5500. Lincomycin

Nomenclature

CAS number: 154-21-2
(2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-d-erythro-α-d-galacto-octopyranoside; lincolnensin; U-10149; NSC-70731.
C18H34N2O6S; mol wt 406.54.
C 53.18%, H 8.43%, N 6.89%, O 23.61%, S 7.89%.

Description and 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).

Chemical structure

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).

Derivative

Hydrochloride hemihydrate.

Nomenclature

Lincocin (Pharmacia & Upjohn).
C18H34N2O6S.HCl.H2O; mol wt 452.01.
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°. [α]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).

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 7179-49-9
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°. [α]D25 +143° (water). pH of a 1% aq. soln: 4.8.

Therapeutic Category

Antibacterial.

Therapeutic Category (Veterinary)

Antibacterial.

Keywords

Antibacterial (Antibiotics); Lincosamides