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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 KeyInChIKey=VYMDGNCVAMGZFE-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
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
Pharmacology
IndicationFor the treatment of backache and ankylosing spondylitis
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.
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
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
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 CodesM01AA01M01BA01M02AA01
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.1 KB)
Interactions
Drug Interactions
Drug
AbciximabPhenylbutazone may increase the anticoagulant activities of Abciximab.
AbirateroneThe metabolism of Phenylbutazone can be decreased when combined with Abiraterone.
AcebutololPhenylbutazone may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Aceclofenac.
AcenocoumarolPhenylbutazone may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Acetylsalicylic acid.
AdapaleneThe risk or severity of adverse effects can be increased when Adapalene is combined with Phenylbutazone.
Alendronic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Alendronic acid.
AliskirenPhenylbutazone may decrease the antihypertensive activities of Aliskiren.
AlprenololPhenylbutazone may decrease the antihypertensive activities of Alprenolol.
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Phenylbutazone.
AmikacinPhenylbutazone may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmiloridePhenylbutazone may decrease the antihypertensive activities of Amiloride.
AmiodaroneThe metabolism of Phenylbutazone can be decreased when combined with Amiodarone.
AncrodPhenylbutazone may increase the anticoagulant activities of Ancrod.
AntipyrineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Antipyrine.
Antithrombin III humanPhenylbutazone may increase the anticoagulant activities of Antithrombin III human.
ApixabanPhenylbutazone may increase the anticoagulant activities of Apixaban.
ApremilastThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Apremilast.
AprepitantThe metabolism of Phenylbutazone can be increased when combined with Aprepitant.
ArdeparinPhenylbutazone may increase the anticoagulant activities of Ardeparin.
ArgatrobanPhenylbutazone may increase the anticoagulant activities of Argatroban.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Phenylbutazone.
ArotinololPhenylbutazone may decrease the antihypertensive activities of Arotinolol.
AtenololPhenylbutazone may decrease the antihypertensive activities of Atenolol.
AzapropazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Azapropazone.
AzelastineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Azelastine.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Phenylbutazone.
BalsalazidePhenylbutazone may increase the nephrotoxic activities of Balsalazide.
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Phenylbutazone.
BecaplerminPhenylbutazone may increase the anticoagulant activities of Becaplermin.
BefunololPhenylbutazone may decrease the antihypertensive activities of Befunolol.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Phenylbutazone.
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Phenylbutazone.
BenoxaprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Benoxaprofen.
BetaxololPhenylbutazone may decrease the antihypertensive activities of Betaxolol.
BevantololPhenylbutazone may decrease the antihypertensive activities of Bevantolol.
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Phenylbutazone.
BisoprololPhenylbutazone may decrease the antihypertensive activities of Bisoprolol.
BivalirudinPhenylbutazone may increase the anticoagulant activities of Bivalirudin.
BopindololPhenylbutazone may decrease the antihypertensive activities of Bopindolol.
BromfenacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Bromfenac.
BufuralolPhenylbutazone may decrease the antihypertensive activities of Bufuralol.
BumetanidePhenylbutazone may decrease the diuretic activities of Bumetanide.
BupranololPhenylbutazone may decrease the antihypertensive activities of Bupranolol.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Phenylbutazone.
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Phenylbutazone.
CapecitabineThe metabolism of Phenylbutazone can be decreased when combined with Capecitabine.
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Phenylbutazone.
CarbamazepineThe metabolism of Phenylbutazone can be increased when combined with Carbamazepine.
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Phenylbutazone.
CarprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Carprofen.
CarteololPhenylbutazone may decrease the antihypertensive activities of Carteolol.
CarvedilolPhenylbutazone may decrease the antihypertensive activities of Carvedilol.
CastanospermineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Castanospermine.
CelecoxibThe risk or severity of adverse effects can be increased when Celecoxib is combined with Phenylbutazone.
CeliprololPhenylbutazone may decrease the antihypertensive activities of Celiprolol.
CeritinibThe serum concentration of Phenylbutazone can be increased when it is combined with Ceritinib.
CertoparinPhenylbutazone may increase the anticoagulant activities of Certoparin.
ChloroquineThe risk or severity of adverse effects can be increased when Chloroquine is combined with Phenylbutazone.
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Phenylbutazone.
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Phenylbutazone.
CholecalciferolThe metabolism of Phenylbutazone can be decreased when combined with Cholecalciferol.
CholestyramineCholestyramine can cause a decrease in the absorption of Phenylbutazone resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Phenylbutazone.
Citric AcidPhenylbutazone may increase the anticoagulant activities of Citric Acid.
ClodronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clodronate.
ClonixinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Clonixin.
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Phenylbutazone.
ClotrimazoleThe metabolism of Phenylbutazone can be decreased when combined with Clotrimazole.
ColesevelamColesevelam can cause a decrease in the absorption of Phenylbutazone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Phenylbutazone resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclosporinePhenylbutazone may increase the nephrotoxic activities of Cyclosporine.
CyclosporineThe metabolism of Phenylbutazone can be decreased when combined with Cyclosporine.
D-LimoneneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with D-Limonene.
Dabigatran etexilatePhenylbutazone may increase the anticoagulant activities of Dabigatran etexilate.
DabrafenibThe serum concentration of Phenylbutazone can be decreased when it is combined with Dabrafenib.
DalteparinPhenylbutazone may increase the anticoagulant activities of Dalteparin.
DanaparoidPhenylbutazone may increase the anticoagulant activities of Danaparoid.
DaunorubicinPhenylbutazone may decrease the excretion rate of Daunorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DeferasiroxThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Deferasirox.
DelavirdineThe metabolism of Phenylbutazone can be decreased when combined with Delavirdine.
DesirudinPhenylbutazone may increase the anticoagulant activities of Desirudin.
DesmopressinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Phenylbutazone.
DextranPhenylbutazone may increase the anticoagulant activities of Dextran.
Dextran 40Phenylbutazone may increase the anticoagulant activities of Dextran 40.
Dextran 70Phenylbutazone may increase the anticoagulant activities of Dextran 70.
Dextran 75Phenylbutazone may increase the anticoagulant activities of Dextran 75.
DiclofenacThe risk or severity of adverse effects can be increased when Diclofenac is combined with Phenylbutazone.
DicoumarolPhenylbutazone may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Diflunisal.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Phenylbutazone.
DihydrostreptomycinPhenylbutazone may decrease the excretion rate of Dihydrostreptomycin which could result in a lower serum level and potentially a reduction in efficacy.
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Phenylbutazone.
DoxorubicinPhenylbutazone may decrease the excretion rate of Doxorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DrospirenonePhenylbutazone may increase the hyperkalemic activities of Drospirenone.
DroxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Droxicam.
Edetic AcidPhenylbutazone may increase the anticoagulant activities of Edetic Acid.
EdoxabanPhenylbutazone may increase the anticoagulant activities of Edoxaban.
EfavirenzThe metabolism of Phenylbutazone can be decreased when combined with Efavirenz.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Phenylbutazone.
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Phenylbutazone.
EnoxaparinPhenylbutazone may increase the anticoagulant activities of Enoxaparin.
EpirizoleThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Epirizole.
EpirubicinPhenylbutazone may decrease the excretion rate of Epirubicin which could result in a lower serum level and potentially a reduction in efficacy.
EplerenonePhenylbutazone may decrease the antihypertensive activities of Eplerenone.
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Phenylbutazone.
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Phenylbutazone.
EsmololPhenylbutazone may decrease the antihypertensive activities of Esmolol.
Etacrynic acidPhenylbutazone may decrease the diuretic activities of Etacrynic acid.
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Phenylbutazone.
Ethyl biscoumacetatePhenylbutazone may increase the anticoagulant activities of Ethyl biscoumacetate.
Etidronic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etidronic acid.
EtodolacThe risk or severity of adverse effects can be increased when Etodolac is combined with Phenylbutazone.
EtofenamateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etofenamate.
EtoricoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Etoricoxib.
EtravirineThe metabolism of Phenylbutazone can be decreased when combined with Etravirine.
Evening primrose oilThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Evening primrose oil.
exisulindThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with exisulind.
FenbufenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Fenbufen.
FenoprofenThe risk or severity of adverse effects can be increased when Fenoprofen is combined with Phenylbutazone.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Phenylbutazone.
FloxuridineThe metabolism of Phenylbutazone can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Phenylbutazone can be decreased when combined with Fluconazole.
FlunixinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Flunixin.
FluorouracilThe metabolism of Phenylbutazone can be decreased when combined with Fluorouracil.
FlurbiprofenThe risk or severity of adverse effects can be increased when Flurbiprofen is combined with Phenylbutazone.
FluvastatinThe metabolism of Phenylbutazone can be decreased when combined with Fluvastatin.
FluvoxamineThe metabolism of Phenylbutazone can be decreased when combined with Fluvoxamine.
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Phenylbutazone.
Fondaparinux sodiumPhenylbutazone may increase the anticoagulant activities of Fondaparinux sodium.
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Phenylbutazone.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Phenylbutazone.
FosphenytoinThe metabolism of Phenylbutazone can be increased when combined with Fosphenytoin.
FramycetinPhenylbutazone may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FurosemidePhenylbutazone may decrease the diuretic activities of Furosemide.
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Phenylbutazone.
GemfibrozilThe metabolism of Phenylbutazone can be decreased when combined with Gemfibrozil.
GentamicinPhenylbutazone may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
HaloperidolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Haloperidol.
HeparinPhenylbutazone may increase the anticoagulant activities of Heparin.
HirulogPhenylbutazone may increase the anticoagulant activities of Hirulog.
HMPL-004The risk or severity of adverse effects can be increased when Phenylbutazone is combined with HMPL-004.
HydralazinePhenylbutazone may decrease the antihypertensive activities of Hydralazine.
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Phenylbutazone.
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Phenylbutazone.
Hygromycin BPhenylbutazone may decrease the excretion rate of Hygromycin B which could result in a lower serum level and potentially a reduction in efficacy.
IbandronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ibandronate.
IbuprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ibuprofen.
IbuproxamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ibuproxam.
IcatibantThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Icatibant.
IdarubicinPhenylbutazone may decrease the excretion rate of Idarubicin which could result in a lower serum level and potentially a reduction in efficacy.
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Phenylbutazone.
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Phenylbutazone.
IndenololPhenylbutazone may decrease the antihypertensive activities of Indenolol.
IndinavirThe metabolism of Phenylbutazone can be decreased when combined with Indinavir.
IndomethacinThe risk or severity of adverse effects can be increased when Indomethacin is combined with Phenylbutazone.
IndoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Indoprofen.
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Phenylbutazone.
IsoxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Isoxicam.
KanamycinPhenylbutazone may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KebuzoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Kebuzone.
KetoconazoleThe metabolism of Phenylbutazone can be decreased when combined with Ketoconazole.
KetoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Phenylbutazone.
LabetalolPhenylbutazone may decrease the antihypertensive activities of Labetalol.
LeflunomideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Leflunomide.
LepirudinPhenylbutazone may increase the anticoagulant activities of Lepirudin.
LevobunololPhenylbutazone may decrease the antihypertensive activities of Levobunolol.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Phenylbutazone.
LithiumThe serum concentration of Lithium can be increased when it is combined with Phenylbutazone.
LornoxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Lornoxicam.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Phenylbutazone.
LovastatinThe metabolism of Phenylbutazone can be decreased when combined with Lovastatin.
LoxoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Loxoprofen.
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Phenylbutazone.
LumacaftorThe serum concentration of Phenylbutazone can be decreased when it is combined with Lumacaftor.
LumiracoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Lumiracoxib.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Magnesium salicylate.
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Phenylbutazone.
Meclofenamic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Meclofenamic acid.
Mefenamic acidThe risk or severity of adverse effects can be increased when Mefenamic acid is combined with Phenylbutazone.
MeloxicamThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Meloxicam.
MesalazinePhenylbutazone may increase the nephrotoxic activities of Mesalazine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Phenylbutazone.
MetamizoleThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Metamizole.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Phenylbutazone.
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Phenylbutazone.
MetipranololPhenylbutazone may decrease the antihypertensive activities of Metipranolol.
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Phenylbutazone.
MetoprololPhenylbutazone may decrease the antihypertensive activities of Metoprolol.
MetrizamidePhenylbutazone may decrease the excretion rate of Metrizamide which could result in a lower serum level and potentially a reduction in efficacy.
MifepristoneThe serum concentration of Phenylbutazone can be increased when it is combined with Mifepristone.
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Phenylbutazone.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Phenylbutazone.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Phenylbutazone.
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Mycophenolate mofetil is combined with Phenylbutazone.
Mycophenolic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Mycophenolic acid.
NabumetoneThe risk or severity of adverse effects can be increased when Nabumetone is combined with Phenylbutazone.
NadololPhenylbutazone may decrease the antihypertensive activities of Nadolol.
NadroparinPhenylbutazone may increase the anticoagulant activities of Nadroparin.
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Phenylbutazone.
NaproxenThe risk or severity of adverse effects can be increased when Naproxen is combined with Phenylbutazone.
NCX 4016The risk or severity of adverse effects can be increased when Phenylbutazone is combined with NCX 4016.
NeomycinPhenylbutazone may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NepafenacThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Nepafenac.
NetilmicinPhenylbutazone may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
NicardipineThe metabolism of Phenylbutazone can be decreased when combined with Nicardipine.
Niflumic AcidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Niflumic Acid.
NimesulideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Nimesulide.
NintedanibThe serum concentration of Nintedanib can be decreased when it is combined with Phenylbutazone.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Phenylbutazone.
OlopatadineThe risk or severity of adverse effects can be increased when Olopatadine is combined with Phenylbutazone.
OlsalazinePhenylbutazone may increase the nephrotoxic activities of Olsalazine.
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Phenylbutazone.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Omacetaxine mepesuccinate.
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Phenylbutazone.
OmeprazoleThe metabolism of Phenylbutazone can be decreased when combined with Omeprazole.
OrgoteinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Orgotein.
OtamixabanPhenylbutazone may increase the anticoagulant activities of Otamixaban.
OxaprozinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Oxaprozin.
OxprenololPhenylbutazone may decrease the antihypertensive activities of Oxprenolol.
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Oxyphenbutazone.
PamidronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Pamidronate.
ParecoxibThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Parecoxib.
ParomomycinPhenylbutazone may decrease the excretion rate of Paromomycin which could result in a lower serum level and potentially a reduction in efficacy.
PenbutololPhenylbutazone may decrease the antihypertensive activities of Penbutolol.
Pentosan PolysulfatePhenylbutazone may increase the anticoagulant activities of Pentosan Polysulfate.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Phenylbutazone.
PhenindionePhenylbutazone may increase the anticoagulant activities of Phenindione.
PhenobarbitalThe metabolism of Phenylbutazone can be increased when combined with Phenobarbital.
PhenprocoumonPhenylbutazone may increase the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Phenylbutazone can be increased when combined with Phenytoin.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Phenylbutazone.
PindololPhenylbutazone may decrease the antihypertensive activities of Pindolol.
PiretanidePhenylbutazone may decrease the diuretic activities of Piretanide.
PirfenidoneThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Pirfenidone.
PiroxicamThe risk or severity of adverse effects can be increased when Piroxicam is combined with Phenylbutazone.
PlicamycinPhenylbutazone may decrease the excretion rate of Plicamycin which could result in a lower serum level and potentially a reduction in efficacy.
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Phenylbutazone.
PractololPhenylbutazone may decrease the antihypertensive activities of Practolol.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Phenylbutazone.
PrimidoneThe metabolism of Phenylbutazone can be increased when combined with Primidone.
ProbenecidThe serum concentration of Phenylbutazone can be increased when it is combined with Probenecid.
PropacetamolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Propacetamol.
PropranololPhenylbutazone may decrease the antihypertensive activities of Propranolol.
Prostaglandin D2The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Phenylbutazone.
Protein CPhenylbutazone may increase the anticoagulant activities of Protein C.
ProtocatechualdehydePhenylbutazone may increase the anticoagulant activities of Protocatechualdehyde.
PTC299The risk or severity of adverse effects can be increased when Phenylbutazone is combined with PTC299.
PuromycinPhenylbutazone may decrease the excretion rate of Puromycin which could result in a lower serum level and potentially a reduction in efficacy.
PyrimethamineThe metabolism of Phenylbutazone can be decreased when combined with Pyrimethamine.
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Phenylbutazone.
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Phenylbutazone.
QuinineThe metabolism of Phenylbutazone can be decreased when combined with Quinine.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Phenylbutazone.
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Phenylbutazone.
ResveratrolThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Resveratrol.
ReviparinPhenylbutazone may increase the anticoagulant activities of Reviparin.
RibostamycinPhenylbutazone may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RifampicinThe metabolism of Phenylbutazone can be increased when combined with Rifampicin.
RifapentineThe metabolism of Phenylbutazone can be increased when combined with Rifapentine.
RisedronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Risedronate.
RivaroxabanPhenylbutazone may increase the anticoagulant activities of Rivaroxaban.
RofecoxibThe risk or severity of adverse effects can be increased when Rofecoxib is combined with Phenylbutazone.
SalicylamideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Salicylamide.
Salicylic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Salicylic acid.
SalsalateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Salsalate.
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Phenylbutazone.
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Phenylbutazone.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Phenylbutazone.
SecobarbitalThe metabolism of Phenylbutazone can be increased when combined with Secobarbital.
SeratrodastThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Seratrodast.
SildenafilThe metabolism of Phenylbutazone can be decreased when combined with Sildenafil.
SorafenibThe metabolism of Phenylbutazone can be decreased when combined with Sorafenib.
SotalolPhenylbutazone may decrease the antihypertensive activities of Sotalol.
SpectinomycinPhenylbutazone may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Phenylbutazone.
SpironolactonePhenylbutazone may decrease the antihypertensive activities of Spironolactone.
SRT501The risk or severity of adverse effects can be increased when Phenylbutazone is combined with SRT501.
StreptomycinPhenylbutazone may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptozocinPhenylbutazone may decrease the excretion rate of Streptozocin which could result in a lower serum level and potentially a reduction in efficacy.
SulfadiazineThe metabolism of Phenylbutazone can be decreased when combined with Sulfadiazine.
SulfamethoxazoleThe metabolism of Phenylbutazone can be decreased when combined with Sulfamethoxazole.
SulfasalazinePhenylbutazone may increase the nephrotoxic activities of Sulfasalazine.
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Phenylbutazone.
SulfisoxazoleThe metabolism of Phenylbutazone can be decreased when combined with Sulfisoxazole.
SulindacThe risk or severity of adverse effects can be increased when Sulindac is combined with Phenylbutazone.
SulodexidePhenylbutazone may increase the anticoagulant activities of Sulodexide.
SuprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Suprofen.
TacrolimusPhenylbutazone may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Phenylbutazone.
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Phenylbutazone.
Technetium Tc-99m MedronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Technetium Tc-99m Medronate.
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Phenylbutazone.
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Phenylbutazone.
TenofovirThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tenofovir.
TenoxicamThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Phenylbutazone.
TepoxalinThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tepoxalin.
TeriflunomideThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Teriflunomide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tiaprofenic acid.
TicagrelorThe metabolism of Phenylbutazone can be decreased when combined with Ticagrelor.
TiclopidineThe metabolism of Phenylbutazone can be decreased when combined with Ticlopidine.
TiludronateThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tiludronate.
TimololPhenylbutazone may decrease the antihypertensive activities of Timolol.
TobramycinPhenylbutazone may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
TolbutamideThe metabolism of Phenylbutazone can be decreased when combined with Tolbutamide.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tolfenamic Acid.
TolmetinThe risk or severity of adverse effects can be increased when Tolmetin is combined with Phenylbutazone.
TorasemidePhenylbutazone may decrease the diuretic activities of Torasemide.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Phenylbutazone.
TranilastThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Tranilast.
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Phenylbutazone.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Phenylbutazone.
TriamterenePhenylbutazone may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Phenylbutazone.
TrimethoprimThe metabolism of Phenylbutazone can be decreased when combined with Trimethoprim.
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Trisalicylate-choline.
ValdecoxibThe risk or severity of adverse effects can be increased when Valdecoxib is combined with Phenylbutazone.
Valproic AcidThe metabolism of Phenylbutazone can be decreased when combined with Valproic Acid.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Phenylbutazone.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Phenylbutazone.
VoriconazoleThe metabolism of Phenylbutazone can be decreased when combined with Voriconazole.
WarfarinPhenylbutazone may increase the anticoagulant activities of Warfarin.
XimelagatranPhenylbutazone may increase the anticoagulant activities of Ximelagatran.
ZafirlukastThe metabolism of Phenylbutazone can be decreased when combined with Zafirlukast.
ZaltoprofenThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Zaltoprofen.
ZileutonThe risk or severity of adverse effects can be increased when Zileuton is combined with Phenylbutazone.
Zoledronic acidThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Zoledronic acid.
ZomepiracThe risk or severity of adverse effects can be increased when Phenylbutazone is combined with Zomepirac.
Food Interactions
  • Take with food to reduce irritation. Avoid alcohol.

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