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CEFOPERAZONE

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Cefoperazone.svg
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ChemSpider 2D Image | 4742 | C25H27N9O8S2
Cefoperazone

Cefoperazone

  • Molecular FormulaC25H27N9O8S2
  • Average mass645.667 Da

Product Ingredients

INGREDIENTUNIICASINCHI KEY
Cefoperazone sodium5FQG9774WD62893-20-3NCFTXMQPRQZFMZ-WERGMSTESA-M

(6R,7R)-7-{[(2R)-2-{[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]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
(6R,7R)-7-[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
263-749-4[EINECS]4742
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo- , (6R,7R)- [ACD/Index Name] 
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-[[(4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)-
62893-19-0[RN]
7-[D-(-)-a-(4-Ethyl-2,3-dioxo-1-piperazinecarboxamido)-a-(4-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic Acid
7U75I1278D

Experimental Properties

PROPERTYVALUESOURCE
melting point (°C)188-190Saikawa, I., Takano, S., Yoshida, C., Takashima, 0..Momonoi, K., Kuroda, S., Komatsu, M., Yasuda, T.and Kodama, Y.; British Patent 1,508,071; April 19,1978; assigned to Toyama Chemical Co., Ltd. and U.S. Patent 4,110,327; August 29,1978; also assigned to Toyama Chemical Co., Ltd.
logP-0.74HANSCH,C ET AL. (1995)

Cefoperazone 
CAS Registry Number: 62893-19-0 
CAS Name: (6R,7R)-7-[[(2R)-[[(4-Ethyl-2,3-dioxo-1-piperazinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidAdditional Names: 7-[D-(-)-a-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-a-(4-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-3-cephem-4-carboxylic acid 
Molecular Formula: C25H27N9O8S2 
Molecular Weight: 645.67 
Percent Composition: C 46.50%, H 4.21%, N 19.52%, O 19.82%, S 9.93% 
Literature References: Broad spectrum third generation cephalosporin antibiotic. Prepn: I. Saikawa et al.,BE837682eidem,US4410522 (1976, 1983 both to Toyama); eidem,Yakugaku Zasshi99, 929 (1979). Stability in aq soln: eidem,ibid. 1207. In vitro activity: M. V. Borobio et al.,Antimicrob. Agents Chemother.17, 129 (1980). Kinetics in rats: J. Fabre et al.,Schweiz. Med. Wochenschr.110, 264 (1980); in humans: A. F. Allaz, ibid.109, 1999 (1979). Review of pharmacology and therapeutic efficacy: R. N. Brogden et al.,Drugs22, 423-460 (1981). Symposium on clinical studies: ibid. Suppl. 1, 1-124. 
Properties: Crystals from acetonitrile/water, mp 169-171° (hydrated). Stable at pH 4.0-7.0; slightly unstable in acid; highly unstable in alkaline soln. 
Melting point: mp 169-171° (hydrated) 
Derivative Type: Sodium salt 
CAS Registry Number: 62893-20-3 
Manufacturers’ Codes: CP-52640-2; T-1551 
Trademarks: Bioperazone (Biopharma); Cefazone (Firma); Cefobid (Pfizer); Cefobine (Pfizer); Cefobis (Pfizer); Cefogram (Metapharma); Cefoneg (Tosi); Cefosint (Proter); Dardum (Lisapharma); Farecef (Lafare); Kefazon (Esseti); Novobiocyl (Francia); Pathozone (Pfizer); Peracef (Pfizer); Perocef (Pulitzer); Tomabef (Aandersen) 
Molecular Formula: C25H26N9NaO8S2 
Molecular Weight: 667.65 
Percent Composition: C 44.97%, H 3.93%, N 18.88%, Na 3.44%, O 19.17%, S 9.61% 
Therap-Cat: Antibacterial., Therap-Cat-Vet: Antibacterial. 
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.

Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.

It was patented in 1974 and approved for medical use in 1981.[1] Cefoperazone/sulbactam (Sulperazon) is a co-formulation with sulbactam.

Cefoperazone is a broad-spectrum cephalosporin antibiotic used for the treatment of bacterial infections in various locations, including the respiratory tract, abdomen, skin, and female genital tracts.

Cefoperazone is a semisynthetic broad-spectrum cephalosporin proposed to be effective against Pseudomonas infections. It is a third-generation antiobiotic agent and it is used in the treatment of various bacterial infections caused by susceptible organisms in the body, including respiratory tract infections, peritonitis, skin infections, endometritis, and bacterial septicemia. While its clinical use has been discontinued in the U.S., cefoperazone is available in several European countries most commonly under the product name, Sulperazon.

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SYN

File:Cefoperazone synthesis.svg

English: I. Saikawa, S. Takano, Y. Shuntaro, C. Yoshida, 0.

Takashima, K. Momonoi, S. Kuroda, M. Komatsu, T. Yasuda, and Y. Kodama, German Offen., DE 2,600,880 (1977); Chem.

Abstr., 87_, 184533b (1977).

SYN

Following is one of the synthesis routes:
alpha-(4-Ethyl-2,3-dioxo-1-piperazinocarbonylamino)-p-hydroxyphenylacetic acid (I) is condensed with 7-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (II) in the presence of ethyl chlorocarbonate and N,O-bis(trimethylsilyl)acetamide in acetonitrile to produce Cefoperazone sodium.

Production Method of Cefoperazone sodium

SYN

Antibiotics

R.S. Vardanyan, V.J. Hruby, in Synthesis of Essential Drugs, 2006

Cefoperazone

Cefoperazone, (6R,7R)-7-[(R)-2-(4-ethyl-2,3-dioxo-1-piperazincarboxamido)-2-(p-hydroxyphenyl)acetamido]-3-[[(1-methyl-1 H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.84), is synthesized by acylating 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl-3-cefem-4-carboxylic acid (32.1.2.24) with a mixed anhydride synthesized from ethyl chloroformate and α-(4-ethylpiperazin-2, 3-dion-1-carbonylamino)-4-hydroxyphenylacetic acid (32.1.2.83), which in turn is synthesized from 4-ethylpiperazin-2,3-dion-1-carboxylic acid (32.1.1.29) and the sodium salt of 4-hydroxyphenylglycine [163–168].

Cefoperazone also has a broad spectrum of antimicrobial action, including most clinically significant microorganisms: Gram-positive, Gram-negative, aerobic, and anaerobic. It is stable with respect to most beta-lactamases of Gram-positive and Gram-negative bacteria.

Cefoperazone is used for bacterial infections of the lower respiratory tract, urinary and sexual tracts, bones, joints, skin, soft tissues, abdominal, and gynecological infections. Synonyms of this drug are cefazon, cefobid, cefobis, and many others.

Spectrum of bacterial susceptibility

Cefoperazone has a broad spectrum of activity and has been used to target bacteria responsible for causing infections of the respiratory and urinary tract, skin, and the female genital tract. The following represents MIC susceptibility data for a few medically significant microorganisms.

  • Haemophilus influenzae: 0.12 – 0.25 µg/ml
  • Staphylococcus aureus: 0.125 – 32 µg/ml
  • Streptococcus pneumoniae: ≤0.007 – 1 µg/ml[2]

Adverse effects

Cefoperazone 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 enzyme vitamin K epoxide reductase) and a reaction with ethanol similar to that produced by disulfiram (Antabuse), due to inhibition of aldehyde dehydrogenase.[3]

Mechanism of action

Cefoperazone exerts its bactericidal effect by inhibiting the bacterial cell wall synthesis, and sulbactam acts as a beta-lactamase inhibitor, to increase the antibacterial activity of cefoperazone against beta-lactamase-producing organisms.

References

  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 9783527607495.
  2. ^ “Cefoperazone (Cefobid) – The Antimicrobial Index Knowledgebase – TOKU-E”antibiotics.toku-e.com.
  3. ^ Stork CM (2006). “Antibiotics, antifungals, and antivirals”. In Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (eds.). Goldfrank’s toxicologic emergencies. New York: McGraw-Hill. p. 847. ISBN 0-07-143763-0. Retrieved 2009-07-03.
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601206
ATC codeJ01DD12 (WHOQJ51DD12 (WHO)
Pharmacokinetic data
ExcretionHepatic
Identifiers
showIUPAC name
CAS Number62893-19-0 
PubChem CID44185
DrugBankDB01329 
ChemSpider40206 
UNII7U75I1278D
KEGGD07645 
ChEMBLChEMBL507674 
CompTox Dashboard (EPA)DTXSID2022759 
ECHA InfoCard100.057.936 
Chemical and physical data
FormulaC25H27N9O8S2
Molar mass645.67 g·mol−1
3D model (JSmol)Interactive image
showSMILES
showInChI
  (verify)

//////////cefoperazone, Antibacterial, Antibiotics, Lactams, Cephalosporins, CP-52640-2,  T-1551, CP 52640-2, T 1551

[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@@]2([H])NC(=O)[C@H](NC(=O)N1CCN(CC)C(=O)C1=O)C1=CC=C(O)C=C1)C(O)=O

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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 LIFE SCIENCES 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 PLUS year tenure till date June 2021, 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, 90 Lakh plus views on dozen plus blogs, 233 countries, 7 continents, 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 33 lakh plus views on New Drug Approvals Blog in 233 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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