(2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 646
• Molecular Formular: C8H9NO5
• Molecular Mass: 199.16076
• Monoisotopic Mass: 199.04807239
• SMILES: O1[C@H]2N([C@H](/C/1=C/CO)C(=O)O)C(=O)C2
• Canonical SMILES: OC(=O)[C@@H]1N2[C@H](O/C/1=C\CO)CC2=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
• InChIKey: HZZVJAQRINQKSD-PBFISZAISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3Z,5R)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: clavulanate
• Synonyms: Clavulanic Acid; Clavulanate

Database IDs

• CAS Number: 58001-44-8
• PubChem SID: 160964109; 46508845
• PubChem CID: 5280980

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3169081
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.6880052
• LogD (pH = 7.4): -4.943672
• Log P: -1.5212076
• Molar Refractivity: 44.2525 cm^3
• Polarizability: 17.05212 Å^3
• Polar Surface Area: 87.07 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.16
• LOG S: 0.23
• Solubility (Water): 3.37e+02 g/l

PROPERTIES

Physical Property

• Solubility: 300 mg/mL (potassium salt)
• Hydrophobicity(logP): -1.5

DETAILS

DrugBank - DB00766

• Drug Groups: approved
• Description: 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 beta-lactam antibiotics prevents antibiotic inactivation by microbial lactamase. [PubChem]
• Indication: For use with Amoxicillin, clavulanic acid is suitable for the treatment of infections with Staph. aureus and Bacteroides fragilis, or with beta-lactamase producing H. influenzae and E. coli.
• Pharmacology: Clavulanic acid, produced by the fermentation of Streptomyces Clavuligerus, is a beta-lactam structurally related to the penicillins. 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.
• Toxicity: Gastrointestinal symptoms including stomach and abdominal pain, vomiting, and diarrhea. Rash, hyperactivity, or drowsiness have also been observed in a small number of patients
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic
• Absorption: 75%
• Half Life: 1.0 hour
• Protein Binding: Low (22 to 30%)
• External Links: Wikipedia