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KEBUZONE…….An antirheumatic agent.

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Kebuzone (or ketophenylbutazone) is a non-steroidal anti-inflammatory drug.

Structural formula

 

4-(3-oxobutyl)-1,2-diphenylpyrazolidine-3,5-dione

UNII-4VD83UL6Y6

853-34-9

4-(3-Oxobutyl)-1,2-diphenyl-3,5-pyrazolidinedione
Additional Names: 1,2-diphenyl-4-(g-ketobutyl)-3,5-pyrazolidinedione; 1,2-diphenyl-4-(3¢-oxobutyl)-3,5-dioxopyrazolidine; ketophenylbutazone; KPB
Trademarks: Chebutan; Chepirol; Chetazolidin (Zeria); Chetil; Copirene; Ketason; Ketazone (Beytout); Pecnon (Sanken); Phloguron (Steiner); Recheton
MF: C19H18N2O3
MW: 322.36
Percent Comp: C 70.79%, H 5.63%, N 8.69%, O 14.89%
Properties: Crystals, mp 115.5-116.5° or 127.5-128.5° depending on cryst form.
Melting point: mp 115.5-116.5° or 127.5-128.5° depending on cryst form
Therap-Cat: Antirheumatic.
  1. BRN 0308507
  2. Chebutan
  3. Chepirol
  4. Chetazolidin
  5. Chetil
  6. Copirene
  7. EINECS 212-715-7
  8. Hichillos
  9. Kebuzone
  10. Kebuzonum
  11. Kebuzonum [INN-Latin]
  12. Keobutane-jade
  13. Ketason
  14. Ketazone
  15. Ketophenylbutazone
  16. Ketophenylbutazonum
  17. KPB
  18. Pecnon
  19. Quebuzona
  20. Quebuzona [INN-Spanish]
  21. Recheton
  22. UNII-4VD83UL6Y6

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

UV – range

Conditions : Concentration – 1 mg / 100 ml
The solvent designation graphics Methanol
Water
0.1М HCl
0.1M NaOH
Maximum absorption 244 nm 237 nm 262 nm
448 404 617
e 14440 13020 19890

IR – spectrum

Wavelength (μm)
Wave number (cm -1 )

Reference

  • UV and IR Spectra. H.-W. Dibbern, R.M. Muller, E. Wirbitzki, 2002 ECV
  • NIST/EPA/NIH Mass Spectral Library 2008
  • Handbook of Organic Compounds. NIR, IR, Raman, and UV-Vis Spectra Featuring Polymers and Surfactants, Jr., Jerry Workman. Academic Press, 2000.
  • Handbook of ultraviolet and visible absorption spectra of organic compounds, K. Hirayama. Plenum Press Data Division, 1967.

Brief background information

ketophenylbutazone.png

Salt ATC Formula MM CAS
M01AA06 C 19 H 18 N 2 O 3 322.36 g / mol 853-34-9
4-(3-oxobutyl)-1,2-di(phenyl)pyrazolidine-3,5-dione
Clinical data
Legal status
?
Identifiers
CAS number 853-34-9 Yes
ATC code M01AA06
PubChem CID 3824
ChemSpider 3692 
UNII 4VD83UL6Y6 Yes
KEGG D01567 Yes
ChEBI CHEBI:31749 
Chemical data
Formula C19H18N2O3 
Mol. mass 322.35782 g/mol

 

Application

  • anti-inflammatory
  • antirheumatic
  • Synthesis pathway
Synthesis of a)


Synthesis b)

Trade names

Country Trade name Manufacturer
Germany Kebuzon Steiner
France Ketazon Beytout
Italy Chetopir Sarm
Ukraine no no

Formulations

  • ampoules of 1 g / 5 ml;
  • 250 mg capsule

Reference

  1. Synthesis of a)
    • Denss, R. et al .: Helv. Chim. Acta (HCACAV) 40, 402 (1957).
    1. material:
      • Kühn, M .: J. Prakt. Chem. (JPCEAO) 156 (II), 103 (1940).
  2. Synthesis b)
    • AT 198 263 (Synfarma; appl. 1955).

References: Prepn: Deuss et al., US 2910481 (1959 to Geigy).

Review of pharmacology: Horakova et al.,Pharmacotherapeutica 1950-1959, 335-350 (1963), C.A. 60, 6072g (1964).

Metabolism: Nemecek et al., Arzneim.-Forsch. 16,1339 (1966); Queisnerova, Nemecek, Cesk. Farm. 20, 55 (1971), C.A. 75, 47077u (1971).

Herrenknecht, Christine; Guernet-Nivaud, Elisabeth; Lafont, Olivier; Guernet, Michel; Gueutin, Claire
Canadian Journal of Chemistry, 1988 ,  v. 66, pg. 1199 – 1202

Cizmarik; Lycka
Pharmazie, 1988 ,  v. 43,  11  pg. 794 – 795

Gueutin-Pelinard, Claire; Nivaud, Elisabeth; Boucly, Patrick; Guernet, Michel
Canadian Journal of Chemistry, 1981 ,  v. 59, pg. 759 – 762

Denss et al.
Helvetica Chimica Acta, 1957 ,  v. 40, pg. 402,406

Patent: CS124279 , 1965 ;Chem.Abstr., 1968 ,  v. 69,   52134r

SPOFA; United Pharmaceutical Work Patent: FR1500627 , 1965 ;Chem.Abstr., 1968 ,  v. 69,   96715k

Nippon Shinyaju Co., Ltd. Patent: US5811547 A1, 1998 ;

Fisnerova,L. et al. Collection of Czechoslovak Chemical Communications, 1974 ,  v. 39, pg. 624 – 633


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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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