Chemicals and Drugs

Clavulanic Acid

A beta-lactam antibiotic produced by the actinobacterium Streptomyces clavuligerus. It is a suicide inhibitor of bacterial beta-lactamase enzymes. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A beta-lactam antibiotic produced by the actinobacterium Streptomyces clavuligerus. It is a suicide inhibitor of bacterial beta-lactamase enzymes. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.

Chemical Identity

Chemical Information

Molecular Formula
C8H9NO5
Molecular Weight
199.16 g/mol
CAS Registry No.
58001-44-8
IUPAC Name
(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChIKey
HZZVJAQRINQKSD-PBFISZAISA-N
SMILES
C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
MeSH Unique ID
D019818
Source
PubChem CID 5280980

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

15 entry terms
  • BRL-14151
  • Clavulanate
  • Clavulanate Potassium
  • Clavulanic Acid, Monopotassium Salt
  • Clavulanic Acid, Monosodium Salt
  • MM-14151
  • Potassium Clavulanate
  • Sodium Clavulanate
  • BRL 14151
  • BRL14151
  • Clavulanate, Potassium
  • Clavulanate, Sodium
  • MM 14151
  • MM14151
  • Potassium, Clavulanate

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analysis, antagonists & inhibitors, biosynthesis, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

98; use CLAVULANIC ACID (NM) 1980-97

MeSH Record

Previous Indexing

  • Clavulanic Acids (1978-1997)
  • Lactams (1976-1982)

MeSH Hierarchy

Tree Numbers

  1. D02w.065w.589w.099w.374.160w
  2. D03w.633.100.300w.374.160w

AMA Style

References

  1. National Library of Medicine. Clavulanic Acid. Medical Subject Headings (MeSH). 2026. Unique ID D019818. http://id.nlm.nih.gov/mesh/2026/D019818
  2. Clavulanic Acid. In: Wikipedia. https://en.wikipedia.org/wiki/Clavulanic_acid
  3. Clavulanic Acid. In: Wikidata. https://www.wikidata.org/wiki/Q415709
  4. Clavulanic Acid. In: PubChem Compound. CID 5280980. https://pubchem.ncbi.nlm.nih.gov/compound/5280980