KEBUZONE…….An antirheumatic agent.

KEBUZONE…….An antirheumatic agent.

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

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
ATC CODE	M01AA06
PUBCHEM	CID 3824
CHEMSPIDER	3692
UNII	4VD83UL6Y6
KEGG	D01567
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

Share this: