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Netilmicin

PubChem CID
441306
Structure
Netilmicin_small.png
Netilmicin_3D_Structure.png
Molecular Formula
Synonyms
  • netilmicin
  • 1-N-Ethylsisomicin
  • 56391-56-1
  • Netilmicina
  • Netilmicine
Molecular Weight
475.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-11
Description
Netilmicin Sulfate can cause developmental toxicity according to state or federal government labeling requirements.
Netilmicin is a semisynthetic 1-N-ethyl derivative of sisomycin, an aminoglycoside antibiotic with action similar to gentamicin, but less ear and kidney toxicity. Netilmicin inhibits protein synthesis in susceptible organisms by binding to the bacterial 30S ribosomal subunit and interfering with mRNA binding and the acceptor tRNA site. The bactericidal effect of netilmiicin is not fully understood.
Netilmicin is an Aminoglycoside Antibacterial.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Netilmicin.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-(ethylamino)-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C21H41N5O7/c1-4-26-13-7-12(24)16(32-19-11(23)6-5-10(8-22)31-19)14(27)17(13)33-20-15(28)18(25-3)21(2,29)9-30-20/h5,11-20,25-29H,4,6-9,22-24H2,1-3H3/t11-,12+,13-,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

CIDUJQMULVCIBT-MQDUPKMGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCN[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]2[C@@H]([C@H]([C@@](CO2)(C)O)NC)O)O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C21H41N5O7
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

56391-57-2

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 PharmGKB ID

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Certomycin
  • Nétromicine
  • Netillin
  • Netilmicin
  • Netilmicin Sulfate
  • Netrocin
  • Netromicina
  • Netromycin
  • Netromycine
  • Sch 20569
  • Sch-20569
  • Sch20569

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
475.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-4.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
475.30059866 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
475.30059866 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
200 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
33
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
673
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
11
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 Solubility

100 mg/mL

3.2.2 LogP

-3

3.2.3 Optical Rotation

Specific optical rotation: +164 deg at 26 °C/D (3 in water)
Budavari, S. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 1996., p. 1112

3.2.4 Decomposition

When heated to decomposition it emits acrid smoke and irritating fumes.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2906

3.2.5 Collision Cross Section

216.82 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

218.55 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

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
3.3.1.1 Human Drugs
Human drug -> Discontinued
Human drug -> Active ingredient (NETILMICIN SULFATE)
Ophthalmological preparations > Anti-infective agents

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

For the treatment of bacteremia, septicaemia, respiratory tract infections, skin and soft-tissue infection, burns, wounds, and peri-operative infections caused by susceptible strains.

6.2 WHO Essential Medicines

Drug
Drug Classes
Ophthalmological preparations > Anti-infective agents
Formulation
Indication
(1) Other specified conjunctivitis; (2) Infectious blepharitis

6.3 FDA Approved Drugs

6.4 FDA Orange Book

6.5 Clinical Trials

6.5.1 EU Clinical Trials Register

6.6 Therapeutic Uses

Gentamycins
National Library of Medicine's Medical Subject Headings online file (MeSH, 1998)
Netilmicin is indicated in the treatment of biliary tract infections caused by susceptible organisms. /Included in US product labeling/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 68
Netilmicin is indicated in the treatment of bone and joint infections caused by susceptible organisms. /Included in US product labeling/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 68
Netilmicin is indicated in the treatment of central nervous system infections caused by susceptible organisms. /Included in US product labeling/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 68
For more Therapeutic Uses (Complete) data for NETILMICIN (13 total), please visit the HSDB record page.

6.7 Drug Warnings

CNS depression, characterized by stupor, flaccidity, coma, or deep respiratory depression, has been reported in very young infants receiving streptomycin at doses that exceeded the maximum recommended amount. However, all aminoglycosides have this potential to cause neuromuscular blockade. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
These aminoglycosides /including netilmicin/ should be used with caution in premature infants and neonates because of these patients' immature renal capability, which may result in prolonged elimination half-life and aminoglycoside-induced toxicity. Dosage adjustments may be required in pediatric patients.
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
Because of their toxicity, aminoglycosides should be used with caution in elderly patients, only after less toxic alternatives have been considered and/or found ineffective. Elderly patients are more likely to have an age-related decrease in renal function. Recommended doses should not be exceeded, and the patient's renal function should be carefully monitored during therapy. Geriatric patients may require smaller daily doses of aminoglycosides in accordance with their increased age, decreased renal function, and, possibly, decreased weight. In addition, loss of hearing may result even in patients with normal renal function. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
Neuromuscular blockade, respiratory paralysis, ototoxicity, and nephrotoxicity may occur following local irrigation and following topical application of aminoglycosides during surgery. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 71
For more Drug Warnings (Complete) data for NETILMICIN (17 total), please visit the HSDB record page.

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

Netilmicin is a semisynthetic, water soluble antibiotic of the aminoglycoside group, produced by the fermentation of Micromonospora inyoensis, a species of actinomycete. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. It is active at low concentrations against a wide variety of pathogenic bacteria including Escherichia coli, bacteria of the Klebsiella-Enterobacter-Serratia group, Citrobacter sp., Proteus sp. (indole-positive and indole-negative), including Proteus mirabilis, P. morganii, P. rettgrei, P. vulgaris, Pseudomonas aeruginosa and Neisseria gonorrhoea. Netilmicin is also active in vitro against isolates of Hemophilus influenzae, Salmonella sp., Shigella sp. and against penicillinase and non-penicillinase-producing Staphylococcus including methicillin-resistant strains. Some strains of Providencia sp., Acinetobacter sp. and Aeromonas sp. are also sensitive to netilmicin. Many strains of the above organisms which are found to be resistant to other aminoglycosides, such as kanamycin, gentamicin, tobramycin and sisomicin, are susceptible to netilmicin in vitro. Occasionally, strains have been identified which are resistant to amikacin but susceptible to netilmicin. The combination of netilmicin and penicillin G has a synergistic bactericidal effect against most strains of Streptococcus faecalis (enterococcus). The combined effect of netilmicin and carbenicillin or ticarcillin is synergistic for many strains of Pseudomonas aeruginosa. In addition, many isolates of Serratia, which are resistant to multiple antibiotics, are inhibited by synergistic combinations of netilmicin with carbenicillin, azlocillin, mezlocillin, cefamandole, cefotaxime or moxalactam. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.

7.2 MeSH Pharmacological Classification

Protein Synthesis Inhibitors
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)
Anti-Bacterial Agents
Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

7.3 FDA Pharmacological Classification

FDA UNII
4O5J85GJJB
Active Moiety
NETILMICIN
Pharmacological Classes
Established Pharmacologic Class [EPC] - Aminoglycoside Antibacterial
Pharmacological Classes
Chemical Structure [CS] - Aminoglycosides
FDA Pharmacology Summary
Netilmicin is an Aminoglycoside Antibacterial.

7.4 ATC Code

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA23 - Netilmicin

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01G - Aminoglycoside antibacterials

J01GB - Other aminoglycosides

J01GB07 - Netilmicin

7.5 Absorption, Distribution and Excretion

Absorption
Rapidly and completely absorbed after IM administration, peak serum levels were achieved within 30-60 minutes. Aminoglycosides are poorly absorbed orally. Topical absorption is also poor unless severe skin damage is present.
Netilmicin is poorly absorbed from the intact GI tract following oral administration. The drug is rapidly and completely absorbed following IM administration.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69
Following absorption, netilmicin rapidly distributes into tissues, sputum, and pericardial, synovial, and peritoneal fluids. ...distributed principally in the extracellular fluid volume... The volume of distribution ...is approximately 20% of body weight. The drug is reportedly 0-30% protein bound.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69
Netilmicin crosses the placenta and has been detected in cord blood. Small amounts of the drug are distributed into milk.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69
...is not metabolized and is excreted unchanged in urine mainly by glomerular filtration. In adults with normal renal function, 74% of a 2 mg/kg dose of netilmicin is excreted unchanged within 24 horus: in adults with creatinine clearances of 30-80 or 10-30 mL/min or in anephric adults, 55, 25, or 15% of the dose is excreted in urine within 24 hours, respectively.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69
Netilmicin is removed by hemodialysis. The drug is also removed by peritoneal dialysis but less readily than by hemodialysis.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69

7.6 Metabolism / Metabolites

No evidence of metabolic transformation, typically 80% is recoverable in the urine within 24 hours

7.7 Biological Half-Life

2.5 hours
The plasma elimination half-life on netilmicin is about 2-2.5 hr following IV or IM administration of a single dose in adults with normal renal function. The serum half-life is reported to be 18 hr in adults with creatinine clearances of 10-30 mL/min and more than 30 hr in anephric adults. The plasma elimination half-life of netilmicin in neonates is inversely related to birthweight and gestational and postnatal age and has been reported to be about 8 or 4.5 hr in neonates less than 7 days of age weighing 1.5-2 or 3-4 kg, respectively. The plasma elimination half-life for children 6 weeks of age and older is 1.5-2 hr.
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69

7.8 Mechanism of Action

Aminoglycosides like netilmicin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically netilmicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes, leaving the bacterium unable to synthesize proteins vital to its growth.
Aminoglycosides are usually bacterial in action. Although the exact mechanism of action has not been fully elucidated, the drugs appear to inhibit protein synthesis in susceptible bacteria by irreversibly binding to 30S ribosomal subunits. /Aminoglycosides/
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 56
/AMINOGLYCOSIDES/ INHIBIT PROTEIN BIOSYNTHESIS & DECR FIDELITY OF TRANSLATION OF GENETIC CODE. /AMINOGLYCOSIDES/
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 1105

8 Use and Manufacturing

8.1 Uses

MEDICATION

8.1.1 Use Classification

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

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H312 (74.5%): Harmful in contact with skin [Warning Acute toxicity, dermal]

H332 (76.4%): Harmful if inhaled [Warning Acute toxicity, inhalation]

H360 (98.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Precautionary Statement Codes

P203, P261, P271, P280, P302+P352, P304+P340, P317, P318, P321, P362+P364, 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 55 reports by companies from 5 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.

9.1.2 Hazard Classes and Categories

Acute Tox. 4 (74.5%)

Acute Tox. 4 (76.4%)

Repr. 1A (98.2%)

9.2 Accidental Release Measures

9.2.1 Disposal Methods

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

9.3 Handling and Storage

9.3.1 Storage Conditions

Commercially available netilmicin sulfate injection should be stored at 2 - 30 °C. /Netilmicin sulfate/
McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 97. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1997 (Plus Supplements)., p. 69

9.4 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Developmental Toxicity

Authoritative List - Prop 65

Report - regardless of intended function of ingredient in the product

9.4.1 FDA Requirements

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
21 CFR 200-299, 300-499, 820, and 860 (4/1/97)

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

10.1.2 Interactions

Concurrent and/or sequential use of 2 or more aminoglycosides by any route or concurrent use of capreomycin with aminoglycosides should be avoided since the potential for ototoxicity, nephrotoxicity, and neuromuscular blockade may be increased; hearing loss may occur and may progress to deafness even after discontinuation of the drug; loss of hearing may be reversible, but usually is permanent; neuromuscular blockade may result in skeletal muscle weakness and respiratory depression or paralysis (apnea). Also, concurrent use of 2 or more aminoglycosides may result in reduced bacterial uptake of each one since the medications compete for the same uptake mechanism. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
Concurrent use of medications with neuromuscular blocking activity, including halogenated hydrocarbon inhalation anesthetics, opioid analgesics, and massive transfusions with citrate anticoagulated blood, with aminoglycosides should be carefully monitored since neuromuscular blockade may be enhanced, resulting in skeletal muscle weakness and respiratory depression or paralysis (apnea); caution is recommended when these medications and aminoglycosides are used concurrently during surgery or in the postoperative period, especially if there is a possibility of incomplete reversal of neuromuscular blockade postoperatively; treatment with anticholinesterase agents or calcium salts may help reverse the blockade. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
Vancomycin and aminoglycosides must often be administered concurrently in the prophylaxis of bacterial endocarditis, in the treatment of endocarditis caused by streptococci and Corynebacteria species, in the treatment of resistant staphylococcal infections, or in penicillin-allergic patients; appropriate monitoring will help to reduce the risk of nephrotoxicity or ototoxicity; renal function determinations, serum aminoglycoside and vancomycin concentrations, dosage reductions, and/or dosage interval adjustments, or alternate antibacterials, may be required. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
Concurrent or sequential use of these medications /nephrotoxic or ototoxic medications/ with aminoglycosides may increase the potential for ototoxicity or nephrotoxicity; hearing loss may occur and may progress to deafness even after discontinuation of the drug and may be reversible, but usually is permanent; serial audiometric function determinations may be required with concurrent or sequential use of other ototoxic antibacterials; renal function determinations may be required. /Aminoglycosides/
USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 70
For more Interactions (Complete) data for NETILMICIN (9 total), please visit the HSDB record page.

10.1.3 Human Toxicity Excerpts

Poison by intravenous, intramuscular, and subcutaneous routes. Human systemic effects by intravenous route: changes to kidney, ureter, and bladder.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p. 2906

10.1.4 Protein Binding

Protein-binding of is low and depends on the test conditions (mainly the concentration of cations in the test medium).

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Nature Journal References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Drug-Drug Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 KEGG: ATC

16.4 KEGG: Drug Groups

16.5 KEGG : Antimicrobials

16.6 WHO ATC Classification System

16.7 FDA Pharm Classes

16.8 ChemIDplus

16.9 ChEMBL Target Tree

16.10 UN GHS Classification

16.11 NORMAN Suspect List Exchange Classification

16.12 CCSBase Classification

16.13 EPA DSSTox Classification

16.14 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. California Office of Environmental Health Hazard Assessment (OEHHA)
  2. DrugBank
    LICENSE
    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
  3. FDA Pharm Classes
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  4. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  6. California Safe Cosmetics Program (CSCP) Product Database
  7. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  8. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. 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
    D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-β-l-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-d-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-N1-ethyl-, sulfate (2:5) (salt)
    https://echa.europa.eu/substance-information/-/substanceinfo/100.054.662
    D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-β-l-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-d-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-N1-ethyl-, sulfate (2:5) (salt) (EC: 260-147-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/41683
  11. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Hazardous Substances Data Bank (HSDB)
  13. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  14. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  15. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  16. WHO Model Lists of Essential Medicines
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) license.
    https://www.who.int/about/policies/publishing/copyright
  17. EU Clinical Trials Register
  18. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  19. Japan Chemical Substance Dictionary (Nikkaji)
  20. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  21. Metabolomics Workbench
  22. Nature Chemical Biology
  23. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Netilmicin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  24. Therapeutic Target Database (TTD)
  25. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  26. Springer Nature
  27. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    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/
  28. Wikidata
  29. Wikipedia
  30. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Protein Synthesis Inhibitors
    https://www.ncbi.nlm.nih.gov/mesh/68011500
  31. PubChem
  32. GHS Classification (UNECE)
  33. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  34. PATENTSCOPE (WIPO)
  35. NCBI
CONTENTS