Cefamandole, セファマンドール ,цефамандол , سيفاماندول , 头孢孟多 ,

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Cefamandole

Cefamandole.svg

ChemSpider 2D Image | Cefamandole | C18H18N6O5S2

Image result for Cefamandole

Cefamandole

セファマンドール

цефамандол [Russian] [INN]
سيفاماندول [Arabic] [INN]
头孢孟多 [Chinese] [INN]
CAS Registry Number: 34444-01-4
CAS Name: (6R,7R)-7-[[(2R)-Hydroxyphenylacetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-D-mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid; 7-D-mandelamido-3-(1-methyl-1,2,3,4-tetrazole-5-thiomethyl)-D3-cephem-4-carboxylic acid; CMT
Manufacturers’ Codes: compd 83405
Molecular Formula: C18H18N6O5S2
Molecular Weight: 462.50
Percent Composition: C 46.74%, H 3.92%, N 18.17%, O 17.30%, S 13.87%
Literature References: Broad-spectrum semi-synthetic cephalosporin antibiotic. Prepn: C. W. Ryan, DE 2018600idem, US3641021 (1970, 1972 to Lilly); J. M. Greene, DE 2312997idem, US 3840531 (1973, 1974 to Lilly). Biological properties: W. E. Wick, D. A. Preston, Antimicrob. Agents Chemother. 1, 221 (1972). Antibacterial activity: S. Eykyn et al., ibid. 3, 657 (1973); H. C. Neu, ibid. 6, 177 (1974); A. D. Russell, J. Antimicrob. Chemother. 1, 97 (1975). Pharmacologic studies: B. R. Meyers et al.,Antimicrob. Agents Chemother. 9, 140 (1976); R. S. Griffith et al., ibid. 10, 814 (1976). Comprehensive description: R. H. Bishara, E. C. Rickard, Anal. Profiles Drug Subs. 9, 125-154 (1980).
Derivative Type: Nafate
CAS Registry Number: 42540-40-9
Trademarks: Bergacef (Bergamon); Cedol (Tiber); Cefam (Magis); Cefiran (Poli); Cemado (Francia); Cemandil (SIT); Fado (Errekappa); Kefadol (Lilly); Kefandol (Lilly); Lampomandol (AGIPS); Mandokef (Lilly); Mandol (Lilly); Mandolsan (San Carlo); Neocefal (Metapharma); Pavecef (IBP)
Molecular Formula: C19H17N6NaO6S2
Molecular Weight: 512.49
Percent Composition: C 44.53%, H 3.34%, N 16.40%, Na 4.49%, O 18.73%, S 12.51%
Properties: White, odorless needles, mp 190° (dec). uv max (H2O): 269 nm (e 10800). pKa 2.6-3.0. Sol in water, methanol. Practically insol in ether, chloroform, benzene, cyclohexane.
Melting point: mp 190° (dec)
pKa: pKa 2.6-3.0
Absorption maximum: uv max (H2O): 269 nm (e 10800)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
  • Use:antibiotic
  • Chemical name:[6R-[6α,7β(R*)]]-7-[(hydroxyphenylacetyl)amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Formula:C18H18N6O5S2
    • MW:462.51 g/mol
    • CAS-RN:34444-01-4
    • InChI Key:OLVCFLKTBJRLHI-AXAPSJFSSA-N
    • InChI:InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
    • EINECS:252-030-0

    Derivatives

    Formate monosodium salt (nafate)

    • Formula:C19H17N6NaO6S2
    • MW:512.50 g/mol
    • CAS-RN:42540-40-9
    • EINECS:255-877-4
    • LD50:3915 mg/kg (M, i.v.);
      2562 mg/kg (R, i.v.)

    Cefamandole (INN, also known as cephamandole) is a second-generation broad-spectrumcephalosporinantibiotic. The clinically used form of cefamandole is the formateestercefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.

    The chemical structure of cefamandole, like that of several other cephalosporins, contains an N-methylthiotetrazole (NMTT or 1-MTT) side chain. As the antibiotic is broken down in the body, it releases free NMTT, which can cause hypoprothrombinemia (likely due to inhibition of the enzymevitamin K epoxide reductase)(vitamin K supplement is recommended during therapy) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.

    Cefamandole has a broad spectrum of activity and can be used to treat bacterial infections of the skin, bones and joints, urinary tract, and lower respiratory tract. The following represents cefamandole MIC susceptibility data for a few medically significant microorganisms.

    • Escherichia coli: 0.12 – 400 μg/ml
    • Haemophilus influenzae: 0.06 – >16 μg/ml
    • Staphylococcus aureus: 0.1 – 12.5 μg/ml

    [1]

    CO2 is generated during the normal constitution of cefamandole and ceftazidime, potentially resulting in an explosive-like reaction in syringes.[2]

    SYNTHESIS

    US 3641021

    US 3840531 US 3974153 US 3903278 US 2018600 US 2065621 DE 2018600 DE 2065621 DE 2730579

    DE 2312997

    Image result for Cefamandole

     

    SYN

    The formylation of 7-aminocephalosporanic acid (I) by the usual techniques produces 7-formamidocephalosporanic acid (II), which is then treated with the sodium salt of 1-methyl-1H-tetrazole-5-thiol (III) to yield 7-formamido-3-(1-methyl-1H-tetrazol-5-ylthio)methyl-3-cephem-4-carboxylic acid (IV). The resulting product (IV) is deformylated affording 7-amino-3-(1-methyl-1H-tetrazol-5-ylthio)methyl-3-cephem-4-carboxylic acid (V), which is finally acylated with anhydro-O-carboxymandelic acid (VI) using the usual techniques.

    References

    1. ^ http://www.toku-e.com/Assets/MIC/Cefamandole%20sodium%20salt.pdf
    2. ^ Stork CM (2006). “Antibiotics, antifungals, and antivirals”. In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA. Goldfrank’s toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
      • US 3 641 021 (Lilly; 8.2.1972; appl. 18.4.1969).
      • DE 2 018 600 (Lilly; appl. 17.4.1970; USA-prior. 18.4.1969).
      • DAS 2 065 621 (Lilly; appl. 17.4.1970; USA-prior. 18.4.1969).
      • US 3 840 531 (Lilly; 8.10.1974; appl. 21.3.1972).
      • US 3 903 278 (Smith Kline Corp.; 2.9.1975; prior. 4.11.1971).
      • DOS 2 730 579 (Pierrel S.p.A.; appl. 6.7.1977; GB-prior. 10.7.1976).
    • preparation and/or purification via the trimethylsilyl-derivatives:

      • DOS 2 711 095 (Lilly; appl. 14.3.1977; USA-prior. 17.3.1976).
    • purification:

      • US 4 115 644 (Lilly; 19.9.1978; appl. 19.9.1978).
      • DOS 2 839 670 (Lilly; appl. 12.9.1978; USA-prior. 19.9.1977).
    • crystalline sodium salt:

      • US 4 054 738 (Lilly; 18.10.1977; appl. 22.12.1975).
      • US 4 168 376 (Lilly; 18.9.1979; appl. 5.6.1978).
    • lithium salt:

      • GB 1 546 757 (Lilly; appl. 10.4.1975; valid from 7.4.1976).
    • O-formyl-derivative:

      • US 3 928 592 (Lilly; 23.12.1975; appl. 21.2.1974).
      • GB 1 493 676 (Lilly; appl. 20.2.1975; USA-prior. 22.2.1974).
      • GB 1 546 898 (Lilly; appl. 7.4.1976; USA-prior. 11.4.1975).
      • DOS 2 506 622 (Lilly; appl. 17.2.1975; USA-prior. 22.2.1974).
    • crystalline sodium salt of O-formylcefamandole:

      • US 4 006 138 (Lilly; 1.2.1977; appl. 11.4.1975).
    • complex of cefamandole sodium with 1,4-dioxane and water:

      • US 3 947 414 (Lilly; 30.3.1976; appl. 23.12.1974).
    • complex of cefamandole sodium with ethyl l-(–)-lactate:

      • US 3 947 415 (Lilly; 30.3.1976; appl. 23.12.1974).
    Cefamandole
    Cefamandole.svg
    Clinical data
    Trade names former Mandol
    AHFS/Drugs.com Micromedex Detailed Consumer Information
    MedlinePlus a601206
    Pregnancy
    category
    Routes of
    administration
    Intramuscularintravenous
    ATC code
    Legal status
    Legal status
    • UK: POM (Prescription only)
    • US: Discontinued
    Pharmacokinetic data
    Protein binding 75%
    Elimination half-life 48 minutes
    Excretion Mostly renal, as unchanged drug
    Identifiers
    CAS Number
    PubChem CID
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    ECHA InfoCard 100.047.285 Edit this at Wikidata
    Chemical and physical data
    Formula C18H18N6O5S2
    Molar mass 462.505 g/mol g·mol−1
    3D model (JSmol)
    /////////////Cefamandole, セファマンドール  ,цефамандол سيفاماندول 头孢孟多 
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