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MedKoo Cat#: 317458 | Name: Cephapirin Sodium
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Description:

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

Cephapirin Sodium is the sodium salt form of cephapirin, a semi-synthetic, broad-spectrum, first-generation cephalosporin antibiotic. It is beta-lactam with bactericidal activity. Cephalosporin antibiotic is effective against gram-negative and gram-positive organisms. Cephapirin sodium inhibits bacterial cell wall synthesis by inhibiting the final transpeptidation step of peptidoglycan synthesis and subsequent cross-linking of peptidoglycan units.

Chemical Structure

Cephapirin Sodium
CAS#24356-60-3 (sodium)

Theoretical Analysis

MedKoo Cat#: 317458

Name: Cephapirin Sodium

CAS#: 24356-60-3 (sodium)

Chemical Formula: C17H16N3NaO6S2

Exact Mass: 0.0000

Molecular Weight: 445.44

Elemental Analysis: C, 45.84; H, 3.62; N, 9.43; Na, 5.16; O, 21.55; S, 14.40

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
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Related CAS #
21593-23-7 (free acid) 24356-60-3 (sodium)
Synonym
Cephapirin Sodium; Cefapirin sodium; Cephap; BL P 1322; BL-P 1322; BLP 1322. NSC 179171
IUPAC/Chemical Name
sodium;(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChi Key
VGEOUKPOQQEQSX-UHFFFAOYSA-M
InChi Code
InChI=1S/C17H17N3O6S2.Na/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);/q;+1/p-1
SMILES Code
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)[O-].[Na+]
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, not in water
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 445.44 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: Hyde B, Brennan M. Does intrauterine cephapirin improve subsequent fertility in cows with clinical endometritis? Vet Rec. 2020 Mar 21;186(11):350-352. doi: 10.1136/vr.m1049. PMID: 32198250. 2: 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. doi: 10.1159/000238709. PMID: 2612233. 3: Cephapirin. Med Lett Drugs Ther. 1974 Jun 21;16(13):53-4. PMID: 4842601. 4: Axelrod J, Meyers BR, Hirschman SZ. Cephapirin: in vitro antibacterial spectrum. Appl Microbiol. 1971 Nov;22(5):904-8. doi: 10.1128/am.22.5.904-908.1971. PMID: 5132096; PMCID: PMC376442. 5: MacNeil L, Rice JJ, Muhammad N, Lauback RG. Stability-indicating liquid chromatographic determination of cephapirin, desacetyl cephapirin and cephapirin lactone in sodium cephapirin bulk and injectable formulations. J Chromatogr. 1986 Jun 27;361:285-90. doi: 10.1016/s0021-9673(01)86917-x. PMID: 3733955. 6: Rubi R, Galan HM. Cephapirin concentrations in prostatic and seminal vesicle tissues. Int J Clin Pharmacol Biopharm. 1979 Feb;17(2):87-9. PMID: 422307. 7: Hyde B, Brennan M. BestBETs for Vets. Vet Rec. 2017 Apr 15;180(15):380-381. doi: 10.1136/vr.j1635. PMID: 28408513. 8: Levison ME, Bran JL, Jepson JH, Kaye D. Neutropenia associated with cephapirin therapy. Antimicrob Agents Chemother. 1972 Feb;1(2):174-6. doi: 10.1128/AAC.1.2.174. PMID: 4680807; PMCID: PMC444188. 9: Chittireddy HNPR, Kumar JVS, Bhimireddy A, Shaik MR, Shaik AH, Alwarthan A, Shaik B. Development and Validation for Quantification of Cephapirin and Ceftiofur by Ultraperformance Liquid Chromatography with Triple Quadrupole Mass Spectrometry. Molecules. 2022 Nov 16;27(22):7920. doi: 10.3390/molecules27227920. PMID: 36432023; PMCID: PMC9696115. 10: 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. PMID: 25375097; PMCID: PMC4223036. 11: Dubuc J, Fauteux V, Villettaz-Robichaud M, Roy JP, Rousseau M, Buczinski S. Short communication: Efficacy of a second intrauterine cephapirin infusion for the treatment of purulent vaginal discharge and endometritis in postpartum dairy cows. J Dairy Sci. 2021 Mar;104(3):3559-3563. doi: 10.3168/jds.2020-19537. Epub 2020 Dec 25. PMID: 33358808. 12: Wiesner P, MacGregor R, Bear D, Berman S, Holmes K, Turck M. Evaluation of a new cephalosporin antibiotic, cephapirin. Antimicrob Agents Chemother. 1972 Apr;1(4):303-9. doi: 10.1128/AAC.1.4.303. PMID: 4208896; PMCID: PMC444212. 13: 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. PMID: 23684021. 14: Creatsas G, Pavlatos M, Lolis D, Kaskarelis D. A study of the kinetics of cephapirin and cephalexin in pregnancy. Curr Med Res Opin. 1980;7(1):43-6. doi: 10.1185/03007998009116514. PMID: 7428412. 15: 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. doi: 10.1021/jf000046b. PMID: 11141270. 16: Barański W, Baryczka A, Zduńczyk S, Tobolski D, Janowski T. Prevalence of subclinical endometritis in dairy cows that recovered after treatment of clinical endometritis with cephapirin and PGF2α. Theriogenology. 2022 Oct 15;192:166-171. doi: 10.1016/j.theriogenology.2022.08.031. Epub 2022 Aug 28. PMID: 36108547. 17: Moats WA, Anderson KL, Rushing JE, Buckley S. Conversion of cephapirin to deacetylcephapirin in milk and tissues of treated animals. J Agric Food Chem. 2000 Feb;48(2):498-502. doi: 10.1021/jf990638y. PMID: 10691664. 18: Wilkins J, Leedom JM, Overturf GD, Baraff LJ. Differential inactivation of cephapirin vs. cephalothin by penicillin-resistant strains of Staphylococcus aureus: a preliminary study. J Infect Dis. 1978 Apr;137(4):494-7. doi: 10.1093/infdis/137.4.494. PMID: 649993. 19: Tison N, Bouchard E, DesCôteaux L, Lefebvre RC. Effectiveness of intrauterine treatment with cephapirin in dairy cows with purulent vaginal discharge. Theriogenology. 2017 Feb;89:305-317. doi: 10.1016/j.theriogenology.2016.09.007. Epub 2016 Sep 29. PMID: 28043367. 20: Burch KH, Quinn EL, Saravolatz LD, Madhavan T, Jovanovich JF, Pohlod D. Cephapirin therapy in infective endocarditis. South Med J. 1983 Apr;76(4):448-52. doi: 10.1097/00007611-198304000-00008. PMID: 6836358.