Phenoxybenzamine - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (8)Enzymes (1)Transporters (3)

Targets (8)Enzymes (1)Transporters (3)Biointeractions (11)

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Dibenzyline

Fenossibenzamina

Fenoxibenzamina

Phenoxybenzamine

Phenoxybenzaminum

POB

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Phenoxybenzamine Hydrochloride	X1IEG24OHL	63-92-3	VBCPVIWPDJVHAN-UHFFFAOYNA-N	Details

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Dibenzyline	Capsule	10 mg/1	Oral	Well Spring Pharmaceutical Corporation	1999-10-01	Not applicable	US
Dibenzyline	Capsule	10 mg/1	Oral	Concordia Pharmaceuticals, Inc	1953-01-26	Not applicable	US
Phenoxybenzamine Hydrochloride	Capsule	10 mg/1	Oral	Prasco, Laboratories	2015-08-11	Not applicable	US

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Phenoxybenzamine Hydrochloride	Capsule	10 mg/1	Oral	West Ward Pharmaceutical	2015-08-10	Not applicable	US
Phenoxybenzamine Hydrochloride	Capsule	10 mg/1	Oral	Par Pharmaceutical	2017-01-24	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Alpha-1A adrenergic receptor	Protein	yes	antagonist	Human	P35348	details
Alpha-2A adrenergic receptor	Protein	yes	antagonist	Human	P08913	details
Alpha-2C adrenergic receptor	Protein	unknown	antagonist	Human	P18825	details
Alpha-2B adrenergic receptor	Protein	unknown	antagonist	Human	P18089	details
Calmodulin	Protein	unknown	inhibitor	Human	P0DP23	details
Beta-2 adrenergic receptor	Protein	unknown	Not Available	Human	P07550	details
Alpha-1B adrenergic receptor	Protein	unknown	antagonist	Human	P35368	details
Alpha-1D adrenergic receptor	Protein	unknown	antagonist	Human	P25100	details

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

Drug	Interaction	Drug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	7,8-DICHLORO-1,2,3,4-TETRAHYDROISOQUINOLINE may increase the hypotensive activities of Phenoxybenzamine.	Experimental
Acebutolol	Phenoxybenzamine may increase the hypotensive activities of Acebutolol.	Approved
Acetazolamide	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Acetazolamide.	Approved, Vet Approved
Aldesleukin	The risk or severity of adverse effects can be increased when Aldesleukin is combined with Phenoxybenzamine.	Approved
Alfuzosin	Alfuzosin may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Aliskiren	Phenoxybenzamine may increase the hypotensive activities of Aliskiren.	Approved, Investigational
Alprenolol	Alprenolol may increase the hypotensive activities of Phenoxybenzamine.	Approved, Withdrawn
Ambrisentan	Phenoxybenzamine may increase the hypotensive activities of Ambrisentan.	Approved, Investigational
Amifostine	Phenoxybenzamine may increase the hypotensive activities of Amifostine.	Approved, Investigational
Amiloride	The risk or severity of adverse effects can be increased when Amiloride is combined with Phenoxybenzamine.	Approved
Amiodarone	The metabolism of Phenoxybenzamine can be decreased when combined with Amiodarone.	Approved, Investigational
Amlodipine	Amlodipine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Amobarbital	Amobarbital may increase the hypotensive activities of Phenoxybenzamine.	Approved, Illicit
Amphotericin B	The risk or severity of adverse effects can be increased when Amphotericin B is combined with Phenoxybenzamine.	Approved, Investigational
Amyl Nitrite	The risk or severity of adverse effects can be increased when Amyl Nitrite is combined with Phenoxybenzamine.	Approved
Apomorphine	The risk or severity of adverse effects can be increased when Apomorphine is combined with Phenoxybenzamine.	Approved, Investigational
Apraclonidine	The risk or severity of adverse effects can be increased when Apraclonidine is combined with Phenoxybenzamine.	Approved
Aprepitant	The serum concentration of Phenoxybenzamine can be increased when it is combined with Aprepitant.	Approved, Investigational
Aripiprazole	Aripiprazole may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Arotinolol	The risk or severity of adverse effects can be increased when Arotinolol is combined with Phenoxybenzamine.	Approved
Arsenic trioxide	The risk or severity of adverse effects can be increased when Arsenic trioxide is combined with Phenoxybenzamine.	Approved, Investigational
Atazanavir	The metabolism of Phenoxybenzamine can be decreased when combined with Atazanavir.	Approved, Investigational
Atenolol	Atenolol may increase the hypotensive activities of Phenoxybenzamine.	Approved
Atomoxetine	The metabolism of Phenoxybenzamine can be decreased when combined with Atomoxetine.	Approved
Azilsartan medoxomil	The risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Phenoxybenzamine.	Approved
Barbexaclone	Barbexaclone may increase the hypotensive activities of Phenoxybenzamine.	Experimental
Barbital	Barbital may increase the hypotensive activities of Phenoxybenzamine.	Illicit
Barnidipine	The risk or severity of adverse effects can be increased when Barnidipine is combined with Phenoxybenzamine.	Approved
Benazepril	Benazepril may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Bendroflumethiazide	Bendroflumethiazide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Benmoxin	Benmoxin may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Bepridil	Phenoxybenzamine may increase the hypotensive activities of Bepridil.	Approved, Withdrawn
Betaxolol	Betaxolol may increase the hypotensive activities of Phenoxybenzamine.	Approved
Bethanidine	Bethanidine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Bexarotene	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Bexarotene.	Approved, Investigational
Bimatoprost	Bimatoprost may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Bisoprolol	Bisoprolol may increase the hypotensive activities of Phenoxybenzamine.	Approved
Boceprevir	The metabolism of Phenoxybenzamine can be decreased when combined with Boceprevir.	Approved, Investigational
Bortezomib	The metabolism of Phenoxybenzamine can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Bosentan.	Approved, Investigational
Bretylium	Phenoxybenzamine may increase the hypotensive activities of Bretylium.	Approved
Brimonidine	Brimonidine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Brimonidine	Brimonidine may increase the antihypertensive activities of Phenoxybenzamine.	Approved
Bromocriptine	The risk or severity of adverse effects can be increased when Bromocriptine is combined with Phenoxybenzamine.	Approved, Investigational
Bumetanide	The risk or severity of adverse effects can be increased when Bumetanide is combined with Phenoxybenzamine.	Approved
Bupivacaine	The risk or severity of adverse effects can be increased when Bupivacaine is combined with Phenoxybenzamine.	Approved, Investigational
Bupranolol	Phenoxybenzamine may increase the hypotensive activities of Bupranolol.	Approved
Canagliflozin	The risk or severity of adverse effects can be increased when Canagliflozin is combined with Phenoxybenzamine.	Approved
Candesartan	Candesartan may increase the hypotensive activities of Phenoxybenzamine.	Approved
Candoxatril	Candoxatril may increase the hypotensive activities of Phenoxybenzamine.	Experimental
Captopril	Phenoxybenzamine may increase the hypotensive activities of Captopril.	Approved
Carbamazepine	The metabolism of Phenoxybenzamine can be increased when combined with Carbamazepine.	Approved, Investigational
Carbetocin	The risk or severity of adverse effects can be increased when Carbetocin is combined with Phenoxybenzamine.	Approved
Caroxazone	Caroxazone may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Carteolol	Carteolol may increase the hypotensive activities of Phenoxybenzamine.	Approved
Carvedilol	Phenoxybenzamine may increase the hypotensive activities of Carvedilol.	Approved, Investigational
Celiprolol	Phenoxybenzamine may increase the hypotensive activities of Celiprolol.	Approved, Investigational
Ceritinib	The serum concentration of Phenoxybenzamine can be increased when it is combined with Ceritinib.	Approved
Chlorothiazide	Chlorothiazide may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Chlorpromazine	The risk or severity of adverse effects can be increased when Chlorpromazine is combined with Phenoxybenzamine.	Approved, Vet Approved
Chlorthalidone	Chlorthalidone may increase the hypotensive activities of Phenoxybenzamine.	Approved
Cilazapril	Phenoxybenzamine may increase the hypotensive activities of Cilazapril.	Approved
Cilnidipine	The risk or severity of adverse effects can be increased when Cilnidipine is combined with Phenoxybenzamine.	Approved
Clarithromycin	The metabolism of Phenoxybenzamine can be decreased when combined with Clarithromycin.	Approved
Clemastine	The metabolism of Phenoxybenzamine can be decreased when combined with Clemastine.	Approved
Clevidipine	The risk or severity of adverse effects can be increased when Clevidipine is combined with Phenoxybenzamine.	Approved
Clofarabine	The risk or severity of adverse effects can be increased when Clofarabine is combined with Phenoxybenzamine.	Approved, Investigational
Clomipramine	The risk or severity of adverse effects can be increased when Clomipramine is combined with Phenoxybenzamine.	Approved, Vet Approved
Clonidine	Clonidine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Clotrimazole	The metabolism of Phenoxybenzamine can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Clozapine	The risk or severity of adverse effects can be increased when Clozapine is combined with Phenoxybenzamine.	Approved
Cobicistat	The metabolism of Phenoxybenzamine can be decreased when combined with Cobicistat.	Approved
Conivaptan	The serum concentration of Phenoxybenzamine can be increased when it is combined with Conivaptan.	Approved, Investigational
Crizotinib	The metabolism of Phenoxybenzamine can be decreased when combined with Crizotinib.	Approved
Cryptenamine	Cryptenamine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Cyclosporine	The metabolism of Phenoxybenzamine can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Cyclothiazide	Cyclothiazide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Dabrafenib	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Dabrafenib.	Approved
Dapagliflozin	The risk or severity of adverse effects can be increased when Dapagliflozin is combined with Phenoxybenzamine.	Approved
Darunavir	The metabolism of Phenoxybenzamine can be decreased when combined with Darunavir.	Approved
Dasatinib	The serum concentration of Phenoxybenzamine can be increased when it is combined with Dasatinib.	Approved, Investigational
Debrisoquin	Phenoxybenzamine may increase the hypotensive activities of Debrisoquin.	Approved
Deferasirox	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Phenoxybenzamine can be decreased when combined with Delavirdine.	Approved
Deserpidine	Phenoxybenzamine may increase the hypotensive activities of Deserpidine.	Approved
Desflurane	The risk or severity of adverse effects can be increased when Desflurane is combined with Phenoxybenzamine.	Approved
Dexamethasone	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dexmedetomidine	The risk or severity of adverse effects can be increased when Dexmedetomidine is combined with Phenoxybenzamine.	Approved, Vet Approved
Diazoxide	Diazoxide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Diclofenamide	The risk or severity of adverse effects can be increased when Diclofenamide is combined with Phenoxybenzamine.	Approved
Dihydralazine	Phenoxybenzamine may increase the hypotensive activities of Dihydralazine.	Investigational
Dihydroergotamine	The metabolism of Phenoxybenzamine can be decreased when combined with Dihydroergotamine.	Approved
Diltiazem	The metabolism of Phenoxybenzamine can be decreased when combined with Diltiazem.	Approved
Dinutuximab	The risk or severity of adverse effects can be increased when Dinutuximab is combined with Phenoxybenzamine.	Approved
Dipyridamole	The risk or severity of adverse effects can be increased when Dipyridamole is combined with Phenoxybenzamine.	Approved
Dorzolamide	Dorzolamide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Doxazosin	Doxazosin may increase the hypotensive activities of Phenoxybenzamine.	Approved
Doxycycline	The metabolism of Phenoxybenzamine can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronedarone	The metabolism of Phenoxybenzamine can be decreased when combined with Dronedarone.	Approved
Duloxetine	Phenoxybenzamine may increase the orthostatic hypotensive activities of Duloxetine.	Approved
Efavirenz	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Efavirenz.	Approved, Investigational
Efonidipine	Phenoxybenzamine may increase the hypotensive activities of Efonidipine.	Approved
Empagliflozin	The risk or severity of adverse effects can be increased when Empagliflozin is combined with Phenoxybenzamine.	Approved
Enalapril	Enalapril may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Enalaprilat	Phenoxybenzamine may increase the hypotensive activities of Enalaprilat.	Approved
Enzalutamide	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Enzalutamide.	Approved
Eplerenone	The risk or severity of adverse effects can be increased when Eplerenone is combined with Phenoxybenzamine.	Approved
Epoprostenol	Phenoxybenzamine may increase the hypotensive activities of Epoprostenol.	Approved
Eprosartan	Eprosartan may increase the hypotensive activities of Phenoxybenzamine.	Approved
Erythromycin	The metabolism of Phenoxybenzamine can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Esmolol	The risk or severity of adverse effects can be increased when Esmolol is combined with Phenoxybenzamine.	Approved
Etacrynic acid	The risk or severity of adverse effects can be increased when Etacrynic acid is combined with Phenoxybenzamine.	Approved
Etravirine	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Etravirine.	Approved
Felodipine	Phenoxybenzamine may increase the hypotensive activities of Felodipine.	Approved, Investigational
Fenoldopam	Fenoldopam may increase the hypotensive activities of Phenoxybenzamine.	Approved
Fimasartan	The risk or severity of adverse effects can be increased when Fimasartan is combined with Phenoxybenzamine.	Approved
Fluconazole	The metabolism of Phenoxybenzamine can be decreased when combined with Fluconazole.	Approved
Fluvoxamine	The metabolism of Phenoxybenzamine can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fosamprenavir	The metabolism of Phenoxybenzamine can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Phenoxybenzamine can be increased when it is combined with Fosaprepitant.	Approved
Fosinopril	Fosinopril may increase the hypotensive activities of Phenoxybenzamine.	Approved
Fosphenytoin	The metabolism of Phenoxybenzamine can be increased when combined with Fosphenytoin.	Approved
Furazolidone	Furazolidone may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Furosemide	The risk or severity of adverse effects can be increased when Furosemide is combined with Phenoxybenzamine.	Approved, Vet Approved
Fusidic Acid	The serum concentration of Phenoxybenzamine can be increased when it is combined with Fusidic Acid.	Approved
Guanabenz	Guanabenz may increase the hypotensive activities of Phenoxybenzamine.	Approved
Guanadrel	Guanadrel may increase the hypotensive activities of Phenoxybenzamine.	Approved
Guanethidine	Phenoxybenzamine may increase the hypotensive activities of Guanethidine.	Approved
Guanfacine	Phenoxybenzamine may increase the hypotensive activities of Guanfacine.	Approved, Investigational
Halothane	The risk or severity of adverse effects can be increased when Halothane is combined with Phenoxybenzamine.	Approved, Vet Approved
Hexamethonium	Phenoxybenzamine may increase the hypotensive activities of Hexamethonium.	Experimental
Hexobarbital	Hexobarbital may increase the hypotensive activities of Phenoxybenzamine.	Approved
Hydracarbazine	Hydracarbazine may increase the hypotensive activities of Phenoxybenzamine.	Experimental
Hydralazine	Phenoxybenzamine may increase the hypotensive activities of Hydralazine.	Approved
Hydrochlorothiazide	Phenoxybenzamine may increase the hypotensive activities of Hydrochlorothiazide.	Approved, Vet Approved
Hydroflumethiazide	Hydroflumethiazide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Idelalisib	The serum concentration of Phenoxybenzamine can be increased when it is combined with Idelalisib.	Approved
Iloprost	Iloprost may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Imatinib	The metabolism of Phenoxybenzamine can be decreased when combined with Imatinib.	Approved
Imidapril	The risk or severity of adverse effects can be increased when Imidapril is combined with Phenoxybenzamine.	Investigational
Imipramine	The risk or severity of adverse effects can be increased when Imipramine is combined with Phenoxybenzamine.	Approved
Indapamide	Indapamide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Indenolol	Phenoxybenzamine may increase the hypotensive activities of Indenolol.	Withdrawn
Indinavir	The metabolism of Phenoxybenzamine can be decreased when combined with Indinavir.	Approved
Indoramin	Phenoxybenzamine may increase the hypotensive activities of Indoramin.	Withdrawn
Iproclozide	Iproclozide may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Iproniazid	Iproniazid may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Irbesartan	Phenoxybenzamine may increase the hypotensive activities of Irbesartan.	Approved, Investigational
Isavuconazonium	The metabolism of Phenoxybenzamine can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isocarboxazid	Isocarboxazid may increase the hypotensive activities of Phenoxybenzamine.	Approved
Isoflurane	The risk or severity of adverse effects can be increased when Isoflurane is combined with Phenoxybenzamine.	Approved, Vet Approved
Isosorbide Dinitrate	The risk or severity of adverse effects can be increased when Isosorbide Dinitrate is combined with Phenoxybenzamine.	Approved
Isosorbide Mononitrate	The risk or severity of adverse effects can be increased when Isosorbide Mononitrate is combined with Phenoxybenzamine.	Approved
Isoxsuprine	The risk or severity of adverse effects can be increased when Isoxsuprine is combined with Phenoxybenzamine.	Approved, Withdrawn
Isradipine	The metabolism of Phenoxybenzamine can be decreased when combined with Isradipine.	Approved
Itraconazole	The metabolism of Phenoxybenzamine can be decreased when combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Phenoxybenzamine can be increased when it is combined with Ivacaftor.	Approved
Ketanserin	Phenoxybenzamine may increase the hypotensive activities of Ketanserin.	Investigational
Ketoconazole	The metabolism of Phenoxybenzamine can be decreased when combined with Ketoconazole.	Approved, Investigational
Labetalol	Labetalol may increase the hypotensive activities of Phenoxybenzamine.	Approved
Lacidipine	Phenoxybenzamine may increase the hypotensive activities of Lacidipine.	Approved
Latanoprost	Latanoprost may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Lercanidipine	Lercanidipine may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Levobunolol	The risk or severity of adverse effects can be increased when Levobunolol is combined with Phenoxybenzamine.	Approved
Levobupivacaine	The risk or severity of adverse effects can be increased when Levobupivacaine is combined with Phenoxybenzamine.	Approved
Levodopa	Phenoxybenzamine may increase the orthostatic hypotensive activities of Levodopa.	Approved
Levosimendan	The risk or severity of adverse effects can be increased when Levosimendan is combined with Phenoxybenzamine.	Approved, Investigational
Lisinopril	Lisinopril may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Lofexidine	Phenoxybenzamine may increase the hypotensive activities of Lofexidine.	Approved, Investigational
Lopinavir	The metabolism of Phenoxybenzamine can be decreased when combined with Lopinavir.	Approved
Losartan	Losartan may increase the hypotensive activities of Phenoxybenzamine.	Approved
Lovastatin	The metabolism of Phenoxybenzamine can be decreased when combined with Lovastatin.	Approved, Investigational
Luliconazole	The serum concentration of Phenoxybenzamine can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The metabolism of Phenoxybenzamine can be increased when combined with Lumacaftor.	Approved
Macitentan	Phenoxybenzamine may increase the hypotensive activities of Macitentan.	Approved
Manidipine	Phenoxybenzamine may increase the hypotensive activities of Manidipine.	Approved
Mannitol	The risk or severity of adverse effects can be increased when Mannitol is combined with Phenoxybenzamine.	Approved, Investigational
Mebanazine	Mebanazine may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Mecamylamine	Mecamylamine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Methazolamide	The risk or severity of adverse effects can be increased when Methazolamide is combined with Phenoxybenzamine.	Approved
Methohexital	Methohexital may increase the hypotensive activities of Phenoxybenzamine.	Approved
Methyclothiazide	The risk or severity of adverse effects can be increased when Methyclothiazide is combined with Phenoxybenzamine.	Approved
Methyldopa	Phenoxybenzamine may increase the hypotensive activities of Methyldopa.	Approved
Methylene blue	Methylene blue may increase the hypotensive activities of Phenoxybenzamine.	Investigational
Methylphenidate	Methylphenidate may decrease the antihypertensive activities of Phenoxybenzamine.	Approved, Investigational
Methylphenobarbital	Methylphenobarbital may increase the hypotensive activities of Phenoxybenzamine.	Approved
Metipranolol	Phenoxybenzamine may increase the hypotensive activities of Metipranolol.	Approved
Metolazone	Metolazone may increase the hypotensive activities of Phenoxybenzamine.	Approved
Metoprolol	Metoprolol may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Metyrosine	Phenoxybenzamine may increase the hypotensive activities of Metyrosine.	Approved
Mibefradil	Phenoxybenzamine may increase the hypotensive activities of Mibefradil.	Withdrawn
Mifepristone	The serum concentration of Phenoxybenzamine can be increased when it is combined with Mifepristone.	Approved, Investigational
Minaprine	Minaprine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Minoxidil	Minoxidil may increase the hypotensive activities of Phenoxybenzamine.	Approved
Mitotane	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Mitotane.	Approved
Moclobemide	Moclobemide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Modafinil	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Modafinil.	Approved, Investigational
Moexipril	Moexipril may increase the hypotensive activities of Phenoxybenzamine.	Approved
Molsidomine	Molsidomine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Morphine	The risk or severity of adverse effects can be increased when Morphine is combined with Phenoxybenzamine.	Approved, Investigational
Moxonidine	Phenoxybenzamine may increase the hypotensive activities of Moxonidine.	Approved
Nabilone	The risk or severity of adverse effects can be increased when Nabilone is combined with Phenoxybenzamine.	Approved, Investigational
Nadolol	Phenoxybenzamine may increase the hypotensive activities of Nadolol.	Approved
Nafcillin	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Nafcillin.	Approved
Naftopidil	Phenoxybenzamine may increase the hypotensive activities of Naftopidil.	Investigational
Nebivolol	Phenoxybenzamine may increase the hypotensive activities of Nebivolol.	Approved, Investigational
Nefazodone	The metabolism of Phenoxybenzamine can be decreased when combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The metabolism of Phenoxybenzamine can be decreased when combined with Nelfinavir.	Approved
Nesiritide	The risk or severity of adverse effects can be increased when Nesiritide is combined with Phenoxybenzamine.	Approved, Investigational
Netupitant	The serum concentration of Phenoxybenzamine can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Phenoxybenzamine can be increased when combined with Nevirapine.	Approved
Nialamide	Nialamide may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Nicardipine	Nicardipine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Nicorandil	Nicorandil may increase the hypotensive activities of Phenoxybenzamine.	Approved
Nifedipine	The risk or severity of adverse effects can be increased when Nifedipine is combined with Phenoxybenzamine.	Approved
Niguldipine	Phenoxybenzamine may increase the hypotensive activities of Niguldipine.	Experimental
Nilotinib	The metabolism of Phenoxybenzamine can be decreased when combined with Nilotinib.	Approved, Investigational
Nilvadipine	Phenoxybenzamine may increase the hypotensive activities of Nilvadipine.	Approved
Nimodipine	Nimodipine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Nisoldipine	Nisoldipine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Nitrendipine	Phenoxybenzamine may increase the hypotensive activities of Nitrendipine.	Approved
Nitric Oxide	The risk or severity of adverse effects can be increased when Nitric Oxide is combined with Phenoxybenzamine.	Approved
Nitroglycerin	The risk or severity of adverse effects can be increased when Nitroglycerin is combined with Phenoxybenzamine.	Approved, Investigational
Nitroprusside	Nitroprusside may increase the hypotensive activities of Phenoxybenzamine.	Approved
Obinutuzumab	Phenoxybenzamine may increase the hypotensive activities of Obinutuzumab.	Approved
Octamoxin	Octamoxin may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Olaparib	The metabolism of Phenoxybenzamine can be decreased when combined with Olaparib.	Approved
Olmesartan	Olmesartan may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Omapatrilat	Omapatrilat may increase the hypotensive activities of Phenoxybenzamine.	Investigational
Osimertinib	The serum concentration of Phenoxybenzamine can be increased when it is combined with Osimertinib.	Approved
Oxprenolol	Phenoxybenzamine may increase the hypotensive activities of Oxprenolol.	Approved
Paclitaxel	The risk or severity of adverse effects can be increased when Paclitaxel is combined with Phenoxybenzamine.	Approved, Vet Approved
Palbociclib	The serum concentration of Phenoxybenzamine can be increased when it is combined with Palbociclib.	Approved
Papaverine	The risk or severity of adverse effects can be increased when Papaverine is combined with Phenoxybenzamine.	Approved
Pargyline	Pargyline may increase the hypotensive activities of Phenoxybenzamine.	Approved
Penbutolol	Phenoxybenzamine may increase the hypotensive activities of Penbutolol.	Approved, Investigational
Pentobarbital	The metabolism of Phenoxybenzamine can be increased when combined with Pentobarbital.	Approved, Vet Approved
Pentolinium	Phenoxybenzamine may increase the hypotensive activities of Pentolinium.	Approved
Pentoxifylline	Pentoxifylline may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Perindopril	Perindopril may increase the hypotensive activities of Phenoxybenzamine.	Approved
Phenelzine	Phenelzine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Pheniprazine	Pheniprazine may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Phenobarbital	The metabolism of Phenoxybenzamine can be increased when combined with Phenobarbital.	Approved
Phenoxypropazine	Phenoxypropazine may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Phentolamine	Phentolamine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Phenytoin	The metabolism of Phenoxybenzamine can be increased when combined with Phenytoin.	Approved, Vet Approved
Pindolol	Phenoxybenzamine may increase the hypotensive activities of Pindolol.	Approved
Pipamperone	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Pipamperone.	Approved
Pirlindole	Pirlindole may increase the hypotensive activities of Phenoxybenzamine.	Approved
Pivhydrazine	Pivhydrazine may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Polythiazide	Phenoxybenzamine may increase the hypotensive activities of Polythiazide.	Approved
Posaconazole	The metabolism of Phenoxybenzamine can be decreased when combined with Posaconazole.	Approved, Investigational, Vet Approved
Pramipexole	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Pramipexole.	Approved, Investigational
Prazosin	Prazosin may increase the hypotensive activities of Phenoxybenzamine.	Approved
Primidone	The metabolism of Phenoxybenzamine can be increased when combined with Primidone.	Approved, Vet Approved
Propofol	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Propofol.	Approved, Investigational, Vet Approved
Propranolol	Propranolol may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Quetiapine	The risk or severity of adverse effects can be increased when Quetiapine is combined with Phenoxybenzamine.	Approved
Quinapril	Quinapril may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Quinine	Quinine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Ramipril	Ramipril may increase the hypotensive activities of Phenoxybenzamine.	Approved
Ranolazine	The metabolism of Phenoxybenzamine can be decreased when combined with Ranolazine.	Approved, Investigational
Rasagiline	Rasagiline may increase the hypotensive activities of Phenoxybenzamine.	Approved
Remifentanil	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Remifentanil.	Approved
Remikiren	Remikiren may increase the hypotensive activities of Phenoxybenzamine.	Approved
Rescinnamine	Phenoxybenzamine may increase the hypotensive activities of Rescinnamine.	Approved
Reserpine	Reserpine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Rifabutin	The metabolism of Phenoxybenzamine can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Phenoxybenzamine can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Phenoxybenzamine can be increased when combined with Rifapentine.	Approved
Rilmenidine	Phenoxybenzamine may increase the hypotensive activities of Rilmenidine.	Investigational
Riociguat	Phenoxybenzamine may increase the hypotensive activities of Riociguat.	Approved
Risperidone	Phenoxybenzamine may increase the hypotensive activities of Risperidone.	Approved, Investigational
Ritonavir	The metabolism of Phenoxybenzamine can be decreased when combined with Ritonavir.	Approved, Investigational
Rituximab	Phenoxybenzamine may increase the hypotensive activities of Rituximab.	Approved
Ropinirole	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Ropinirole.	Approved, Investigational
Ropivacaine	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Ropivacaine.	Approved
Rotigotine	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Rotigotine.	Approved
Sacubitril	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sacubitril.	Approved
Safrazine	Safrazine may increase the hypotensive activities of Phenoxybenzamine.	Withdrawn
Saprisartan	Phenoxybenzamine may increase the hypotensive activities of Saprisartan.	Experimental
Saquinavir	The metabolism of Phenoxybenzamine can be decreased when combined with Saquinavir.	Approved, Investigational
Secobarbital	Secobarbital may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Selegiline	Selegiline may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational, Vet Approved
Selexipag	Phenoxybenzamine may increase the hypotensive activities of Selexipag.	Approved
Sevoflurane	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sevoflurane.	Approved, Vet Approved
Sildenafil	Sildenafil may increase the antihypertensive activities of Phenoxybenzamine.	Approved, Investigational
Siltuximab	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Phenoxybenzamine can be increased when it is combined with Simeprevir.	Approved
Sitaxentan	Phenoxybenzamine may increase the hypotensive activities of Sitaxentan.	Approved, Investigational, Withdrawn
Sodium Nitrite	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sodium Nitrite.	Approved
Sotalol	The risk or severity of adverse effects can be increased when Sotalol is combined with Phenoxybenzamine.	Approved
Spirapril	Phenoxybenzamine may increase the hypotensive activities of Spirapril.	Approved
Spironolactone	The risk or severity of adverse effects can be increased when Spironolactone is combined with Phenoxybenzamine.	Approved
St. John's Wort	The serum concentration of Phenoxybenzamine can be decreased when it is combined with St. John's Wort.	Nutraceutical
Stiripentol	The serum concentration of Phenoxybenzamine can be increased when it is combined with Stiripentol.	Approved
Streptokinase	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Streptokinase.	Approved
Sufentanil	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Sufentanil.	Approved, Investigational
Sulfisoxazole	The metabolism of Phenoxybenzamine can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Tadalafil	Tadalafil may increase the antihypertensive activities of Phenoxybenzamine.	Approved, Investigational
Tamsulosin	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tamsulosin.	Approved, Investigational
Telaprevir	The metabolism of Phenoxybenzamine can be decreased when combined with Telaprevir.	Withdrawn
Telithromycin	The metabolism of Phenoxybenzamine can be decreased when combined with Telithromycin.	Approved
Telmisartan	Phenoxybenzamine may increase the hypotensive activities of Telmisartan.	Approved, Investigational
Temocapril	Phenoxybenzamine may increase the hypotensive activities of Temocapril.	Experimental, Investigational
Terazosin	The risk or severity of adverse effects can be increased when Terazosin is combined with Phenoxybenzamine.	Approved
Terlipressin	Phenoxybenzamine may increase the hypotensive activities of Terlipressin.	Approved, Investigational
Thalidomide	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Thalidomide.	Approved, Investigational, Withdrawn
Thiamylal	Thiamylal may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Thiopental	Thiopental may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Thioridazine	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Thioridazine.	Withdrawn
Tibolone	Phenoxybenzamine may increase the hypotensive activities of Tibolone.	Approved
Ticlopidine	The metabolism of Phenoxybenzamine can be decreased when combined with Ticlopidine.	Approved
Ticrynafen	Phenoxybenzamine may increase the hypotensive activities of Ticrynafen.	Withdrawn
Timolol	Timolol may increase the hypotensive activities of Phenoxybenzamine.	Approved
Tizanidine	The risk or severity of adverse effects can be increased when Tizanidine is combined with Phenoxybenzamine.	Approved
Tocilizumab	The serum concentration of Phenoxybenzamine can be decreased when it is combined with Tocilizumab.	Approved
Tolazoline	Tolazoline may increase the hypotensive activities of Phenoxybenzamine.	Approved, Vet Approved
Tolcapone	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tolcapone.	Approved, Withdrawn
Toloxatone	Toloxatone may increase the hypotensive activities of Phenoxybenzamine.	Approved
Torasemide	Torasemide may increase the hypotensive activities of Phenoxybenzamine.	Approved
Trandolapril	Trandolapril may increase the hypotensive activities of Phenoxybenzamine.	Approved
Trans-2-Phenylcyclopropylamine	Trans-2-Phenylcyclopropylamine may increase the hypotensive activities of Phenoxybenzamine.	Experimental
Tranylcypromine	Tranylcypromine may increase the hypotensive activities of Phenoxybenzamine.	Approved
Travoprost	Travoprost may increase the hypotensive activities of Phenoxybenzamine.	Approved
Treprostinil	Treprostinil may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Tretinoin	The risk or severity of adverse effects can be increased when Phenoxybenzamine is combined with Tretinoin.	Approved, Investigational, Nutraceutical
Triamterene	The risk or severity of adverse effects can be increased when Triamterene is combined with Phenoxybenzamine.	Approved
Trichlormethiazide	Phenoxybenzamine may increase the hypotensive activities of Trichlormethiazide.	Approved, Vet Approved
Trimazosin	Phenoxybenzamine may increase the hypotensive activities of Trimazosin.	Experimental
Trimethaphan	Phenoxybenzamine may increase the hypotensive activities of Trimethaphan.	Approved
Udenafil	Udenafil may increase the antihypertensive activities of Phenoxybenzamine.	Approved, Investigational
Unoprostone	Phenoxybenzamine may increase the hypotensive activities of Unoprostone.	Approved
Valsartan	Valsartan may increase the hypotensive activities of Phenoxybenzamine.	Approved, Investigational
Vardenafil	Vardenafil may increase the antihypertensive activities of Phenoxybenzamine.	Approved
Venlafaxine	The metabolism of Phenoxybenzamine can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Phenoxybenzamine can be decreased when combined with Verapamil.	Approved
Vinpocetine	Phenoxybenzamine may increase the hypotensive activities of Vinpocetine.	Investigational
Voriconazole	The metabolism of Phenoxybenzamine can be decreased when combined with Voriconazole.	Approved, Investigational
Xylometazoline	Phenoxybenzamine may increase the hypotensive activities of Xylometazoline.	Approved
Yohimbine	Yohimbine may decrease the antihypertensive activities of Phenoxybenzamine.	Approved, Vet Approved
Ziprasidone	The metabolism of Phenoxybenzamine can be decreased when combined with Ziprasidone.	Approved

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
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

Resource	Link
Human Metabolome Database (HMDB)	HMDB15061
KEGG Compound	C07435
PubChem Compound	4768
PubChem Substance	46507191
ChemSpider	4604
BindingDB	50017679
ChEBI	8077
ChEMBL	CHEMBL753
Therapeutic Targets Database	DAP000478
PharmGKB	PA450919
RxList	http://www.rxlist.com/cgi/generic3/phenoxybenz.htm
Drugs.com	http://www.drugs.com/cdi/phenoxybenzamine.html
Wikipedia	Phenoxybenzamine

ATC Codes

C04AX02 — Phenoxybenzamine

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (73.8 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
2	Completed	Treatment	Cardiopulmonary Bypass / Open-heart Surgery	1
2	Unknown Status	Treatment	Congenital Heart Disease (CHD)	1
3	Recruiting	Treatment	Paraganglioma / Pheochromocytomas	1
4	Recruiting	Treatment	Pheochromocytomas	1
Not Available	Unknown Status	Treatment	Cardiopulmonary Bypass / Congenital Heart Surgery	1

Pharmacoeconomics

Manufacturers

Wellspring pharmaceutical corp

Packagers

Dosage forms

Form	Route	Strength
Capsule	Oral	10 mg/1

Prices

Unit description	Cost	Unit
Phenoxybenzamine hcl powd	42.35USD	g
Dibenzyline 10 mg capsule	8.61USD	capsule

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	39 °C	PhysProp
logP	4.7	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0103 mg/mL	ALOGPS
logP	4.26	ALOGPS
logP	4.64	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	7.97	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.92 m³·mol^-1	ChemAxon
Polarizability	34.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9629
Caco-2 permeable	+	0.7367
P-glycoprotein substrate	Substrate	0.6059
P-glycoprotein inhibitor I	Inhibitor	0.6043
P-glycoprotein inhibitor II	Inhibitor	0.5871
Renal organic cation transporter	Inhibitor	0.7955
CYP450 2C9 substrate	Non-substrate	0.6666
CYP450 2D6 substrate	Non-substrate	0.6013
CYP450 3A4 substrate	Substrate	0.5937
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Non-inhibitor	0.7714
CYP450 2D6 inhibitor	Inhibitor	0.8931
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.6682
Ames test	AMES toxic	0.9107
Carcinogenicity	Non-carcinogens	0.7565
Biodegradation	Not ready biodegradable	0.9973
Rat acute toxicity	2.1163 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.7145
hERG inhibition (predictor II)	Inhibitor	0.5874

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

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

Details

1. Alpha-1A adrenergic receptor

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

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 ]
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 ]
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 ]
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 ]
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 ]

Details

2. Alpha-2A adrenergic receptor

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

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 ]

Details

3. Alpha-2C adrenergic receptor

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

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 ]

Details

4. Alpha-2B adrenergic receptor

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

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 ]

Details

5. Calmodulin

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:: P0DP23
Molecular Weight:: 16837.47 Da

References

Cimino M, Weiss B: Characteristics of the binding of phenoxybenzamine to calmodulin. Biochem Pharmacol. 1988 Jul 15;37(14):2739-45. [PubMed:3134891 ]
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 ]
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 ]
Earl CQ, Prozialeck WC, Weiss B: Interaction of alpha adrenergic antagonists with calmodulin. Life Sci. 1984 Jul 30;35(5):525-34. [PubMed:6146911 ]
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 ]

Details

6. Beta-2 adrenergic receptor

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

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 ]

Details

7. Alpha-1B adrenergic receptor

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

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 ]

Details

8. Alpha-1D adrenergic receptor

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

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

Details

1. Cytochrome P450 3A4

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

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

Details

1. Solute carrier family 22 member 2

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

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 ]
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 ]

Details

2. Solute carrier family 22 member 1

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

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 ]

Details

3. Solute carrier family 22 member 3

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

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 July 18, 2017 16:54

Get DrugBank to go!

Structure for DB00925 (Phenoxybenzamine)

Targets

References

References

References

References

References

References

References

References

Enzymes

References

Transporters

References

References

References