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MedKoo Cat#: 597953 | Name: Pirlimycin HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pirlimycin Hydrochloride is a semi-synthetic lincosaminide antibiotic. Pirlimycin Hydrochloride is a Clindamycin analog.

Chemical Structure

Pirlimycin HCl
Pirlimycin HCl
CAS#78822-40-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 597953

Name: Pirlimycin HCl

CAS#: 78822-40-9 (HCl)

Chemical Formula: C17H33Cl3N2O5S

Exact Mass: 482.1176

Molecular Weight: 483.87

Elemental Analysis: C, 42.20; H, 6.87; Cl, 21.98; N, 5.79; O, 16.53; S, 6.63

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Related CAS #
79548-73-5 (free base) 78822-40-9 (HCl)
Synonym
Pirlimycin hydrochloride; Pirlimycin HCl; U 57930E; U-57930E; U57930E; Pirsue;
IUPAC/Chemical Name
(2S,4R)-N-((1S,2S)-2-chloro-1-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)propyl)-4-ethylpiperidine-2-carboxamide dihydrochloride
InChi Key
WOOZGIRLEZDLSO-RWMVMHIMSA-N
InChi Code
InChI=1S/C17H31ClN2O5S.2ClH/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);2*1H/t8-,9+,10-,11+,12-,13+,14+,15+,17+;;/m0../s1
SMILES Code
CC[C@@H]1CCN[C@H](C(N[C@@H]([C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O)[C@@H](Cl)C)=O)C1.Cl.Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pirlimycin Hydrochloride is a semi-synthetic lincosaminide antibiotic.
In vitro activity:
The in vitro activity of U-57930E, a pipecolic acid amide of clindamycin, was compared with those of clindamycin, ampicillin, carbenicillin and tetracycline against 321 anaerobic clinical isolates. The MIC (micrograms/ml) of U-57930E that inhibited 95% Bacteroides fragilis, Peptococcus prevotii, B. melaninogenicus and P. asaccharolyticus was 0.0625; 0.03125 for Peptostreptococcus anaerobius, B. vulgatus, Propionibacterium and Peptococcus species. All strains of Clostridium perfringens were inhibited by 0.5 microgram/ml of U-57930E. Both clindamycin and U-57930E showed similar MIC values for all strains of Fusobacterium nucleatum and Propionibacterium acnes tested. The MIC values for ampicillin, carbenicillin and tetracycline were within the expected range. U-57930E had a 4 approximately 8 fold lower MIC than clindamycin and is significantly active against anaerobic bacteria. Reference: J Antibiot (Tokyo). 1983 Jan;36(1):42-6. https://pubmed.ncbi.nlm.nih.gov/6678915/
In vivo activity:
The purpose of this study was to determine the effect of intramammary pirlimycin on the fecal microbiome of dairy cattle. In part 1 of the study, treated heifers (T1) were given intramammary pirlimycin into one infected quarter once daily for 2 d at 24-h intervals, according to the label instructions. Control heifers received no treatment. In part 2 of the study, treated heifers (T2) were given intramammary pirlimycin into one infected quarter once daily for 8 d at 24-h intervals, according to the label instructions. Intramammary pirlimycin induced a significant change in the composition of the fecal microbiota by d 2 in the treated groups. Based on calculated intra-subject similarities, intramammary pirlimycin was associated with a significant acute change in the fecal microbiota of dairy heifers and that chance reversed when the antimicrobial exposure was brief, but sustained following longer exposure. Reference: J Dairy Sci. 2020 Apr;103(4):3459-3469. https://pubmed.ncbi.nlm.nih.gov/32037172/

Preparing Stock Solutions

The following data is based on the product molecular weight 483.87 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Qadri SM, Karim MR, Flournoy DJ. In vitro activity of U-57930E against anaerobic bacteria and its comparison with clindamycin, ampicillin, carbenicillin and tetracycline. J Antibiot (Tokyo). 1983 Jan;36(1):42-6. doi: 10.7164/antibiotics.36.42. PMID: 6678915. 2. Dhawan VK, Bansal MB, Thadepalli H. In vitro activity of pipecolic acid amide of clindamycin (U-57930E) on anaerobic bacteria compared with those of clindamycin, cefoxitin, and chloramphenicol. Antimicrob Agents Chemother. 1982 Aug;22(2):350-1. doi: 10.1128/AAC.22.2.350. PMID: 6927289; PMCID: PMC183741. 3. Adkins PRF, Ericsson AC, Middleton JR, Witzke MC. The effect of intramammary pirlimycin hydrochloride on the fecal microbiome of early-lactation heifers. J Dairy Sci. 2020 Apr;103(4):3459-3469. doi: 10.3168/jds.2019-17554. Epub 2020 Feb 7. PMID: 32037172. 4. Roy JP, Du Tremblay D, DesCôteaux 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. PMID: 17955903; PMCID: PMC1940276.
In vitro protocol:
1. Qadri SM, Karim MR, Flournoy DJ. In vitro activity of U-57930E against anaerobic bacteria and its comparison with clindamycin, ampicillin, carbenicillin and tetracycline. J Antibiot (Tokyo). 1983 Jan;36(1):42-6. doi: 10.7164/antibiotics.36.42. PMID: 6678915. 2. Dhawan VK, Bansal MB, Thadepalli H. In vitro activity of pipecolic acid amide of clindamycin (U-57930E) on anaerobic bacteria compared with those of clindamycin, cefoxitin, and chloramphenicol. Antimicrob Agents Chemother. 1982 Aug;22(2):350-1. doi: 10.1128/AAC.22.2.350. PMID: 6927289; PMCID: PMC183741.
In vivo protocol:
1. Adkins PRF, Ericsson AC, Middleton JR, Witzke MC. The effect of intramammary pirlimycin hydrochloride on the fecal microbiome of early-lactation heifers. J Dairy Sci. 2020 Apr;103(4):3459-3469. doi: 10.3168/jds.2019-17554. Epub 2020 Feb 7. PMID: 32037172. 2. Roy JP, Du Tremblay D, DesCôteaux 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. PMID: 17955903; PMCID: PMC1940276.
1: 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. 2: 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. 3: Jiang W, Beier RC, Luo P, Zhai P, Wu N, Lin G, Wang X, Xu G. Analysis of Pirlimycin Residues in Beef Muscle, Milk, and Honey by a Biotin-Streptavidin-Amplified Enzyme-Linked Immunosorbent Assay. J Agric Food Chem. 2016 Jan 13;64(1):364-70. doi: 10.1021/acs.jafc.5b05711. Epub 2015 Dec 31. PubMed PMID: 26671277. 4: Gillespie BE, Moorehead H, Lunn P, Dowlen HH, Johnson DL, Lamar KC, Lewis MJ, Ivey SJ, Hallberg JW, Chester ST, Oliver SP. Efficacy of extended pirlimycin hydrochloride therapy for treatment of environmental Streptococcus spp and Staphylococcus aureus intramammary infections in lactating dairy cows. Vet Ther. 2002 Winter;3(4):373-80. PubMed PMID: 12584673. 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. 6: Middleton JR, Timms LL, Bader GR, Lakritz J, Luby CD, Steevens BJ. Effect of prepartum intramammary treatment with pirlimycin hydrochloride on prevalence of early first-lactation mastitis in dairy heifers. J Am Vet Med Assoc. 2005 Dec 15;227(12):1969-74. PubMed PMID: 16379636. 7: Oliver SP, Gillespie BE, Ivey SJ, Lewis MJ, Johnson DL, Lamar KC, Moorehead H, Dowlen HH, Chester ST, Hallberg JW. Influence of prepartum pirlimycin hydrochloride or penicillin-novobiocin therapy on mastitis in heifers during early lactation. J Dairy Sci. 2004 Jun;87(6):1727-31. PubMed PMID: 15453485. 8: 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 Jul;45(4):1466. doi: 10.2134/jeq2015.06.0266er. PubMed PMID: 27380099. 9: 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. 10: Oliver SP, Almeida RA, Gillespie BE, Ivey SJ, Moorehead H, Lunn P, Dowlen HH, Johnson DL, Lamar KC. Efficacy of extended pirlimycin therapy for treatment of experimentally induced Streptococcus uberis intramammary infections in lactating dairy cattle. Vet Ther. 2003 Fall;4(3):299-308. PubMed PMID: 15136992. 11: Apparao D, Oliveira L, Ruegg PL. Relationship between results of in vitro susceptibility tests and outcomes following treatment with pirlimycin hydrochloride in cows with subclinical mastitis associated with gram-positive pathogens. J Am Vet Med Assoc. 2009 Jun 1;234(11):1437-46. doi: 10.2460/javma.234.11.1437. PubMed PMID: 19480625. 12: Oliver SP, Headrick SI, Gillespie BE, Lewis MJ, Johnson DL, Lamar KC, Moorehead H, Dowlen HH, Hallberg JW. Intramammary infections in heifers during early lactation following intramammary infusion of pirlimycin hydrochloride or penicillin-novobiocin at the first milking after parturition. J Dairy Res. 2007 May;74(2):211-7. Epub 2007 Jan 17. PubMed PMID: 17227598. 13: Garcia-Rodriguez JA, Garcia-Sanchez JE, Prieto J, Sanchez de S Lorenzo A. Activity of pirlimycin (U57930E) against strains of the Bacteroides fragilis group. Antimicrob Agents Chemother. 1982 Nov;22(5):893-4. PubMed PMID: 7181494; PubMed Central PMCID: PMC185677. 14: Heller DN. Determination and confirmation of pirlimycin residue in bovine milk and liver by liquid chromatography/thermospray mass spectrometry: interlaboratory study. J AOAC Int. 1996 Sep-Oct;79(5):1054-61. PubMed PMID: 8823914. 15: Deluyker HA, Van Oye SN, Boucher JF. Factors affecting cure and somatic cell count after pirlimycin treatment of subclinical mastitis in lactating cows. J Dairy Sci. 2005 Feb;88(2):604-14. PubMed PMID: 15653527. 16: 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. 17: 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. 18: Shah JA, Weber DJ. High-performance liquid chromatographic assay of pirlimycin in human serum and urine using 9-fluorenylmethylchloroformate. J Chromatogr. 1984 Jul 13;309(1):95-105. PubMed PMID: 6480775. 19: Roy JP, Du Tremblay D, DesCôteaux 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. 20: Thornsberry C, Marler JK, Watts JL, Yancey RJ Jr. Activity of pirlimycin against pathogens from cows with mastitis and recommendations for disk diffusion tests. Antimicrob Agents Chemother. 1993 May;37(5):1122-6. PubMed PMID: 8517701; PubMed Central PMCID: PMC187914.

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