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Details

Stereochemistry RACEMIC
Molecular Formula C18H22ClNO
Molecular Weight 303.826
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENOXYBENZAMINE

SMILES

CC(COC1=CC=CC=C1)N(CCCl)CC2=CC=CC=C2

InChI

InChIKey=QZVCTJOXCFMACW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Phenoxybenzamin (marketed under the trade name Dibenzyline) is an alpha-adrenergic antagonist with long duration of action. It is indicated in the treatment of pheochromocytoma, to control episodes of hypertension and sweating. If tachycardia is excessive, it may be necessary to use a beta-blocking agent concomitantly. 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. Phenoxybenzamine hydrochloride 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. Twenty to percent of orally administered phenoxybenzamine appears to be absorbed in the active form. The half-life of orally administered phenoxybenzamine hydrochloride is not known; however, the half-life of intravenously administered drug is approximately 24 hours. Demonstrable effects with intravenous administration persist for at least 3 to 4 days, and the effects of daily administration are cumulative for nearly a week. The following adverse reactions have been observed, but there are insufficient data to support an estimate of their frequency: Postural hypotension, tachycardia, inhibition of ejaculation, nasal congestion, and miosis. These so-called “side effects” are actually evidence of adrenergic blockade and vary according to the degree of blockade. Miscellaneous: Gastrointestinal irritation, drowsiness, fatigue.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DIBENZYLINE
PubMed

PubMed

TitleDatePubMed
Efficacy and safety of doxazosin for perioperative management of patients with pheochromocytoma.
2002 Aug
Norepinephrine release is reduced by I(1)-receptors in addition to alpha(2)-adrenoceptors.
2003 Dec
Comparative efficacies and durations of action of phenoxybenzamine, verapamil/nitroglycerin solution, and papaverine as topical antispasmodics for radial artery coronary bypass grafting.
2003 Dec
Remifentanil in the management of laparoscopic resection of phaeochromocytoma--case reports.
2003 Nov
Pretreatment with phenoxybenzamine attenuates the radial artery's vasoconstrictor response to alpha-adrenergic stimuli.
2003 Nov
Role of alpha-adrenergic receptors in the effect of the beta-adrenergic receptor ligands, CGP 12177, bupranolol, and SR 59230A, on the contraction of rat intrapulmonary artery.
2004 Apr
Involvement of different receptors in pituitary adenylate cyclase activating polypeptide induced open field activity in rats.
2004 Feb
Pheochromocytoma and pregnancy: a case report and review of anesthetic management.
2004 Feb
Release and functional role of neuropeptide Y as a sympathetic modulator in human saphenous vein biopsies.
2004 Jan
Effect of moderate pressure distention on the human saphenous vein vasomotor function.
2004 Jan
Medicinal plants in Suriname: hypotensive effect of Gossypium barbadense.
2004 Mar
Alteration of the critical arteriovenous oxygen saturation relationship by sustained afterload reduction after the Norwood procedure.
2004 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Initially, 10 mg twice a day. Dosage should be increased every other day, usually to 20 to 40 mg 2 or 3 times a day, until an optimal dosage is obtained, as judged by blood pressure control.
Route of Administration: Oral
Name Type Language
PHENOXYBENZAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENOXYBENZAMINE [INN]
Common Name English
BENSYLYT
Common Name English
BENZYLYT
Common Name English
(+/-)-PHENOXYBENZAMINE
Common Name English
DIBENYLIN
Common Name English
N-(2-CHLOROETHYL)-N-(1-METHYL-2-PHENOXYETHYL)BENZENEMETHANAMINE
Systematic Name English
BENZENEMETHANAMINE, N-(2-CHLOROETHYL)-N-(1-METHYL-2-PHENOXYETHYL)-
Systematic Name English
DIBENZYLINE
Brand Name English
PHENOXYBENZAMINE [HSDB]
Common Name English
BENZYLAMINE, N-(2-CHLOROETHYL)-N-(1-METHYL-2-PHENOXYETHYL)-
Systematic Name English
DIBENYLINE
Common Name English
PHENOXYBENZAMINE [VANDF]
Common Name English
N-(2-CHLOROETHYL)-N-(1-METHYL-2-PHENOXYETHYL)BENZYLAMINE
Systematic Name English
PHENOXYBENZAMINE [MI]
Common Name English
N-PHENOXYISOPROPYL-N-BENZYL-.BETA.-CHLOROETHYLAMINE
Systematic Name English
PHENOXYBENZAMINE [WHO-DD]
Common Name English
688A
Common Name English
Classification Tree Code System Code
NDF-RT N0000000099
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
WHO-ATC C04AX02
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
NDF-RT N0000175553
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
WHO-VATC QC04AX02
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
Code System Code Type Description
RXCUI
8149
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY RxNorm
INN
608
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
PUBCHEM
4768
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY SWITZERF
CAS
102737-84-8
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
SUPERSEDED
MESH
D010643
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
HSDB
59-96-1
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
ChEMBL
CHEMBL753
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-446-8
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
EVMPD
SUB09778MIG
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
WIKIPEDIA
PHENOXYBENZAMINE
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
DRUG BANK
DB00925
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
MERCK INDEX
M8638
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY Merck Index
IUPHAR
7268
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
NCI_THESAURUS
C62065
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
CAS
59-96-1
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY
EPA CompTox
59-96-1
Created by admin on Tue Mar 06 11:53:58 UTC 2018 , Edited by admin on Tue Mar 06 11:53:58 UTC 2018
PRIMARY