Pirlimycin

Pirlimycin

File:Pirlimycin structure.svg
Systematic (IUPAC) name
Methyl(2S-cis)-7-chloro-6,7,8-trideoxy-6[[(4-ethyl-2-piperidinyl) carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside
Clinical data
Routes of administration	Intramammary
Identifiers
CAS Number	79548-73-5 Y
ATCvet code	QJ51FF90 (WHO)
ChemSpider	138508 N
UNII	LM19JT6G5K N
KEGG	D08391 Y
ChEMBL	CHEMBL1652611 N
Chemical data
Formula	C17H31ClN2O5S
Molecular mass	410.164 g/mol
SMILES CC[C@@H]1CCN[C@@H](C1)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
InChI InChI=1S/C17H31ClN2O5S/c1-4-9-5-6-19-10(7-9)16(24)20-11(8(2)18)15-13(22)12(21)14(23)17(25-15)26-3/h8-15,17,19,21-23H,4-7H2,1-3H3,(H,20,24)/t8-,9+,10-,11+,12-,13+,14+,15+,17+/m0/s1 N Key:HBJOXQRURQPDEX-MHXMMLMNSA-N N
NY (what is this?)  (verify)

Pirlimycin hydrochloride belongs to the lincosamide class of antimicrobials. Under the trade name Pirsue, it is used in the treatment of mastitis in cattle.

Activity

Pirlimycin is active against Gram-positive bacteria, specifically Staphylococcus aureus and coagulase negative species of Staphylococcus and Streptococcus. It has no activity against Gram-negative bacteria.

Mechanism of action

It is bacteriostatic and acts by inhibiting bacterial protein synthesis via binding with the 50S subunit of the ribosome.