Showing posts with label KEBUZONE. Show all posts
Showing posts with label KEBUZONE. Show all posts

Saturday 29 November 2014

KEBUZONE…….An antirheumatic agent.

KEBUZONE…….An antirheumatic agent.

Kebuzone.png

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

Structural formula


4-(3-oxobutyl)-1,2-diphenylpyrazolidine-3,5-dione
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 GRAPHICSMETHANOL
WATER
0.1М HCL
0.1M NAOH
Maximum absorption244 nm-237 nm262 nm
448-404617
e14440-1302019890

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
SALTATCFORMULAMMCAS
-M01AA0619 H 18 N 2 O 3322.36 g / mol853-34-9
4-(3-oxobutyl)-1,2-di(phenyl)pyrazolidine-3,5-dione
CLINICAL DATA
LEGAL STATUS
?
IDENTIFIERS
CAS NUMBER853-34-9 Yes
ATC CODEM01AA06
PUBCHEMCID 3824
CHEMSPIDER3692 
UNII4VD83UL6Y6 Yes
KEGGD01567 Yes
CHEBICHEBI:31749 
CHEMICAL DATA
FORMULAC19H18N2O3 
MOL. MASS322.35782 g/mol

Application

  • anti-inflammatory
  • antirheumatic
  • Synthesis pathway
SYNTHESIS OF A)


SYNTHESIS B)

Trade names

COUNTRYTRADE NAMEMANUFACTURER
GermanyKebuzonSteiner
FranceKetazonBeytout
ItalyChetopirSarm
Ukrainenono

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