Clavulanic acid

Clavulanic acid
Clinical data
Pronunciation	/ˌklævjʊˈlænɪk/
Other names	RX-10100; Serdaxin; Zoraxel
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B1; ;
Routes of; administration	Oral, IV
ATC code	J01CR (WHO) (combinations with penicillins);
Legal status
Legal status	AU: S4 (Prescription only); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Oral: 45–64%
Protein binding	~25%
Metabolism	Unknown
Metabolites	Two minor metabolites
Onset of action	≤0.67–2 hours (TmaxTooltip time to peak concentrations)
Elimination half-life	0.8–1.2 hours
Excretion	Urine: 35–65% (unchanged; within 6 hours)
Identifiers
	IUPAC name (2R,5R,Z)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	58001-44-8 ;
PubChem CID	5280980;
DrugBank	DB00766 ;
ChemSpider	4444466 ;
UNII	23521W1S24;
KEGG	D07711 ;
ChEBI	CHEBI:48947 ;
ChEMBL	ChEMBL777 ;
CompTox Dashboard (EPA)	DTXSID2022830 ;
ECHA InfoCard	100.055.500
Chemical and physical data
Formula	C8H9NO5
Molar mass	199.162 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1[C@H](C(/O[C@@H]1C2)=C/CO)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 ; Key:HZZVJAQRINQKSD-PBFISZAISA-N ;
	(verify)

Clavulanic acid is a β-lactam drug that functions as a mechanism-based β-lactamase inhibitor. While not effective by itself as an antibiotic, when combined with penicillin-group antibiotics, it can overcome antibiotic resistance in bacteria that secrete β-lactamase, which otherwise inactivates most penicillins.

In its most common preparations, potassium clavulanate (clavulanic acid as a salt of potassium) is combined with:

amoxicillin (co-amoxiclav, trade names Augmentin, Clavulin, Tyclav, Clavaseptin (veterinary), Clavamox (veterinary), Synulox (veterinary), and others)
ticarcillin (co-ticarclav, trade name Timentin)

Clavulanic acid was patented in 1974.^[3] In addition to its β-lactamase inhibition, clavulanic acid shows off-target activity in the nervous system by upregulating the glutamate transporter 1 (GLT-1) and has been studied in the potential treatment of a variety of central nervous system disorders.^[1]^[4]

^ ^a ^b ^c ^d ^e Cite error: The named reference Balcazar-OchoaVentura-MartínezÁngeles-López2024 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f "Clavulanic acid: Uses, Interactions, Mechanism of Action". DrugBank Online. 8 July 2014. Retrieved 5 November 2024.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495.
^ Cite error: The named reference AdisInsight was invoked but never defined (see the help page).