Cefamandole Nafate | CAS#42540-40-9 |

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

MedKoo CAT#: 317382

CAS#: 42540-40-9

Description: 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

CAS# 42540-40-9

Instruction

Theoretical Analysis

MedKoo Cat#: 317382
Name: Cefamandole Nafate
CAS#: 42540-40-9
Chemical Formula: C19H17N6NaO6S2
Exact Mass: 0.00
Molecular Weight: 512.490
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
5g	USD 350	2 Weeks
10g	USD 585	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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Cefamandole Nafate featured