Pirlimycin

For research use only. Not for therapeutic Use.

  • CAT Number: M008732
  • CAS Number: 79548-73-5
  • Molecular Formula: C17H31ClN2O5S
  • Molecular Weight: 411.00
  • Purity: ≥95%
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Pirlimycin(Cat No.:M008732)is a lincosamide antibiotic used primarily in veterinary medicine to treat bovine mastitis caused by Gram-positive bacteria, including Staphylococcus and Streptococcus species. It inhibits bacterial protein synthesis by binding to the 50S ribosomal subunit, preventing peptide elongation. With its broad-spectrum antibacterial activity and targeted efficacy, pirlimycin is administered as an intramammary infusion, offering a practical solution for dairy cattle infections. Its favorable pharmacokinetics and low resistance profile enhance its effectiveness, making pirlimycin a valuable tool in veterinary antibiotic therapies and mastitis management strategies.


Catalog Number M008732
CAS Number 79548-73-5
Synonyms

Pirlimycin;Methyl 7-chloro-6,7,8-trideoxy-6-[[[(2S,4R)-4-ethyl-2-piperidinyl]carbonyl]amino]-1-thio-L-threo-α-D-galacto-octopyranoside;L-Threo-alpha-galacto-octopyranoside, methyl 7-chloro-6,7,8-trideoxy-6-((((2S,4R)-4-ethyl-2-piperidinyl)carbonyl)am

Molecular Formula C17H31ClN2O5S
Purity ≥95%
Target Antibiotic
Solubility Soluble in DMSO
Appearance White solid
Storage Store at -20°C
IUPAC Name (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-4-ethylpiperidine-2-carboxamide
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
InChIKey HBJOXQRURQPDEX-MHXMMLMNSA-N
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
Reference

1: Ray P, Knowlton KF, Shang C, Xia K. Method development and validation: solid Phase extraction-ultra performance liquid chromatography-tandem mass spectrometry quantification of pirlimycin in bovine feces and urine. J AOAC Int. 2014 Nov-Dec;97(6):1730-6. PubMed PMID: 25632451.<br />
2: Kulesza SB, Maguire RO, Xia K, Cushman J, Knowlton K, Ray P. Manure Injection Affects the Fate of Pirlimycin in Surface Runoff and Soil. J Environ Qual. 2016 Mar;45(2):511-8. doi: 10.2134/jeq2015.06.0266. PubMed PMID: 27065398.<br />
3: Birkenmeyer RD, Kroll SJ, Lewis C, Stern KF, Zurenko GE. Synthesis and antimicrobial activity of clindamycin analogues: pirlimycin, 1,2 a potent antibacterial agent. J Med Chem. 1984 Feb;27(2):216-23. PubMed PMID: 6363698.<br />
4: Kopia GA, Driscoll EM, Yeung KF, Lucchesi BR. Antiarrhythmic and cardiovascular actions of the new antibiotic agent pirlimycin adenylate. Pharmacology. 1983;27(5):255-66. PubMed PMID: 6606809.<br />
5: Whittem T. Pharmacokinetics and milk discard times of pirlimycin after intramammary infusion: a population approach. J Vet Pharmacol Ther. 1999 Feb;22(1):41-51. PubMed PMID: 10211716.<br />
6: Hornish RE, Roof RD, Wiest JR. Pirlimycin residue in bovine liver–a case of reverse metabolism. Analyst. 1998 Dec;123(12):2463-7. PubMed PMID: 10435279.<br />
7: Roy JP, Du Tremblay D, DesC&ocirc;teaux L, Messier S, Scholl D, Bouchard E. Effect of precalving intramammary treatment with pirlimycin in nulliparous Holstein heifers. Can J Vet Res. 2007 Oct;71(4):283-91. PubMed PMID: 17955903; PubMed Central PMCID: PMC1940276.

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