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
SMILES
CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC=CC(O)=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)
DescriptionCurator'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
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2095203 |
3.7 nM [Kd] | ||
Target ID: CHEMBL2094251 |
16.6 nM [Kd] | ||
Target ID: CHEMBL2095158 |
5.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | REGITINE Approved UsePhentolamine 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 Date1952 |
|||
| Primary | REGITINE Approved UsePhentolamine 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 Date1952 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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: |
unhealthy, 26–83 |
Disc. AE: Rhinitis, Vomiting... AEs leading to discontinuation/dose reduction: Rhinitis Sources: Vomiting Nausea Diarrhea Headache Dizziness Tachycardia |
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: |
unhealthy, 28–80 |
Disc. AE: Dyspnea, Tachycardia... AEs leading to discontinuation/dose reduction: Dyspnea (0.84%) Sources: 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%) |
5 mg single, intravenous|intramuscular Recommended Dose: 5 mg Route: intravenous|intramuscular Route: single Dose: 5 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Myocardial infarction, Cerebrovascular spasm... AEs leading to discontinuation/dose reduction: Myocardial infarction Sources: Cerebrovascular spasm Cerebral vascular occlusion Hypotension |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 26–83 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| 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: |
unhealthy, 28–80 |
| Cerebral vascular occlusion | Disc. AE | 5 mg single, intravenous|intramuscular Recommended Dose: 5 mg Route: intravenous|intramuscular Route: single Dose: 5 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Cerebrovascular spasm | Disc. AE | 5 mg single, intravenous|intramuscular Recommended Dose: 5 mg Route: intravenous|intramuscular Route: single Dose: 5 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hypotension | Disc. AE | 5 mg single, intravenous|intramuscular Recommended Dose: 5 mg Route: intravenous|intramuscular Route: single Dose: 5 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
| Myocardial infarction | Disc. AE | 5 mg single, intravenous|intramuscular Recommended Dose: 5 mg Route: intravenous|intramuscular Route: single Dose: 5 mg Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats. | 1975 |
|
| Evidence for separate peptide sequences related to the lipolytic and magnesium-accumulating activities of ACTH. Analogy with adrenergic receptors. | 1977 Apr |
|
| 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 |
|
| Chronic treatment with antidepressant drugs: potentiation of apomorphine-induced aggressive behaviour in rats. | 1979 Aug |
|
| 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 |
|
| Pharmacological characterisation of the alpha-adrenoceptors responsible for a decrease of blood pressure in the nucleus tractus solitarii of the rat. | 1981 Sep |
|
| [Acute and chronic cardiac decompensation: is vasodilator therapy useful?]. | 1982 Jan 14 |
|
| 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 |
|
| Contribution of alpha-adrenoceptor activation to the pathogenesis of norepinephrine cardiomyopathy. | 1983 Apr |
|
| 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 |
|
| Sympathetic mechanisms in poststenotic myocardial ischemia. | 1986 |
|
| Antagonism of cocaine-induced hepatotoxicity by the alpha adrenergic antagonists phentolamine and yohimbine. | 1987 Aug |
|
| Cardiac myonecrosis in hypertensive crisis associated with monoamine oxidase inhibitor therapy. | 1987 May |
|
| Prostaglandins inhibit endogenous pain control mechanisms by blocking transmission at spinal noradrenergic synapses. | 1988 Apr |
|
| Involvement of beta 2-adrenoceptor-mediated mechanisms in the cardiovascular responses to alpha 1- and alpha 2-adrenoceptor antagonism in conscious, unrestrained, Long Evans and Brattleboro rats. | 1988 Jan |
|
| Propranolol antagonizes hypotension induced by alpha-blockers but not by sodium nitroprusside or methacholine. | 1989 Feb |
|
| 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 |
|
| Comparison of a mixture of papaverine, phentolamine and prostaglandin E1 with other intracavernous injections. | 1994 |
|
| 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 |
|
| KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues. | 1995 Aug |
|
| Effects of chronic NO synthase inhibition in rats on renin-angiotensin system and sympathetic nervous system. | 1995 Jun |
|
| 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 |
|
| [The vasodilation and its mechanism of C-type natriuretic peptide]. | 2001 May |
|
| Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane. | 2004 Aug |
|
| [Lessons learned from anesthetic management of pheochromocytoma resection: a report of three cases]. | 2004 Dec |
|
| Enhancement of PAI-1 mRNA in cardiovascular cells after kainate injection is mediated through the sympathetic nervous system. | 2005 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 |
|
| Phentolamine mesylate for accelerating recovery from lip and tongue anesthesia. | 2010 Oct |
|
| Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
| Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model. | 2013 Dec |
Patents
Sample Use Guides
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
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.
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WHO-VATC |
QV03AB36
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NCI_THESAURUS |
C29713
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NDF-RT |
N0000175553
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WHO-ATC |
C04AB01
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WHO-ATC |
V03AB36
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NDF-RT |
N0000000099
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WHO-VATC |
QC04AB01
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100000082263
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C62066
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DTXSID4023462
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8153
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5775
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50-60-2
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D010646
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502
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Z468598HBV
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Z468598HBV
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DB00692
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3382
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m8646
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PHENTOLAMINE
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8081
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SUB09785MIG
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CHEMBL597
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2142
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200-053-1
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
