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Meropenem

PubChem CID
441130
Structure
Meropenem_small.png
Meropenem_3D_Structure.png
Molecular Formula
Synonyms
  • meropenem
  • 96036-03-2
  • Merrem
  • Meropenem anhydrous
  • Meropenemum
Molecular Weight
383.5 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-11
Description
Meropenem is a carbapenemcarboxylic acid in which the azetidine and pyrroline rings carry 1-hydroxymethyl and in which the azetidine and pyrroline rings carry 1-hydroxymethyl and 5-(dimethylcarbamoyl)pyrrolidin-3-ylthio substituents respectively. It has a role as an antibacterial drug, an antibacterial agent and a drug allergen. It is a carbapenemcarboxylic acid, a pyrrolidinecarboxamide, an alpha,beta-unsaturated monocarboxylic acid and an organic sulfide.
Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death. In August 2017, a combination antibacterial therapy under the market name vabomere was approved for treatment of adult patients with complicated urinary tract infections (cUTI). Vabomere consists of meropenem and [DB12107] and is intravenously admininstered. The treatment aims to resolve infection-related symptoms and achieve negative urine culture, where the infections are proven or strongly suspected to be caused by susceptible bacteria.
Meropenem anhydrous is a Penem Antibacterial.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Meropenem.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

DMJNNHOOLUXYBV-PQTSNVLCSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H25N3O5S
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

119478-56-7

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 RXCUI

2.3.14 Wikidata

2.3.15 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 3-(5-dimethylcarbamoylpyrrolidin-3-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid
  • meropenem
  • Merrem
  • Penem
  • Ronem
  • SM 7338
  • SM-7338
  • SM7338

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
383.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
-2.4
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
383.15149208 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
383.15149208 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
135 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
679
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
6
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Solubility

Sparingly
5.63e+00 g/L

3.2.3 LogP

-0.6
-0.6

3.2.4 Stability / Shelf Life

Solutions of Meropenem (Meropenem concentrations ranging from 1 to 20 mg/mL) in Water for Injection or Sodium Chloride Injection 0.9% (for up to 4 hours) or in Dextrose Injection 5% (for up to 2 hours) at controlled room temperatures 15-25 °C (59-77 °F) are stable in plastic tubing and volume control devices of common intravenous infusion sets. Solutions of Meropenem (Meropenem concentrations ranging from 1 to 20 mg/mL) in Water for Injection or Sodium Chloride Injection 0.9% (for up to 48 hours) or in Dextrose Injection 5% (for up to 6 hours) are stable at 4 °C (39 °F) in plastic syringes.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
Freshly prepared solutions of Meropenem should be used whenever possible. However, constituted solutions of Meropenem maintain satisfactory potency at controlled room temperature 15-25 °C (59-77 °F) or under refrigeration at 4 °C (39 °F) ... . Solutions of intravenous Meropenem should not be frozen.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
Meropenem injection vials constituted with sterile Water for Injection for bolus administration (up to 50 mg/mL of Meropenem) may be stored for up to 2 hours at controlled room temperature 15-25 °C (59-77 °F) or for up to 12 hours at 4 °C (39 °F).
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
Solutions of Meropenem (Meropenem concentrations ranging from 2.5 to 20 mg/mL) in Baxter Minibag Plus bags with Sodium Chloride Injection 0.9% may be stored for up to 4 hours at controlled room temperatures 15-25 °C (59-77 °F) or for up to 24 hours at 4 °C (39 °F). Solutions of Meropenem (Meropenem concentrations ranging from 2.5 to 20 mg/mL) in Baxter Minibag Plus bags with Dextrose Injection 5% may be stored up to 1 hour at controlled room temperatures 15-25 °C (59-77 °F) or for up to 6 hours at 4 °C (39 °F).
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
Meropenem infusion vials constituted with Sodium Chloride Injection 0.9% (Meropenem concentrations ranging from 2.5 to 50 mg/mL) are stable for up to 2 hours at controlled room temperature 15-25 °C (59-77 °F) or for up to 18 hours at 4 °C (39 °F). Infusion vials of Meropenem constituted with Dextrose Injection 5% (Meropenem concentrations ranging from 2.5 to 50 mg/mL) are stable for up to 1 hour at controlled room temperature 15-25 °C (59-77 °F) or for up to 8 hours at 4 °C (39 °F).
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

3.2.5 Collision Cross Section

190.79 Ų [M+H]+

192.42 Ų [M-H]-

S61 | UJICCSLIB | Collision Cross Section (CCS) Library from UJI | DOI:10.5281/zenodo.3549476

3.2.6 Other Experimental Properties

White to pale yellow crystalline powder. Sparingly soluble in water; very slightly soluble in hydrated ethanol /Meropenem trihydrate/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1018
The solution varies from colorless to yellow depending on the concentration. The pH of freshly constituted solutions is between 7.3 and 8.3. Meropenem is soluble in 5% monobasic potassium phosphate solution ... and practically insoluble in acetone or ether. /Meropenem trihydrate/
US Natl Inst Health; DailyMed. Current Medical Information. Available from, as of Jan 27, 2012: https://dailymed.nlm.nih.gov/dailymed/about.cfm

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Antibiotics
S6 | ITNANTIBIOTIC | Antibiotic List from the ITN MSCA ANSWER | DOI:10.5281/zenodo.2621956
S57 | GREEKPHARMA | Suspect Pharmaceuticals from the National Organization of Medicine, Greece | DOI:10.5281/zenodo.3248883
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals -> unsed in Switzerland 2014-2016
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Anti-Infective Agents; Carbapenems
Human drug -> Prescription
Human drug -> Prescription; Discontinued; Active ingredient (MEROPENEM)
Paediatric drug

Antituberculosis medicines

Watch group antibiotics

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 LC-MS

MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
384.159
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

70.065132 100

68.049515 76.88

110.071228 28.67

84.044380 18.55

384.158783 14.16

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4.2 IR Spectra

4.2.1 FTIR Spectra

Instrument Name
Bio-Rad FTS
Technique
KBr0
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/16068>16068</a>
Lot Number
0459369-26
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/16068>16068</a>
Lot Number
0459369-26
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For use as single agent therapy for the treatment of the following infections when caused by susceptible isolates of the designated microorganisms: complicated skin and skin structure infections due to Staphylococcus aureus (b-lactamase and non-b-lactamase producing, methicillin-susceptible isolates only), Streptococcus pyogenes, Streptococcus agalactiae, viridans group streptococci, Enterococcus faecalis (excluding vancomycin-resistant isolates), Pseudomonas aeruginosa, Escherichia coli, Proteus mirabilis, Bacteroides fragilis and Peptostreptococcus species; complicated appendicitis and peritonitis caused by viridans group streptococci, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, and Peptostreptococcus species. Also for use in the treatment of bacterial meningitis caused by Streptococcus pneumoniae, Haemophilus influenzae (b-lactamase and non-b-lactamase-producing isolates), and Neisseria meningitidis.
Treatment of bacterial sepsis, Treatment of bacterial meningitis

7.2 LiverTox Summary

Meropenem is a carbapenem antibiotic with broad spectrum of activity that is administered intravenously and used for severe bacterial infections due to sensitive agents. Meropenem is a common cause of mild transient aminotransferase elevations and can rarely result in clinically apparent, cholestatic liver injury.

7.3 Drug Classes

Breast Feeding; Lactation; Anti-Infective Agents; Carbapenems
Antiinfective Agents

7.4 WHO Essential Medicines

Drug
Drug Classes
Antituberculosis medicines
Formulation
Parenteral - General injections - IV: 500 mg in vial (as trihydrate) powder for injection; 1 g in vial (as trihydrate) powder for injection
Indication
Multi-drug resistant Mycobacterium tuberculosis
Drug
Drug Classes
Watch group antibiotics
Formulation
Parenteral - General injections - IV: 500 mg in vial (as trihydrate) powder for injection; 1 g in vial (as trihydrate) powder for injection
Indication
(1) Neonatal meningitis; (2) Peritonitis (severe); (3) Peritoneal abscess (severe); (4) Neutropenia (high-risk)

7.5 FDA Approved Drugs

7.6 FDA Orange Book

7.7 FDA National Drug Code Directory

7.8 Drug Labels

Drug and label
Active ingredient and drug

7.9 Clinical Trials

7.9.1 ClinicalTrials.gov

7.9.2 EU Clinical Trials Register

7.9.3 NIPH Clinical Trials Search of Japan

7.10 EMA Drug Information

Type
Paediatric investigation
Active Substance
Therapeutic Area
Infectious diseases
Drug Form
Powder for solution for injection/infusion
Administration Route
Intravenous use
Decision Type
PM: decision on the application for modification of an agreed PIP
Decision Date
2016-03-18

7.11 Therapeutic Uses

Anti-Bacterial Agents
National Library of Medicine's Medical Subject Headings online file (MeSH, 2012)
Meropenem is used for the treatment of intra-abdominal infections, including complicated appendicitis and peritonitis, caused by susceptible bacteria. The drug may be used as monotherapy for the treatment of intra-abdominal infections caused by susceptible viridans streptococci, Escherichia coli, Klebsiella pneumonia, Pseudomonas aeruginosa, Bacteroides fragilis, B. thetaiotaomicron, or Peptostreptococcus. Because meropenem has a broad spectrum of antibacterial activity, the drug may be used empirically to treat intra-abdominal infections before identification of the causative organism. /Included in US product labeling/
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 186
Meropenem is used for the treatment of bacterial meningitis caused by susceptible Streptococcus pneumoniae, Haemophilus influenzae (including beta-lactamase-producing strains), or Neisseria meningitidis in children 3 months of age and older. /Included in US product labeling/
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 187
The drug also is used in the treatment of meningitis in adults. /NOT included in US product labeling/
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 187
For more Therapeutic Uses (Complete) data for Meropenem (20 total), please visit the HSDB record page.

7.12 Drug Warnings

Serious and occasionally fatal hypersensitivity reactions (e.g., anaphylaxis) reported with beta-lactams. If hypersensitivity occurs, discontinue meropenem and institute appropriate therapy as indicated (e.g., epinephrine, corticosteroids, and maintenance of an adequate airway and oxygen).
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 189
Adverse effects reported in 1% or more of patients receiving meropenem including GI effects (diarrhea, nausea, vomiting, constipation), local reactions (pain and inflammation at injection site, phlebitis/thrombophlebitis), headache, anemia, rash, pruritus, sepsis, apnea, shock, glossitis, and oral candidiasis.
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 190
Seizures and other adverse CNS effects reported during meropenem therapy, especially in those with underlying CNS disorders (e.g., brain lesions, history of seizures), bacterial meningitis, or compromised renal function. Do not exceed recommended dosage, especially in those with known factors that predispose to seizures. Anticonvulsant therapy should be continued in those with known seizure disorders. If focal tremors, myoclonus, or seizures occur, evaluate the patient neurologically, initiate anticonvulsant therapy if necessary, and determine whether meropenem dosage should be decreased or the drug discontinued.
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 189
Partial cross-allergenicity among beta-lactam antibiotics, including penicillins, cephalosporins, and other beta-lactams. Prior to initiation of meropenem therapy, make careful inquiry concerning previous hypersensitivity reactions to meropenem, cephalosporins, penicillins, or other drugs.
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 189
For more Drug Warnings (Complete) data for Meropenem (8 total), please visit the HSDB record page.

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Meropenem is a broad-spectrum carbapenem antibiotic. It is active against Gram-positive and Gram-negative bacteria. Meropenem exerts its action by penetrating bacterial cells readily and interfering with the synthesis of vital cell wall components, which leads to cell death.

8.2 MeSH Pharmacological Classification

Anti-Bacterial Agents
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
YOP6PX0BAO
Active Moiety
MEROPENEM ANHYDROUS
Pharmacological Classes
Chemical Structure [CS] - Carbapenems
Pharmacological Classes
Established Pharmacologic Class [EPC] - Penem Antibacterial
FDA Pharmacology Summary
Meropenem anhydrous is a Penem Antibacterial.
2 of 2
Non-Proprietary Name
MEROPENEM
Pharmacological Classes
Carbapenems [CS]; Penem Antibacterial [EPC]

8.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DH - Carbapenems

J01DH02 - Meropenem

8.5 Absorption, Distribution and Excretion

Route of Elimination
Approximately 70% of the intravenously administered dose is recovered as unchanged meropenem in the urine over 12 hours, after which little further urinary excretion is detectable.
Approximately 70% of the intravenously administered dose is recovered as unchanged meropenem in the urine over 12 hours, after which little further urinary excretion is detectable. Urinary concentrations of meropenem in excess of 10 ug/mL are maintained for up to 5 hours after a 500 mg dose.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
Meropenem is distributed into most body tissues and fluids, including bronchial mucosa, lung, bile, gynecologic tissue (endometrium, myometrium, ovary, cervix, fallopian tube), muscle, heart valves, skin, interstitial and peritoneal fluid, and CSF. Plasma protein binding is approximately 2%. The drug is partially metabolized to at least one microbiologically inactive metabolite. About 70% of an IV dose is eliminated in urine as unchanged drug by tubular secretion and glomerular filtration.
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 190
At the end of a 30 minute intravenous infusion of a single dose of Meropenem for injection (IV) in healthy volunteers, mean peak plasma concentrations of meropenem are approximately 23 ug/mL (range 14-26) for the 500 mg dose and 49 ug/mL (range 39-58) for the 1 g dose. A 5-minute intravenous bolus injection of Meropenem for injection (IV) in healthy volunteers results in mean peak plasma concentrations of approximately 45 ug/mL (range 18-65) for the 500 mg dose and 112 ug/mL (range 83-140) for the 1 g dose. Following intravenous doses of 500 mg, mean plasma concentrations of meropenem usually decline to approximately 1 ug/mL at 6 hours after administration. No accumulation of meropenem in plasma was observed with regimens using 500 mg administered every 8 hours or 1 g administered every 6 hours in healthy volunteers with normal renal function.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011).

8.6 Metabolism / Metabolites

Primarily excreted unchanged. There is one metabolite which is microbiologically inactive.
There is one metabolite of meropenem that is microbiologically inactive.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

8.7 Biological Half-Life

Approximately 1 hour in adults and children 2 years of age and older with normal renal function. Approximately 1.5 hours in children 3 months to 2 years of age.
The plasma half-life of meropenem is approximately 1 hour in adults with normal renal function and 1.5 hours in children 3 months to 2 years of age. Plasma half-life is increased and clearance of the drug is decreased in patients with renal impairment.
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 190

8.8 Mechanism of Action

The bactericidal activity of meropenem results from the inhibition of cell wall synthesis. Meropenem readily penetrates the cell wall of most Gram-positive and Gram-negative bacteria to reach penicillin-binding- protein (PBP) targets. Its strongest affinities are toward PBPs 2, 3 and 4 of Escherichia coli and Pseudomonas aeruginosa; and PBPs 1, 2 and 4 of Staphylococcus aureus.
The bactericidal activity of meropenem results from the inhibition of cell wall synthesis. Meropenem readily penetrates the cell wall of most Gram-positive and Gram-negative bacteria to reach penicillin-binding-protein (PBP) targets. Its strongest affinities are toward PBPs 2, 3 and 4 of Escherichia coli and Pseudomonas aeruginosa; and PBPs 1, 2, and 4 of Staphylococcus aureus. Bactericidal concentrations (defined as a 3 log10 reduction in cell counts within 12 to 24 hours) are typically 1-2 times the bacteriostatic concentrations of meropenem, with the exception of Listeria monocytogenes, against which lethal activity is not observed.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

8.9 Human Metabolite Information

8.9.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9 Use and Manufacturing

9.1 Uses

MEDICATION

Use (kg) in Switzerland (2009): >100

Use (kg; approx.) in Germany (2009): >2500

Use (kg; exact) in Germany (2009): 3586

Use (kg) in USA (2002): 1110

Consumption (g per capita) in Switzerland (2009): 0.013

Consumption (g per capita; approx.) in Germany (2009): 0.031

Consumption (g per capita; exact) in Germany (2009): 0.044

Consumption (g per capita) in the USA (2002): 0.0039

Excretion rate: 0.7

Calculated removal (%): 75.1

9.1.1 Use Classification

Human Drugs -> EU pediatric investigation plans
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9.2 Methods of Manufacturing

Preparation: M. Sunagawa et al., EP 126587; M. Sunagawa, US 4943569 (1984, 1990 both to Sumitomo)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1018

9.3 Formulations / Preparations

Table: Meropenem (Trihydrate) Preparations
Route of Administration
Parenteral
Dosage Form
For injection, for IV use only
Strength
500 mg (of anhydrous meropenem)
Brand or Generic Name (Manufacturer)
Merrem IV (AstraZeneca)
Route of Administration
Parenteral
Dosage Form
For injection, for IV use only
Strength
1 g (of anhydrous meropenem)
Brand or Generic Name (Manufacturer)
Merrem IV (AstraZeneca)
American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 190

10 Identification

10.1 Analytic Laboratory Methods

The present work reports a microbiological assay, applying the cylinder-plate method, for the determination of meropenem in powder for injection.
Mendez AS et al; J Pharm Biomed Anal 37 (4): 649-53 (2005)

10.2 Clinical Laboratory Methods

A sensitive and rapid HPLC assay for the determination of the beta-lactam antibiotics ceftazidime and meropenem in serum and bronchial secretions is described. HPLC-integrated sample preparation allows direct injection of serum samples without any pretreatment. Sputum samples need only a simple homogenisation and volume measurement but no liquefying reagents are necessary.
Ehrlich M et al; J Chromatogr B Biomed Sci Appl 751 (2): 357-63 (2001)
A simple and sensitive high-performance liquid chromatography (HPLC) method with ultraviolet (UV) detection has been developed and validated for simultaneous quantification of five beta-lactam antibiotics in human plasma: cefepim, ceftazidim, cefuroxim, meropenem and piperacillin. The plasma sample, after spiked with ceforanid as an internal standard (IS), was submitted to a solid-phase extraction (SPE) prior to HPLC analysis. A chromatographic separation was achieved on a C8 symmetry column with a mobile phase consisting of an acetonitrile and phosphate buffer (pH 7.4) mixture in a gradient mode. Detection was carried out at a wavelength between 200 and 400 nm.
Denooz R, Charlier C; J Chromatogr B Analyt Technol Biomed Life Sci 864 (1-2): 161-7 (2008)
A rapid, accurate and sensitive liquid chromatographic assay with on-line solid-phase extraction for determination of meropenem in serum is described. Sample was directly injected onto the extraction column for sample clean-up and extraction. Thereafter, using an on-line column-switching system the drug was quantitatively transferred and separated on a C18 analytical column. Ultraviolet absorption at 298 nm was used for detection. The assay was linear from 1 to 100 micrograms/mL. Recovery was 98.5%. Based on a 20-microliters sample volume (serum- water, 1:1, v/v), detection limit was 0.1 microgram/mL.
Bompadre S et al: J Chromatogr A 812 (1-2): 249-53 (1998)
Concentration determination of meropenem, a carbapenem antibiotic, using a capillary electrophoresis method by direct injection of serum samples without any pretreatment is described herein. Sodium tetraborate (25 mM)-sodium hydroxide (0.1 M) containing sodium dodecyl sulfate (90 mM) is used as a run buffer (pH 10.0). Meropenem is detected at its absorption maximum at 297 nm. Migration time of meropenem is approximately 7.2 min, and the detection limit of the assay is 2.0 mg/L at a signal-to-noise ratio of 3.0. The relative standard deviations of intra- and interassay accuracies are 3.43-8.87% and 4.28-8.54%, respectively, at a nominal concentration of 6.3-100.0 mg/L, and their recovery rates are 94-111% and 92-105%, respectively.
Kitahashi T, Furuta I; J Chromatogr Sci 43 (8): 430-3 (2005)

11 Safety and Hazards

11.1 Hazards Identification

11.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H315 (76.9%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (23.1%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (76.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H334 (23.1%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

H335 (76.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 13 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

11.1.2 Hazard Classes and Categories

Skin Irrit. 2 (76.9%)

Skin Sens. 1 (23.1%)

Eye Irrit. 2 (76.9%)

Resp. Sens. 1 (23.1%)

STOT SE 3 (76.9%)

Skin Irrit. 2 (93.2%)

Eye Irrit. 2 (93.2%)

STOT SE 3 (16.9%)

11.1.3 Fire Potential

This material is assumed to be combustible.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)

11.2 Fire Fighting

11.2.1 Fire Fighting Procedures

As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)
Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)

11.3 Accidental Release Measures

11.3.1 Cleanup Methods

Spill Response: Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labelled container for disposal. Wash spill site.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)

11.3.2 Disposal Methods

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

11.3.3 Preventive Measures

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Engineering controls such as exhaust ventilation are recommended.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)
As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)
As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)

11.4 Exposure Control and Personal Protection

11.4.1 Personal Protective Equipment (PPE)

Respiratory Protection: Use a NIOSH approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used. Gloves: Chemically compatible. Eye Protection: Safety Glasses. Protective Clothing: Protect exposed skin.
United States Pharmacopeial Convention, Inc (USP); MSDS Database Online; Material Safety Data Sheet: Meropenem; Catalog Number: 1392454; (Revision Date: April 3, 2006)

11.5 Regulatory Information

11.5.1 FDA Requirements

The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including meropenem, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
DHHS/FDA; Electronic Orange Book-Approved Drug Products with Therapeutic Equivalence Evaluations. Available from, as of March 5, 2012: https://www.fda.gov/cder/ob/

12 Toxicity

12.1 Toxicological Information

12.1.1 Hepatotoxicity

Serum aminotransferase elevations have been reported in 1% to 6% of recipients of intravenous meropenem when given for up to 14 days. These elevations are usually transient, mild and asymptomatic; and rarely require dose adjustment. Meropenem has also been linked to rare cases of cholestatic jaundice that usually arises after 1 to 3 weeks of therapy. Immunoallergic features may be present, but are rarely prominent. Autoantibodies are rare. Most cases are mild and self-limited, but at least one instance of vanishing bile duct syndrome related to meropenem therapy has been published (Case 1). Meropenem has not been reported to cause acute liver failure.

Likelihood score: D (possible rare cause of clinically apparent liver injury).

12.1.2 Drug Induced Liver Injury

Compound
meropenem
DILI Annotation
Less-DILI-Concern
Severity Grade
3
Label Section
Warnings and precautions
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

12.1.3 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Although no information is available on the use of meropenem during breastfeeding, milk levels appear to be low and beta-lactams are generally not expected to cause adverse effects in breastfed infants. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with beta-lactams, but these effects have not been adequately evaluated. Vaborbactam, which is available in combination with meropenem in the product Vabomere, has not been studied in nursing mothers, but the combination is expected to have similar concerns as with meropenem alone.

◉ Effects in Breastfed Infants

A mother received meropenem 1 gram IV every 8 hours for 7 days while exclusively breastfeeding her newborn. When questioned later, she stated that her infant had no oral thrush, watery diarrhea, or diaper dermatitis that required antifungal therapy during the month following her meropenem therapy.

An infant was breastfed (extent not stated) until the 4th month postpartum. At 2 months of age, his mother was given a 2-week course of tobramycin and meropenem (dosage not specified) for a cystic fibrosis exacerbation. The infant displayed no change in stool pattern during the maternal treatment and had normal renal function at 6 months of age.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

12.1.4 Acute Effects

12.1.5 Interactions

Case reports in the literature have shown that co-administration of carbapenems, including meropenem, to patients receiving valproic acid or divalproex sodium results in a reduction in valproic acid concentrations. The valproic acid concentrations may drop below the therapeutic range as a result of this interaction, therefore increasing the risk of breakthrough seizures. Although the mechanism of this interaction is unknown, data from in vitro and animal studies suggest that carbapenems may inhibit the hydrolysis of valproic acid's glucuronide metabolite (VPA-g) back to valproic acid, thus decreasing the serum concentrations of valproic acid. If administration of Meropenem for injection is necessary, then supplemental anti-convulsant therapy should be considered
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
Probenecid competes with meropenem for active tubular secretion, resulting in increased plasma concentrations of meropenem. Co-administration of probenecid with meropenem is not recommended.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

12.1.6 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 160-1

12.1.7 Human Toxicity Excerpts

/CASE REPORTS/ A male patient was hospitalized as a case of pneumonia. He was diabetic, hypertensive and post Hepatitis "C". He reported skin eruption following administration of meropenem. Skin biopsy revealed acute generalized exanthematous pustulosis. ... The diagnosis was made after excluding all other possible causes. Dermatologists and clinicians must be aware of this .. unusual side effect.
Khalel MH et al; Indian J Dermatol 55 (2): 176-7 (2010)
/CASE REPORTS/ Vanishing bile duct syndrome is a rare and potentially life-threatening disorder in which progressive destruction and disappearance of small intrahepatic bile ducts occur, with resultant cholestasis. The mechanism by which biliary epithelial cells are damaged and intrahepatic bile ducts are lost has not been fully elucidated. However, many etiologies have been reported,and several drugs have been implicated. Meropenem is a widely used, well tolerated broad-spectrum carbapenem antibiotic indicated for the treatment of intraabdominal infections, complicated skin and skin structure infections, and pediatric bacterial meningitis. We describe what we believe is the first reported case of meropenem-induced vanishing bile duct syndrome. A 60-year-old woman was diagnosed with vanishing bile duct syndrome after being treated with meropenem for a left temporal lobe brain abscess. Three weeks after starting the drug, the patient developed mixed hepatocellular and cholestatic liver injury with jaundice and pruritus.Meropenem-induced liver injury was suspected, and the drug was discontinued. Diagnostic tests ruled out other causes of cholestasis, including infectious and immunologic conditions. A liver biopsy, performed due to persistent liver injury, demonstrated an absence of bile ducts, which, in conjunction with the patient's clinical course, was consistent with the diagnosis of vanishing bile duct syndrome. Several months after the cessation of meropenem, the patient's liver function test results improved. Use of the Naranjo adverse drug reaction probability scale indicated a probable relationship (score of 6) between the patient's development of vanishing bile duct syndrome and meropenem therapy. A high index of suspicion is necessary to diagnose vanishing bile duct syndrome and other types of drug induced liver injury. Clinicians should consider vanishing bile duct syndrome as a potential diagnosis in patients receiving meropenem who have prolonged cholestasis, especially after other more probable causes have been excluded.
Schumaker AL, Okulicz JF; Pharmacotherapy 30 (9): 953 (2010)
/GENOTOXICITY/ Genetic toxicity studies were performed with meropenem using the ... cultured human lymphocytes cytogenic assay ... . There was no evidence of mutagenic potential found in /this test/.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

12.1.8 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ In mice and rats, large intravenous doses of meropenem (2200-4000 mg/kg) have been associated with ataxia, dyspnea, convulsions, and mortalities.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Reproductive studies were performed with meropenem in rats at doses up to 1000 mg/kg/day, and cynomolgus monkeys at doses up to 360 mg/kg/day (on the basis of AUC comparisons, approximately 1.8 times and 3.7 times, respectively, to the human exposure at the usual dose of 1 g every 8 hours). There was no reproductive toxicity seen
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem
/GENOTOXICITY/ Genetic toxicity studies were performed with meropenem using the bacterial reverse mutation test, the Chinese hamster ovary HGPRT assay, ... and the mouse micronucleus test. There was no evidence of mutagenic potential found in any of these tests.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

12.1.9 Populations at Special Risk

Meropenem for injection (IV) is contraindicated in patients with known hypersensitivity to any component of this product or to other drugs in the same class or in patients who have demonstrated anaphylactic reactions to beta-lactams.
US Natl Inst Health; DailyMed. Current Medication Information for MEROPENEM injection, powder, for solution (October 2011). Available from, as of February 8, 2012: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=meropenem

12.1.10 Protein Binding

Approximately 2%.

13 Associated Disorders and Diseases

14 Literature

14.1 Consolidated References

14.2 NLM Curated PubMed Citations

14.3 Springer Nature References

14.4 Thieme References

14.5 Wiley References

14.6 Chemical Co-Occurrences in Literature

14.7 Chemical-Gene Co-Occurrences in Literature

14.8 Chemical-Disease Co-Occurrences in Literature

15 Patents

15.1 Depositor-Supplied Patent Identifiers

15.2 WIPO PATENTSCOPE

15.3 FDA Orange Book Patents

15.4 Chemical Co-Occurrences in Patents

15.5 Chemical-Disease Co-Occurrences in Patents

15.6 Chemical-Gene Co-Occurrences in Patents

16 Interactions and Pathways

16.1 Protein Bound 3D Structures

16.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

16.2 Chemical-Target Interactions

16.3 Drug-Drug Interactions

17 Biological Test Results

17.1 BioAssay Results

18 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

19 Classification

19.1 MeSH Tree

19.2 NCI Thesaurus Tree

19.3 ChEBI Ontology

19.4 KEGG: ATC

19.5 KEGG: Drug Groups

19.6 KEGG : Antimicrobials

19.7 WHO ATC Classification System

19.8 FDA Pharm Classes

19.9 ChemIDplus

19.10 ChEMBL Target Tree

19.11 UN GHS Classification

19.12 NORMAN Suspect List Exchange Classification

19.13 EPA DSSTox Classification

19.14 LOTUS Tree

19.15 FDA Drug Type and Pharmacologic Classification

19.16 EPA Substance Registry Services Tree

19.17 MolGenie Organic Chemistry Ontology

20 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    (4R,5S,6S)-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
    https://echa.europa.eu/substance-information/-/substanceinfo/100.169.299
    (4R,5S,6S)-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-3-pyrrolidinyl]thio]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (EC: 641-424-1)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/174186
  6. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Hazardous Substances Data Bank (HSDB)
  8. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  9. ChEBI
  10. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. LiverTox
  12. LOTUS - the natural products occurrence database
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    https://lotus.nprod.net/
  13. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  14. Open Targets
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    https://platform-docs.opentargets.org/licence
  15. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  16. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  17. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  18. Drug Gene Interaction database (DGIdb)
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    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  19. Therapeutic Target Database (TTD)
  20. DailyMed
  21. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
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    https://www.ema.europa.eu/en/about-us/legal-notice
  23. Drugs and Lactation Database (LactMed)
  24. Drugs@FDA
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
    MEROPENEM AND SODIUM CHLORIDE IN DUPLEX CONTAINER
    https://www.accessdata.fda.gov/scripts/cder/daf/
  25. WHO Model Lists of Essential Medicines
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    https://www.who.int/about/policies/publishing/copyright
  26. EU Clinical Trials Register
  27. FDA Orange Book
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  28. National Drug Code (NDC) Directory
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  29. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    MEROPENEM
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  30. Japan Chemical Substance Dictionary (Nikkaji)
  31. KEGG
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    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  32. MassBank of North America (MoNA)
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    https://mona.fiehnlab.ucdavis.edu/documentation/license
  33. Metabolomics Workbench
  34. NIPH Clinical Trials Search of Japan
  35. NLM RxNorm Terminology
    LICENSE
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  36. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  37. Protein Data Bank in Europe (PDBe)
  38. RCSB Protein Data Bank (RCSB PDB)
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    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  39. SpectraBase
  40. Springer Nature
  41. Thieme Chemistry
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    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
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  43. Wikipedia
  44. Wiley
  45. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  46. PubChem
  47. GHS Classification (UNECE)
  48. EPA Substance Registry Services
  49. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  50. PATENTSCOPE (WIPO)
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