MedKoo Cat#: 317382 | Name: Cefamandole Nafate
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Description:

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

Cefamandole nafate is a pro-drug that is hydrolyzed by plasma esterases to produce cefamandole, second-generation cephalosporin antibiotic with bactericidal activity. Cefamandole nafate is used to study the effects of expression and inhibition of PBP 2A and other penicillin-binding proteins (PDPs) on bacterial cell wall mucopeptide synthesis. Cefamandole 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. This results in the weakening of the bacterial cell wall and causes cell lysis.

Chemical Structure

Cefamandole Nafate
Cefamandole Nafate
CAS#42540-40-9

Theoretical Analysis

MedKoo Cat#: 317382

Name: Cefamandole Nafate

CAS#: 42540-40-9

Chemical Formula: C19H17N6NaO6S2

Exact Mass: 0.0000

Molecular Weight: 512.49

Elemental Analysis: C, 44.53; H, 3.34; N, 16.40; Na, 4.49; O, 18.73; S, 12.51

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
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Synonym
Cefamandole Nafate; Cephamandole nafate; Cemandil sodium salt; Cefamandol nafato; O-Formylcefamandole sodium; Mandol
IUPAC/Chemical Name
sodium;(6R,7R)-7-[[(2R)-2-formyloxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChi Key
ICZOIXFFVKYXOM-YCLOEFEOSA-M
InChi Code
InChI=1S/C19H18N6O6S2.Na/c1-24-19(21-22-23-24)33-8-11-7-32-17-12(16(28)25(17)13(11)18(29)30)20-15(27)14(31-9-26)10-5-3-2-4-6-10;/h2-6,9,12,14,17H,7-8H2,1H3,(H,20,27)(H,29,30);/q;+1/p-1/t12-,14-,17-;/m1./s1
SMILES Code
CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)OC=O)SC2)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 512.49 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: Donelli G, Francolini I, Romoli D, Guaglianone E, Piozzi A, Ragunath C, Kaplan JB. Synergistic activity of dispersin B and cefamandole nafate in inhibition of staphylococcal biofilm growth on polyurethanes. Antimicrob Agents Chemother. 2007 Aug;51(8):2733-40. Epub 2007 Jun 4. PubMed PMID: 17548491; PubMed Central PMCID: PMC1932551. 2: Lee HS, Zee OP, Kwon KI. Simultaneous determination of cefamandole and cefamandole nafate in human plasma and urine by high-performance liquid chromatography with column switching. J Chromatogr. 1990 Jun 29;528(2):425-33. PubMed PMID: 2384580. 3: Henley MB, Jones RE, Wyatt RW, Hofmann A, Cohen RL. Prophylaxis with cefamandole nafate in elective orthopedic surgery. Clin Orthop Relat Res. 1986 Aug;(209):249-54. PubMed PMID: 3731606. 4: Bosso JA, Townsend RJ. Stability of clindamycin phosphate and ceftizoxime sodium, cefoxitin sodium, cefamandole nafate, or cefazolin sodium in two intravenous solutions. Am J Hosp Pharm. 1985 Oct;42(10):2211-4. PubMed PMID: 3864367. 5: Accardo FM, Mancuso A, Granese D, Dugo C. [Cefamandole nafate in short-term prophylaxis in obstetric and gynecologic surgery]. Minerva Ginecol. 1983 May;35(5):351-6. Italian. PubMed PMID: 6877656. 6: Frable RA, Klink PR, Engel GL, Mundell EE. Stability of cefamandole nafate injection with parenteral solutions and additives. Am J Hosp Pharm. 1982 Apr;39(4):622-7. PubMed PMID: 7082453. 7: Das Gupta V, Stewart KR. Stability of cefamandole nafate and cefoxitin sodium solutions. Am J Hosp Pharm. 1981 Jun;38(6):875-9. PubMed PMID: 7246563. 8: Indelicato JM, Stewart BA, Engel GL. Formylation of glucose by cefamandole nafate at alkaline pH. J Pharm Sci. 1980 Oct;69(10):1183-8. PubMed PMID: 7420288. 9: Custer GM, Briggs BR, Smith RE. Cefamandole nafate and blood coagulation. Ohio State Med J. 1980 Aug;76(8):517-21. PubMed PMID: 7402519. 10: Foster TS, Shrewsbury RP, Coonrod JD. Bioavailability and pain study of cefamandole nafate. J Clin Pharmacol. 1980 Aug-Sep;20(8-9):526-33. PubMed PMID: 7000857. 11: Di Nola F, Eandi M, Capra E, Soranzo ML, Bosio G, Bramato C, Salassa B, Andrini L, Robecchi GA. [Pharmacokinetics and clinical studies of a new cephalosporin: cefamandole nafate]. Minerva Med. 1980 May 26;71(21):1515-24. Italian. PubMed PMID: 7383410. 12: Nielsen RL, Wolen R, Luft FC, Ozawa T. Hydrolysis of cefamandole nafate in dialysis patients. Antimicrob Agents Chemother. 1979 Nov;16(5):683-5. PubMed PMID: 526012; PubMed Central PMCID: PMC352930. 13: Winely CL, Spears JC, Scott JK. Comparison of cefamandole nafate to cefamandole by microbiological assay. Antimicrob Agents Chemother. 1979 Sep;16(3):424-6. PubMed PMID: 41479; PubMed Central PMCID: PMC352872. 14: Ekwall E, Holmgren EB, Lundbergh P, Svanbom M, Tunevall G. Cefamandole nafate: an evaluation of antibacterial activity, serum levels, clinical effect, and incidence of side reactions in 58 patients. Scand J Infect Dis. 1979;11(2):135-9. PubMed PMID: 462128. 15: Wold JS, Joost RR, Black HR, Griffith RS. Hydrolysis of cefamandole nafate to cefamandole in vivo. J Infect Dis. 1978 May;137 Suppl:S17-S24. PubMed PMID: 650001. 16: Kalinkova GN, Opalchenova G. Estimation of the two sample preparation techniques for infrared spectroscopic identification of Cefamandole nafate in solid state. Pharmeur Sci Notes. 2007 Sep;2007(1):9-13. PubMed PMID: 17993089. 17: Jelińska A, Zajac M, Gostomska J, Szczepaniak M. Kinetics of cefamandole nafate degradation in solid phase. Farmaco. 2003 Apr;58(4):309-13. PubMed PMID: 12727540. 18: Das Gupta V, Stewart KR, Dela Torre M. Chemical stabilities of cefamandole nafate and metronidazole when mixed together for intravenous infusion. J Clin Hosp Pharm. 1985 Dec;10(4):379-83. PubMed PMID: 4093509. 19: Hemsell DL, Cunningham FG, Nobles B. Evaluation of cefamandole nafate for the treatment of acute gonococcal salpingitis. Obstet Gynecol. 1983 May;61(5):635-40. PubMed PMID: 6403898. 20: Rudd EG, Long WH, Dillon MB. Febrile morbidity following cefamandole nafate intrauterine irrigation during cesarean section. Am J Obstet Gynecol. 1981 Sep 1;141(1):12-6. PubMed PMID: 7270617.