Pirlimycin

Pirlimycin
Clinical data
Trade names	Pirsue
Routes of; administration	Intramammary
ATCvet code	QJ51FF90 (WHO) ;
Legal status
Legal status	EU: Rx-only;
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 ;
ChemSpider	138508 ;
UNII	LM19JT6G5K; 8S09O559AQ;
KEGG	D08391 ; D05501;
ChEMBL	ChEMBL1652611 ; 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 ; Key:HBJOXQRURQPDEX-MHXMMLMNSA-N ; Key:CHAZSEMQYSZBFN-RWMVMHIMSA-N;
	(what is this?) (verify)

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]

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]}

References

^ ^a ^b ^c "Pirsue EPAR". European Medicines Agency (EMA). 29 January 2001. Retrieved 26 December 2024.
^ "Pirsue PI". Union Register of medicinal products. 31 January 2001. Retrieved 26 December 2024.
^ Thornsberry C, Marler JK, Watts JL, Yancey RJ (May 1993). "Activity of pirlimycin against pathogens from cows with mastitis and recommendations for disk diffusion tests". Antimicrobial Agents and Chemotherapy. 37 (5): 1122–6. doi:10.1128/AAC.37.5.1122. PMC 187914. PMID 8517701.
^ Hogeveen H (2005). Mastitis in dairy production: current knowledge and future solutions. Wageningen: Wageningen Academic Publishers. p. 55. ISBN 978-90-76998-70-1.
^ "USP: Pirlimycin" (PDF). Archived from the original (PDF) on 9 May 2009. Retrieved 28 June 2009.

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[Pirsue_EPAR-1] "Pirsue EPAR". European Medicines Agency (EMA). 29 January 2001. Retrieved 26 December 2024.

[2] "Pirsue PI". Union Register of medicinal products. 31 January 2001. Retrieved 26 December 2024.

[Thornsberry_1993-3] Thornsberry C, Marler JK, Watts JL, Yancey RJ (May 1993). "Activity of pirlimycin against pathogens from cows with mastitis and recommendations for disk diffusion tests". Antimicrobial Agents and Chemotherapy. 37 (5): 1122–6. doi:10.1128/AAC.37.5.1122. PMC 187914. PMID 8517701.

[4] Hogeveen H (2005). Mastitis in dairy production: current knowledge and future solutions. Wageningen: Wageningen Academic Publishers. p. 55. ISBN 978-90-76998-70-1.

[5] "USP: Pirlimycin" (PDF). Archived from the original (PDF) on 9 May 2009. Retrieved 28 June 2009.

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