Clindamycin
Title: Clindamycin
CAS Registry Number: 18323-44-9
CAS Name: Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-1-methyl-4-propyl-2-pyrrolidinyl]carbonyl]amino]-1-thio-L-threo-a-D-galacto-octopyranoside
Additional Names: 7(S)-chloro-7-deoxylincomycin; 7-deoxy-7(S)-chlorolincomycin; clinimycin (rescinded)
Manufacturers' Codes: U-21251
Molecular Formula: C18H33ClN2O5S
Molecular Weight: 424.98
Percent Composition: C 50.87%, H 7.83%, Cl 8.34%, N 6.59%, O 18.82%, S 7.55%
Literature References: Semi-synthetic antibiotic prepd from lincomycin, q.v. Prepn: Magerlein et al., Antimicrob. Agents Chemother. 1966, 727. Manuf process: R. D. Birkenmeyer, US 3475407 (1969 to Upjohn). Synthesis and structure: R. D. Birkenmeyer, F. Kagan, J. Med. Chem. 13, 616 (1970). Stability studies: Oesterling, J. Pharm. Sci. 59, 63 (1970). Activity studies: McGehee et al., Am. J. Med. Sci. 256, 279 (1968); D. A. Leigh, J. Antimicrob. Chemother. 7(suppl. A), 3 (1981). Toxicology: J. E. Gray et al., Toxicol. Appl. Pharmacol. 21, 516 (1972). Comprehensive description of the hydrochloride: L. W. Brown, W. F. Beyer, Anal. Profiles Drug Subs. 10, 75-91 (1981).
Properties: Yellow, amorphous solid. [a]D +214° (chloroform).
Optical Rotation: [a]D +214° (chloroform)
 
Derivative Type: Hydrochloride
CAS Registry Number: 21462-39-5; 58207-19-5 (monohydrate)
Trademarks: Antirobe (Pharmacia & Upjohn); Clinsol (Virbac); Clintabs (Virbac); Dalacin C (Pharmacia & Upjohn); Sobelin (Pharmacia)
Molecular Formula: C18H33ClN2O5S.HCl
Molecular Weight: 461.44
Percent Composition: C 46.85%, H 7.43%, Cl 15.37%, N 6.07%, O 17.34%, S 6.95%
Properties: Various hydrated forms exist. White crystals from ethanol-ethyl acetate, mp 141-143° (anhydrous). [a]D +144° (H2O). pKa 7.6. Sol in water, pyridine, ethanol, DMF. LD50 in mice (mg/kg): 245 i.v.; 361 i.p.; 2618 orally (Gray).
Melting point: mp 141-143°
pKa: pKa 7.6
Optical Rotation: [a]D +144° (H2O)
Toxicity data: LD50 in mice (mg/kg): 245 i.v.; 361 i.p.; 2618 orally (Gray)
 
Derivative Type: 2-Dihydrogen phosphate
CAS Registry Number: 24729-96-2
Manufacturers' Codes: U-28508
Trademarks: Cleocin (Pharmacia & Upjohn); Dalacin T (Pharmacia & Upjohn); Klimicin (Lek); Zindaclin (Epitan)
Molecular Formula: C18H34ClN2O8PS
Molecular Weight: 504.96
Percent Composition: C 42.81%, H 6.79%, Cl 7.02%, N 5.55%, O 25.35%, P 6.13%, S 6.35%
Properties: Sol in water.
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Lincosamides.

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