Loracarbef
Title: Loracarbef
CAS Registry Number: 121961-22-6
CAS Name: (6R,7S)-7-[[(2R)-Aminophenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid monohydrate
Additional Names: (6R,7S)-3-chloro-7-[(R)-phenylglycinamido]-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid monohydrate; carbacefaclor
Manufacturers' Codes: KT-3777; LY-163892 monohydrate
Trademarks: Lorabid (Lilly)
Molecular Formula: C16H16ClN3O4.H2O
Molecular Weight: 367.78
Percent Composition: C 52.25%, H 4.93%, Cl 9.64%, N 11.43%, O 21.75%
Literature References: Carbacephem analog of cefaclor, q.v. Prepn: T. Hirata et al., EP 14476; eidem, US 4708956 (1980, 1987 both to Kyowa Hakko); I. Matsukuma et al., Chem. Pharm. Bull. 37, 1239 (1989). Prepn of the crystalline monohydrate: C. E. Pasini, EP 311366 (1989 to Lilly). Enantioselective synthesis: C. C. Bodurow et al., Tetrahedron Lett. 30, 2321 (1989). Antibacterial spectrum: K. Sato et al., J. Antibiot. 42, 1844 (1989). b-Lactamase stability: R. N. Jones, A. L. Barry, Eur. J. Clin. Microbiol. 6, 570 (1987). Pharmacology in animals: T. Shetler et al., Arzneim.-Forsch. 43, 60 (1993). Pharmacokinetics in children: J. D. Nelson et al., Antimicrob. Agents Chemother. 32, 1738 (1988).
Properties: mp 205-215° (dec) (Matsukuma). [a]D21 +34.0° (c = 0.35 in water).
Melting point: mp 205-215° (dec) (Matsukuma)
Optical Rotation: [a]D21 +34.0° (c = 0.35 in water)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Carbacephems.

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