Identification

Name
Phenoxybenzamine
Accession Number
DB00925  (APRD00651)
Type
Small Molecule
Groups
Approved
Description

An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator. [PubChem]

Structure
Thumb
Synonyms
  • Fenossibenzamina
  • Fenoxibenzamina
  • Phenoxybenzamine
  • Phenoxybenzaminum
  • POB
Product Ingredients
IngredientUNIICASInChI Key
Phenoxybenzamine HydrochlorideX1IEG24OHL63-92-3VBCPVIWPDJVHAN-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DibenzylineCapsule10 mg/1OralWell Spring Pharmaceutical Corporation1999-10-012017-10-31Us
DibenzylineCapsule10 mg/1OralConcordia Pharmaceuticals, Inc1953-01-26Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Phenoxybenzamine HydrochlorideCapsule10 mg/1OralPrasco, Laboratories2015-08-11Not applicableUs
Phenoxybenzamine HydrochlorideCapsule10 mg/1OralWest Ward Pharmaceutical2015-08-10Not applicableUs
Phenoxybenzamine HydrochlorideCapsule10 mg/1OralPar Pharmaceutical2017-01-24Not applicableUs
International/Other Brands
Dibenzyline
Categories
UNII
0TTZ664R7Z
CAS number
59-96-1
Weight
Average: 303.826
Monoisotopic: 303.138992038
Chemical Formula
C18H22ClNO
InChI Key
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

Pharmacology

Indication

For the treatment of phaeochromocytoma (malignant), benign prostatic hypertrophy and malignant essential hypertension.

Structured Indications
Pharmacodynamics

Phenoxybenzamine 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 action

Phenoxybenzamine 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.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
antagonist
Human
AAlpha-2A adrenergic receptor
antagonist
Human
UAlpha-2C adrenergic receptor
antagonist
Human
UAlpha-2B adrenergic receptor
antagonist
Human
UCalmodulin
inhibitor
Human
UBeta-2 adrenergic receptorNot AvailableHuman
UAlpha-1B adrenergic receptor
antagonist
Human
UAlpha-1D adrenergic receptor
antagonist
Human
Absorption

Twenty to 30 percent of orally administered phenoxybenzamine appears to be absorbed in the active form.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

24 hours

Clearance
Not Available
Toxicity

Symptoms 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Phenoxybenzamine.Experimental
AcebutololPhenoxybenzamine may increase the hypotensive activities of Acebutolol.Approved, Investigational
AcemetacinThe therapeutic efficacy of Phenoxybenzamine can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
Acetyl sulfisoxazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Acetyl sulfisoxazole.Approved, Vet Approved
AldesleukinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Aldesleukin.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
AliskirenPhenoxybenzamine may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Phenoxybenzamine.Approved, Withdrawn
AmbrisentanPhenoxybenzamine may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostinePhenoxybenzamine may increase the hypotensive activities of Amifostine.Approved, Investigational
AmilorideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Amiloride.Approved
AmiodaroneThe metabolism of Phenoxybenzamine can be decreased when combined with Amiodarone.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Phenoxybenzamine.Approved
AmobarbitalAmobarbital may increase the hypotensive activities of Phenoxybenzamine.Approved, Illicit
AmphetamineAmphetamine may increase the hypotensive activities of Phenoxybenzamine.Approved, Illicit, Investigational
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Phenoxybenzamine.Approved, Investigational
Amyl NitriteThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Amyl Nitrite.Approved
ApalutamideThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Apalutamide.Approved, Investigational
ApomorphineThe risk or severity of adverse effects can be increased when Apomorphine is combined with Phenoxybenzamine.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Apraclonidine.Approved
AprepitantThe serum concentration of Phenoxybenzamine can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleAripiprazole may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Phenoxybenzamine.Investigational
Arsenic trioxideThe risk or severity of adverse effects can be increased when Arsenic trioxide is combined with Phenoxybenzamine.Approved, Investigational
AtazanavirThe metabolism of Phenoxybenzamine can be decreased when combined with Atazanavir.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Phenoxybenzamine.Approved
AtomoxetineThe metabolism of Phenoxybenzamine can be decreased when combined with Atomoxetine.Approved
AvanafilAvanafil may increase the antihypertensive activities of Phenoxybenzamine.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Azilsartan medoxomil.Approved, Investigational
BarbexacloneBarbexaclone may increase the hypotensive activities of Phenoxybenzamine.Experimental
BarbitalBarbital may increase the hypotensive activities of Phenoxybenzamine.Illicit
BarnidipinePhenoxybenzamine may increase the antihypertensive activities of Barnidipine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Phenoxybenzamine.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
BepridilPhenoxybenzamine may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
BethanidineBethanidine may increase the hypotensive activities of Phenoxybenzamine.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Phenoxybenzamine.Experimental
BimatoprostBimatoprost may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Phenoxybenzamine.Approved
BoceprevirThe metabolism of Phenoxybenzamine can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Phenoxybenzamine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Bosentan.Approved, Investigational
BQ-123Phenoxybenzamine may increase the hypotensive activities of BQ-123.Investigational
BretyliumPhenoxybenzamine may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Phenoxybenzamine.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Phenoxybenzamine.Experimental
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Phenoxybenzamine.Approved, Investigational
BumetanideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Bumetanide.Approved
BupivacaineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Phenoxybenzamine.Approved, Investigational
BupranololPhenoxybenzamine may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Phenoxybenzamine.Experimental
CafedrinePhenoxybenzamine may increase the hypotensive activities of Cafedrine.Investigational
CanagliflozinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Canagliflozin.Approved
CandesartanPhenoxybenzamine may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilCandesartan cilexetil may increase the hypotensive activities of Phenoxybenzamine.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Phenoxybenzamine.Experimental
CaptoprilPhenoxybenzamine may increase the hypotensive activities of Captopril.Approved
CarbamazepineThe metabolism of Phenoxybenzamine can be increased when combined with Carbamazepine.Approved, Investigational
CarbetocinThe risk or severity of adverse effects can be increased when Carbetocin is combined with Phenoxybenzamine.Approved, Investigational
CaroxazoneCaroxazone may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Phenoxybenzamine.Approved
CarvedilolPhenoxybenzamine may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololPhenoxybenzamine may increase the hypotensive activities of Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Ceritinib.Approved
ChlorothiazideChlorothiazide may increase the hypotensive activities of Phenoxybenzamine.Approved, Vet Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Phenoxybenzamine.Approved, Investigational, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Phenoxybenzamine.Approved
CicletaninePhenoxybenzamine may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilPhenoxybenzamine may increase the hypotensive activities of Cilazapril.Approved
CilnidipineThe risk or severity of adverse effects can be increased when Cilnidipine is combined with Phenoxybenzamine.Approved, Investigational
ClarithromycinThe metabolism of Phenoxybenzamine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Phenoxybenzamine can be decreased when combined with Clemastine.Approved, Investigational
ClevidipineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Clevidipine.Approved, Investigational
ClofarabineThe risk or severity of adverse effects can be increased when Clofarabine is combined with Phenoxybenzamine.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Phenoxybenzamine.Approved, Investigational, Vet Approved
ClonidineClonidine may increase the hypotensive activities of Phenoxybenzamine.Approved
CloranololPhenoxybenzamine may increase the hypotensive activities of Cloranolol.Experimental
ClotrimazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Clozapine is combined with Phenoxybenzamine.Approved
CobicistatThe metabolism of Phenoxybenzamine can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Conivaptan can be increased when it is combined with Phenoxybenzamine.Approved, Investigational
CrizotinibThe metabolism of Phenoxybenzamine can be decreased when combined with Crizotinib.Approved
CryptenamineCryptenamine may increase the hypotensive activities of Phenoxybenzamine.Approved
CyclopenthiazidePhenoxybenzamine may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Phenoxybenzamine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyclothiazideCyclothiazide may increase the hypotensive activities of Phenoxybenzamine.Approved
DabrafenibThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Dabrafenib.Approved, Investigational
DapagliflozinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Dapagliflozin.Approved
DarunavirThe metabolism of Phenoxybenzamine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Dasatinib.Approved, Investigational
DebrisoquinDebrisoquin may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
DeferasiroxThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelaprilPhenoxybenzamine may increase the hypotensive activities of Delapril.Experimental
DelavirdineThe metabolism of Phenoxybenzamine can be decreased when combined with Delavirdine.Approved
DeserpidinePhenoxybenzamine may increase the hypotensive activities of Deserpidine.Approved
DesfluraneThe risk or severity of adverse effects can be increased when Desflurane is combined with Phenoxybenzamine.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Dexmedetomidine.Approved, Vet Approved
DiazoxideDiazoxide may increase the hypotensive activities of Phenoxybenzamine.Approved
DiclofenamideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Diclofenamide.Approved, Investigational
DiethylnorsperminePhenoxybenzamine may increase the hypotensive activities of Diethylnorspermine.Investigational
DihydralazineDihydralazine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
DihydroergotamineThe metabolism of Phenoxybenzamine can be decreased when combined with Dihydroergotamine.Approved, Investigational
DiltiazemThe metabolism of Phenoxybenzamine can be decreased when combined with Diltiazem.Approved, Investigational
DinutuximabThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Dinutuximab.Approved, Investigational
DipyridamoleThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Dipyridamole.Approved
DorzolamideDorzolamide may increase the hypotensive activities of Phenoxybenzamine.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Phenoxybenzamine.Approved
DoxycyclineThe metabolism of Phenoxybenzamine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Phenoxybenzamine can be decreased when combined with Dronedarone.Approved
DuloxetinePhenoxybenzamine may increase the orthostatic hypotensive activities of Duloxetine.Approved
EfonidipinePhenoxybenzamine may increase the hypotensive activities of Efonidipine.Approved, Investigational
EmpagliflozinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Empagliflozin.Approved
EnalaprilEnalapril may increase the hypotensive activities of Phenoxybenzamine.Approved, Vet Approved
EnalaprilatPhenoxybenzamine may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Phenoxybenzamine.Experimental
EnzalutamideThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Enzalutamide.Approved
EpanololPhenoxybenzamine may increase the hypotensive activities of Epanolol.Experimental
EplerenoneThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Eplerenone.Approved
EpoprostenolPhenoxybenzamine may increase the hypotensive activities of Epoprostenol.Approved
EprosartanEprosartan may increase the hypotensive activities of Phenoxybenzamine.Approved
ErythromycinThe metabolism of Phenoxybenzamine can be decreased when combined with Erythromycin.Approved, Investigational, Vet Approved
EsmololThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Esmolol.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Etacrynic acid.Approved, Investigational
FelodipinePhenoxybenzamine may increase the hypotensive activities of Felodipine.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Phenoxybenzamine.Approved
Ferulic acidPhenoxybenzamine may increase the hypotensive activities of Ferulic acid.Experimental
FimasartanThe risk or severity of adverse effects can be increased when Fimasartan is combined with Phenoxybenzamine.Approved, Investigational
FluconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Fluconazole.Approved, Investigational
FluvoxamineThe metabolism of Phenoxybenzamine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Phenoxybenzamine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Phenoxybenzamine can be increased when it is combined with Fosaprepitant.Approved
FosinoprilFosinopril may increase the hypotensive activities of Phenoxybenzamine.Approved
FosphenytoinThe metabolism of Phenoxybenzamine can be increased when combined with Fosphenytoin.Approved, Investigational
FurazolidoneFurazolidone may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational, Vet Approved
FurosemideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Phenoxybenzamine can be increased when it is combined with Fusidic Acid.Approved, Investigational
GuanabenzGuanabenz may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Phenoxybenzamine.Approved
GuanazodinePhenoxybenzamine may increase the hypotensive activities of Guanazodine.Experimental
GuanethidinePhenoxybenzamine may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
GuanoclorPhenoxybenzamine may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzPhenoxybenzamine may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanPhenoxybenzamine may increase the hypotensive activities of Guanoxan.Experimental
HalothaneThe risk or severity of adverse effects can be increased when Halothane is combined with Phenoxybenzamine.Approved, Vet Approved
HarmalineHarmaline may increase the hypotensive activities of Phenoxybenzamine.Experimental
HexamethoniumPhenoxybenzamine may increase the hypotensive activities of Hexamethonium.Experimental
HexobarbitalHexobarbital may increase the hypotensive activities of Phenoxybenzamine.Approved
HydracarbazineHydracarbazine may increase the hypotensive activities of Phenoxybenzamine.Experimental
HydralazineHydralazine may increase the hypotensive activities of Phenoxybenzamine.Approved
HydrochlorothiazidePhenoxybenzamine may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
IdelalisibThe metabolism of Phenoxybenzamine can be decreased when combined with Idelalisib.Approved
IloprostThe risk or severity of adverse effects can be increased when Iloprost is combined with Phenoxybenzamine.Approved, Investigational
ImatinibThe metabolism of Phenoxybenzamine can be decreased when combined with Imatinib.Approved
ImidaprilThe risk or severity of adverse effects can be increased when Imidapril is combined with Phenoxybenzamine.Investigational
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Phenoxybenzamine.Approved
IndapamideIndapamide may increase the hypotensive activities of Phenoxybenzamine.Approved
IndenololPhenoxybenzamine may increase the hypotensive activities of Indenolol.Withdrawn
IndinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Indinavir.Approved
IndoraminIndoramin may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
IrbesartanPhenoxybenzamine may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsavuconazoleThe serum concentration of Phenoxybenzamine can be increased when it is combined with Isavuconazole.Approved, Investigational
IsavuconazoniumThe metabolism of Phenoxybenzamine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Phenoxybenzamine.Approved
IsofluraneThe risk or severity of adverse effects can be increased when Isoflurane is combined with Phenoxybenzamine.Approved, Vet Approved
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Isosorbide Dinitrate.Approved, Investigational
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Isosorbide Mononitrate.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Isoxsuprine.Approved, Withdrawn
IsradipineThe metabolism of Phenoxybenzamine can be decreased when combined with Isradipine.Approved, Investigational
ItraconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Phenoxybenzamine can be increased when it is combined with Ivacaftor.Approved
KetanserinKetanserin may increase the hypotensive activities of Phenoxybenzamine.Investigational
KetoconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolLabetalol may increase the hypotensive activities of Phenoxybenzamine.Approved
LacidipinePhenoxybenzamine may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Levobunolol.Approved
LevobupivacaineThe risk or severity of adverse effects can be increased when Levobupivacaine is combined with Phenoxybenzamine.Approved, Investigational
LevodopaPhenoxybenzamine may increase the orthostatic hypotensive activities of Levodopa.Approved
LevosimendanThe risk or severity of adverse effects can be increased when Levosimendan is combined with Phenoxybenzamine.Approved, Investigational
LinsidominePhenoxybenzamine may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilLisinopril may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
LofexidinePhenoxybenzamine may increase the hypotensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Lopinavir.Approved
LorpiprazoleThe serum concentration of Phenoxybenzamine can be increased when it is combined with Lorpiprazole.Approved
LosartanLosartan may increase the hypotensive activities of Phenoxybenzamine.Approved
LovastatinThe metabolism of Phenoxybenzamine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Phenoxybenzamine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Phenoxybenzamine can be increased when combined with Lumacaftor.Approved
MacitentanPhenoxybenzamine may increase the hypotensive activities of Macitentan.Approved
ManidipinePhenoxybenzamine may increase the hypotensive activities of Manidipine.Approved, Investigational
MannitolThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Mannitol.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MethazolamideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Methazolamide.Approved
MethohexitalMethohexital may increase the hypotensive activities of Phenoxybenzamine.Approved
MethoserpidinePhenoxybenzamine may increase the hypotensive activities of Methoserpidine.Experimental
MethyclothiazideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Methyclothiazide.Approved
MethyldopaPhenoxybenzamine may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Phenoxybenzamine.Approved, Investigational
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Phenoxybenzamine.Approved
MetipranololPhenoxybenzamine may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Phenoxybenzamine.Approved
MetoprololMetoprolol may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MetyrosinePhenoxybenzamine may increase the hypotensive activities of Metyrosine.Approved
MibefradilPhenoxybenzamine may increase the hypotensive activities of Mibefradil.Investigational, Withdrawn
MifepristoneThe serum concentration of Phenoxybenzamine can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineMinaprine may increase the hypotensive activities of Phenoxybenzamine.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MirodenafilMirodenafil may increase the antihypertensive activities of Phenoxybenzamine.Investigational
MitotaneThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Mitotane.Approved
MoclobemideMoclobemide may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MoexiprilMoexipril may increase the hypotensive activities of Phenoxybenzamine.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Phenoxybenzamine.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
MuzoliminePhenoxybenzamine may increase the hypotensive activities of Muzolimine.Experimental
NabiloneThe risk or severity of adverse effects can be increased when Nabilone is combined with Phenoxybenzamine.Approved, Investigational
NadololPhenoxybenzamine may increase the hypotensive activities of Nadolol.Approved
NaftopidilPhenoxybenzamine may increase the hypotensive activities of Naftopidil.Investigational
NebivololPhenoxybenzamine may increase the hypotensive activities of Nebivolol.Approved, Investigational
NefazodoneThe metabolism of Phenoxybenzamine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Nelfinavir.Approved
NesiritideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Nesiritide.Approved, Investigational
NetupitantThe serum concentration of Phenoxybenzamine can be increased when it is combined with Netupitant.Approved, Investigational
NevirapineThe metabolism of Phenoxybenzamine can be increased when combined with Nevirapine.Approved
NialamideNialamide may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
NicorandilNicorandil may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
NifedipineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Nifedipine.Approved
NiguldipinePhenoxybenzamine may increase the hypotensive activities of Niguldipine.Experimental
NilotinibThe metabolism of Phenoxybenzamine can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipinePhenoxybenzamine may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
NisoldipineNisoldipine may increase the hypotensive activities of Phenoxybenzamine.Approved
NitrendipinePhenoxybenzamine may increase the hypotensive activities of Nitrendipine.Approved, Investigational
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Phenoxybenzamine.Approved
NitroglycerinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Nitroglycerin.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
Nitrous acidThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Nitrous acid.Approved, Investigational
ObinutuzumabPhenoxybenzamine may increase the hypotensive activities of Obinutuzumab.Approved, Investigational
OctamoxinOctamoxin may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
OlaparibThe metabolism of Phenoxybenzamine can be decreased when combined with Olaparib.Approved
OlmesartanOlmesartan may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Phenoxybenzamine.Investigational
OsimertinibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Osimertinib.Approved
OxprenololPhenoxybenzamine may increase the hypotensive activities of Oxprenolol.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Phenoxybenzamine.Approved, Vet Approved
PalbociclibThe serum concentration of Phenoxybenzamine can be increased when it is combined with Palbociclib.Approved, Investigational
PapaverineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Papaverine.Approved, Investigational
PargylinePargyline may increase the hypotensive activities of Phenoxybenzamine.Approved
PenbutololPhenoxybenzamine may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentobarbitalThe metabolism of Phenoxybenzamine can be increased when combined with Pentobarbital.Approved, Investigational, Vet Approved
PentoliniumPhenoxybenzamine may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Phenoxybenzamine.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
PhenobarbitalThe metabolism of Phenoxybenzamine can be increased when combined with Phenobarbital.Approved, Investigational
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
PhentolaminePhentolamine may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenytoinThe metabolism of Phenoxybenzamine can be increased when combined with Phenytoin.Approved, Vet Approved
PinacidilPinacidil may increase the hypotensive activities of Phenoxybenzamine.Approved
PindololPhenoxybenzamine may increase the hypotensive activities of Pindolol.Approved, Investigational
PipamperoneThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Pipamperone.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Phenoxybenzamine.Approved
PitolisantThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Pitolisant.Approved, Investigational
PivhydrazinePivhydrazine may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
Platelet Activating FactorPhenoxybenzamine may increase the hypotensive activities of Platelet Activating Factor.Experimental
PolythiazidePhenoxybenzamine may increase the hypotensive activities of Polythiazide.Approved
PosaconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramipexoleThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Pramipexole.Approved, Investigational
PrazosinPrazosin may increase the hypotensive activities of Phenoxybenzamine.Approved
PrimidoneThe metabolism of Phenoxybenzamine can be increased when combined with Primidone.Approved, Vet Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
PropofolThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Propofol.Approved, Investigational, Vet Approved
PropranololPropranolol may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
QuetiapineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Quetiapine.Approved
QuinaprilQuinapril may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Phenoxybenzamine.Approved
RamiprilRamipril may increase the hypotensive activities of Phenoxybenzamine.Approved
RanolazineThe metabolism of Phenoxybenzamine can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the hypotensive activities of Phenoxybenzamine.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Remifentanil.Approved
RemikirenRemikiren may increase the hypotensive activities of Phenoxybenzamine.Approved
RescinnaminePhenoxybenzamine may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
RifabutinThe metabolism of Phenoxybenzamine can be increased when combined with Rifabutin.Approved, Investigational
RifampicinThe metabolism of Phenoxybenzamine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Phenoxybenzamine can be increased when combined with Rifapentine.Approved, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
RiociguatPhenoxybenzamine may increase the hypotensive activities of Riociguat.Approved
RisperidonePhenoxybenzamine may increase the hypotensive activities of Risperidone.Approved, Investigational
RituximabPhenoxybenzamine may increase the hypotensive activities of Rituximab.Approved
RopiniroleThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Ropivacaine.Approved
RotigotineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Rotigotine.Approved
RucaparibThe metabolism of Phenoxybenzamine can be decreased when combined with Rucaparib.Approved, Investigational
SacubitrilThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sacubitril.Approved
SafrazineSafrazine may increase the hypotensive activities of Phenoxybenzamine.Withdrawn
SaprisartanPhenoxybenzamine may increase the hypotensive activities of Saprisartan.Experimental
SaquinavirThe metabolism of Phenoxybenzamine can be decreased when combined with Saquinavir.Approved, Investigational
SarilumabThe therapeutic efficacy of Phenoxybenzamine can be decreased when used in combination with Sarilumab.Approved, Investigational
SecobarbitalSecobarbital may increase the hypotensive activities of Phenoxybenzamine.Approved, Vet Approved
SelegilineSelegiline may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational, Vet Approved
SelexipagPhenoxybenzamine may increase the hypotensive activities of Selexipag.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sevoflurane.Approved, Vet Approved
SildenafilSildenafil may increase the antihypertensive activities of Phenoxybenzamine.Approved, Investigational
SiltuximabThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Siltuximab.Approved, Investigational
SimeprevirThe serum concentration of Phenoxybenzamine can be increased when it is combined with Simeprevir.Approved
SitaxentanPhenoxybenzamine may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SotalolThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sotalol.Approved
SpiraprilPhenoxybenzamine may increase the hypotensive activities of Spirapril.Approved
SpironolactoneThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Phenoxybenzamine can be decreased when it is combined with St. John's Wort.Approved, Investigational, Nutraceutical
StiripentolThe serum concentration of Phenoxybenzamine can be increased when it is combined with Stiripentol.Approved
StreptokinaseThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Streptokinase.Approved, Investigational
SufentanilThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sufentanil.Approved, Investigational
SulfisoxazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TadalafilTadalafil may increase the antihypertensive activities of Phenoxybenzamine.Approved, Investigational
TalinololPhenoxybenzamine may increase the hypotensive activities of Talinolol.Investigational
TamsulosinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tamsulosin.Approved, Investigational
TelaprevirThe metabolism of Phenoxybenzamine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Phenoxybenzamine can be decreased when combined with Telithromycin.Approved
TelmisartanPhenoxybenzamine may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilPhenoxybenzamine may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerazosinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Terazosin.Approved
TerlipressinPhenoxybenzamine may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatinePhenoxybenzamine may increase the hypotensive activities of Tetrahydropalmatine.Investigational
ThalidomideThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Thalidomide.Approved, Investigational, Withdrawn
TheodrenalinePhenoxybenzamine may increase the hypotensive activities of Theodrenaline.Investigational
ThiamylalThiamylal may increase the hypotensive activities of Phenoxybenzamine.Approved, Vet Approved
ThiopentalThiopental may increase the hypotensive activities of Phenoxybenzamine.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Thioridazine.Approved, Withdrawn
TibolonePhenoxybenzamine may increase the hypotensive activities of Tibolone.Approved, Investigational
TiclopidineThe metabolism of Phenoxybenzamine can be decreased when combined with Ticlopidine.Approved
TicrynafenPhenoxybenzamine may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Phenoxybenzamine.Approved
TizanidineThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tizanidine.Approved, Investigational
TocilizumabThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Tocilizumab.Approved
TolazolineTolazoline may increase the hypotensive activities of Phenoxybenzamine.Approved, Vet Approved
TolcaponeThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tolcapone.Approved, Withdrawn
TolonidinePhenoxybenzamine may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Phenoxybenzamine.Approved
TorasemideTorasemide may increase the hypotensive activities of Phenoxybenzamine.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Phenoxybenzamine.Approved
TranylcypromineTranylcypromine may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
TravoprostTravoprost may increase the hypotensive activities of Phenoxybenzamine.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
TretinoinThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tretinoin.Approved, Investigational, Nutraceutical
TriamtereneThe risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Triamterene.Approved
TrichlormethiazidePhenoxybenzamine may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Phenoxybenzamine.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
UdenafilUdenafil may increase the antihypertensive activities of Phenoxybenzamine.Approved, Investigational
UnoprostonePhenoxybenzamine may increase the hypotensive activities of Unoprostone.Approved, Investigational
UrapidilUrapidil may increase the hypotensive activities of Phenoxybenzamine.Investigational
ValsartanValsartan may increase the hypotensive activities of Phenoxybenzamine.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Phenoxybenzamine.Approved
VemurafenibThe serum concentration of Phenoxybenzamine can be decreased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Phenoxybenzamine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Phenoxybenzamine can be decreased when combined with Verapamil.Approved
VincaminePhenoxybenzamine may increase the hypotensive activities of Vincamine.Experimental
VinpocetinePhenoxybenzamine may increase the hypotensive activities of Vinpocetine.Investigational
VoriconazoleThe metabolism of Phenoxybenzamine can be decreased when combined with Voriconazole.Approved, Investigational
XipamidePhenoxybenzamine may increase the hypotensive activities of Xipamide.Experimental
XylometazolinePhenoxybenzamine may increase the hypotensive activities of Xylometazoline.Approved, Investigational
YohimbineYohimbine may decrease the antihypertensive activities of Phenoxybenzamine.Approved, Investigational, Vet Approved
ZiprasidoneThe metabolism of Phenoxybenzamine can be decreased when combined with Ziprasidone.Approved
ZofenoprilPhenoxybenzamine may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

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
Human Metabolome Database
HMDB0015061
KEGG Compound
C07435
PubChem Compound
4768
PubChem Substance
46507191
ChemSpider
4604
BindingDB
50017679
ChEBI
8077
ChEMBL
CHEMBL753
Therapeutic Targets Database
DAP000478
PharmGKB
PA450919
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phenoxybenzamine
ATC Codes
C04AX02 — Phenoxybenzamine
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentCardiopulmonary Bypass / Open-heart Surgery1
2Unknown StatusTreatmentCongenital Heart Disease (CHD)1
3RecruitingTreatmentParaganglioma / Pheochromocytomas1
4CompletedTreatmentPheochromocytomas1
Not AvailableTerminatedTreatmentCardiopulmonary Bypass / Congenital Heart Surgery1

Pharmacoeconomics

Manufacturers
  • Wellspring pharmaceutical corp
Packagers
  • Gallipot
  • Murfreesboro Pharmaceutical Nursing Supply
  • Wellspring Pharmaceutical
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)39 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylmethylamines
Alternative Parents
Phenoxy compounds / Phenol ethers / Benzylamines / Aralkylamines / Alkyl aryl ethers / Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives / Alkyl chlorides
Substituents
Benzylamine / Phenoxy compound / Phenol ether / Phenylmethylamine / Alkyl aryl ether / Aralkylamine / Tertiary aliphatic amine / Tertiary amine / Ether / Organopnictogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aromatic amine (CHEBI:8077)

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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
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 oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
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
Uniprot Name
Alpha-2C adrenergic receptor
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...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
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...
Gene Name
CALM1
Uniprot ID
P0DP23
Uniprot Name
Calmodulin
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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
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
Uniprot Name
Alpha-1D adrenergic receptor
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
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, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
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
Uniprot Name
Solute carrier family 22 member 3
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]

Drug created on June 13, 2005 07:24 / Updated on May 02, 2018 01:18