Cloxacillin
Title: Cloxacillin
CAS Registry Number: 61-72-3
CAS Name: (2S,5R,6R)-6-[[[3-(2-Chlorophenyl)-5-methyl-4-isoxazolyl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Additional Names: [3-(o-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin; [5-methyl-3-(o-chlorophenyl)-4-isoxazolyl]penicillin; 6-[3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido]penicillanic acid
Molecular Formula: C19H18ClN3O5S
Molecular Weight: 435.88
Percent Composition: C 52.35%, H 4.16%, Cl 8.13%, N 9.64%, O 18.35%, S 7.36%
Literature References: Semi-synthetic antibiotic related to penicillin; chlorinated deriv of oxacillin, q.v. Prepn: F. P. Doyle, J. H. C. Nayler, US 2996501 (1961); F. P. Doyle et al., J. Chem. Soc. 1963, 5838. Manuf: Ind. Chem. 39, 513 (1963), C.A. 60, 1543a (1964). Properties and pharmacology: J. H. C. Nayler et al., Nature 195, 1264 (1962). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description: D. L. Mays, Anal. Profiles Drug Subs. 4, 113-136 (1975).
 
Derivative Type: Sodium salt monohydrate
CAS Registry Number: 7081-44-9; 642-78-4 (anhydrous)
Additional Names: Sodium cloxacillin
Manufacturers' Codes: BRL-1621
Trademarks: Cloxapen (GSK); Cloxypen (BMS); Ekvacillin (AstraZeneca); Latocillin (Chassot); Orbenin (GSK); Methocillin-S (Meiji); Tegopen (BMS)
Molecular Formula: C19H17ClN3NaO5S.H2O
Molecular Weight: 475.88
Percent Composition: C 47.95%, H 4.02%, Cl 7.45%, N 8.83%, Na 4.83%, O 20.17%, S 6.74%
Properties: Microcryst powder, dec 170°. [a]D20 +163° (c = 1 in water). pH of 1% aq soln = 6.0-7.5. Sol in water, methanol, ethanol, pyridine, ethylene glycol. LD50 in rats, mice (mg/kg): 1630 ±112, 1280 ±50 i.p. (Goldenthal).
Optical Rotation: [a]D20 +163° (c = 1 in water)
Toxicity data: LD50 in rats, mice (mg/kg): 1630 ±112, 1280 ±50 i.p. (Goldenthal)
 
Derivative Type: Benzathine salt
CAS Registry Number: 23736-58-5
Trademarks: Dry Clox (Wyeth); Noroclox (Norbrook)
Molecular Formula: C54H56Cl2N8O10S2
Molecular Weight: 1112.11
Percent Composition: C 58.32%, H 5.08%, Cl 6.38%, N 10.08%, O 14.39%, S 5.77%
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.

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