Lincomycin

Lincomycin

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a609005
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	IM/IV
ATC code	J01FF02 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	N/A
Biological half-life	5.4 ± 1.0 hours after IM or IV administration
Excretion	renal and biliary
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 Y
PubChem CID	3000540
DrugBank	DB01627 N
ChemSpider	2272112 Y
UNII	BOD072YW0F
KEGG	D00223 Y
ChEBI	CHEBI:6472 N
ChEMBL	CHEMBL1447 Y
ECHA InfoCard	100.005.296
Chemical and physical data
Formula	C18H34N2O6S
Molar mass	406.538 g/mol
3D model (Jmol)	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 Y Key:OJMMVQQUTAEWLP-KIDUDLJLSA-N Y
NY (what is this?)

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.

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.

Intramuscular administration of a single dose of 600 mg of Lincomycin produces average peak serum levels of 11.6 micrograms/ml at 60 minutes, and maintains therapeutic levels for 17 to 20 hours, for most susceptible gram-positive organisms. Urinary excretion after this dose ranges from 1.8 to 24.8 percent (mean: 17.3 percent).

A two-hour intravenous infusion of 600 mg of Lincomycin achieves average peak serum levels of 15.9 micrograms/ml and yields therapeutic levels for 14 hours for most susceptible gram-positive organisms. Urinary excretion ranges from 4.9 to 30.3 percent (mean: 13.8 percent).

The biological half-life after IM or IV administration is 5.4 ± 1.0 hours. The serum half-life of lincomycin may be prolonged in patients with severe impairment of renal function, compared to patients with normal renal function. In patients with abnormal hepatic function, serum half-life may be twofold longer than in patients with normal hepatic function. Hemodialysis and peritoneal dialysis are not effective in removing lincomycin from the serum.