Clavulanic acid

Class: Beta-lactamase inhibitor (clavam, bicyclic beta-lactam without a penicillin or cephalosporin nucleus)

Details of activity:	Binds irreversibly to beta-lactamases, mainly class A enzymes. No intrinsic antibacterial activity
Combined with other compounds:	Yes
Description:	Streptomyces natural product. Only available as a combination product, oral and parenteral application
Year first mentioned:	1976
Development status:	Approved, off-patent

Chemical structure(s):
Canonical SMILES:	C(=C/1\[C@H](C(=O)O)N2C(=O)C[C@H]2O1)/CO
Isomeric SMILES:	C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
InChI:	InChI=1S/C8H9NO5/c10-2-1-4-7(8(12)13)9-5(11)3-6(9)14-4/h1,6-7,10H,2-3H2,(H,12,13)/b4-1-/t6-,7-/m1/s1
InChI Key:	HZZVJAQRINQKSD-PBFISZAISA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5280980

External links:
Guide to Pharmacology:	clavulanic acid
Main Source:	https://www.jstage.jst.go.jp/article/antibiotics1968/29/6/29_6_668/_pdf/-char/en
Citations:	https://pubs.acs.org/doi/10.1021/acs.jmedchem.9b01279 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2806661/ https://www.ncbi.nlm.nih.gov/pmc/articles/PMC358033/pdf/cmr00055-0121.pdf