Cefoxitin | CAS#35607-66-0 | cephamycin antibiotic

MedKoo Cat#: 461226 | Name: Cefoxitin

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Description:

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

Cefoxitin is a second-generation cephamycin antibiotic. It was synthesized in order to create an antibiotic with a broader spectrum.

Chemical Structure

Cefoxitin

CAS#35607-66-0 (free)

Theoretical Analysis

MedKoo Cat#: 461226

Name: Cefoxitin

CAS#: 35607-66-0 (free)

Chemical Formula: C16H17N3O7S2

Exact Mass: 427.0508

Molecular Weight: 427.44

Elemental Analysis: C, 44.96; H, 4.01; N, 9.83; O, 26.20; S, 15.00

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 350.00	2 Weeks
1g	USD 950.00	2 Weeks

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Related CAS #

35607-66-0 (free) 33564-30-6 (sodium)

Synonym

Cefoxitin; Cefoxitinum; Rephoxitin; Mefoxin; CEPHOXITIN; Cefoxitina

IUPAC/Chemical Name

(6R,7S)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key

WZOZEZRFJCJXNZ-ZBFHGGJFSA-N

InChi Code

InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1

SMILES Code

O=C(C(N12)=C(COC(N)=O)CS[C@]2([H])[C@@](NC(CC3=CC=CS3)=O)(OC)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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 427.44 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.

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

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Antimicrob Agents Chemother. 2014 Jun;58(6):3570-1. doi: 10.1128/AAC.02763-14. Epub 2014 Apr 14. PubMed PMID: 24733469; PubMed Central PMCID: PMC4068483. 4: Mitchell SM, Ullman JL, Teel AL, Watts RJ. pH and temperature effects on the hydrolysis of three β-lactam antibiotics: ampicillin, cefalotin and cefoxitin. Sci Total Environ. 2014 Jan 1;466-467:547-55. doi: 10.1016/j.scitotenv.2013.06.027. Epub 2013 Aug 13. PubMed PMID: 23948499. 5: Dien Bard J, Hindler JA, Gold HS, Limbago B. Rationale for eliminating Staphylococcus breakpoints for β-lactam agents other than penicillin, oxacillin or cefoxitin, and ceftaroline. Clin Infect Dis. 2014 May;58(9):1287-96. doi: 10.1093/cid/ciu043. Epub 2014 Jan 22. PubMed PMID: 24457339; PubMed Central PMCID: PMC5734619. 6: Serres A, Gibold L, Dalmasso G, Robin F, Bonnet R, Delmas J. Evaluation of the efficiency of cefoxitin/cefepime combination against Enterobacteriaceae resistant to expanded-spectrum cephalosporins. Int J Antimicrob Agents. 2015 Jan;45(1):86-7. doi: 10.1016/j.ijantimicag.2014.10.001. Epub 2014 Oct 22. PubMed PMID: 25459401. 7: Isla A, Trocóniz IF, de Tejada IL, Vázquez S, Canut A, López JM, Solinís MÁ, Rodríguez Gascón A. Population pharmacokinetics of prophylactic cefoxitin in patients undergoing colorectal surgery. Eur J Clin Pharmacol. 2012 May;68(5):735-45. doi: 10.1007/s00228-011-1206-1. Epub 2012 Jan 15. PubMed PMID: 22246211. 8: Moine P, Mueller SW, Schoen JA, Rothchild KB, Fish DN. Pharmacokinetic and Pharmacodynamic Evaluation of a Weight-Based Dosing Regimen of Cefoxitin for Perioperative Surgical Prophylaxis in Obese and Morbidly Obese Patients. Antimicrob Agents Chemother. 2016 Sep 23;60(10):5885-93. doi: 10.1128/AAC.00585-16. Print 2016 Oct. PubMed PMID: 27458209; PubMed Central PMCID: PMC5038324. 9: Mambie A, Vuotto F, Poitrenaud D, Weyrich P, Cannesson O, Dessein R, Faure K, Guery B, Galpérine T. Cefoxitin: An alternative to carbapenems in urinary tract infections due to extended-spectrum beta-lactamase-producing Enterobacteriaceae. Med Mal Infect. 2016 Jun;46(4):215-9. doi: 10.1016/j.medmal.2016.04.008. PubMed PMID: 27210283. 10: Ahire JJ, Dicks LM. Antimicrobial Hyaluronic Acid-Cefoxitin Sodium Thin Films Produced by Electrospraying. Curr Microbiol. 2016 Aug;73(2):236-41. doi: 10.1007/s00284-016-1057-1. Epub 2016 May 5. PubMed PMID: 27146506. 11: Skalweit MJ, Li M, Conklin BC, Taracila MA, Hutton RA. N152G, -S, and -T substitutions in CMY-2 β-lactamase increase catalytic efficiency for cefoxitin and inactivation rates for tazobactam. Antimicrob Agents Chemother. 2013 Apr;57(4):1596-602. doi: 10.1128/AAC.01334-12. Epub 2013 Jan 14. PubMed PMID: 23318801; PubMed Central PMCID: PMC3623365. 12: Toma O, Suntrup P, Stefanescu A, London A, Mutch M, Kharasch E. Pharmacokinetics and tissue penetration of cefoxitin in obesity: implications for risk of surgical site infection. Anesth Analg. 2011 Oct;113(4):730-7. doi: 10.1213/ANE.0b013e31821fff74. Epub 2011 Jun 3. PubMed PMID: 21642605. 13: Sóki J, Gonzalez SM, Urbán E, Nagy E, Ayala JA. Molecular analysis of the effector mechanisms of cefoxitin resistance among Bacteroides strains. J Antimicrob Chemother. 2011 Nov;66(11):2492-500. doi: 10.1093/jac/dkr339. Epub 2011 Aug 25. PubMed PMID: 21873290. 14: Lepeule R, Ruppé E, Le P, Massias L, Chau F, Nucci A, Lefort A, Fantin B. Cefoxitin as an alternative to carbapenems in a murine model of urinary tract infection due to Escherichia coli harboring CTX-M-15-type extended-spectrum β-lactamase. Antimicrob Agents Chemother. 2012 Mar;56(3):1376-81. doi: 10.1128/AAC.06233-11. Epub 2012 Jan 3. PubMed PMID: 22214774; PubMed Central PMCID: PMC3294923. 15: Liberman MA, Greason KL, Frame S, Ragland JJ. Single-dose cefotetan or cefoxitin versus multiple-dose cefoxitin as prophylaxis in patients undergoing appendectomy for acute nonperforated appendicitis. 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Pharmacokinetics and pharmacodynamics of total and unbound cefoxitin and cefotetan in healthy volunteers. J Antimicrob Chemother. 1989 Jan;23(1):99-106. PubMed PMID: 2745258.