Lincomycin

Lincomycin 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. It was released for medical use in September 1964.

Lincomycin
Clinical data
Trade namesBiocine, Lincocin
AHFS/Drugs.comMonograph
MedlinePlusa609005
Routes of
administration
IM/IV
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityN/A
Elimination half-life5.4 ± 1.0 h after IM or IV administration
Excretionrenal and biliary
Identifiers
  • (2S,4R)-N-[(1R,2R)-2-Hydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.296
Chemical and physical data
FormulaC18H34N2O6S
Molar mass406.54 g·mol−1
3D model (JSmol)
  • O=C(N[C@@H]([C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O)[C@H](O)C)[C@H]2N(C)C[C@H](CCC)C2
  • 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 Y
  • Key:OJMMVQQUTAEWLP-KIDUDLJLSA-N Y
 NY (what is this?)  (verify)
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