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Identification
NamePhenylbutazone
Accession NumberDB00812  (APRD00409, DB08343)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionA 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)
Structure
Thumb
Synonyms
3,5-Dioxo-1,2-diphenyl-4-n-butylpyrazolidine
4-BUTYL-1,2-diphenyl-pyrazolidine-3,5-dione
4-n-Butyl-1,2-diphenyl-3,5-pyrazolidinedione
Fenilbutazona
Phenbutazone
Phenylbutazon
Phenylbutazone
Phenylbutazonum
External Identifiers
  • USAF Ge-15
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novo-butazone Tab 100mgTablet100 mgOralNovopharm Limited1976-12-312005-08-10Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Phenylbutazone Tab 100mgTablet100 mgOralApotex Inc1976-12-312009-09-18Canada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AzolidNot Available
Brand mixtures
NameLabellerIngredients
Alka Phenyl TabDuchesnay Inc
Alka Phenylbutazone TabPro Doc Limitee
Phenylone Plus TabMedic Laboratory LtÉe
SaltsNot Available
Categories
UNIIGN5P7K3T8S
CAS number50-33-9
WeightAverage: 308.3743
Monoisotopic: 308.152477894
Chemical FormulaC19H20N2O2
InChI KeyVYMDGNCVAMGZFE-UHFFFAOYSA-N
InChI
InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
IUPAC Name
4-butyl-1,2-diphenylpyrazolidine-3,5-dione
SMILES
CCCCC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1
Pharmacology
IndicationFor the treatment of backache and ankylosing spondylitis
Structured Indications Not Available
PharmacodynamicsPhenylbutazone 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 actionPhenylbutazone 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Prostaglandin G/H synthase 2Proteinyes
inhibitor
HumanP35354 details
Prostacyclin synthaseProteinyes
inhibitor
HumanQ16647 details
Prostaglandin G/H synthase 1Proteinyes
inhibitor
HumanP23219 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, 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
PathwayCategorySMPDB ID
Phenylbutazone Action PathwayDrug actionSMP00701
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with 16-Bromoepiandrosterone.Investigational
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with 19-norandrostenedione.Experimental, Illicit
4-AndrostenedioneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with 4-Androstenedione.Experimental, Illicit
5-androstenedioneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with 5-androstenedione.Experimental, Illicit
AbciximabPhenylbutazone may increase the anticoagulant activities of Abciximab.Approved
AbirateroneThe metabolism of Phenylbutazone can be decreased when combined with Abiraterone.Approved
AcebutololPhenylbutazone may decrease the antihypertensive activities of Acebutolol.Approved
AceclofenacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Aceclofenac.Approved
AcenocoumarolPhenylbutazone may increase the anticoagulant activities of Acenocoumarol.Approved
AcetovanilloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Acetovanillone.Investigational
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Acetylsalicylic acid.Approved, Vet Approved
AclarubicinPhenylbutazone may decrease the excretion rate of Aclarubicin which could result in a higher serum level.Investigational
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Phenylbutazone.Approved
AlclometasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Alclometasone.Approved
AldosteroneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Aldosterone.Experimental
Alendronic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Alendronic acid.Approved
AliskirenPhenylbutazone may decrease the antihypertensive activities of Aliskiren.Approved, Investigational
AlprenololPhenylbutazone may decrease the antihypertensive activities of Alprenolol.Approved, Withdrawn
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Phenylbutazone.Approved, Investigational
AmcinonideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Amcinonide.Approved
AmikacinPhenylbutazone may decrease the excretion rate of Amikacin which could result in a higher serum level.Approved, Vet Approved
AmiloridePhenylbutazone may decrease the antihypertensive activities of Amiloride.Approved
AmiodaroneThe metabolism of Phenylbutazone can be decreased when combined with Amiodarone.Approved, Investigational
AmrubicinPhenylbutazone may decrease the excretion rate of Amrubicin which could result in a higher serum level.Approved, Investigational
AncrodPhenylbutazone may increase the anticoagulant activities of Ancrod.Investigational
AnecortaveThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Anecortave.Investigational
AnisodamineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Anisodamine.Investigational
annamycinPhenylbutazone may decrease the excretion rate of annamycin which could result in a higher serum level.Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Antipyrine.Approved
Antithrombin III humanPhenylbutazone may increase the anticoagulant activities of Antithrombin III human.Approved
Aop200704Phenylbutazone may decrease the antihypertensive activities of Aop200704.Investigational
ApixabanPhenylbutazone may increase the anticoagulant activities of Apixaban.Approved
ApramycinPhenylbutazone may decrease the excretion rate of Apramycin which could result in a higher serum level.Experimental, Vet Approved
ApremilastThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Apremilast.Approved, Investigational
AprepitantThe metabolism of Phenylbutazone can be increased when combined with Aprepitant.Approved, Investigational
ArbekacinPhenylbutazone may decrease the excretion rate of Arbekacin which could result in a higher serum level.Approved
ArdeparinPhenylbutazone may increase the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanPhenylbutazone may increase the anticoagulant activities of Argatroban.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Phenylbutazone.Approved, Investigational
ArotinololPhenylbutazone may decrease the antihypertensive activities of Arotinolol.Approved
AtenololPhenylbutazone may decrease the antihypertensive activities of Atenolol.Approved
AzapropazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Azapropazone.Withdrawn
AzelastineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Azelastine.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Phenylbutazone.Approved
BalsalazidePhenylbutazone may increase the nephrotoxic activities of Balsalazide.Approved, Investigational
BecaplerminPhenylbutazone may increase the anticoagulant activities of Becaplermin.Approved, Investigational
BeclomethasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Beclomethasone.Investigational
Beclomethasone dipropionateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Beclomethasone dipropionate.Approved, Investigational
BefunololPhenylbutazone may decrease the antihypertensive activities of Befunolol.Experimental
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Phenylbutazone.Approved, Investigational
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Phenylbutazone.Approved
BenoxaprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Benoxaprofen.Withdrawn
BeraprostThe therapeutic efficacy of Beraprost can be decreased when used in combination with Phenylbutazone.Investigational
BetamethasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Betamethasone.Approved, Vet Approved
BetaxololPhenylbutazone may decrease the antihypertensive activities of Betaxolol.Approved
Betulinic AcidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Betulinic Acid.Investigational
BevantololPhenylbutazone may decrease the antihypertensive activities of Bevantolol.Approved
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Phenylbutazone.Approved, Investigational
BisoprololPhenylbutazone may decrease the antihypertensive activities of Bisoprolol.Approved
BivalirudinPhenylbutazone may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BopindololPhenylbutazone may decrease the antihypertensive activities of Bopindolol.Approved
BromfenacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Bromfenac.Approved
BucillamineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Bucillamine.Investigational
BucindololPhenylbutazone may decrease the antihypertensive activities of Bucindolol.Investigational
BudesonideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Budesonide.Approved
BufuralolPhenylbutazone may decrease the antihypertensive activities of Bufuralol.Experimental, Investigational
BumetanidePhenylbutazone may decrease the diuretic activities of Bumetanide.Approved
BupranololPhenylbutazone may decrease the antihypertensive activities of Bupranolol.Approved
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Phenylbutazone.Approved
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Phenylbutazone.Experimental
CapecitabineThe metabolism of Phenylbutazone can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Phenylbutazone.Approved
CarbamazepineThe metabolism of Phenylbutazone can be increased when combined with Carbamazepine.Approved, Investigational
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Phenylbutazone.Approved
CarprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Carprofen.Approved, Vet Approved, Withdrawn
CarteololPhenylbutazone may decrease the antihypertensive activities of Carteolol.Approved
CarvedilolPhenylbutazone may decrease the antihypertensive activities of Carvedilol.Approved, Investigational
CastanospermineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Castanospermine.Experimental
CelecoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Celecoxib.Approved, Investigational
CeliprololPhenylbutazone may decrease the antihypertensive activities of Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Phenylbutazone can be increased when it is combined with Ceritinib.Approved
CertoparinPhenylbutazone may increase the anticoagulant activities of Certoparin.Approved
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Phenylbutazone.Approved, Vet Approved
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Phenylbutazone.Approved
CholecalciferolThe metabolism of Phenylbutazone can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholestyramineCholestyramine can cause a decrease in the absorption of Phenylbutazone resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CiclesonideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ciclesonide.Approved, Investigational
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Phenylbutazone.Approved
CinoxacinPhenylbutazone may increase the neuroexcitatory activities of Cinoxacin.Approved, Withdrawn
CiprofloxacinPhenylbutazone may increase the neuroexcitatory activities of Ciprofloxacin.Approved, Investigational
Citric AcidPhenylbutazone may increase the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClobetasolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clobetasol.Investigational
Clobetasol propionateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clobetasol propionate.Approved
ClocortoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clocortolone.Approved
ClodronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clodronate.Approved, Investigational, Vet Approved
ClonixinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clonixin.Approved
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Phenylbutazone.Vet Approved
ClotrimazoleThe metabolism of Phenylbutazone can be decreased when combined with Clotrimazole.Approved, Vet Approved
ColesevelamColesevelam can cause a decrease in the absorption of Phenylbutazone resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Phenylbutazone resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Cortisone acetateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Cortisone acetate.Approved
CurcuminThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Curcumin.Investigational
CyclosporinePhenylbutazone may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CyclosporineThe metabolism of Phenylbutazone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with D-Limonene.Investigational
Dabigatran etexilatePhenylbutazone may increase the anticoagulant activities of Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Phenylbutazone can be decreased when it is combined with Dabrafenib.Approved
DalteparinPhenylbutazone may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidPhenylbutazone may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DaunorubicinPhenylbutazone may decrease the excretion rate of Daunorubicin which could result in a higher serum level.Approved
DeferasiroxThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Deferasirox.Approved, Investigational
dehydroepiandrosterone sulfateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with dehydroepiandrosterone sulfate.Investigational
DelavirdineThe metabolism of Phenylbutazone can be decreased when combined with Delavirdine.Approved
DesirudinPhenylbutazone may increase the anticoagulant activities of Desirudin.Approved
DesmopressinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Desmopressin.Approved
DesoximetasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Desoximetasone.Approved
Desoxycorticosterone acetateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Desoxycorticosterone acetate.Approved
Desoxycorticosterone PivalateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Desoxycorticosterone Pivalate.Experimental, Vet Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Dexamethasone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Dexamethasone isonicotinate.Vet Approved
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Phenylbutazone.Approved
DextranPhenylbutazone may increase the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Phenylbutazone may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Phenylbutazone may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Phenylbutazone may increase the anticoagulant activities of Dextran 75.Approved
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Phenylbutazone.Approved, Vet Approved
DicoumarolPhenylbutazone may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Diflorasone.Approved
DiflunisalThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Diflunisal.Approved
DifluocortoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Difluocortolone.Approved
DifluprednateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Difluprednate.Approved
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Phenylbutazone.Approved
DihydrostreptomycinPhenylbutazone may decrease the excretion rate of Dihydrostreptomycin which could result in a higher serum level.Vet Approved
DinoprostThe therapeutic efficacy of Dinoprost can be decreased when used in combination with Phenylbutazone.Investigational
Dinoprost TromethamineThe therapeutic efficacy of Dinoprost Tromethamine can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Phenylbutazone.Approved
DoxorubicinPhenylbutazone may decrease the excretion rate of Doxorubicin which could result in a higher serum level.Approved, Investigational
DrospirenonePhenylbutazone may increase the hyperkalemic activities of Drospirenone.Approved
DroxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Droxicam.Approved
DuvelisibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Duvelisib.Investigational
E6201The risk or severity of adverse effects can be increased when Phenylbutazone is combined with E6201.Investigational
EbselenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ebselen.Investigational
Edetic AcidPhenylbutazone may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanPhenylbutazone may increase the anticoagulant activities of Edoxaban.Approved
EfavirenzThe metabolism of Phenylbutazone can be decreased when combined with Efavirenz.Approved, Investigational
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Phenylbutazone.Approved, Vet Approved
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Phenylbutazone.Approved
EnoxacinPhenylbutazone may increase the neuroexcitatory activities of Enoxacin.Approved
EnoxaparinPhenylbutazone may increase the anticoagulant activities of Enoxaparin.Approved
EpirizoleThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Epirizole.Approved
EpirubicinPhenylbutazone may decrease the excretion rate of Epirubicin which could result in a higher serum level.Approved
EplerenonePhenylbutazone may decrease the antihypertensive activities of Eplerenone.Approved
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Phenylbutazone.Approved
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Phenylbutazone.Approved
EquileninThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Equilenin.Experimental
EquilinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Equilin.Approved
EsmololPhenylbutazone may decrease the antihypertensive activities of Esmolol.Approved
EstroneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Estrone.Approved
Estrone sulfateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Estrone sulfate.Approved
Etacrynic acidPhenylbutazone may decrease the diuretic activities of Etacrynic acid.Approved
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Phenylbutazone.Approved, Investigational
Ethyl biscoumacetatePhenylbutazone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Etidronic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etidronic acid.Approved
EtodolacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etofenamate.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etoricoxib.Approved, Investigational
EtravirineThe metabolism of Phenylbutazone can be decreased when combined with Etravirine.Approved
Evening primrose oilThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Evening primrose oil.Approved
exisulindThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with exisulind.Investigational
FenbufenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fenbufen.Approved
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Phenylbutazone.Approved
FenprostaleneThe therapeutic efficacy of Fenprostalene can be decreased when used in combination with Phenylbutazone.Vet Approved
FleroxacinPhenylbutazone may increase the neuroexcitatory activities of Fleroxacin.Approved
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Phenylbutazone.Approved, Withdrawn
FloxuridineThe metabolism of Phenylbutazone can be decreased when combined with Floxuridine.Approved
fluasteroneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with fluasterone.Investigational
FluconazoleThe metabolism of Phenylbutazone can be decreased when combined with Fluconazole.Approved
FludrocortisoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fludrocortisone.Approved
FluindionePhenylbutazone may increase the anticoagulant activities of Fluindione.Investigational
FlumequinePhenylbutazone may increase the neuroexcitatory activities of Flumequine.Withdrawn
FlumethasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Flumethasone.Approved, Vet Approved
FlunisolideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Flunisolide.Approved, Investigational
FlunixinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Flunixin.Vet Approved
Fluocinolone AcetonideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluocinolone Acetonide.Approved, Investigational, Vet Approved
FluocinonideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluocinonide.Approved, Investigational
FluocortoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluocortolone.Approved, Withdrawn
FluorometholoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluorometholone.Approved
FluorouracilThe metabolism of Phenylbutazone can be decreased when combined with Fluorouracil.Approved
FluprednideneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluprednidene.Approved, Withdrawn
FluprednisoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluprednisolone.Approved
FluprostenolThe therapeutic efficacy of Fluprostenol can be decreased when used in combination with Phenylbutazone.Vet Approved
FlurandrenolideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Flurandrenolide.Approved
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Phenylbutazone.Approved, Investigational
Fluticasone furoateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluticasone furoate.Approved
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fluticasone Propionate.Approved
FluvastatinThe metabolism of Phenylbutazone can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Phenylbutazone can be decreased when combined with Fluvoxamine.Approved, Investigational
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Phenylbutazone.Approved, Nutraceutical, Vet Approved
FondaparinuxPhenylbutazone may increase the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumPhenylbutazone may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Phenylbutazone.Experimental
FormestaneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Formestane.Approved, Investigational, Withdrawn
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Phenylbutazone.Approved
FosphenytoinThe metabolism of Phenylbutazone can be increased when combined with Fosphenytoin.Approved
FramycetinPhenylbutazone may decrease the excretion rate of Framycetin which could result in a higher serum level.Approved
FurosemidePhenylbutazone may decrease the diuretic activities of Furosemide.Approved, Vet Approved
GabexatePhenylbutazone may increase the anticoagulant activities of Gabexate.Investigational
GarenoxacinPhenylbutazone may increase the neuroexcitatory activities of Garenoxacin.Investigational
GatifloxacinPhenylbutazone may increase the neuroexcitatory activities of Gatifloxacin.Approved, Investigational
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Phenylbutazone.Approved, Withdrawn
GemfibrozilThe metabolism of Phenylbutazone can be decreased when combined with Gemfibrozil.Approved
GemifloxacinPhenylbutazone may increase the neuroexcitatory activities of Gemifloxacin.Approved, Investigational
GeneticinPhenylbutazone may decrease the excretion rate of Geneticin which could result in a higher serum level.Experimental
GentamicinPhenylbutazone may decrease the excretion rate of Gentamicin which could result in a higher serum level.Approved, Vet Approved
GENTAMICIN C1APhenylbutazone may decrease the excretion rate of GENTAMICIN C1A which could result in a higher serum level.Experimental
GrepafloxacinPhenylbutazone may increase the neuroexcitatory activities of Grepafloxacin.Withdrawn
HaloperidolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Haloperidol.Approved
HE3286The risk or severity of adverse effects can be increased when Phenylbutazone is combined with HE3286.Investigational
HeparinPhenylbutazone may increase the anticoagulant activities of Heparin.Approved, Investigational
HigenamineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Higenamine.Investigational
HirulogPhenylbutazone may increase the anticoagulant activities of Hirulog.Experimental
HMPL-004The risk or severity of adverse effects can be increased when Phenylbutazone is combined with HMPL-004.Investigational
HydralazinePhenylbutazone may decrease the antihypertensive activities of Hydralazine.Approved
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Hydrocortisone.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Phenylbutazone.Approved
Hygromycin BPhenylbutazone may decrease the excretion rate of Hygromycin B which could result in a higher serum level.Vet Approved
IbandronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ibandronate.Approved, Investigational
IbuprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ibuprofen.Approved
IbuproxamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ibuproxam.Withdrawn
IcatibantThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Icatibant.Approved
IdarubicinPhenylbutazone may decrease the excretion rate of Idarubicin which could result in a higher serum level.Approved
idraparinuxPhenylbutazone may increase the anticoagulant activities of idraparinux.Investigational
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Phenylbutazone.Approved, Investigational
ImidaprilThe risk or severity of adverse effects can be increased when Imidapril is combined with Phenylbutazone.Investigational
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Phenylbutazone.Approved
IndenololPhenylbutazone may decrease the antihypertensive activities of Indenolol.Withdrawn
IndinavirThe metabolism of Phenylbutazone can be decreased when combined with Indinavir.Approved
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Phenylbutazone.Approved, Investigational
IndoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Indoprofen.Withdrawn
INNO-206Phenylbutazone may decrease the excretion rate of INNO-206 which could result in a higher serum level.Investigational
IrbesartanThe metabolism of Phenylbutazone can be decreased when combined with Irbesartan.Approved, Investigational
IsoxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Isoxicam.Withdrawn
IstaroximeThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Istaroxime.Investigational
KanamycinPhenylbutazone may decrease the excretion rate of Kanamycin which could result in a higher serum level.Approved, Vet Approved
KebuzoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Kebuzone.Experimental
KetoconazoleThe metabolism of Phenylbutazone can be decreased when combined with Ketoconazole.Approved, Investigational
KetoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ketoprofen.Approved, Vet Approved
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Phenylbutazone.Approved
LabetalolPhenylbutazone may decrease the antihypertensive activities of Labetalol.Approved
LatanoprostThe therapeutic efficacy of Latanoprost can be decreased when used in combination with Phenylbutazone.Approved, Investigational
LeflunomideThe metabolism of Phenylbutazone can be decreased when combined with Leflunomide.Approved, Investigational
LepirudinPhenylbutazone may increase the anticoagulant activities of Lepirudin.Approved
LevobunololPhenylbutazone may decrease the antihypertensive activities of Levobunolol.Approved
LevofloxacinPhenylbutazone may increase the neuroexcitatory activities of Levofloxacin.Approved, Investigational
LimaprostThe therapeutic efficacy of Limaprost can be decreased when used in combination with Phenylbutazone.Approved
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Phenylbutazone.Approved, Investigational
LisofyllineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Lisofylline.Investigational
LithiumThe serum concentration of Lithium can be increased when it is combined with Phenylbutazone.Approved
LomefloxacinPhenylbutazone may increase the neuroexcitatory activities of Lomefloxacin.Approved
LornoxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Lornoxicam.Approved
LosartanThe metabolism of Phenylbutazone can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Phenylbutazone can be decreased when combined with Lovastatin.Approved, Investigational
LoxoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Loxoprofen.Approved
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Phenylbutazone.Approved, Investigational
LumacaftorThe serum concentration of Phenylbutazone can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Lumiracoxib.Approved, Investigational
LuprostiolThe therapeutic efficacy of Luprostiol can be decreased when used in combination with Phenylbutazone.Vet Approved
Magnesium salicylateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Magnesium salicylate.Approved
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Phenylbutazone.Approved
ME-609The risk or severity of adverse effects can be increased when Phenylbutazone is combined with ME-609.Investigational
Meclofenamic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Meclofenamic acid.Approved, Vet Approved
MedrysoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Medrysone.Approved
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Phenylbutazone.Approved
MelengestrolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Melengestrol.Vet Approved
MeloxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Meloxicam.Approved, Vet Approved
MesalazinePhenylbutazone may increase the nephrotoxic activities of Mesalazine.Approved
MetamizoleThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Metamizole.Withdrawn
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Phenylbutazone.Approved
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Phenylbutazone.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Methylprednisolone.Approved, Vet Approved
MetipranololPhenylbutazone may decrease the antihypertensive activities of Metipranolol.Approved
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Phenylbutazone.Approved
MetoprololPhenylbutazone may decrease the antihypertensive activities of Metoprolol.Approved, Investigational
MetrizamidePhenylbutazone may decrease the excretion rate of Metrizamide which could result in a higher serum level.Approved
MifepristoneThe serum concentration of Phenylbutazone can be increased when it is combined with Mifepristone.Approved, Investigational
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Phenylbutazone.Approved
MizoribineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Mizoribine.Investigational
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Phenylbutazone.Approved
MometasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Mometasone.Approved, Vet Approved
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Phenylbutazone.Approved
MoxifloxacinPhenylbutazone may increase the neuroexcitatory activities of Moxifloxacin.Approved, Investigational
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Phenylbutazone.Approved, Investigational
Mycophenolic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Mycophenolic acid.Approved
NabumetoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Nabumetone.Approved
NadololPhenylbutazone may decrease the antihypertensive activities of Nadolol.Approved
NadroparinPhenylbutazone may increase the anticoagulant activities of Nadroparin.Approved
NafamostatPhenylbutazone may increase the anticoagulant activities of Nafamostat.Investigational
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Phenylbutazone.Approved
Nalidixic AcidPhenylbutazone may increase the neuroexcitatory activities of Nalidixic Acid.Approved
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Phenylbutazone.Approved, Vet Approved
NCX 1022The risk or severity of adverse effects can be increased when Phenylbutazone is combined with NCX 1022.Investigational
NCX 4016The risk or severity of adverse effects can be increased when Phenylbutazone is combined with NCX 4016.Investigational
NeaminePhenylbutazone may decrease the excretion rate of Neamine which could result in a higher serum level.Experimental
NemonoxacinPhenylbutazone may increase the neuroexcitatory activities of Nemonoxacin.Investigational
NeomycinPhenylbutazone may decrease the excretion rate of Neomycin which could result in a higher serum level.Approved, Vet Approved
NepafenacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Nepafenac.Approved
NetilmicinPhenylbutazone may decrease the excretion rate of Netilmicin which could result in a higher serum level.Approved
NicardipineThe metabolism of Phenylbutazone can be decreased when combined with Nicardipine.Approved
Niflumic AcidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Niflumic Acid.Approved
NimesulideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Nimesulide.Approved, Withdrawn
NitroaspirinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Nitroaspirin.Investigational
NorfloxacinPhenylbutazone may increase the neuroexcitatory activities of Norfloxacin.Approved
OfloxacinPhenylbutazone may increase the neuroexcitatory activities of Ofloxacin.Approved
Oleoyl estroneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Oleoyl estrone.Investigational
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Phenylbutazone.Approved, Investigational
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Phenylbutazone.Approved
OlsalazinePhenylbutazone may increase the nephrotoxic activities of Olsalazine.Approved
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Omacetaxine mepesuccinate.Approved
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Phenylbutazone.Investigational
OmeprazoleThe metabolism of Phenylbutazone can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OrgoteinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Orgotein.Vet Approved
OtamixabanPhenylbutazone may increase the anticoagulant activities of Otamixaban.Investigational
OxaprozinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Oxaprozin.Approved
OxprenololPhenylbutazone may decrease the antihypertensive activities of Oxprenolol.Approved
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Oxyphenbutazone.Withdrawn
PamidronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Pamidronate.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Paramethasone.Approved
ParecoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Parecoxib.Approved
ParomomycinPhenylbutazone may decrease the excretion rate of Paromomycin which could result in a higher serum level.Approved, Investigational
PazufloxacinPhenylbutazone may increase the neuroexcitatory activities of Pazufloxacin.Investigational
PefloxacinPhenylbutazone may increase the neuroexcitatory activities of Pefloxacin.Approved
PenbutololPhenylbutazone may decrease the antihypertensive activities of Penbutolol.Approved, Investigational
Pentosan PolysulfatePhenylbutazone may increase the anticoagulant activities of Pentosan Polysulfate.Approved
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Phenylbutazone.Approved
PhenindionePhenylbutazone may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Phenylbutazone can be increased when combined with Phenobarbital.Approved
PhenprocoumonPhenylbutazone may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe metabolism of Phenylbutazone can be increased when combined with Phenytoin.Approved, Vet Approved
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Phenylbutazone.Approved, Investigational
PindololPhenylbutazone may decrease the antihypertensive activities of Pindolol.Approved
PirarubicinPhenylbutazone may decrease the excretion rate of Pirarubicin which could result in a higher serum level.Investigational
PiretanidePhenylbutazone may decrease the diuretic activities of Piretanide.Experimental
PirfenidoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Pirfenidone.Investigational
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Phenylbutazone.Approved, Investigational
PlicamycinPhenylbutazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Withdrawn
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Phenylbutazone.Approved
PractololPhenylbutazone may decrease the antihypertensive activities of Practolol.Approved
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Phenylbutazone.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Prasterone.Approved, Nutraceutical
PrednicarbateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Prednicarbate.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Prednisolone.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Prednisone.Approved, Vet Approved
PregnenoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Pregnenolone.Experimental
PrimidoneThe metabolism of Phenylbutazone can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Phenylbutazone can be increased when it is combined with Probenecid.Approved
PropacetamolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Propacetamol.Approved
PropranololPhenylbutazone may decrease the antihypertensive activities of Propranolol.Approved, Investigational
Prostaglandin B2The therapeutic efficacy of Prostaglandin B2 can be decreased when used in combination with Phenylbutazone.Experimental
Prostaglandin D2The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Phenylbutazone.Experimental, Investigational
Prostaglandin G2The therapeutic efficacy of Prostaglandin G2 can be decreased when used in combination with Phenylbutazone.Experimental
ProstaleneThe therapeutic efficacy of Prostalene can be decreased when used in combination with Phenylbutazone.Vet Approved
Protein CPhenylbutazone may increase the anticoagulant activities of Protein C.Approved
Protein S humanPhenylbutazone may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydePhenylbutazone may increase the anticoagulant activities of Protocatechualdehyde.Approved
PrulifloxacinPhenylbutazone may increase the neuroexcitatory activities of Prulifloxacin.Investigational
PTC299The risk or severity of adverse effects can be increased when Phenylbutazone is combined with PTC299.Investigational
PuromycinPhenylbutazone may decrease the excretion rate of Puromycin which could result in a higher serum level.Experimental
PyrimethamineThe metabolism of Phenylbutazone can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Phenylbutazone.Approved, Investigational
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Phenylbutazone.Approved
QuinineThe metabolism of Phenylbutazone can be decreased when combined with Quinine.Approved
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Phenylbutazone.Approved
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Phenylbutazone.Approved
ResveratrolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Resveratrol.Experimental, Investigational
ReviparinPhenylbutazone may increase the anticoagulant activities of Reviparin.Approved
RibostamycinPhenylbutazone may decrease the excretion rate of Ribostamycin which could result in a higher serum level.Approved
RifampicinThe metabolism of Phenylbutazone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Phenylbutazone can be increased when combined with Rifapentine.Approved
RimexoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Rimexolone.Approved
RisedronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Risedronate.Approved, Investigational
RivaroxabanPhenylbutazone may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Rofecoxib.Investigational, Withdrawn
RosoxacinPhenylbutazone may increase the neuroexcitatory activities of Rosoxacin.Approved
SacubitrilThe risk or severity of adverse effects can be increased when Sacubitril is combined with Phenylbutazone.Approved
SalicylamideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Salicylamide.Approved
Salicylic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Salicylic acid.Approved, Vet Approved
SalsalateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Salsalate.Approved
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Phenylbutazone.Experimental
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Phenylbutazone.Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Phenylbutazone.Approved
SecobarbitalThe metabolism of Phenylbutazone can be increased when combined with Secobarbital.Approved, Vet Approved
SeratrodastThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Seratrodast.Approved, Investigational
SildenafilThe metabolism of Phenylbutazone can be decreased when combined with Sildenafil.Approved, Investigational
SisomicinPhenylbutazone may decrease the excretion rate of Sisomicin which could result in a higher serum level.Investigational
SorafenibThe metabolism of Phenylbutazone can be decreased when combined with Sorafenib.Approved, Investigational
SotalolPhenylbutazone may decrease the antihypertensive activities of Sotalol.Approved
SP1049CPhenylbutazone may decrease the excretion rate of SP1049C which could result in a higher serum level.Investigational
SparfloxacinPhenylbutazone may increase the neuroexcitatory activities of Sparfloxacin.Approved
SpectinomycinPhenylbutazone may decrease the excretion rate of Spectinomycin which could result in a higher serum level.Approved, Vet Approved
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Phenylbutazone.Approved
SpironolactonePhenylbutazone may decrease the antihypertensive activities of Spironolactone.Approved
SRT501The risk or severity of adverse effects can be increased when Phenylbutazone is combined with SRT501.Investigational
StreptomycinPhenylbutazone may decrease the excretion rate of Streptomycin which could result in a higher serum level.Approved, Vet Approved
StreptozocinPhenylbutazone may decrease the excretion rate of Streptozocin which could result in a higher serum level.Approved
SulfadiazineThe metabolism of Phenylbutazone can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Phenylbutazone can be decreased when combined with Sulfamethoxazole.Approved
SulfasalazinePhenylbutazone may increase the nephrotoxic activities of Sulfasalazine.Approved
SulfisoxazoleThe metabolism of Phenylbutazone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Phenylbutazone.Approved
SulodexidePhenylbutazone may increase the anticoagulant activities of Sulodexide.Approved, Investigational
SulprostoneThe therapeutic efficacy of Sulprostone can be decreased when used in combination with Phenylbutazone.Investigational
SuprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Suprofen.Approved, Withdrawn
TacrolimusPhenylbutazone may increase the nephrotoxic activities of Tacrolimus.Approved, Investigational
TafluprostThe therapeutic efficacy of Tafluprost can be decreased when used in combination with Phenylbutazone.Approved
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Phenylbutazone.Approved
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Phenylbutazone.Approved
Technetium tc 99m etidronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Technetium tc 99m etidronate.Approved
Technetium Tc-99m MedronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Technetium Tc-99m Medronate.Approved
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Phenylbutazone.Approved, Investigational
TemafloxacinPhenylbutazone may increase the neuroexcitatory activities of Temafloxacin.Withdrawn
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Phenylbutazone.Experimental, Investigational
TenofovirThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tenofovir.Approved, Investigational
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Phenylbutazone.Approved
TepoxalinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tepoxalin.Vet Approved
TeriflunomideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Teriflunomide.Approved
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tiaprofenic acid.Approved
TicagrelorThe metabolism of Phenylbutazone can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Phenylbutazone can be decreased when combined with Ticlopidine.Approved
TiludronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tiludronate.Approved, Vet Approved
TimololPhenylbutazone may decrease the antihypertensive activities of Timolol.Approved
TinoridineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tinoridine.Investigational
TixocortolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tixocortol.Approved
TobramycinPhenylbutazone may decrease the excretion rate of Tobramycin which could result in a higher serum level.Approved, Investigational
TolbutamideThe metabolism of Phenylbutazone can be decreased when combined with Tolbutamide.Approved
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tolfenamic Acid.Approved
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Phenylbutazone.Approved
TorasemidePhenylbutazone may decrease the diuretic activities of Torasemide.Approved
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Phenylbutazone.Approved
TranilastThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tranilast.Approved, Investigational
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Phenylbutazone.Approved
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Phenylbutazone.Approved, Investigational
TriamcinoloneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Triamcinolone.Approved, Vet Approved
TriamterenePhenylbutazone may decrease the antihypertensive activities of Triamterene.Approved
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Phenylbutazone.Approved, Vet Approved
TrimethoprimThe metabolism of Phenylbutazone can be decreased when combined with Trimethoprim.Approved, Vet Approved
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Trisalicylate-choline.Approved
TrovafloxacinPhenylbutazone may increase the neuroexcitatory activities of Trovafloxacin.Approved, Withdrawn
UnoprostoneThe therapeutic efficacy of Unoprostone can be decreased when used in combination with Phenylbutazone.Approved
ValdecoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Valdecoxib.Investigational, Withdrawn
Valproic AcidThe metabolism of Phenylbutazone can be decreased when combined with Valproic Acid.Approved, Investigational
ValrubicinPhenylbutazone may decrease the excretion rate of Valrubicin which could result in a higher serum level.Approved
ValsartanThe metabolism of Phenylbutazone can be decreased when combined with Valsartan.Approved, Investigational
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Phenylbutazone.Approved
VoriconazoleThe metabolism of Phenylbutazone can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinPhenylbutazone may increase the anticoagulant activities of Warfarin.Approved
XimelagatranPhenylbutazone may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Ym150Phenylbutazone may increase the anticoagulant activities of Ym150.Investigational
ZafirlukastThe metabolism of Phenylbutazone can be decreased when combined with Zafirlukast.Approved, Investigational
ZaltoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Zaltoprofen.Approved
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with Phenylbutazone.Approved, Investigational, Withdrawn
Zoledronic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Zoledronic acid.Approved
ZomepiracThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Zomepirac.Withdrawn
ZorubicinPhenylbutazone may decrease the excretion rate of Zorubicin which could result in a higher serum level.Experimental
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.
References
Synthesis Reference

Dieter Rahtz, Henning Koch, Erich Gerhards, “Hydroxy phenylbutazone derivatives and their preparation.” U.S. Patent US3968219, issued January, 1971.

US3968219
General ReferencesNot Available
External Links
ATC CodesM01BA01M01AA01M02AA01
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.1 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9931
Caco-2 permeable+0.6185
P-glycoprotein substrateNon-substrate0.7632
P-glycoprotein inhibitor INon-inhibitor0.5423
P-glycoprotein inhibitor IIInhibitor0.5596
Renal organic cation transporterNon-inhibitor0.866
CYP450 2C9 substrateNon-substrate0.6378
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5439
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorInhibitor0.5752
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.5968
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5233
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.7995
BiodegradationNot ready biodegradable0.9881
Rat acute toxicity2.7753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9469
hERG inhibition (predictor II)Non-inhibitor0.892
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Novartis pharmaceuticals corp
  • Ivax pharmaceuticals inc
  • Mutual pharmaceutical co inc
  • Sandoz inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
TabletOral100 mg
Prices
Unit descriptionCostUnit
Phenylbutazone powder1.16USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point105 °CPhysProp
water solubility47.5 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.16SANGSTER (1994)
logS-3.81ADME Research, USCD
pKa4.5SERJEANT,EP & DEMPSEY,B (1979)
Predicted Properties
PropertyValueSource
Water Solubility0.144 mg/mLALOGPS
logP2.81ALOGPS
logP4.14ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)5.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity88.76 m3·mol-1ChemAxon
Polarizability34.15 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.03 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • 1,3-dicarbonyl compound
  • Pyrazolidinone
  • Monocyclic benzene moiety
  • Pyrazolidine
  • Carboxylic acid hydrazide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. Arifah AK, Lees P: Pharmacodynamics and pharmacokinetics of phenylbutazone in calves. J Vet Pharmacol Ther. 2002 Aug;25(4):299-309. [PubMed:12213119 ]
  2. Takada Y, Bhardwaj A, Potdar P, Aggarwal BB: Nonsteroidal anti-inflammatory agents differ in their ability to suppress NF-kappaB activation, inhibition of expression of cyclooxygenase-2 and cyclin D1, and abrogation of tumor cell proliferation. Oncogene. 2004 Dec 9;23(57):9247-58. [PubMed:15489888 ]
  3. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-i synthase activity
Specific Function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q16647
Molecular Weight:
57103.385 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Reed GA, Griffin IO, Eling TE: Inactivation of prostaglandin H synthase and prostacyclin synthase by phenylbutazone. Requirement for peroxidative metabolism. Mol Pharmacol. 1985 Jan;27(1):109-14. [PubMed:3917545 ]
  4. Marnett LJ, Siedlik PH, Ochs RC, Pagels WR, Das M, Honn KV, Warnock RH, Tainer BE, Eling TE: Mechanism of the stimulation of prostaglandin H synthase and prostacyclin synthase by the antithrombotic and antimetastatic agent, nafazatrom. Mol Pharmacol. 1984 Sep;26(2):328-35. [PubMed:6434940 ]
  5. Tobin T, Chay S, Kamerling S, Woods WE, Weckman TJ, Blake JW, Lees P: Phenylbutazone in the horse: a review. J Vet Pharmacol Ther. 1986 Mar;9(1):1-25. [PubMed:3517382 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Zitova A, Hynes J, Kollar J, Borisov SM, Klimant I, Papkovsky DB: Analysis of activity and inhibition of oxygen-dependent enzymes by optical respirometry on the LightCycler system. Anal Biochem. 2010 Feb 15;397(2):144-51. doi: 10.1016/j.ab.2009.10.029. Epub 2009 Oct 20. [PubMed:19849999 ]
  2. Beretta C, Garavaglia G, Cavalli M: COX-1 and COX-2 inhibition in horse blood by phenylbutazone, flunixin, carprofen and meloxicam: an in vitro analysis. Pharmacol Res. 2005 Oct;52(4):302-6. [PubMed:15939622 ]
  3. Morton AJ, Campbell NB, Gayle JM, Redding WR, Blikslager AT: Preferential and non-selective cyclooxygenase inhibitors reduce inflammation during lipopolysaccharide-induced synovitis. Res Vet Sci. 2005 Apr;78(2):189-92. [PubMed:15563928 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
  2. Uwai Y, Saito H, Inui K: Interaction between methotrexate and nonsteroidal anti-inflammatory drugs in organic anion transporter. Eur J Pharmacol. 2000 Dec 1;409(1):31-6. [PubMed:11099697 ]
  3. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [PubMed:10220563 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [PubMed:12130730 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23