MedKoo Cat#: 412492 | Name: Cefazolin free base
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Description:

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

Cefazolin is a semisynthetic cephalosporin analog with broad-spectrum antibiotic action due to inhibition of bacterial cell wall synthesis. It attains high serum levels and is excreted quickly via the urine. Cefazolin inhibits synthesis of bacterial cell wall. Cefazolin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity, which results in the weakening of the bacterial cell wall and cell lysis.

Chemical Structure

Cefazolin free base
Cefazolin free base
CAS#25953-19-9 (free base)

Theoretical Analysis

MedKoo Cat#: 412492

Name: Cefazolin free base

CAS#: 25953-19-9 (free base)

Chemical Formula: C14H14N8O4S3

Exact Mass: 454.0300

Molecular Weight: 454.49

Elemental Analysis: C, 37.00; H, 3.10; N, 24.65; O, 14.08; S, 21.16

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
500mg USD 950.00 2 Weeks
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Synonym
Cefazolin (free base); HSDB-3213; HSDB3213 HSDB 3213
IUPAC/Chemical Name
5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-7-(((1H-tetrazol-1-yl)acetyl)amino)-, (6R-trans)-
InChi Key
MLYYVTUWGNIJIB-BXKDBHETSA-N
InChi Code
InChI=1S/C14H14N8O4S3/c1-6-17-18-14(29-6)28-4-7-3-27-12-9(11(24)22(12)10(7)13(25)26)16-8(23)2-21-5-15-19-20-21/h5,9,12H,2-4H2,1H3,(H,16,23)(H,25,26)/t9-,12-/m1/s1
SMILES Code
O=C(C(N12)=C(CSC3=NN=C(C)S3)CS[C@]2([H])[C@H](NC(CN4N=NN=C4)=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
>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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 454.49 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: Quintiliani R, Nightingale CH. Cefazolin. Ann Intern Med. 1978 Nov;89(5 Pt 1):650-6. doi: 10.7326/0003-4819-89-5-650. PMID: 362999. 2: Griffith RS. Cefazolin. Adv Clin Pharmacol. 1974;8:123-7. PMID: 4468727. 3: Yourassowsky E, Peromet M, Schoutens E. La cefazoline [Cefazolin]. Acta Clin Belg. 1975;30(5):449-50. French. doi: 10.1080/17843286.1975.11717034. PMID: 1221750. 4: Ortiz A. Cefazolin-induced neurotoxicity. Clin Infect Dis. 1992 Feb;14(2):624. doi: 10.1093/clinids/14.2.624. PMID: 1554860. 5: Sanderson H. Prophylactic cefazolin. Lancet. 1980 Mar 15;1(8168 Pt 1):605-6. doi: 10.1016/s0140-6736(80)91102-2. PMID: 6102335. 6: Plotkin GR. Cefazolin vs penicillin. JAMA. 1979 Oct 26;242(17):1849. doi: 10.1001/jama.242.17.1849e. PMID: 113571. 7: Gudiol C, Cuervo G, Shaw E, Pujol M, Carratalà J. Pharmacotherapeutic options for treating Staphylococcus aureus bacteremia. Expert Opin Pharmacother. 2017 Dec;18(18):1947-1963. doi: 10.1080/14656566.2017.1403585. Epub 2017 Dec 4. PMID: 29115883. 8: Albarellos GA, Montoya L, Passini SM, Lupi MP, Lorenzini PM, Landoni MF. Cefazolin pharmacokinetics in cats under surgical conditions. J Feline Med Surg. 2017 Oct;19(10):992-997. doi: 10.1177/1098612X16666594. Epub 2016 Sep 8. PMID: 27609113. 9: Raff MJ, Rogers JH, Barnwell PA, Waterman NG. Cefazolin in the treatment of pneumonia. Int J Clin Pharmacol Biopharm. 1978 Feb;16(2):78-82. PMID: 24596. 10: Suna J, Alphonso N. Cefazolin prophylaxis in children undergoing cardiac surgery-is it too little too late? Eur J Cardiothorac Surg. 2021 Dec 27;61(1):34-35. doi: 10.1093/ejcts/ezab327. PMID: 34269388. 11: Qureshi F, Romeiser JL, Murphy PF, Go RA, Abola R. A quality assurance initiative on improving cefazolin perioperative redose compliance. Int J Qual Health Care. 2022 Oct 8;34(4):mzac073. doi: 10.1093/intqhc/mzac073. PMID: 36103371. 12: Patel RP, Jacob J, Sedeeq M, Ming LC, Wanandy T, Zaidi STR, Peterson GM. Stability of Cefazolin in Polyisoprene Elastomeric Infusion Devices. Clin Ther. 2018 Apr;40(4):664-667. doi: 10.1016/j.clinthera.2018.02.009. Epub 2018 Feb 26. PMID: 29496321. 13: Honda H, Murakami S, Tokuda Y, Tagashira Y, Takamatsu A. Critical National Shortage of Cefazolin in Japan: Management Strategies. Clin Infect Dis. 2020 Oct 23;71(7):1783-1789. doi: 10.1093/cid/ciaa216. PMID: 32133482. 14: Koizumi R, Kusama Y, Asai Y, Yoshiaki G, Muraki Y, Ohmagari N. Effects of the cefazolin shortage on the sales, cost, and appropriate use of other antimicrobials. BMC Health Serv Res. 2021 Oct 19;21(1):1118. doi: 10.1186/s12913-021-07139-z. PMID: 34663315; PMCID: PMC8523201. 15: Gonzalez OJ, Renberg WC, Roush JK, KuKanich B, Warner M. Pharmacokinetics of cefazolin for prophylactic administration to dogs. Am J Vet Res. 2017 Jun;78(6):695-701. doi: 10.2460/ajvr.78.6.695. PMID: 28541147. 16: Tchaick RM, Sá MPBO, Figueira FRM, Paz KC, Ferraz ÁAB, Moraes FR Neto. Cefazolin Concentration in the Mediastinal Adipose Tissue of Patients Undergoing Cardiac Surgery. Braz J Cardiovasc Surg. 2017 Jul-Aug;32(4):239-244. doi: 10.21470/1678-9741-2016-0031. PMID: 28977194; PMCID: PMC5613718. 17: Dubrovsky G, Huynh N, Rouch JD, Koulakis JP, Nicolau DP, Sutherland CA, Putterman S, Dunn JCY. Subcutaneous cefazolin to reduce surgical site infections in a porcine model. J Surg Res. 2018 Apr;224:156-159. doi: 10.1016/j.jss.2017.11.056. Epub 2017 Dec 28. PMID: 29506833. 18: Ishibiki K, Shimada J. [Cefazolin sodium]. Jpn J Antibiot. 1994 Apr;47(4):333-40. Japanese. PMID: 8201763. 19: Smelter D, Hayney M, Sakoulas G, Rose W. Is the Success of Cefazolin plus Ertapenem in Methicillin-Susceptible Staphylococcus aureus Bacteremia Based on Release of Interleukin-1 Beta? Antimicrob Agents Chemother. 2022 Feb 15;66(2):e0216621. doi: 10.1128/aac.02166-21. Epub 2022 Jan 3. PMID: 34978891; PMCID: PMC8846438. 20: Asada M, Nagata M, Mizuno T, Uchida T, Takahashi H, Makita K, Arai H, Kijima S, Echizen H, Yasuhara M. Population pharmacokinetics of cefazolin before, during and after cardiopulmonary bypass in adult patients undergoing cardiac surgery. Eur J Clin Pharmacol. 2021 May;77(5):735-745. doi: 10.1007/s00228-020-03045-1. Epub 2020 Nov 19. PMID: 33211137.