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MedKoo Cat#: 584327 | Name: Cefapirin
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Description:

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

Cefapirin is an antibiotic effective against gram-negative and gram-positive organisms.

Chemical Structure

Cefapirin
CAS#21593-23-7 (free acid)

Theoretical Analysis

MedKoo Cat#: 584327

Name: Cefapirin

CAS#: 21593-23-7 (free acid)

Chemical Formula: C17H17N3O6S2

Exact Mass: 423.0559

Molecular Weight: 423.46

Elemental Analysis: C, 48.22; H, 4.05; N, 9.92; O, 22.67; S, 15.14

Price and Availability

Size Price Availability Quantity
5mg USD 325.00 2 Weeks
10mg USD 585.00 2 Weeks
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Related CAS #
21593-23-7 (free acid) 24356-60-3 (sodium)
Synonym
Cefapirin; Cephapirin; Cefapirine; Cefadyl;
IUPAC/Chemical Name
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridinylthio)acetyl)amino)-, (6R-trans)-
InChi Key
UQLLWWBDSUHNEB-CZUORRHYSA-N
InChi Code
InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
SMILES Code
O=C(C(N12)=C(COC(C)=O)CS[C@]2([H])[C@H](NC(CSC3=CC=NC=C3)=O)C1=O)O
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 423.46 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
1: Cagnardi P, Locatelli C, Ferraresi C, Bronzo V, Carli S, Villa R, Zonca A. Pharmacokinetics in foremilk and antimicrobial activity of cephapirin following intramammary administration in healthy and Staphylococcus aureus-infected cows. N Z Vet J. 2014 May;62(3):146-51. doi: 10.1080/00480169.2013.865295. Epub 2014 Jan 9. PubMed PMID: 24224523. 2: Hausler K, Godden SM, Schneider MJ, Lightfield AR, Bulthaus M, Haines D. Hot topic: investigating the risk of violative meat residues in bob veal calves fed colostrum from cows treated at dry-off with cephapirin benzathine. J Dairy Sci. 2013 Apr;96(4):2349-2355. doi: 10.3168/jds.2012-5891. Epub 2013 Feb 15. PubMed PMID: 23415519. 3: Gorden PJ, van der List M, Lehman FD, Lantz RK, Constable PD. Elimination kinetics of cephapirin sodium in milk after an 8-day extended therapy program of daily intramammary infusion in healthy lactating Holstein-Friesian cows. J Dairy Sci. 2013 Jul;96(7):4455-64. doi: 10.3168/jds.2012-6487. Epub 2013 May 16. PubMed PMID: 23684021. 4: Berendsen BJ, Essers ML, Mulder PP, van Bruchem GD, Lommen A, van Overbeek WM, Stolker LA. Newly identified degradation products of ceftiofur and cephapirin impact the analytical approach for quantitative analysis of kidney. J Chromatogr A. 2009 Nov 13;1216(46):8177-86. doi: 10.1016/j.chroma.2009.04.003. Epub 2009 Apr 9. PubMed PMID: 19406407. 5: Ray P, Knowlton KF, Shang C, Xia K. Development and validation of a UPLC-MS/MS method to monitor cephapirin excretion in dairy cows following intramammary infusion. PLoS One. 2014 Nov 6;9(11):e112343. doi: 10.1371/journal.pone.0112343. eCollection 2014. PubMed PMID: 25375097; PubMed Central PMCID: PMC4223036. 6: Heller DN, Kaplan DA, Rummel NG, von Bredow J. Identification of cephapirin metabolites and degradants in bovine milk by electrospray ionization--ion trap tandem mass spectrometry. J Agric Food Chem. 2000 Dec;48(12):6030-5. PubMed PMID: 11141270. 7: Denis-Robichaud J, Dubuc J. Randomized clinical trial of intrauterine cephapirin infusion in dairy cows for the treatment of purulent vaginal discharge and cytological endometritis. J Dairy Sci. 2015 Oct;98(10):6856-64. doi: 10.3168/jds.2014-9129. Epub 2015 Jul 22. PubMed PMID: 26210270. 8: el-Komy AA. Disposition kinetics and bioavailability of piperacillin and cephapirin in mares. Dtsch Tierarztl Wochenschr. 1995 Jun;102(6):244-8. PubMed PMID: 8582260. 9: Nickerson SC, Owens WE, Fox LK, Scheifinger CC, Shryock TR, Spike TE. Comparison of tilmicosin and cephapirin as therapeutics for Staphylococcus aureus mastitis at dry-off. J Dairy Sci. 1999 Apr;82(4):696-703. PubMed PMID: 10212455. 10: Apparao MD, Ruegg PL, Lago A, Godden S, Bey R, Leslie K. Relationship between in vitro susceptibility test results and treatment outcomes for gram-positive mastitis pathogens following treatment with cephapirin sodium. J Dairy Sci. 2009 Jun;92(6):2589-97. doi: 10.3168/jds.2008-1693. PubMed PMID: 19447991. 11: Robson HG, Bowmer MI. Treatment of pneumonia and other serious bacterial infections with cephapirin. Antimicrob Agents Chemother. 1974 Sep;6(3):274-81. PubMed PMID: 15830473; PubMed Central PMCID: PMC444637. 12: Roy JP, DesCôteaux L, DuTremblay D, Beaudry F, Elsener J. Efficacy of a 5-day extended therapy program during lactation with cephapirin sodium in dairy cows chronically infected with Staphylococcus aureus. Can Vet J. 2009 Dec;50(12):1257-62. PubMed PMID: 20190974; PubMed Central PMCID: PMC2777288. 13: Runciman DJ, Anderson GA, Malmo J. Comparison of two methods of detecting purulent vaginal discharge in postpartum dairy cows and effect of intrauterine cephapirin on reproductive performance. Aust Vet J. 2009 Sep;87(9):369-78. doi: 10.1111/j.1751-0813.2009.00469.x. PubMed PMID: 19703140. 14: Stockler RM, Morin DE, Lantz RK, Hurley WL, Constable PD. Effect of milk fraction on concentrations of cephapirin and desacetylcephapirin in bovine milk after intramammary infusion of cephapirin sodium. J Vet Pharmacol Ther. 2009 Aug;32(4):345-52. doi: 10.1111/j.1365-2885.2008.01048.x. PubMed PMID: 19614839. 15: Fry W, Ximenes J, Siskin SB. Concentrations of cephapirin sodium in plasma and gynecologic tissue after a single preoperative dose. Int J Clin Pharmacol Ther Toxicol. 1980;18(2):92-6. PubMed PMID: 7372381. 16: Juzwiak JS, Brown MP, Gronwall R, Houston AE. Effect of probenecid administration on cephapirin pharmacokinetics and concentrations in mares. Am J Vet Res. 1989 Oct;50(10):1742-7. PubMed PMID: 2802305. 17: Barza M, Melethil S, Berger S, Ernst EC. Comparative pharmacokinetics of cefamandole, cephapirin, and cephalothin in healthy subjects and effect of repeated dosing. Antimicrob Agents Chemother. 1976 Sep;10(3):421-5. PubMed PMID: 984783; PubMed Central PMCID: PMC429764. 18: Vidal Pan C, González Quintela A, Román García J, Millán I, Martin Martin F, Moya Mir M. Cephapirin-induced neutropenia. Chemotherapy. 1989;35(6):449-53. PubMed PMID: 2612233. 19: Owens WE, Nickerson SC, Washburn PJ, Ray CH. Efficacy of a cephapirin dry cow product for treatment of experimentally induced Staphylococcus aureus mastitis in heifers. J Dairy Sci. 1991 Oct;74(10):3376-82. PubMed PMID: 1744267. 20: Shimizu T. Comparison of absorption and excretion of cefazolin with cephalothin and cephapirin. Jpn J Antibiot. 1975 Aug;28(4):542-8. PubMed PMID: 1160145.