Lincomycin

Lincomycin
Clinical data
Trade names	Biocine, Lincocin
AHFS/Drugs.com	Monograph
MedlinePlus	a609005
Routes of; administration	IM/IV
ATC code	J01FF02 (WHO) QJ51FF02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	N/A
Elimination half-life	5.4 ± 1.0 h after IM or IV administration
Excretion	Kidney and bile duct
Identifiers
	IUPAC name (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	154-21-2 ;
PubChem CID	3000540;
DrugBank	DB01627 ;
ChemSpider	2272112 ;
UNII	BOD072YW0F;
KEGG	D00223 ;
ChEBI	CHEBI:6472 ;
ChEMBL	ChEMBL1447 ;
CompTox Dashboard (EPA)	DTXSID3023215 ;
ECHA InfoCard	100.005.296
Chemical and physical data
Formula	C18H34N2O6S
Molar mass	406.54 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:OJMMVQQUTAEWLP-KIDUDLJLSA-N ;
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Lincomycin is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis.^[3] 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.^[4] It was released for medical use in September 1964.^[5]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ Macleod AJ, Ross HB, Ozere RL, Digout G (November 1964). "Lincomycin: A New Antibiotic Active Against Staphylococci and Other Gram-Positive Cocci: Clinical and Laboratory Studies". Canadian Medical Association Journal. 91 (20): 1056–1060. PMC 1928283. PMID 14217764.
^ Birkenmeyer RD, Kagan F (July 1970). "Lincomycin. XI. Synthesis and structure of clindamycin. A potent antibacterial agent". Journal of Medicinal Chemistry. 13 (4): 616–619. doi:10.1021/jm00298a007. PMID 4916317.
^ Duncan IB, Jeans B (September 1965). "Lincomycin in hospital practice". Canadian Medical Association Journal. 93 (13): 685–691. PMC 1928825. PMID 5828940.