Pirlimycin

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

Pirlimycin

Clinical data
Routes of administration	Intramammary
ATCvet code	QJ51FF90 (WHO)
Identifiers
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
CAS Number	79548-73-5 Y
ChemSpider	138508 N
UNII	LM19JT6G5K
KEGG	D08391 Y
ChEMBL	ChEMBL1652611 N
CompTox Dashboard (EPA)	DTXSID30904249
Chemical and physical data
Formula	C17H31ClN2O5S
Molar mass	410.95 g·mol−1
3D model (JSmol)	Interactive image
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)

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.