Kebuzone: Difference between revisions

Kebuzone
Clinical data

ATC code	M01AA06 (WHO)
Identifiers
IUPAC name 4-(3-oxobutyl)-1,2-di(phenyl)pyrazolidine-3,5-dione
CAS Number	853-34-9^Y
PubChem CID	3824
ChemSpider	3692^N
UNII	4VD83UL6Y6
KEGG	D01567^Y
ChEBI	CHEBI:31749^N
CompTox Dashboard (EPA)	DTXSID00234500
ECHA InfoCard	100.011.560
Chemical and physical data
Formula	C₁₉H₁₈N₂O₃
Molar mass	322.35782 g/mol g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(=O)CCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI InChI=1S/C19H18N2O3/c1-14(22)12-13-17-18(23)20(15-8-4-2-5-9-15)21(19(17)24)16-10-6-3-7-11-16/h2-11,17H,12-13H2,1H3^N Key:LGYTZKPVOAIUKX-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

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

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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-'''Kebuzone''' (or '''ketophenylbutazone''') is a [[non-steroidal anti-inflammatory drug]]. Incorporation of a carbonyl group into the alkyl [[side chain]] (''[[cf.]]'' [[butazone]]) also proved compatible with biological activity.
+'''Kebuzone''' (or '''ketophenylbutazone''') is a [[non-steroidal anti-inflammatory drug]].
-==Synthesis==
-The key intermediate is obtainable by [[Michael addition]] of the anion from [[diethyl malonate]] to [[methyl vinyl ketone]] followed by ketalization with [[ethylene glycol]]. Condensation with [[hydrazobenzene]] leads to pyrazolodione; hydrolysis of the ketone affords [[ketazone]].
-[[File:Kebuzone synthesis.svg|thumb|center|700px|Kebuzone synthesis: {{US patent|2910481}}]]
 {{Anti-inflammatory and antirheumatic products}}

Revision as of 12:32, 10 January 2015