Lincomycin - CAS 154-21-2

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

PubChem Substance ID:355177016

Molecular Formula: C18H34N2O6S

Molecular Weight:406.538

Purity: ≥95%

Online inquiry

* For research use only. Not for human or veterinary use.

Synonym

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;

Property

Molecular Formula:	C18H34N2O6S
Molecular Weight	406.538
Purity	≥95%
Storage	-20°C

Computed Descriptor

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