Pirlimycin

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Pirlimycin
Structural formula
Space-filling model of pirlimycin molecule
Clinical data
Routes of
administration
Intramammary
ATCvet code
Identifiers
  • 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
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H31ClN2O5S
Molar mass410.95 g·mol−1
3D model (JSmol)
  • 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=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
 ☒NcheckY (what is this?)  (verify)

Pirlimycin hydrochloride belongs to the lincosamide class of antimicrobials. Under the trade name Pirsue,[1] it is used in the treatment of mastitis in cattle.[2][3]

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.[4]

Mechanism of action

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

References

  1. ^ Pirsue Sterile Solution
  2. ^ 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.
  3. ^ Hogeveen H (2005). Mastitis in dairy production: current knowledge and future solutions. Wageningen: Wageningen Academic Publishers. p. 55. ISBN 978-90-76998-70-1.
  4. ^ "USP: Pirlimycin" (PDF). Archived from the original (PDF) on 2009-05-09. Retrieved 2009-06-28.