'Esteve';Alindor;Alka Butazolidin;Alkabutazona;Alqoverin;Ambene;Anerval;Anpuzone;Antadol;Anuspiramin;Apo-Phenylbutazone;Arthrizon;Artizin;Artrizin;Artrizone;Artropan;Azdid;Azobutyl;Azolid;B.T.Z.;Benzone;Betazed;Bizolin;Bizolin 200;Bunetzone;Busone;Buta Phen;Butacompren;Butacote;Butadion;Butadiona;Butadione;Butagesic;Butalgina;Butalidon;Butaluy;Butapirazol;Butapirazole;Butapyrazole;Butarecbon;Butartril;Butartrina;Butatron;Butazina;Butazolidin;Butazolidine;Butazona;Butazone;Bute;Butidiona;Butiwas-Simple;Butone;Butoz;Butylpyrin;Buvetzone;Buzon;Chembutazone;Cotylbutazone;Digibutina;Diossidone;Diozol;Diphebuzol;Diphenylbutazone;Ecobutazone;Elmedal;Equi Bute;Equipalazone;Eributazone;Exrheudon N;Febuzina;Fenartil;Fenibutal;Fenibutasan;Fenibutazona;Fenibutol;Fenilbutazona;Fenilbutina;Fenilbutine;Fenilidina;Fenotone;Fenylbutazon;Ia-But;Intalbut;Intrabutazone;Intrazone;Ipsoflame;Kadol;Lingel;Malgesic;Mepha-Butazon;Mephabutazon;Mephabutazone;Merizone;Nadazone;Nadozone;Neo-Zoline;Novophenyl;Phebuzin;Phebuzine;Phenbutazol;Phenbutazone;Phenopyrine;Phenyl-Mobuzon;Phenylbutaz;Phenylbutazonum;Phenyzene;Phenyzone;Pirarreumol "B";Pirarreumol B;Praecirheumin;Pyrabutol;Pyrazolidin;Rectofasa;Reudo;Reudox;Reumasyl;Reumazin;Reumazol;Reumune;Reumuzol;Reupolar;Robizon-V;Robizone;Robizone-V;Rubatone;Scanbutazone;Schemergin;Shigrodin;Tazone;Tencodyne;Tetnor;Tevcodyne;Therazone;Ticinil;Todalgil;Usaf Ge-15;Uzone;VAC-10;Wescozone;Zolaphen;Zolidinum;

A drug that has anti-inflammatory, antipyretic, and analgesic activities. It is especially effective in the treatment of ankylosing spondylitis. It also is useful in rheumatoid arthritis and Reiter's syndrome (investigational indication). Although phenylbutazone is effective in gouty arthritis, risk/benefit considerations indicate that this drug should not be employed for this disease. (From AMA Drug Evaluations Annual, 1994, p1822)

• Ivax pharmaceuticals inc
• Mutual pharmaceutical co inc
• Novartis pharmaceuticals corp
• Sandoz inc
• Sanofi aventis us llc
• Watson laboratories inc

• C.O. Truxton Inc.
• Jaapharm Canada Inc.
• Medisca Inc.

Synthesis Reference	Not Available
General Reference	Not Available

Type	small molecule

Classes

Phenylhydrazines Anilines

Substructures

Pyrazolones Amino Ketones Benzene and Derivatives Pyrazolidines Heterocyclic compounds Aromatic compounds Carboxamides and Derivatives Hydrazine Derivatives Phenylhydrazines Anilines

ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;

Indication	For the treatment of backache and ankylosing spondylitis
Pharmacodynamics	Phenylbutazone is a synthetic, pyrazolone derivative. It is a nonhormonal anti-inflammatory, antipyretic compound useful in the management of inflammatory conditions. The apparent analgesic effect is probably related mainly to the compound's anti-inflammatory properties and arise from its ability to reduce production of prostaglandin H and prostacyclin. Prostaglandins act on a variety of cells such as vascular smooth muscle cells causing constriction or dilation, on platelets causing aggregation or disaggregation and on spinal neurons causing pain. Prostacylcin causes vascular constriction platelet disaggregation
Mechanism of action	Phenylbutazone binds to and inactivates prostaglandin H synthase and prostacyclin synthase through peroxide (H2O2) mediated deactivation. The reduced production of prostaglandin leads to reduced inflammation of the surrounding tissues.
Absorption	Not Available
Volume of distribution	Not Available
Protein binding	Not Available
Metabolism	Not Available
Route of elimination	Not Available
Half life	Not Available
Clearance	Not Available
Toxicity	Oral, LD50 = 238 mg/kg (mouse); Oral, LD50 = 781 mg/kg (rabbit); Oral, LD50 = 245 mg/kg (rat); Oral, LD50 = 375 mg/kg (rat)
Affected organisms	Humans and other mammals
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 105 °C PhysProp water solubility 47.5 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.16 SANGSTER (1994) logS -3.81 ADME Research, USCD pKa 4.5 SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties	Property Value Source water solubility 1.44e-01 g/l ALOGPS logP 2.81 ALOGPS logP 4.14 ChemAxon logS -3.3 ALOGPS pKa (strongest acidic) 5.13 ChemAxon physiological charge -1 ChemAxon hydrogen acceptor count 2 ChemAxon hydrogen donor count 0 ChemAxon polar surface area 40.62 ChemAxon rotatable bond count 5 ChemAxon refractivity 88.76 ChemAxon polarizability 34.15 ChemAxon

Drug	Interaction
Acenocoumarol	The NSAID, phenylbutazone, may increase the anticoagulant effect of acenocoumarol.
Acetohexamide	Phenylbutazone may increase the effect of acetohexamide.
Anisindione	The NSAID, phenylbutazone, may increase the anticoagulant effect of anisindione.
Chlorpropamide	Phenylbutazone increases the effect of the hypoglycemic agent
Dicumarol	The NSAID, phenylbutazone, may increase the anticoagulant effect of dicumarol.
Ethotoin	The NSAID, phenylbutazone, may increase the hydantoin effect of ethotoin.
Fosphenytoin	The NSAID, phenylbutazone, may increase the hydantoin effect of fosphenytoin.
Gliclazide	Phenylbutazone increases the effect of the hypoglycemic agent
Glipizide	Phenylbutazone increases the effect of the hypoglycemic agent
Glisoxepide	Phenylbutazone increases the effect of the hypoglycemic agent
Glyburide	Phenylbutazone increases the effect of the hypoglycemic agent
Glycodiazine	Phenylbutazone increases the effect of the hypoglycemic agent
Lithium	The NSAID, phenylbutazone, may decrease the renal excretion of lithium. Increased risk of lithium toxicity.
Mephenytoin	The NSAID, phenylbutazone, may increase the hydantoin effect of mephenytoin.
Methotrexate	The NSAID, phenylbutazone, may decrease the renal excretion of methotrexate. Increased risk of methotrexate toxicity.
Phenytoin	The NSAID, phenylbutazone, may increase the therapeutic and adverse effects of phenytoin.
Tolazamide	Phenylbutazone increases the effect of the hypoglycemic agent
Tolbutamide	Phenylbutazone increases the effect of the hypoglycemic agent
Warfarin	The NSAID, phenylbutazone, may increase the anticoagulant effect of warfarin.

• Take with food to reduce irritation. Avoid alcohol.