MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 597952 | Name: Pirlimycin
Featured

Description:

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

Pirlimycin is a lincosamide antibiotic that is effective against Gram-positive bacteria, including Staphylococcus, Streptococcus, Bacteroides, and Plasmodium. Pirlimycin inhibits bacterial protein synthesis by binding to the 50S subunit of the ribosome. Pirlimycin has been used by veterinarians in the treatment of mastitis in dairy cattle.

Chemical Structure

Pirlimycin
Pirlimycin
CAS#79548-73-5 (free base)

Theoretical Analysis

MedKoo Cat#: 597952

Name: Pirlimycin

CAS#: 79548-73-5 (free base)

Chemical Formula: C17H31ClN2O5S

Exact Mass: 410.1642

Molecular Weight: 410.95

Elemental Analysis: C, 49.69; H, 7.60; Cl, 8.63; N, 6.82; O, 19.47; S, 7.80

Price and Availability

Size Price Availability Quantity
1mg USD 550.00 2 Weeks
5mg USD 1,150.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
79548-73-5 (free base) 78822-40-9 (HCl)
Synonym
Pirlimycin; Pirlimycina; Pirlimycinum;
IUPAC/Chemical Name
(2S,4S)-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
InChi Key
HBJOXQRURQPDEX-DGZHSVRSSA-N
InChi Code
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
SMILES Code
O=C([C@H]1NCC[C@@H](C1)CC)N[C@H]([C@@H](Cl)C)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O
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 (RU 38882), a lincosamide antibiotic, is active against Gram-positive bacteria.
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 410.95 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: Bechtold V, Petzl W, Huber-Schlenstedt R, Gangl A, Sorge US. Antimicrobial resistance of Streptococcus dysgalactiae, Streptococcus agalactiae, and Streptococcus canis in quarter milk samples from Bavaria, Southern Germany, between 2012 and 2022. J Dairy Sci. 2024 May 31:S0022-0302(24)00840-3. doi: 10.3168/jds.2023-24555. Epub ahead of print. PMID: 38825124. 2: Shawver S, Ishii S, Strickland MS, Badgley B. Soil type and moisture content alter soil microbial responses to manure from cattle administered antibiotics. Environ Sci Pollut Res Int. 2024 Apr;31(18):27259-27272. doi: 10.1007/s11356-024-32903-z. Epub 2024 Mar 20. PMID: 38507165; PMCID: PMC11052774. 3: Sweeney MT, Gunnett L, Kumar DM, Lunt BL, Moulin V, Barrett M, Gurjar A, Doré E, Pedraza JR, Bade D, Machin C. Antimicrobial susceptibility of mastitis pathogens isolated from North American dairy cattle, 2011-2022. Vet Microbiol. 2024 Apr;291:110015. doi: 10.1016/j.vetmic.2024.110015. Epub 2024 Feb 8. PMID: 38340554. 4: Kolar QK, Goncalves JL, Erskine RJ, Ruegg PL. Comparison of Minimum Inhibitory Concentrations of Selected Antimicrobials for Non-Aureus Staphylococci, Enterococci, Lactococci, and Streptococci Isolated from Milk Samples of Cows with Clinical Mastitis. Antibiotics (Basel). 2024 Jan 18;13(1):91. doi: 10.3390/antibiotics13010091. PMID: 38247650; PMCID: PMC10812473. 5: Karell J, Petzl W, Gangl A, Huber-Schlenstedt R, Sorge US. Changes in antimicrobial resistance of Staphylococcus aureus in bovine quarter milk samples from southern Germany between 2012 and 2022. J Dairy Sci. 2024 Jun;107(6):3802-3812. doi: 10.3168/jds.2023-23997. Epub 2023 Nov 16. PMID: 37977447. 6: Leite de Campos J, Gonçalves JL, Kates A, Steinberger A, Sethi A, Suen G, Shutske J, Safdar N, Goldberg T, Ruegg PL. Variation in partial direct costs of treating clinical mastitis among 37 Wisconsin dairy farms. J Dairy Sci. 2023 Dec;106(12):9276-9286. doi: 10.3168/jds.2023-23388. Epub 2023 Aug 23. PMID: 37641286. 7: Palladini G, Garbarino C, Luppi A, Russo S, Filippi A, Arrigoni N, Massella E, Ricchi M. Comparison between broth microdilution and agar disk diffusion methods for antimicrobial susceptibility testing of bovine mastitis pathogens. J Microbiol Methods. 2023 Sep;212:106796. doi: 10.1016/j.mimet.2023.106796. Epub 2023 Aug 5. PMID: 37544431. 8: Koike H, Hayashi M, Kazama K, Yoshikawa S, Hayashi H, Ohba Y, Matsushima Y, Nagano C, Kanda M, Otsuka K, Sasamoto T. Validation and application of an immunochromatographic test to detect four macrolides and two lincosamides in raw cow milk. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2023 Apr;40(4):528-541. doi: 10.1080/19440049.2023.2177504. Epub 2023 Feb 27. PMID: 36848530. 9: Kawai K, Kurumisawa T, Shinozuka Y, Higuchi H, Iwano H, Hayashi T, Ozawa M, Koike R, Uchiyama M. Antimicrobial susceptibility of bovine clinical mastitis pathogens in Japan and development of a simplified agar disk diffusion method for clinical practice. J Vet Med Sci. 2023 Feb 1;85(2):143-148. doi: 10.1292/jvms.21-0450. Epub 2022 Dec 20. PMID: 36543185; PMCID: PMC10017299. 10: Kulesza SB, Maguire R, Xia K, Ray P, Knowlton K. Effect of temperature, pH, and soil texture on pirlimycin fate in dairy manure-amended soils. J Environ Qual. 2022 Nov;51(6):1310-1318. doi: 10.1002/jeq2.20410. Epub 2022 Nov 4. PMID: 36068016. 11: McDougall S, Penry J, Dymock D. Antimicrobial susceptibilities in dairy herds that differ in dry cow therapy usage. J Dairy Sci. 2021 Aug;104(8):9142-9163. doi: 10.3168/jds.2020-19925. Epub 2021 May 15. PMID: 34001359. 12: Keenum I, Williams RK, Ray P, Garner ED, Knowlton KF, Pruden A. Combined effects of composting and antibiotic administration on cattle manure-borne antibiotic resistance genes. Microbiome. 2021 Apr 1;9(1):81. doi: 10.1186/s40168-021-01006-z. PMID: 33795006; PMCID: PMC8017830. 13: Fuenzalida MJ, Furmaga E, Aulik N. Antimicrobial resistance in Klebsiella species from milk specimens submitted for bovine mastitis testing at the Wisconsin Veterinary Diagnostic Laboratory, 2008-2019. JDS Commun. 2021 Mar 19;2(3):148-152. doi: 10.3168/jdsc.2020-0031. PMID: 36339509; PMCID: PMC9623802. 14: Le HTV, Maguire RO, Xia K. Spatial distribution and temporal change of antibiotics in soils amended with manure using two field application methods. Sci Total Environ. 2021 Mar 10;759:143431. doi: 10.1016/j.scitotenv.2020.143431. Epub 2020 Nov 1. PMID: 33172639. 15: Woodward AP, Morin D, Whittem T. Population physiologically based modeling of pirlimycin milk concentrations in dairy cows. J Dairy Sci. 2020 Nov;103(11):10639-10650. doi: 10.3168/jds.2020-18760. Epub 2020 Sep 10. PMID: 32921458. 16: Naushad S, Nobrega DB, Naqvi SA, Barkema HW, De Buck J. Genomic Analysis of Bovine Staphylococcus aureus Isolates from Milk To Elucidate Diversity and Determine the Distributions of Antimicrobial and Virulence Genes and Their Association with Mastitis. mSystems. 2020 Jul 7;5(4):e00063-20. doi: 10.1128/mSystems.00063-20. PMID: 32636332; PMCID: PMC7343304. 17: El Garch F, Youala M, Simjee S, Moyaert H, Klee R, Truszkowska B, Rose M, Hocquet D, Valot B, Morrissey I, de Jong A; VetPath Study Group. Antimicrobial susceptibility of nine udder pathogens recovered from bovine clinical mastitis milk in Europe 2015-2016: VetPath results. Vet Microbiol. 2020 Jun;245:108644. doi: 10.1016/j.vetmic.2020.108644. Epub 2020 May 11. PMID: 32456822. 18: Li MM, Ray P, Knowlton KF, Pruden A, Xia K, Teets C, Du P. Fate of pirlimycin and antibiotic resistance genes in dairy manure slurries in response to temperature and pH adjustment. Sci Total Environ. 2020 Mar 25;710:136310. doi: 10.1016/j.scitotenv.2019.136310. Epub 2019 Dec 26. PMID: 32050366. 19: 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. 20: Tomazi T, Freu G, Alves BG, de Souza Filho AF, Heinemann MB, Veiga Dos Santos M. Genotyping and antimicrobial resistance of Streptococcus uberis isolated from bovine clinical mastitis. PLoS One. 2019 Oct 22;14(10):e0223719. doi: 10.1371/journal.pone.0223719. PMID: 31639136; PMCID: PMC6805098.

View History

Pirmitegravir

Pirmitegravir