Lincomycin

  • CAT Number: R063125
  • CAS Number: 154-21-2
  • Molecular Formula: C18H34N2O6S
  • Molecular Weight: 406.538
  • Purity: ≥95%
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Lincomycin (CAS 154-21-2), also known as U-10149, is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. Although similar in structure, antibacterial spectrum, and mechanism of action to macrolides, lincomycin is also effective against other organisms including actinomycetes and some species of Mycoplasma and Plasmodium. However, 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.

Catalog Number R063125
CAS Number 154-21-2
Synonyms

(2S-trans)-Methyl 6,8-Dideoxy-6-[[(1-methyl-4-propyl-2-pyrrolidinyl)carbonyl?]amino]-1-thio-D-erythro-α-D-galacto-octopyranoside; Lincocin; Lincogap; NSC 70731; U 10149a;

Molecular Formula

C18H34N2O6S

Purity 95%
Storage -20°C
IUPAC Name (2S,4R)-N-[(1R,2R)-2-hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
InChI InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
InChIKey OJMMVQQUTAEWLP-KIDUDLJLSA-N
SMILES CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)O
Reference

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1:Treatment rates for injectable tiamulin and lincomycin as an estimate of morbidity in a swine herd with endemic swine dysentery. Walczak K, Friendship R, Brockoff E, Greer A, Poljak Z.Can Vet J. 2017 May;58(5):472-481. PMID: 28487591<br />
2:Aptamer-molecularly imprinted sensor base on electrogenerated chemiluminescence energy transfer for detection of lincomycin. Li S, Liu C, Yin G, Zhang Q, Luo J, Wu N.Biosens Bioelectron. 2017 May 15;91:687-691. doi: 10.1016/j.bios.2017.01.038. Epub 2017 Jan 19. PMID: 28119249<br />
3:Novel lnu(G) gene conferring resistance to lincomycin by nucleotidylation, located on Tn6260 from Enterococcus faecalis E531. Zhu XQ, Wang XM, Li H, Shang YH, Pan YS, Wu CM, Wang Y, Du XD, Shen JZ.J Antimicrob Chemother. 2017 Apr 1;72(4):993-997. doi: 10.1093/jac/dkw549. PMID: 28039271<br />
4:Development of a heterologous enzyme-linked immunosorbent assay for the detection of clindamycin and lincomycin residues in edible animal tissues. He J, Wu N, Luo P, Guo P, Qu J, Zhang S, Zou X, Wu F, Xie H, Wang C, Jiang W.Meat Sci. 2017 Mar;125:137-142. doi: 10.1016/j.meatsci.2016.11.024. Epub 2016 Dec 1. PMID: 27951465<br />
5:Synthesis and antibacterial activity of novel lincomycin derivatives. II. Exploring (7S)-7-(5-aryl-1,3,4-thiadiazol-2-yl-thio)-7-deoxylincomycin derivatives. Kumura K, Wakiyama Y, Ueda K, Umemura E, Watanabe T, Kumura M, Yoshida T, Ajito K.J Antibiot (Tokyo). 2017 May;70(5):655-663. doi: 10.1038/ja.2016.139. Epub 2016 Dec 7. PMID: 27924113<br />
6:Identification of a Novel Lincomycin Resistance Mutation Associated with Activation of Antibiotic Production in Streptomyces coelicolor A3(2). Wang G, Izawa M, Yang X, Xu D, Tanaka Y, Ochi K.Antimicrob Agents Chemother. 2017 Jan 24;61(2). pii: e02247-16. doi: 10.1128/AAC.02247-16. Print 2017 Feb. PMID: 27919888<br />
7:Improvement of lincomycin production by mutant selection and metabolic regulation. Pang X, Zheng Y, Qiao X, Mao Q, Ma Q, Ye R.Prep Biochem Biotechnol. 2016 Aug 15. doi: 10.1080/10826068.2016.1207083. [Epub ahead of print] PMID: 27715470<br />
8:Synthesis and structure-activity relationships of novel lincomycin derivatives part 3: discovery of the 4-(pyrimidin-5-yl)phenyl group in synthesis of 7(S)-thiolincomycin analogs. Wakiyama Y, Kumura K, Umemura E, Masaki S, Ueda K, Sato Y, Watanabe T, Hirai Y, Ajito K.J Antibiot (Tokyo). 2017 Jan;70(1):52-64. doi: 10.1038/ja.2016.114. Epub 2016 Oct 5. PMID: 27703159<br />
9:Lincomycin-Induced Acute Generalized Exanthematous Pustulosis Confirmed by Delayed Reading of Intradermal Testing. Salem C B, Fathallah N, Slim R, Ziadi S, Ghariani N.Ann Pharmacother. 2016 Oct;50(10):894-5. doi: 10.1177/1060028016657554. Epub 2016 Jul 1. No abstract available. PMID: 27371545<br />
10:Cometabolic degradation of lincomycin in a Sequencing Batch Biofilm Reactor (SBBR) and its microbial community. Li Y, Zhou J, Gong B, Wang Y, He Q.Bioresour Technol. 2016 Aug;214:589-95. doi: 10.1016/j.biortech.2016.04.085. Epub 2016 Apr 19. PMID: 27183234

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