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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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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 30 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri, Dr T.V. Radhakrishnan and Dr B. K. Kulkarni, etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him Open superstar worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 30 year tenure till date Dec 2017, Around 35 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 50 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 19 lakh plus views on New Drug Approvals Blog in 216 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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