Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Clavulanic acid [INN:BAN]
RN: 58001-44-8
UNII: 23521W1S24
InChIKey: HZZVJAQRINQKSD-PBFISZAISA-N

Note

  • Clavulanic acid and its salts and esters. The acid is a suicide inhibitor of bacterial beta-lactamase enzymes from Streptomyces clavuligerus. Administered alone, it has only weak antibacterial activity against most organisms, but given in combination with other beta-lactam antibiotics it prevents antibiotic inactivation by microbial lactamase.

Molecular Formula

  • C8-H9-N-O5

Molecular Weight

  • 199.1611
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • beta-Lactamase Inhibitor
  • beta-Lactamase Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Natural Product
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Clavulanic acid
  • Clavulanic acid [INN:BAN]

MeSH Heading

  • Clavulanic acid

Synonyms

  • (Z)-(2R,5R)-3-(2-Hydroxyethyliden)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 3008-B
  • Acide clavulanique
  • Acide clavulanique [INN-French]
  • Acido clavulanico
  • Acido clavulanico [INN-Spanish]
  • Acidum clavulanicum
  • Acidum clavulanicum [INN-Latin]
  • Antibiotic MM 14151
  • BRL 14151
  • BRN 0787059
  • Clavulanate
  • Clavulanic acid
  • Clavulansaeure
  • Clavulansaeure [INN]
  • EINECS 261-069-2
  • MM 14151
  • UNII-23521W1S24

Systematic Names

  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • 4-Oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3-(2-hydroxyethylidene)-7-oxo-, (2R-(2-alpha,3Z,5-alpha))-
  • Clavulanic acid

Registry Numbers

CAS Registry Number

  • 58001-44-8

FDA UNII

  • 23521W1S24

Related Registry Numbers

  • 57943-81-4 (mono-hydrochloride-salt)
  • 61177-45-5 (mono-potassium-salt)

System Generated Number

  • 0058001448

Structure Descriptors

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

InChIKey

HZZVJAQRINQKSD-PBFISZAISA-N

Smiles

C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1531mg/kg (1531mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
mouse LD50 intravenous 4gm/kg (4000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(1), Pg. 129, 1980.
mouse LD50 oral 4526mg/kg (4526mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
mouse LD50 subcutaneous 2185mg/kg (2185mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
rat LD50 intraperitoneal 1399mg/kg (1399mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
rat LD50 oral 7936mg/kg (7936mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.
rat LD50 subcutaneous 1393mg/kg (1393mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 16, Pg. 590, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.040 (none)   EST
Atmospheric OH Rate Constant 1.61E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.