Clavulanic acid

Clavulanic acid

Clinical data

Pronunciation
/ˌklævjuːˈlænᵻk ˈæsᵻd/

AHFS/Drugs.com
International Drug Names

Pregnancy
category

B (United States)
B1 (Aust)

Routes of
administration
by mouth, IV

ATC code
J01CR (WHO) (combinations with penicillins)

Legal status

Legal status

Schedule 4 (Au) rx only

Pharmacokinetic data

Bioavailability
“well absorbed”

Metabolism
hepatic (extensive)

Biological half-life
1 hour

Excretion
renal (30–40%)

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 Y

PubChem (CID)
5280980

DrugBank
DB00766 Y

ChemSpider
4444466 Y

UNII
23521W1S24 Y

KEGG
D07711 Y

ChEBI
CHEBI:48947 Y

ChEMBL
CHEMBL777 Y

ECHA InfoCard
100.055.500

Chemical and physical data

Formula
C8H9NO5

Molar mass
199.16 g/mol

3D model (Jmol)
Interactive image

SMILES

O=C2N1[[email protected]](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 Y

Key:HZZVJAQRINQKSD-PBFISZAISA-N Y

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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 form, the potassium salt potassium clavulanate is combined with:

amoxicillin (co-amoxiclav, trade names Augmentin, Tyclav (Beximco), Synulox [veterinary], and others) or
ticarcillin (co-ticarclav, trade name Timentin).

Clavulanic acid is an example of a clavam.
Clavulanic acid was patented in 1974.[1]

Contents

1 Uses
2 Sources
3 Biosynthesis
4 History
5 Adverse effects
6 References

Uses[edit]
For the treatment of pyelonephritis during pregnancy, and for the treatment of pyelonephritis caused by gram-positive organisms, amoxicillin or amoxicillin-clavulanate potassium is preferred.
Sources[edit]
The name is derived from strains of Streptomyces clavuligerus, which produces clavulanic acid.[2][3]
Clavulanic acid is biosynthetically generated from the amino acid arginine and the sugar glyceraldehyde 3-phosphate.
Biosynthesis[edit]

The intermediates of the biosynthesis of Clavulanic Acid[4]

With the β-lactam like structure, clavulanic
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