Clavulanic Acid

Title: Clavulanic Acid
CAS Registry Number: 58001-44-8
CAS Name: [2R-(2a,3Z,5a)]-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Manufacturers' Codes: MM 14151
Molecular Formula: C8H9NO5
Molecular Weight: 199.16
Percent Composition: C 48.25%, H 4.55%, N 7.03%, O 40.17%
Literature References: b-Lactamase inhibitor. Antibiotic produced by Streptomyces clavuligerus; first reported naturally occurring fused b-lactam containing oxygen. Isoln: M. Cole et al., DE 2517316 (1975 to Beecham), C.A. 84, 72635t (1976); A. G. Brown et al., J. Antibiot. 29, 668 (1976). Structure, x-ray crystallography: T. T. Howarth et al., Chem. Commun. 1976, 266. Total synthesis of (±)-form: P. H. Bentley et al., ibid. 1977, 748, 905; eidem, Tetrahedron Lett. 1979, 1889. b-Lactamase inhibition and antibacterial spectrum: C. Reading, M. Cole, Antimicrob. Agents Chemother. 11, 852 (1977). Mechanism of action: B. G. Spratt et al., ibid. 12, 406 (1977). Antibacterial activity, pharmacology and clinical efficacy of combination with amoxicillin: A. P. Ball et al., Lancet 1, 620 (1980); R. N. Brogden et al., Drugs 22, 337-362 (1981). In vitro and in vivo synergism with ticarcillin: R. Sutherland et al., Am. J. Med. 79, Suppl. 5B, 13 (1985).
Derivative Type: Combination of potassium salt with amoxicillin trihydrate
Additional Names: Co-amoxiclav
Trademarks: Amoksiklav (Lek); Augmentin (SKB); Ciblor (Inava); Clavamox (Pfizer); Clavulin (SKB); Klavocin (Pliva); Neo-Duplamox (ISF); Synulox (Pfizer)
Derivative Type: Combination of potassium salt with ticarcillin disodium
CAS Registry Number: 116876-37-0
Trademarks: Betabactyl (SKB); Timentin (SKB)
Derivative Type: Methyl ester
Molecular Formula: C9H11NO5
Molecular Weight: 213.19
Percent Composition: C 50.70%, H 5.20%, N 6.57%, O 37.52%
Properties: Oil. [a]D22 +38°.
Optical Rotation: [a]D22 +38°
Derivative Type: p-Nitrobenzyl ester
Molecular Formula: C15H14N2O7
Molecular Weight: 334.28
Percent Composition: C 53.90%, H 4.22%, N 8.38%, O 33.50%
Properties: Monoclinic crystals, mp 117.5-118°.
Melting point: mp 117.5-118°
Therap-Cat: Combination with b-lactam antibiotics as antibacterial.
Therap-Cat-Vet: Combination with b-lactam antibiotics as antibacterial.
Keywords: Antibacterial Adjuncts; ?Lactamase Inhibitors.
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