U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C17H19N3O
Molecular Weight 281.3523
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENTOLAMINE

SMILES

CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC(O)=CC=C3

InChI

InChIKey=MRBDMNSDAVCSSF-UHFFFAOYSA-N
InChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15/h2-8,11,21H,9-10,12H2,1H3,(H,18,19)

HIDE SMILES / InChI
Molecular Formula C17H19N3O
Molecular Weight 281.3523
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00692 | https://www.drugs.com/pro/phentolamine.html | http://reference.medscape.com/drug/regitine-oraverse-phentolamine-342392 | https://www.ncbi.nlm.nih.gov/pubmed/26180030

Phentolamine (trade name Regitine) is a reversible nonselective α-adrenergic antagonist used for the control of hypertensive emergencies, most notably due to pheochromocytoma. Phentolamine produces its therapeutic actions by competitively blocking alpha-adrenergic receptors (primarily excitatory responses of smooth muscle and exocrine glands), 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. The action of phentolamine on the alpha-adrenergic receptors is relatively transient and the blocking effect is incomplete. The drug is more effective in antagonizing responses to circulating epinephrine and/or norepinephrine than in antagonizing responses to mediator released at the adrenergic nerve ending. Phentolamine also stimulates β-adrenergic receptors and produces a positive inotropic and chronotropic effect on the heart and increases cardiac output. Phentolamine is indicated for the prevention or control of hypertensive episodes that may occur in a patient with pheochromocytoma as a result of stress or manipulation during preoperative preparation and surgical excision. Phentolamine is indicated for the prevention or treatment of dermal necrosis and sloughing following intravenous administration or extravasation of norepinephrine. Phentolamine is also indicated for the diagnosis of pheochromocytoma by the Phentolamine blocking test. Acute and prolonged hypotensive episodes, tachycardia, and cardiac arrhythmias have been reported. In addition, weakness, dizziness, flushing, orthostatic hypotension, nasal stuffiness, nausea, vomiting, and diarrhea may occur.

Originator

Tappi, G.|Forni, P.V.
3
Sources: Annali di Chimica Applicata (1948), 38, 602-13.

Approval Year

1952
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2737
 3.7 nM [Kd]
Antagonist
2737
 16.6 nM [Kd]
Antagonist
2737
 5.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
REGITINE

Approved Use

Phentolamine Mesylate for Injection is indicated for the prevention or control of hypertensive episodes that may occur in a patient with pheochromocytoma as a result of stress or manipulation during preoperative preparation and surgical excision. Phentolamine Mesylate for Injection is indicated for the prevention or treatment of dermal necrosis and sloughing following intravenous administration or extravasation of norepinephrine. Phentolamine Mesylate for Injection is also indicated for the diagnosis of pheochromocytoma by the phentolamine blocking test.

Launch Date

-5.6557437E11
Primary
Approved
8307
REGITINE

Approved Use

Phentolamine Mesylate for Injection is indicated for the prevention or control of hypertensive episodes that may occur in a patient with pheochromocytoma as a result of stress or manipulation during preoperative preparation and surgical excision. Phentolamine Mesylate for Injection is indicated for the prevention or treatment of dermal necrosis and sloughing following intravenous administration or extravasation of norepinephrine. Phentolamine Mesylate for Injection is also indicated for the diagnosis of pheochromocytoma by the phentolamine blocking test.

Launch Date

-5.6557437E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
67.05 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/24452521
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENTOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
197.59 ng × h/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/24452521
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENTOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.32 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/24452521
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENTOLAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Disc. AE: Rhinitis, Vomiting...
AEs leading to
discontinuation/dose reduction:
Rhinitis
Vomiting
Nausea
Diarrhea
Headache
Dizziness
Tachycardia
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Disc. AE: Dyspnea, Tachycardia...
AEs leading to
discontinuation/dose reduction:
Dyspnea (0.84%)
Tachycardia (0.84%)
Epistaxis (0.84%)
Cephalgia (0.84%)
Flushing (serious, 0.84%)
Chest pain (serious, 0.84%)
Shortness of breath (serious, 0.84%)
Tachycardia (serious, 0.84%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
5 mg single, intravenous|intramuscular
Recommended
Dose: 5 mg
Route: intravenous|intramuscular
Route: single
Dose: 5 mg
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
unhealthy
Health Status: unhealthy
Condition: Pheochromocytoma
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
Disc. AE: Myocardial infarction, Cerebrovascular spasm...
AEs leading to
discontinuation/dose reduction:
Myocardial infarction
Cerebrovascular spasm
Cerebral vascular occlusion
Hypotension
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
AEs

AEs

AESignificanceDosePopulation
Diarrhea Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Dizziness Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Headache Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Nausea Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Rhinitis Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Tachycardia Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Vomiting Disc. AE
80 mg 10 times / month multiple, oral
Highest studied dose
Dose: 80 mg, 10 times / month
Route: oral
Route: multiple
Dose: 80 mg, 10 times / month
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
unhealthy, 26–83
n = 691
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 26–83
Sex: M
Population Size: 691
Sources:
https://pubmed.ncbi.nlm.nih.gov/12152116
Page: p.268
Cephalgia 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Dyspnea 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Epistaxis 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Tachycardia 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Chest pain serious, 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Flushing serious, 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Shortness of breath serious, 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Tachycardia serious, 0.84%
Disc. AE
40 mg 1 times / day multiple, oral
Studied dose
Dose: 40 mg, 1 times / day
Route: oral
Route: multiple
Dose: 40 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
unhealthy, 28–80
n = 119
Health Status: unhealthy
Condition: Erectile dysfunction
Age Group: 28–80
Sex: M
Population Size: 119
Sources:
https://pubmed.ncbi.nlm.nih.gov/12161768
Page: S51
Cerebral vascular occlusion Disc. AE
5 mg single, intravenous|intramuscular
Recommended
Dose: 5 mg
Route: intravenous|intramuscular
Route: single
Dose: 5 mg
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
unhealthy
Health Status: unhealthy
Condition: Pheochromocytoma
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
Cerebrovascular spasm Disc. AE
5 mg single, intravenous|intramuscular
Recommended
Dose: 5 mg
Route: intravenous|intramuscular
Route: single
Dose: 5 mg
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
unhealthy
Health Status: unhealthy
Condition: Pheochromocytoma
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
Hypotension Disc. AE
5 mg single, intravenous|intramuscular
Recommended
Dose: 5 mg
Route: intravenous|intramuscular
Route: single
Dose: 5 mg
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
unhealthy
Health Status: unhealthy
Condition: Pheochromocytoma
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
Myocardial infarction Disc. AE
5 mg single, intravenous|intramuscular
Recommended
Dose: 5 mg
Route: intravenous|intramuscular
Route: single
Dose: 5 mg
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
unhealthy
Health Status: unhealthy
Condition: Pheochromocytoma
Sources:
https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=fe1e10f5-4ff3-4616-9534-489648d88d33&type=display
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:8081
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8081
ChemicalBook
CB6665216
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6665216
MolPort
MolPort-000-771-097
https://www.molport.com/shop/molecule-link/MolPort-000-771-097
MolPort
MolPort-001-783-569
https://www.molport.com/shop/molecule-link/MolPort-001-783-569
ZINC
ZINC000000020251
http://zinc15.docking.org/substances/ZINC000000020251
eMolecules
31790003
https://www.emolecules.com/cgi-bin/more?vid=31790003
eMolecules
975745
https://www.emolecules.com/cgi-bin/more?vid=975745
PubMed

PubMed

TitleDatePubMed
Positive phentolamine test in hypertension induced by a nasal decongestant.
1969 Apr 17
Use of phentolamine in acute myocardial infarction associated with hypertension and left ventricular failure.
1973 Apr
Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats.
1975
[Effect of several neuroleptic, adreno-, sympatho- and cholinolytic substances on the development of experimental cerebral edema induced by nicotine].
1977 May-Jun
A study of the sympathomimetic action of guanethidine on the isolated anococcygeus muscle of the rat.
1978 Feb
Three cases of sinoatrial block induced by anticonvulsants.
1978 Jul
Central action of narcotic analgesics. Part III. The role of endogenous noradrenaline in hyperactivity induced by morphine or fentanyl in mice.
1978 Jul-Aug
Oral therapy with phentolamine in chronic congestive heart failure.
1979 Apr
DDT-induced myoclonus: serotonin and alpha noradrenergic interaction.
1979 Feb
Noradrenergic influences on sound-induced seizures.
1980 Aug
Effects of clonidine on canine cardiac neuroeffector structures controlling heart rate.
1980 Oct
Electrophysiologic properties of hydralazine in man.
1980 Sep
Noninvasive assessment of load reduction in chronic congestive heart failure patients.
1981 Aug
Hypertensive crisis resulting from avocados and a MAO inhibitor.
1981 Nov
Mediation of renin release in essential hypertension by alpha-adrenoreceptors.
1981 Nov-Dec
Alpha-adrenoceptor blockade by phentolamine causes beta-adrenergic vasodilation by increased catecholamine release due to presynaptic alpha-blockade.
1982 Jan-Feb
The effects of cigarette smoke and nicotine on platelet thrombus formation in stenosed dog coronary arteries: inhibition with phentolamine.
1982 Mar
Some functional changes in experimentally induced cardiac overload.
1983
Role of autonomic nervous system in the pathogenesis of angina pectoris.
1983 Feb
A nonhuman primate model for evaluating the potential of antihypertensive drugs to cause orthostatic hypotension.
1983 May
Involvement of adenosine receptor activities in aggressive responses produced by clonidine in mice.
1984
Pharmacological, hemodynamic and autonomic nervous system mechanisms responsible for the blood pressure and heart rate lowering effects of pergolide in rats.
1984 Mar
Dissociation of epinephrine's hyperglycemic and anorectic effect.
1985 Mar
Hypertension after epidural meperidine.
1985 Nov
Sympathetic mechanisms in poststenotic myocardial ischemia.
1986
Prostaglandins inhibit endogenous pain control mechanisms by blocking transmission at spinal noradrenergic synapses.
1988 Apr
Complications of phenylpropanolamine.
1989 Apr
Propranolol antagonizes hypotension induced by alpha-blockers but not by sodium nitroprusside or methacholine.
1989 Feb
Treatment of peripheral ischemia secondary to lidocaine containing epinephrine.
1989 Jul
An improved vasoactive drug combination for a pharmacological erection program.
1991 Dec
Presynaptic alpha 2-autoreceptors in brain cortex: alpha 2D in the rat and alpha 2A in the rabbit.
1993 Jul
Sodium bicarbonate alleviates penile pain induced by intracavernous injections for erectile dysfunction.
1993 May
The involvement of noradrenaline, 5-hydroxytryptamine and acetylcholine in imipramine-induced seizures in mice.
1993 Oct 15
Further characterization of human alpha 2-adrenoceptor subtypes: [3H]RX821002 binding and definition of additional selective drugs.
1994 Jan 24
Reasons for high drop-out rate with self-injection therapy for impotence.
1994 Sep
Involvement of the sympathetic postganglionic neuron in capsaicin-induced secondary hyperalgesia in the rat.
1995 Mar
Contribution of peripheral alpha 1A-adrenoceptors to pain induced by formalin or by alpha-methyl-5-hydroxytryptamine plus noradrenaline.
1996 Apr 22
Cocaine-associated myocardial infarction.
1996 Aug
Neural mechanism of pressor action of nitric oxide synthase inhibitor in anesthetized monkeys.
1996 Sep
[Effect of morphine chloride on contractility of small intestinal muscle in vitro or in vivo and its mechanisms].
2008 May
A new homogeneous high-throughput screening assay for profiling compound activity on the human ether-a-go-go-related gene channel.
2009 Nov 1
Limited clinical value of bacterial cocaine esterase in cocaine toxicity.
2010 May
Phentolamine mesylate for accelerating recovery from lip and tongue anesthesia.
2010 Oct
Cell membrane chromatography competitive binding analysis for characterization of α1A adrenoreceptor binding interactions.
2011 Jul
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Insights into the mechanisms mediating hyperglycemic and stressogenic outcomes in rats treated with monocrotophos, an organophosphorus insecticide.
2012 Mar 29
Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease.
2012 Oct
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013 Dec
Comparative pathophysiology, toxicology, and human cancer risk assessment of pharmaceutical-induced hibernoma.
2013 Dec 15
Acute effects of a sarin-like organophosphorus agent, bis(isopropyl methyl)phosphonate, on cardiovascular parameters in anaesthetized, artificially ventilated rats.
2013 Oct 1
Patents

Patents

CH262433
3

Sample Use Guides

In Vivo Use Guide
Prevention or control of hypertensive episodes in the patient with pheochromo-cytoma. For preoperative reduction of elevated blood pressure, 5 mg of Phentolamine mesylate (1 mg for children) is injected intravenously or intramuscularly 1 or 2 hours before surgery, and repeated if necessary. During surgery, Phentolamine mesylate (5 mg for adults, 1 mg for children) is administered intravenously as indicated, to help prevent or control paroxysms of hypertension, tachycardia, respiratory depression, convulsions, or other effects of epinephrine intoxication.
Route of Administration: Other
In Vitro Use Guide
Cancer cell lines, PC-3, DU-145, NCI/ADR-RES, and SKOV3 were used for activity evaluation. Cells were seeded in 96-well plates. After 24 hr, cells were fixed with 10% trichloroacetic acid (TCA) representing cell population at time zero (T0). After additional incubation of 0.1% DMSO or phentolamine for 48 hr, cells were fixed with 10% TCA and SRB at 0.4% (w/v) in 1% acetic acid was added to stain cells. Unbound SRB was washed out. SRB bound cells were solubilized with 10mM Trizma base.
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:51:33 UTC 2022
Edited
by admin
on Fri Dec 16 16:51:33 UTC 2022
Record UNII
Z468598HBV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PHENTOLAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENTOLAMINE [MI]
Common Name English
Phentolamine [WHO-DD]
Common Name English
3-((4,5-DIHYDRO-1H-IMIDAZOL-2-YLMETHYL)(4-METHYLPHENYL)AMINO)PHENOL
Systematic Name English
PHENTOLAMIN
Common Name English
phentolamine [INN]
Common Name English
PHENTOLAMINE [HSDB]
Common Name English
PHENTOLAMINE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QV03AB36
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
NCI_THESAURUS C29713
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
NDF-RT N0000175553
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
WHO-ATC C04AB01
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
WHO-ATC V03AB36
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
NDF-RT N0000000099
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
WHO-VATC QC04AB01
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
Code System Code Type Description
NCI_THESAURUS
C62066
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
EPA CompTox
DTXSID4023462
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
RXCUI
8153
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY RxNorm
PUBCHEM
5775
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
CAS
50-60-2
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
MESH
D010646
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
IUPHAR
502
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
FDA UNII
Z468598HBV
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
DAILYMED
Z468598HBV
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
DRUG BANK
DB00692
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
HSDB
3382
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
MERCK INDEX
M8646
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY Merck Index
WIKIPEDIA
PHENTOLAMINE
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
CHEBI
8081
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
EVMPD
SUB09785MIG
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
INN
22
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
ChEMBL
CHEMBL597
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
DRUG CENTRAL
2142
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-053-1
Created by admin on Fri Dec 16 16:51:33 UTC 2022 , Edited by admin on Fri Dec 16 16:51:33 UTC 2022
PRIMARY
Related Record Type Details
Structure of PHENTOLAMINE MESYLATE
SALT/SOLVATE -> PARENT
ALPHA-1A ADRENERGIC RECEPTOR
TARGET -> AGONIST
Structure of PHENTOLAMINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
ALPHA-2A ADRENERGIC RECEPTOR
TARGET -> AGONIST
SHORT-ACTING
Related Record Type Details
Structure of PHENTOLAMINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966