Pirlimycin

Pirlimycin, sold under the brand name Pirsue, is used in the treatment of mastitis in cattle.^[1][3][4] It is used as the salt pirlimycin hydrochloride and it belongs to the lincosamide class of antimicrobials.^[1]

Pirlimycin

Clinical data
Trade names	Pirsue
Routes of administration	Intramammary
ATCvet code	QJ51FF90 (WHO)
Legal status
Legal status	EU: Rx-only[1][2]
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 8S09O559AQ
KEGG	D08391 Y D05501
ChEMBL	ChEMBL1652611 N ChEMBL3989899
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 Key:CHAZSEMQYSZBFN-RWMVMHIMSA-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.^[5]

Mechanism of action

It is bacteriostatic and acts by inhibiting bacterial protein synthesis via binding with the 50S subunit of the ribosome.^{[citation needed]}