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Identification
NamePhenoxybenzamine
Accession NumberDB00925  (APRD00651)
TypeSmall Molecule
GroupsApproved
DescriptionAn alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator. [PubChem]
Structure
Thumb
Synonyms
Dibenzyline
Fenossibenzamina
Fenoxibenzamina
Phenoxybenzamine
Phenoxybenzaminum
POB
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dibenzylinecapsule10 mg/1oralConcordia Pharmaceuticals Inc.1953-01-26Not applicableUs
Dibenzylinecapsule10 mg/1oralWell Spring Pharmaceutical Corporation1999-10-01Not applicableUs
Phenoxybenzamine Hydrochloridecapsule10 mg/1oralPrasco Laboratories2015-08-11Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Phenoxybenzamine Hydrochloridecapsule10 mg/1oralRoxane Laboratories, Inc.2015-08-10Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Phenoxybenzamine Hydrochloride
Thumb
  • InChI Key: VBCPVIWPDJVHAN-UHFFFAOYNA-N
  • Monoisotopic Mass: 339.115669777
  • Average Mass: 340.287
DBSALT000480
Categories
UNII0TTZ664R7Z
CAS number59-96-1
WeightAverage: 303.826
Monoisotopic: 303.138992038
Chemical FormulaC18H22ClNO
InChI KeyInChIKey=QZVCTJOXCFMACW-UHFFFAOYSA-N
InChI
InChI=1S/C18H22ClNO/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3
IUPAC Name
benzyl(2-chloroethyl)(1-phenoxypropan-2-yl)amine
SMILES
CC(COC1=CC=CC=C1)N(CCCl)CC1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Aralkylamine
  • Alkyl aryl ether
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of phaeochromocytoma (malignant), benign prostatic hypertrophy and malignant essential hypertension.
PharmacodynamicsPhenoxybenzamine is indicated for the control of episodes of hypertension and sweating that occur with a disease called pheochromocytoma. If tachycardia is excessive, it may be necessary to use a beta-blocking agent concomitantly. Phenoxybenzamine is a long-acting, adrenergic, alpha-receptor blocking agent which can produce and maintain "chemical sympathectomy" by oral administration. It increases blood flow to the skin, mucosa and abdominal viscera, and lowers both supine and erect blood pressures. It has no effect on the parasympathetic system. Phenoxybenzamine works by blocking alpha receptors in certain parts of the body. Alpha receptors are present in the muscle that lines the walls of blood vessels. When the receptors are blocked by Phenoxybenzamine, the muscle relaxes and the blood vessels widen. This widening of the blood vessels results in a lowering of blood pressure.
Mechanism of actionPhenoxybenzamine produces its therapeutic actions by blocking alpha receptors, leading to a muscle relaxation and a widening of the blood vessels. This widening of the blood vessels results in a lowering of blood pressure.
Related Articles
AbsorptionTwenty to 30 percent of orally administered phenoxybenzamine appears to be absorbed in the active form.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life24 hours
ClearanceNot Available
ToxicitySymptoms of overdose are largely the result of block of the sympathetic nervous system and of the circulating epinephrine. They may include postural hypotension resulting in dizziness or fainting, tachycardia, particularly postural, vomiting; lethargy, and shock.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9629
Caco-2 permeable+0.7367
P-glycoprotein substrateSubstrate0.6059
P-glycoprotein inhibitor IInhibitor0.6043
P-glycoprotein inhibitor IIInhibitor0.5871
Renal organic cation transporterInhibitor0.7955
CYP450 2C9 substrateNon-substrate0.6666
CYP450 2D6 substrateNon-substrate0.6013
CYP450 3A4 substrateSubstrate0.5937
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.7714
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6682
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7565
BiodegradationNot ready biodegradable0.9973
Rat acute toxicity2.1163 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7145
hERG inhibition (predictor II)Inhibitor0.5874
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Wellspring pharmaceutical corp
Packagers
Dosage forms
FormRouteStrength
Capsuleoral10 mg/1
Prices
Unit descriptionCostUnit
Phenoxybenzamine hcl powd42.35USD g
Dibenzyline 10 mg capsule8.61USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point39 °CPhysProp
logP4.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0103 mg/mLALOGPS
logP4.26ALOGPS
logP4.64ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)7.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity88.92 m3·mol-1ChemAxon
Polarizability34.09 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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 ReferenceNot Available
General References
  1. Caine M, Perlberg S, Meretyk S: A placebo-controlled double-blind study of the effect of phenoxybenzamine in benign prostatic obstruction. Br J Urol. 1978 Dec;50(7):551-4. [PubMed:88984 ]
  2. Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]
External Links
ATC CodesC04AX02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.8 KB)
Interactions
Drug Interactions
Drug
7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Phenoxybenzamine.
AcebutololPhenoxybenzamine may increase the hypotensive activities of Acebutolol.
AlfuzosinAlfuzosin may increase the hypotensive activities of Phenoxybenzamine.
AliskirenPhenoxybenzamine may increase the hypotensive activities of Aliskiren.
AlprenololAlprenolol may increase the hypotensive activities of Phenoxybenzamine.
AmbrisentanPhenoxybenzamine may increase the hypotensive activities of Ambrisentan.
AmifostinePhenoxybenzamine may increase the hypotensive activities of Amifostine.
AmiodaroneThe metabolism of Phenoxybenzamine can be decreased when combined with Amiodarone.
AmlodipineAmlodipine may increase the hypotensive activities of Phenoxybenzamine.
AprepitantThe serum concentration of Phenoxybenzamine can be increased when it is combined with Aprepitant.
AtazanavirThe metabolism of Phenoxybenzamine can be decreased when combined with Atazanavir.
AtenololAtenolol may increase the hypotensive activities of Phenoxybenzamine.
AtomoxetineThe metabolism of Phenoxybenzamine can be decreased when combined with Atomoxetine.
BenazeprilBenazepril may increase the hypotensive activities of Phenoxybenzamine.
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Phenoxybenzamine.
BenmoxinBenmoxin may increase the hypotensive activities of Phenoxybenzamine.
BepridilPhenoxybenzamine may increase the hypotensive activities of Bepridil.
BetaxololBetaxolol may increase the hypotensive activities of Phenoxybenzamine.
BethanidineBethanidine may increase the hypotensive activities of Phenoxybenzamine.
BexaroteneThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Bexarotene.
BimatoprostBimatoprost may increase the hypotensive activities of Phenoxybenzamine.
BisoprololBisoprolol may increase the hypotensive activities of Phenoxybenzamine.
BoceprevirThe metabolism of Phenoxybenzamine can be decreased when combined with Boceprevir.
BortezomibThe metabolism of Phenoxybenzamine can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Bosentan.
BosentanPhenoxybenzamine may increase the hypotensive activities of Bosentan.
BretyliumPhenoxybenzamine may increase the hypotensive activities of Bretylium.
BrimonidinePhenoxybenzamine may increase the hypotensive activities of Brimonidine.
BrimonidineBrimonidine may increase the antihypertensive activities of Phenoxybenzamine.
BupranololPhenoxybenzamine may increase the hypotensive activities of Bupranolol.
CandesartanCandesartan may increase the hypotensive activities of Phenoxybenzamine.
CandoxatrilCandoxatril may increase the hypotensive activities of Phenoxybenzamine.
CaptoprilPhenoxybenzamine may increase the hypotensive activities of Captopril.
CarbamazepineThe metabolism of Phenoxybenzamine can be increased when combined with Carbamazepine.
CaroxazoneCaroxazone may increase the hypotensive activities of Phenoxybenzamine.
CarteololCarteolol may increase the hypotensive activities of Phenoxybenzamine.
CarvedilolPhenoxybenzamine may increase the hypotensive activities of Carvedilol.
CeliprololPhenoxybenzamine may increase the hypotensive activities of Celiprolol.
CeritinibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Ceritinib.
ChlorothiazideChlorothiazide may increase the hypotensive activities of Phenoxybenzamine.
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Phenoxybenzamine.
CilazaprilPhenoxybenzamine may increase the hypotensive activities of Cilazapril.
ClarithromycinThe metabolism of Phenoxybenzamine can be decreased when combined with Clarithromycin.
ClemastineThe metabolism of Phenoxybenzamine can be decreased when combined with Clemastine.
ClonidineClonidine may increase the hypotensive activities of Phenoxybenzamine.
ClotrimazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Clotrimazole.
CobicistatThe metabolism of Phenoxybenzamine can be decreased when combined with Cobicistat.
ConivaptanThe serum concentration of Phenoxybenzamine can be increased when it is combined with Conivaptan.
CrizotinibThe metabolism of Phenoxybenzamine can be decreased when combined with Crizotinib.
CryptenamineCryptenamine may increase the hypotensive activities of Phenoxybenzamine.
CyclosporineThe metabolism of Phenoxybenzamine can be decreased when combined with Cyclosporine.
CyclothiazideCyclothiazide may increase the hypotensive activities of Phenoxybenzamine.
DabrafenibThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Dabrafenib.
DarunavirThe metabolism of Phenoxybenzamine can be decreased when combined with Darunavir.
DasatinibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Dasatinib.
DebrisoquinPhenoxybenzamine may increase the hypotensive activities of Debrisoquin.
DeferasiroxThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Phenoxybenzamine can be decreased when combined with Delavirdine.
DeserpidinePhenoxybenzamine may increase the hypotensive activities of Deserpidine.
DexamethasoneThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Dexamethasone.
DiazoxideDiazoxide may increase the hypotensive activities of Phenoxybenzamine.
DihydroergotamineThe metabolism of Phenoxybenzamine can be decreased when combined with Dihydroergotamine.
DiltiazemDiltiazem may increase the hypotensive activities of Phenoxybenzamine.
DorzolamideDorzolamide may increase the hypotensive activities of Phenoxybenzamine.
DoxazosinDoxazosin may increase the hypotensive activities of Phenoxybenzamine.
DoxycyclineThe metabolism of Phenoxybenzamine can be decreased when combined with Doxycycline.
DronedaroneThe metabolism of Phenoxybenzamine can be decreased when combined with Dronedarone.
EfavirenzThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Efavirenz.
EfonidipinePhenoxybenzamine may increase the hypotensive activities of Efonidipine.
EnalaprilEnalapril may increase the hypotensive activities of Phenoxybenzamine.
EnalaprilatPhenoxybenzamine may increase the hypotensive activities of Enalaprilat.
EnzalutamideThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Enzalutamide.
EpoprostenolPhenoxybenzamine may increase the hypotensive activities of Epoprostenol.
EprosartanEprosartan may increase the hypotensive activities of Phenoxybenzamine.
ErythromycinThe metabolism of Phenoxybenzamine can be decreased when combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Eslicarbazepine acetate.
EtravirineThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Etravirine.
FelodipinePhenoxybenzamine may increase the hypotensive activities of Felodipine.
FenoldopamFenoldopam may increase the hypotensive activities of Phenoxybenzamine.
FluconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Fluconazole.
FluvoxamineThe metabolism of Phenoxybenzamine can be decreased when combined with Fluvoxamine.
FosamprenavirThe metabolism of Phenoxybenzamine can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Phenoxybenzamine can be increased when it is combined with Fosaprepitant.
FosinoprilFosinopril may increase the hypotensive activities of Phenoxybenzamine.
FosphenytoinThe metabolism of Phenoxybenzamine can be increased when combined with Fosphenytoin.
FurazolidoneFurazolidone may increase the hypotensive activities of Phenoxybenzamine.
Fusidic AcidThe serum concentration of Phenoxybenzamine can be increased when it is combined with Fusidic Acid.
GuanabenzGuanabenz may increase the hypotensive activities of Phenoxybenzamine.
GuanadrelGuanadrel may increase the hypotensive activities of Phenoxybenzamine.
GuanethidinePhenoxybenzamine may increase the hypotensive activities of Guanethidine.
GuanfacinePhenoxybenzamine may increase the hypotensive activities of Guanfacine.
HexamethoniumPhenoxybenzamine may increase the hypotensive activities of Hexamethonium.
HydracarbazineHydracarbazine may increase the hypotensive activities of Phenoxybenzamine.
HydralazinePhenoxybenzamine may increase the hypotensive activities of Hydralazine.
HydrochlorothiazidePhenoxybenzamine may increase the hypotensive activities of Hydrochlorothiazide.
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Phenoxybenzamine.
IdelalisibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Idelalisib.
IloprostIloprost may increase the hypotensive activities of Phenoxybenzamine.
ImatinibThe metabolism of Phenoxybenzamine can be decreased when combined with Imatinib.
IndapamideIndapamide may increase the hypotensive activities of Phenoxybenzamine.
IndenololPhenoxybenzamine may increase the hypotensive activities of Indenolol.
IndinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Indinavir.
IndoraminPhenoxybenzamine may increase the hypotensive activities of Indoramin.
IproclozideIproclozide may increase the hypotensive activities of Phenoxybenzamine.
IproniazidIproniazid may increase the hypotensive activities of Phenoxybenzamine.
IrbesartanPhenoxybenzamine may increase the hypotensive activities of Irbesartan.
IsavuconazoniumThe metabolism of Phenoxybenzamine can be decreased when combined with Isavuconazonium.
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Phenoxybenzamine.
IsradipineIsradipine may increase the hypotensive activities of Phenoxybenzamine.
ItraconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Itraconazole.
IvacaftorThe serum concentration of Phenoxybenzamine can be increased when it is combined with Ivacaftor.
KetoconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Ketoconazole.
LabetalolLabetalol may increase the hypotensive activities of Phenoxybenzamine.
LacidipinePhenoxybenzamine may increase the hypotensive activities of Lacidipine.
LatanoprostLatanoprost may increase the hypotensive activities of Phenoxybenzamine.
LercanidipineLercanidipine may increase the hypotensive activities of Phenoxybenzamine.
LisinoprilLisinopril may increase the hypotensive activities of Phenoxybenzamine.
LofexidinePhenoxybenzamine may increase the hypotensive activities of Lofexidine.
LopinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Lopinavir.
LosartanLosartan may increase the hypotensive activities of Phenoxybenzamine.
LovastatinThe metabolism of Phenoxybenzamine can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Phenoxybenzamine can be increased when it is combined with Luliconazole.
MacitentanPhenoxybenzamine may increase the hypotensive activities of Macitentan.
ManidipinePhenoxybenzamine may increase the hypotensive activities of Manidipine.
MebanazineMebanazine may increase the hypotensive activities of Phenoxybenzamine.
MecamylamineMecamylamine may increase the hypotensive activities of Phenoxybenzamine.
MethyldopaPhenoxybenzamine may increase the hypotensive activities of Methyldopa.
Methylene blueMethylene blue may increase the hypotensive activities of Phenoxybenzamine.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Phenoxybenzamine.
MetipranololPhenoxybenzamine may increase the hypotensive activities of Metipranolol.
MetolazoneMetolazone may increase the hypotensive activities of Phenoxybenzamine.
MetoprololMetoprolol may increase the hypotensive activities of Phenoxybenzamine.
MibefradilPhenoxybenzamine may increase the hypotensive activities of Mibefradil.
MifepristoneThe metabolism of Phenoxybenzamine can be decreased when combined with Mifepristone.
MinaprineMinaprine may increase the hypotensive activities of Phenoxybenzamine.
MinoxidilMinoxidil may increase the hypotensive activities of Phenoxybenzamine.
MitotaneThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Mitotane.
MoclobemideMoclobemide may increase the hypotensive activities of Phenoxybenzamine.
ModafinilThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Modafinil.
MoexiprilMoexipril may increase the hypotensive activities of Phenoxybenzamine.
MolsidomineMolsidomine may increase the hypotensive activities of Phenoxybenzamine.
MoxonidinePhenoxybenzamine may increase the hypotensive activities of Moxonidine.
NadololPhenoxybenzamine may increase the hypotensive activities of Nadolol.
NafcillinThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Nafcillin.
NebivololPhenoxybenzamine may increase the hypotensive activities of Nebivolol.
NefazodoneThe metabolism of Phenoxybenzamine can be decreased when combined with Nefazodone.
NelfinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Phenoxybenzamine can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Phenoxybenzamine can be decreased when combined with Nevirapine.
NialamideNialamide may increase the hypotensive activities of Phenoxybenzamine.
NicardipineNicardipine may increase the hypotensive activities of Phenoxybenzamine.
NicorandilPhenoxybenzamine may increase the hypotensive activities of Nicorandil.
NiguldipinePhenoxybenzamine may increase the hypotensive activities of Niguldipine.
NilotinibThe metabolism of Phenoxybenzamine can be decreased when combined with Nilotinib.
NilvadipinePhenoxybenzamine may increase the hypotensive activities of Nilvadipine.
NimodipineNimodipine may increase the hypotensive activities of Phenoxybenzamine.
NisoldipineNisoldipine may increase the hypotensive activities of Phenoxybenzamine.
NitrendipinePhenoxybenzamine may increase the hypotensive activities of Nitrendipine.
NitroprussideNitroprusside may increase the hypotensive activities of Phenoxybenzamine.
ObinutuzumabPhenoxybenzamine may increase the hypotensive activities of Obinutuzumab.
OctamoxinOctamoxin may increase the hypotensive activities of Phenoxybenzamine.
OlaparibThe metabolism of Phenoxybenzamine can be decreased when combined with Olaparib.
OlmesartanOlmesartan may increase the hypotensive activities of Phenoxybenzamine.
OmapatrilatOmapatrilat may increase the hypotensive activities of Phenoxybenzamine.
OsimertinibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Osimertinib.
OxprenololPhenoxybenzamine may increase the hypotensive activities of Oxprenolol.
PalbociclibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Palbociclib.
PargylinePhenoxybenzamine may increase the hypotensive activities of Pargyline.
PenbutololPhenoxybenzamine may increase the hypotensive activities of Penbutolol.
PentobarbitalThe metabolism of Phenoxybenzamine can be increased when combined with Pentobarbital.
PentoliniumPhenoxybenzamine may increase the hypotensive activities of Pentolinium.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Phenoxybenzamine.
PerindoprilPerindopril may increase the hypotensive activities of Phenoxybenzamine.
PhenelzinePhenelzine may increase the hypotensive activities of Phenoxybenzamine.
PheniprazinePheniprazine may increase the hypotensive activities of Phenoxybenzamine.
PhenobarbitalThe metabolism of Phenoxybenzamine can be increased when combined with Phenobarbital.
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Phenoxybenzamine.
PhentolaminePhentolamine may increase the hypotensive activities of Phenoxybenzamine.
PhenytoinThe metabolism of Phenoxybenzamine can be increased when combined with Phenytoin.
PinacidilPhenoxybenzamine may increase the hypotensive activities of Pinacidil.
PindololPhenoxybenzamine may increase the hypotensive activities of Pindolol.
PirlindolePirlindole may increase the hypotensive activities of Phenoxybenzamine.
PivhydrazinePivhydrazine may increase the hypotensive activities of Phenoxybenzamine.
PolythiazidePhenoxybenzamine may increase the hypotensive activities of Polythiazide.
PosaconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Posaconazole.
PrazosinPrazosin may increase the hypotensive activities of Phenoxybenzamine.
PrimidoneThe metabolism of Phenoxybenzamine can be increased when combined with Primidone.
PropranololPropranolol may increase the hypotensive activities of Phenoxybenzamine.
QuinaprilQuinapril may increase the hypotensive activities of Phenoxybenzamine.
QuinineQuinine may increase the hypotensive activities of Phenoxybenzamine.
RamiprilRamipril may increase the hypotensive activities of Phenoxybenzamine.
RanolazineThe metabolism of Phenoxybenzamine can be decreased when combined with Ranolazine.
RasagilineRasagiline may increase the hypotensive activities of Phenoxybenzamine.
RemikirenRemikiren may increase the hypotensive activities of Phenoxybenzamine.
RescinnaminePhenoxybenzamine may increase the hypotensive activities of Rescinnamine.
ReserpineReserpine may increase the hypotensive activities of Phenoxybenzamine.
RifabutinThe metabolism of Phenoxybenzamine can be increased when combined with Rifabutin.
RifampicinThe metabolism of Phenoxybenzamine can be increased when combined with Rifampicin.
RifapentineThe metabolism of Phenoxybenzamine can be increased when combined with Rifapentine.
RiociguatPhenoxybenzamine may increase the hypotensive activities of Riociguat.
RitonavirThe metabolism of Phenoxybenzamine can be decreased when combined with Ritonavir.
RituximabPhenoxybenzamine may increase the hypotensive activities of Rituximab.
SafrazineSafrazine may increase the hypotensive activities of Phenoxybenzamine.
SaprisartanPhenoxybenzamine may increase the hypotensive activities of Saprisartan.
SaquinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Saquinavir.
SelegilineSelegiline may increase the hypotensive activities of Phenoxybenzamine.
SelexipagPhenoxybenzamine may increase the hypotensive activities of Selexipag.
SildenafilSildenafil may increase the antihypertensive activities of Phenoxybenzamine.
SiltuximabThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Phenoxybenzamine can be increased when it is combined with Simeprevir.
SitaxentanPhenoxybenzamine may increase the hypotensive activities of Sitaxentan.
SpiraprilPhenoxybenzamine may increase the hypotensive activities of Spirapril.
St. John's WortThe serum concentration of Phenoxybenzamine can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Phenoxybenzamine can be increased when it is combined with Stiripentol.
SulfisoxazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Sulfisoxazole.
TadalafilTadalafil may increase the antihypertensive activities of Phenoxybenzamine.
TelaprevirThe metabolism of Phenoxybenzamine can be decreased when combined with Telaprevir.
TelithromycinThe metabolism of Phenoxybenzamine can be decreased when combined with Telithromycin.
TelmisartanPhenoxybenzamine may increase the hypotensive activities of Telmisartan.
TemocaprilPhenoxybenzamine may increase the hypotensive activities of Temocapril.
TerlipressinPhenoxybenzamine may increase the hypotensive activities of Terlipressin.
TibolonePhenoxybenzamine may increase the hypotensive activities of Tibolone.
TiclopidineThe metabolism of Phenoxybenzamine can be decreased when combined with Ticlopidine.
TicrynafenPhenoxybenzamine may increase the hypotensive activities of Ticrynafen.
TimololTimolol may increase the hypotensive activities of Phenoxybenzamine.
TocilizumabThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Tocilizumab.
TolazolineTolazoline may increase the hypotensive activities of Phenoxybenzamine.
ToloxatoneToloxatone may increase the hypotensive activities of Phenoxybenzamine.
TorasemideTorasemide may increase the hypotensive activities of Phenoxybenzamine.
TrandolaprilTrandolapril may increase the hypotensive activities of Phenoxybenzamine.
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Phenoxybenzamine.
TranylcypromineTranylcypromine may increase the hypotensive activities of Phenoxybenzamine.
TravoprostTravoprost may increase the hypotensive activities of Phenoxybenzamine.
TreprostinilTreprostinil may increase the hypotensive activities of Phenoxybenzamine.
TrichlormethiazidePhenoxybenzamine may increase the hypotensive activities of Trichlormethiazide.
TrimazosinPhenoxybenzamine may increase the hypotensive activities of Trimazosin.
TrimethaphanPhenoxybenzamine may increase the hypotensive activities of Trimethaphan.
UdenafilUdenafil may increase the antihypertensive activities of Phenoxybenzamine.
UnoprostonePhenoxybenzamine may increase the hypotensive activities of Unoprostone.
ValsartanValsartan may increase the hypotensive activities of Phenoxybenzamine.
VardenafilVardenafil may increase the antihypertensive activities of Phenoxybenzamine.
VenlafaxineThe metabolism of Phenoxybenzamine can be decreased when combined with Venlafaxine.
VerapamilThe metabolism of Phenoxybenzamine can be decreased when combined with Verapamil.
VoriconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Voriconazole.
XylometazolinePhenoxybenzamine may increase the hypotensive activities of Xylometazoline.
YohimbineYohimbine may decrease the antihypertensive activities of Phenoxybenzamine.
ZiprasidoneThe metabolism of Phenoxybenzamine can be decreased when combined with Ziprasidone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Stam WB, Van der Graaf PH, Saxena PR: Analysis of alpha 1L-adrenoceptor pharmacology in rat small mesenteric artery. Br J Pharmacol. 1999 Jun;127(3):661-70. [PubMed:10401556 ]
  2. Michel MC, Hanft G, Gross G: Functional studies on alpha 1-adrenoceptor subtypes mediating inotropic effects in rat right ventricle. Br J Pharmacol. 1994 Feb;111(2):539-46. [PubMed:7911719 ]
  3. Yu Y, Koss MC: Functional characterization of alpha-adrenoceptors mediating pupillary dilation in rats. Eur J Pharmacol. 2003 Jun 20;471(2):135-40. [PubMed:12818701 ]
  4. Salles J, Gascon S, Badia A: Sustained increase in rat myocardial alpha 1A-adrenoceptors induced by 6-hydroxydopamine treatment involves a decelerated receptor turnover. Naunyn Schmiedebergs Arch Pharmacol. 1996 Mar;353(4):408-16. [PubMed:8935707 ]
  5. Suzuki E, Tsujimoto G, Tamura K, Hashimoto K: Two pharmacologically distinct alpha 1-adrenoceptor subtypes in the contraction of rabbit aorta: each subtype couples with a different Ca2+ signalling mechanism and plays a different physiological role. Mol Pharmacol. 1990 Nov;38(5):725-36. [PubMed:1978244 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Thioesterase binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
References
  1. Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Protein homodimerization activity
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name:
ADRA2C
Uniprot ID:
P18825
Molecular Weight:
49521.585 Da
References
  1. Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Epinephrine binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular Weight:
49565.8 Da
References
  1. Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Titin binding
Specific Function:
Calmodulin mediates the control of a large number of enzymes, ion channels, aquaporins and other proteins by Ca(2+). Among the enzymes to be stimulated by the calmodulin-Ca(2+) complex are a number of protein kinases and phosphatases. Together with CCP110 and centrin, is involved in a genetic pathway that regulates the centrosome cycle and progression through cytokinesis.
Gene Name:
CALM1
Uniprot ID:
P62158
Molecular Weight:
16837.47 Da
References
  1. Cimino M, Weiss B: Characteristics of the binding of phenoxybenzamine to calmodulin. Biochem Pharmacol. 1988 Jul 15;37(14):2739-45. [PubMed:3134891 ]
  2. Suko J, Wyskovsky W, Pidlich J, Hauptner R, Plank B, Hellmann G: Calcium release from calmodulin and its C-terminal or N-terminal halves in the presence of the calmodulin antagonists phenoxybenzamine and melittin measured by stopped-flow fluorescence with Quin 2 and intrinsic tyrosine. Inhibition of calmodulin-dependent protein kinase of cardiac sarcoplasmic reticulum. Eur J Biochem. 1986 Sep 15;159(3):425-34. [PubMed:3758070 ]
  3. Lukas TJ, Marshak DR, Watterson DM: Drug-protein interactions: isolation and characterization of covalent adducts of phenoxybenzamine and calmodulin. Biochemistry. 1985 Jan 1;24(1):151-7. [PubMed:3994963 ]
  4. Earl CQ, Prozialeck WC, Weiss B: Interaction of alpha adrenergic antagonists with calmodulin. Life Sci. 1984 Jul 30;35(5):525-34. [PubMed:6146911 ]
  5. Kuromi H, Yoshihara M, Kidokoro Y: An inhibitory role of calcineurin in endocytosis of synaptic vesicles at nerve terminals of Drosophila larvae. Neurosci Res. 1997 Feb;27(2):101-13. [PubMed:9100252 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein homodimerization activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular Weight:
46458.32 Da
References
  1. Frang H, Cockcroft V, Karskela T, Scheinin M, Marjamaki A: Phenoxybenzamine binding reveals the helical orientation of the third transmembrane domain of adrenergic receptors. J Biol Chem. 2001 Aug 17;276(33):31279-84. Epub 2001 Jun 6. [PubMed:11395517 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Minneman KP, Theroux TL, Hollinger S, Han C, Esbenshade TA: Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes. Mol Pharmacol. 1994 Nov;46(5):929-36. [PubMed:7969082 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Minneman KP, Theroux TL, Hollinger S, Han C, Esbenshade TA: Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes. Mol Pharmacol. 1994 Nov;46(5):929-36. [PubMed:7969082 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Toxin transporter activity
Specific Function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular Weight:
61279.485 Da
References
  1. Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [PubMed:12110607 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23