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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

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

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
THE EFFECT OF L-3, 4-DIHYDROXYPHENYLALANINE AND DL-5-HYDROXYTRYPTOPHAN ON RIGIDITY AND TREMOR INDUCED BY RESERPINE, CHLORPROMAZINE AND PHENOXYBENZAMINE.
1964 Apr
Evidence for antagonistic activity of endothelin for clonidine induced hypotension and bradycardia.
1992
[Comparison of selective alpha-1 blockades for alpha-receptors in human hypertrophied prostatic adenomas].
1992 Mar
[Prevention and release of epidural-morphine-induced urinary retention with phenoxybenzamine and neostigmine].
2000 Dec
[Sympathetically maintained pain syndrome--a case report].
2001
Pheochromocytoma in a pregnant woman with multiple endocrine neoplasia type 2a.
2001 Dec
Brief pretreatment of radial artery conduits with phenoxybenzamine prevents vasoconstriction long term.
2001 Dec
Changes in blood glucose and plasma insulin levels induced by bradykinin in anaesthetized rats.
2001 Nov
Responsiveness, affinity constants and receptor reserves for serotonin on aortae of aged normotensive and hypertensive rats.
2001 Oct
Rapid preparation of a patient with pheochromocytoma with labetolol and magnesium sulfate.
2001 Oct
Evaluation of functional response of cerebral arteries by a new morphometric technique.
2001 Oct 8
Agmatine, an endogenous ligand at imidazoline binding sites, does not antagonize the clonidine-mediated blood pressure reaction.
2002 Feb
alpha(1A)-adrenoceptors mediate sympathetically evoked pupillary dilation in rats.
2002 Feb
Cerebrovascular effects of intravenous dopamine infusions in fetal sheep.
2002 Feb
The action of orexin A on passive avoidance learning. Involvement of transmitters.
2002 Mar 15
Analgesia in phasic and tonic pain tests in a pharmacological model of autotomy.
2002 Nov
The role of alpha1D-adrenoceptors in prostatic contraction examined using protection studies.
2002 Oct-Dec
Neurotransmitter release in an arterial preparation and the action of alpha-adrenoceptor antagonists.
2002 Oct-Dec
One hundred years of adrenaline.
2003 Aug
Phenoxybenzamine treatment is insufficient to prevent spasm in the radial artery: the effect of other vasodilators.
2003 Aug
Phaeochromocytoma--views on current management.
2003 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
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens.
2003 Jul
Elevation of the nasal mucosal surface temperature after warming of the feet occurs via a neural reflex.
2003 Jun
Studies of alpha-adrenoceptor antagonists on sympathetic mydriasis in rabbits.
2003 Jun
Pheochromocytoma unmasked by imipramine in an 8-year-old girl.
2003 Jun
Biochemical diagnosis of pheochromocytoma: how to distinguish true- from false-positive test results.
2003 Jun
Functional characterization of alpha-adrenoceptors mediating pupillary dilation in rats.
2003 Jun 20
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
Photoperiod modulates the effects of norepinephrine on lymphocyte proliferation in Siberian hamsters.
2003 Oct
Involvement of transmitters in pituitary adenylate cyclase-activating polypeptide-induced hyperthermia.
2003 Oct 15
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
Increased reactivity of murine mesenteric veins to adrenergic agonists: functional evidence supporting increased alpha1-adrenoceptor reserve in veins compared with arteries.
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
Substance Class Chemical
Created
by admin
on Tue Mar 06 11:53:58 UTC 2018
Edited
by admin
on Tue Mar 06 11:53:58 UTC 2018
Record UNII
0TTZ664R7Z
Record Status Validated (UNII)
Record Version
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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
Related Record Type Details
TARGET -> AGONIST
TARGET -> AGONIST
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
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ACTIVE MOIETY