Lincomycin is a lincosamide antibiotic that comes from the actinomyces Streptomyces lincolnensis. It has been structurally modified by thionyl chloride to its more commonly known 7-chloro-7-deoxy derivative, clindamycin. It is available under the brand name of Lincobect and Lincocin in Pakistan. Although similar in structure, antibacterial spectrum, and mechanism of action to macrolides, lincomycin is also effective against other organisms including actinomycetes, mycoplasma, and some species of Plasmodium. Because of its adverse effects and toxicity, it is rarely used today and reserved for patients allergic to penicillin or where bacteria have developed resistance. Lincomycin is an antibiotic classified as a constituent of the lincosamide group, which typically feature a 6,8-dideoxy-6-aminooctose lincosamine.[1] In Lincomycin A, this sugar moiety (referred to as methylthiolincosamide) is linked via an amide bond to an amino acid derivative (referred to as propylhygric acid). Lincomycin biosynthesis occurs via a biphasic pathway producing propylproline and methylthiolincosamide followed by condensation of these subunits to N-demethyllincomycin and methyllation by S-adenosylmethionine to produce the antibiotic lincomycin. In the biosynthesis of the amino acid moiety of lincomycin, tyrosine comprises seven of the nine carbons in the prophylhygric acid, while the remaining two carbons are added in reactions with S-adenosylmethionine.[2][3][4][5] Glucose is converted via glycolysis and the hexose monophosphate pathway to phosphoenolpyruvate and erythrose-4-phosphate, respectively, which are converted via the shikimate pathway to tyrosine and dihydroxyphenylalanine. Although the multistep conversion of dihydroxyphenylalanine to propylproline remains unknown, experiments involving accumulation of 1,2,3,6-tetradehydro-propylproline in mutants lacking a reductase requiring lincomycin cosynthetic factor suggests a biosynthetic scheme that Kuo and coworkers have modified from Brahme et al.[4][5] to accommodate the remaining steps leading to propylproline.[6][7] Synonyms: (2S-trans)-Methyl 6,8-dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl]amino]-1-thio-D-threo-a-D-galacto-octopyranoside, Lincocin hydrochloride CAS No: 859-18-7 Molecular Formula: C18H34N2O6SHCl Molecular Weight: 443 Appearance: White to off-white powder Purity: As reported Infrared: Conforms to reference Activity: 790ug/mg (Anhydrous) Water (KF): 3.1-4.6% pH: 3.5-5.5 Optical Rotation: [a] = +135-150 Residual Solvents: 1-butanol: 5000ppm Lincomycin B: 5% Endotoxin: 0.50 IU/mg Solubility: Water Storage and Stability: May be stored at RT for short-term only. Long-term storage is recommended at 4C. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
Molecular Weight:
443
Purity:
As reported
Form:
White to off-white powder
CAS Number:
[859-18-7]
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