An official website of the United States government

Sulbactam

PubChem CID
130313
Structure
Sulbactam_small.png
Sulbactam_3D_Structure.png
Molecular Formula
Synonyms
  • SULBACTAM
  • 68373-14-8
  • Betamaze
  • Penicillanic Acid Sulfone
  • Sulbactamum
Molecular Weight
233.24 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2025-01-18
Description
Sulbactam is a member of penicillanic acids. It is a conjugate acid of a sulbactam(1-).
Sulbactam is a beta (β)-lactamase inhibitor and a derivative of the basic penicillin nucleus. When given in combination with β-lactam antibiotics, sulbactam produces a synergistic effect as it blocks the enzyme responsible for drug resistance by hydrolyzing β-lactams.
Sulbactam is a beta Lactamase Inhibitor. The mechanism of action of sulbactam is as a beta Lactamase Inhibitor.
See also: Sulbactam Sodium (has salt form); Sulbactam Pivoxil (is active moiety of); Sulbactam Benzathine (is active moiety of).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Sulbactam.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

FKENQMMABCRJMK-RITPCOANSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C8H11NO5S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

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 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 RXCUI

2.3.13 Wikidata

2.3.14 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Bétamaze
  • Combactam
  • CP 45899
  • CP-45899
  • CP45899
  • Penicillanic Acid Sulfone
  • Sodium, Sulbactam
  • Sulbactam
  • Sulbactam Sodium
  • Sulfone, Penicillanic Acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
233.24 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
233.03579362 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
233.03579362 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
100 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
446
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
2
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 Melting Point

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Antibiotics
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

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

Source of Spectrum
J-55-5114-10
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Sulbactam is used in combination with other antibacterial agents. With [ampicillin], it is used to treat skin and skin structure infections, intra-abdominal infections, and gynecological infections caused by susceptible bacteria. In combination with [durlobactam], sulbactam is indicated in adults for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia (HABP/VABP), caused by susceptible isolates of _Acinetobacter baumannii-calcoaceticus_ complex.

7.2 Drug Labels

Drug and label

7.3 Clinical Trials

7.3.1 ClinicalTrials.gov

7.3.2 EU Clinical Trials Register

7.3.3 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

When given together with beta-lactam antibiotics, sulbactam broadens their antibacterial spectrum by blocking the enzyme involved in their hydrolysis. Sulbactam alone possesses weak intrinsic antibacterial activity except against the _Neisseriaceae_, _Acinetobacter spp._, and _Bacteroides fragilis_ as it can bind to the penicillin-binding proteins. Sulbactam restores the activity of beta-lactam antibiotics against a range of beta-lactamase-producing gram-positive and gram-negative bacteria.

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.)
beta-Lactamase Inhibitors
Endogenous substances and drugs that inhibit or block the activity of BETA-LACTAMASES. (See all compounds classified as beta-Lactamase Inhibitors.)

8.3 FDA Pharmacological Classification

FDA UNII
S4TF6I2330
Active Moiety
SULBACTAM
Pharmacological Classes
Established Pharmacologic Class [EPC] - beta Lactamase Inhibitor
Pharmacological Classes
Mechanisms of Action [MoA] - beta Lactamase Inhibitors
FDA Pharmacology Summary
Sulbactam is a beta Lactamase Inhibitor. The mechanism of action of sulbactam is as a beta Lactamase Inhibitor.

8.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CG - Beta-lactamase inhibitors

J01CG01 - Sulbactam

8.5 Absorption, Distribution and Excretion

Absorption
Sulbactam is poorly absorbed after oral administration. Peak serum concentrations of ampicillin and sulbactam are reached following a 15-minute intravenous infusion. After the intravenous administration of 2000 mg of ampicillin plus 1000 mg sulbactam, peak sulbactam serum levels corresponded to 48 to 88 mcg/mL. After the intravenous administration of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels corresponded to 21 to 40 mcg/mL. After an intramuscular injection of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels ranged from 6 to 24 mcg/mL.
Route of Elimination
When given in combination with ampicillin in individuals with normal renal function, approximately 75 to 85% of the drug is excreted unchanged in the urine during the first eight hours after administration.
Volume of Distribution
The steady-state volumes of distribution range from 12.2 to 16.3 L. Sulbactam exhibits extensive distribution in extracellular fluids and tissues. Penetration of sulbactam into cerebrospinal fluid is enhanced in the presence of inflamed meninges.
Clearance
Eenal clearance is approximately 12 L/h following infusion over 15 to 30 minutes.

8.6 Metabolism / Metabolites

Metabolism of sulbactam has not been characterized.

8.7 Biological Half-Life

In healthy volunteers, the half-life is approximately one hour.

8.8 Mechanism of Action

Sulbactam is a competitive, irreversible bacterial beta (β)-lactamase inhibitor. It is reported to be more potent against class C beta-lactamases.

9 Use and Manufacturing

9.1 Uses

Use (kg; approx.) in Germany (2009): >10000

Use (kg; exact) in Germany (2009): 27580

Use (kg) in USA (2002): 6920

Consumption (g per capita; approx.) in Germany (2009): 0.122

Consumption (g per capita; exact) in Germany (2009): 0.337

Consumption (g per capita) in the USA (2002): 0.0245

Excretion rate: 0.8

Calculated removal (%): 75.1

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 98.7% (78 of 79) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 1.3% (1 of 79) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H302 (51.9%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (46.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H334 (46.8%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

Precautionary Statement Codes

P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, 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 79 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 1 of 79 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 6 notifications provided by 78 of 79 reports by companies with hazard statement code(s).

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.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (51.9%)

Skin Sens. 1 (46.8%)

Resp. Sens. 1 (46.8%)

10.2 Regulatory Information

REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

11 Toxicity

11.1 Toxicological Information

11.1.1 Protein Binding

Sulbactam is approximately 38% reversibly bound to plasma proteins.

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Drug-Drug Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: ATC

17.5 KEGG: Drug Groups

17.6 KEGG : Antimicrobials

17.7 WHO ATC Classification System

17.8 FDA Pharm Classes

17.9 ChemIDplus

17.10 ChEMBL Target Tree

17.11 UN GHS Classification

17.12 NORMAN Suspect List Exchange Classification

17.13 EPA DSSTox Classification

17.14 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
    (2S,5R)-3,3-Dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid
    https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50021954
  2. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  3. 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
  4. 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/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  7. 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
  8. 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
  9. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
    4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S,5R)-
    https://www.epa.govt.nz/industry-areas/hazardous-substances/guidance-for-importers-and-manufacturers/hazardous-substances-databases/
  10. ChEBI
  11. 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
  12. 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
  13. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  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. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  16. DailyMed
  17. EU Clinical Trials Register
  18. Japan Chemical Substance Dictionary (Nikkaji)
  19. 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
  20. Metabolomics Workbench
  21. NIPH Clinical Trials Search of Japan
  22. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  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/
    Sulbactam
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  24. Protein Data Bank in Europe (PDBe)
  25. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    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
  26. SpectraBase
    (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure 4,4-dioxid
    https://spectrabase.com/spectrum/GQAqhlMmlfh
  27. Springer Nature
  28. Thieme Chemistry
    LICENSE
    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/
  29. 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/
  30. Wikidata
  31. Wikipedia
  32. 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
  33. PubChem
  34. GHS Classification (UNECE)
  35. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  36. PATENTSCOPE (WIPO)
CONTENTS