Lincomycin
Title: Lincomycin
CAS Registry Number: 154-21-2
CAS Name: (2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-erythro-a-D-galacto-octopyranoside
Additional Names: lincolnensin
Manufacturers' Codes: U-10149; NSC-70731
Molecular Formula: C18H34N2O6S
Molecular Weight: 406.54
Percent Composition: C 53.18%, H 8.43%, N 6.89%, O 23.61%, S 7.89%
Literature References: Antibiotic produced by Streptomyces lincolnensis var. lincolnensis. Isoln: D. J. Mason et al., Antimicrob. Agents Chemother. 1962, 555; R. R. Herr, M. E. Bergy, ibid. 560; M. E. Bergy et al., US 3086912 (1963 to Upjohn). Structure: Hoeksema et al., J. Am. Chem. Soc. 86, 4223 (1964). Synthesis: Magerlein, Tetrahedron Lett. 1970, 33. Stereoselective synthesis: S. Knapp, P. J. Kukkola, J. Org. Chem. 55, 1632 (1990). Mechanism of action: F. N. Chang in Antibiotics vol. 5(pt. 1), F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 127-134. Clinical study: F. Puleo et al., Gazz. Med. Ital. 138, 401 (1979). Toxicity data: Gray et al., Toxicol. Appl. Pharmacol. 6, 476 (1964). Comprehensive description: H. Y. Muti, F. H. Al-Hajjar, Anal. Profiles Drug Subs. Excip. 23, 269-319 (1994).
Properties: Free base, pKa¢ 7.6. More stable in salt form. Sol in methanol, lower alcohols, ethyl acetate, acetone, chloroform. Slightly sol in water (Bergy).
pKa: pKa¢ 7.6
 
Derivative Type: Hydrochloride hemihydrate
Trademarks: Lincocin (Pharmacia & Upjohn)
Molecular Formula: C18H34N2O6S.HCl.½H2O
Molecular Weight: 452.01
Percent Composition: C 47.83%, H 8.03%, N 6.20%, O 23.01%, S 7.09%, Cl 7.84%
Properties: Crystals from acetone, mp 135-140°. Also reported as mp 146-148°. [a]D25 +137° (water). No uv absorption. pKa¢ 7.60. Freely sol in water, methanol, ethanol; sparingly sol in most organic solvents other than hydrocarbons. LD50 in mice, rats (g/kg): 1 i.p.; 4 orally (Gray).
Melting point: mp 135-140°; mp 146-148°
pKa: pKa¢ 7.60
Optical Rotation: [a]D25 +137° (water)
Toxicity data: LD50 in mice, rats (g/kg): 1 i.p.; 4 orally (Gray)
 
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 7179-49-9
Trademarks: Albiotic (Pharmacia); Lincomix (Pharmacia & Upjohn)
Properties: White or almost white crystalline powder. odorless or with a slight mercaptan-like odor and a bitter taste. mp 156-158°. [a]D25 +143° (water). pH of a 1% aq. soln: 4.8.
Melting point: mp 156-158°
Optical Rotation: [a]D25 +143° (water)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Lincosamides.

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