Structure via PubChem · Public domain (PubChem)
clavulanic acid
Sign in to saveAlso known as clavulonic acid, (Z)-(2R,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Β-lactam molecule used as β-lactamase inhibitor to overcome antibiotic resistance in bacteria
Chemical data
- Formula
- C8H9NO5
- Molecular weight
- 199.16 g/mol
- IUPAC name
- (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
- InChIKey
- HZZVJAQRINQKSD-PBFISZAISA-N
- XLogP
- -1.2
- Polar surface area
- 87.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1984
- Admin. routes
- oral, parenteral
- Indications
- infection, obesity, cocaine dependence, osteomyelitis
via ChEMBL · EBI
Research
10,059 papers- Clavulanic Acid and its Potential Therapeutic Effects on the Central Nervous System.Archives of medical research · 2024
- Pharmacokinetics of Clavulanic Acid in the Pediatric Population: A Systematic Literature Review.Clinical pharmacokinetics · 2022
- Clavulanic acid: a review.Biotechnology advances · 2008
- How Clavulanic Acid Inhibits Serine β-Lactamases.Chembiochem : a European journal of chemical biology · 2024
- Clavulanic acid biosynthesis and genetic manipulation for its overproduction.Applied microbiology and biotechnology · 2010
via PubMed
Wikidata facts
- Subclass of
- alkaloid
- Has part
- carbon
- Mass
- 199.048
- Has use
- medication
Show 9 more facts
- subject has role
- beta-lactamase inhibitors
- found in taxon
- Streptomyces clavuligerus
- route of administration
- intravenous infusion and defusion
- chemical formula
- C₈H₉NO₅
- isomeric SMILES
- C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
- canonical SMILES
- C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
- Commons category
- Clavulanic acid
- medical condition treated
- urinary tract infection
- World Health Organisation international non-proprietary name
- acidum clavulanicum
Sources (6)
via Wikidata · CC0