CLAVULANIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H9NO5
Molecular Weight	199.1608
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12CC(=O)N1[C@@H](C(O)=O)\C(O2)=C\CO

InChI

InChIKey=HZZVJAQRINQKSD-PBFISZAISA-N

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

HIDE SMILES / InChI

Molecular Formula	C8H9NO5
Molecular Weight	199.1608
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description

Clavulanic acid is produced by the fermentation of Streptomyces clavuligerus. It is a β-lactam structurally related to the penicillins and possesses the ability to inactivate a wide variety of β-lactamases by blocking the active sites of these enzymes. Clavulanic acid is particularly active against the clinically important plasmid-mediated β-lactamases frequently responsible for transferred drug resistance to penicillins and cephalosporins. Clavulanic acid is used in conjunction with amoxicillin for the treatment of bronchitis and urinary tract, skin, and soft tissue infections caused by beta-lactamase producing organisms. Clavulanic acid competitively and irreversibly inhibits a wide variety of beta-lactamases, commonly found in microorganisms resistant to penicillins and cephalosporins. Binding and irreversibly inhibiting the beta-lactamase results in a restauration of the antimicrobial activity of beta-lactam antibiotics against lactamase-secreting-resistant bacteria. By inactivating beta-lactamase (the bacterial resistance protein), the accompanying penicillin/cephalosporin drugs may be made more potent as well.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-lactamase TEM 12	Inhibitor 8,297		0.09 µM [IC50]
Beta-lactamase 16	Inhibitor 8,297		80.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Lower respiratory tract infections 51	Curative	Approved 8,429	Augmentin
Otitis media 41	Curative	Approved 8,429	Augmentin
Sinusitis 26	Curative	Approved 8,429	Augmentin
Urinary tract infections 205	Curative	Approved 8,429	Augmentin
Skin and skin structure infections 80	Curative	Approved 8,429	Augmentin

C_max

Value	Dose	Co-administered	Analyte	Population
2.63 μg/mL	125 mg single, oral	AMOXICILLIN	CLAVULANIC ACID plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
5.49 μg × h/mL	125 mg single, oral	AMOXICILLIN	CLAVULANIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1 h	125 mg single, oral	AMOXICILLIN	CLAVULANIC ACID plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 mg/kg 1 times / day steady, oral Recommended	unhealthy, 2 months to 12 years n = 575	Other AEs: Diarrhea, Rash urticarial...
125 mg 1 times / day steady, oral Recommended	unhealthy, adult	Other AEs: Loose stools, Nausea...

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AEs

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AE	Significance	Dose	Population
Diaper rash		10 mg/kg 1 times / day steady, oral Recommended	unhealthy, 2 months to 12 years n = 575
Diarrhea		10 mg/kg 1 times / day steady, oral Recommended	unhealthy, 2 months to 12 years n = 575
Rash urticarial		10 mg/kg 1 times / day steady, oral Recommended	unhealthy, 2 months to 12 years n = 575
Vaginitis	1%	125 mg 1 times / day steady, oral Recommended	unhealthy, adult
Vomiting	1%	125 mg 1 times / day steady, oral Recommended	unhealthy, adult

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:48947	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:48947
ChemicalBook	CB9722501	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9722501
ZINC	ZINC000003830569	http://zinc15.docking.org/substances/ZINC000003830569

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PubMed

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Title	Date	PubMed
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis?	1995 Dec	8592990
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470
Suppression of the growth of six potentially-pathogenic mycobacteria by beta-lactam/beta-lactamase-inhibitors.	1997	9467917

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Patents

Sample Use Guides

In Vivo Use Guide

Adults The usual adult dose is one 500 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 12 hours or one 250 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 8 hours. For more severe infections and infections of the respiratory tract, the dose should be one 875 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 12 hours or one 500 mg/125 mg Amoxicillin and Clavulanate Potassium Tablet every 8 hours. Adults who have difficulty swallowing may be given the 125 mg/31.25 mg per 5 mL or 250 mg/62.5 mg per 5 mL suspension in place of the 500 mg/125 mg tablet. The 200 mg/28.5 mg per 5 mL suspension or the 400 mg/57 mg per 5 mL suspension may be used in place of the 875 mg/125 mg tablet.

Route of Administration: Oral

In Vitro Use Guide

The purified beta-lactamase enzyme focused at pI 5.4 and was strongly inhibited in vitro by clavulanic acid (IC50 = 0.09 uM).