Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H19N3O.ClH |
| Molecular Weight | 317.813 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC=CC(O)=C3
InChI
InChIKey=TUEJFGFQYKDAPM-UHFFFAOYSA-N
InChI=1S/C17H19N3O.ClH/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);1H
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 |
|---|---|---|
| Comparative pathophysiology, toxicology, and human cancer risk assessment of pharmaceutical-induced hibernoma. | 2013-12-15 |
|
| Neural mechanism of pressor action of nitric oxide synthase inhibitor in anesthetized monkeys. | 1996-09 |
|
| Cocaine-associated myocardial infarction. | 1996-08 |
|
| Contribution of peripheral alpha 1A-adrenoceptors to pain induced by formalin or by alpha-methyl-5-hydroxytryptamine plus noradrenaline. | 1996-04-22 |
|
| KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues. | 1995-08 |
|
| Effects of chronic NO synthase inhibition in rats on renin-angiotensin system and sympathetic nervous system. | 1995-06 |
|
| Involvement of the sympathetic postganglionic neuron in capsaicin-induced secondary hyperalgesia in the rat. | 1995-03 |
|
| Reasons for high drop-out rate with self-injection therapy for impotence. | 1994-09 |
|
| Further characterization of human alpha 2-adrenoceptor subtypes: [3H]RX821002 binding and definition of additional selective drugs. | 1994-01-24 |
|
| Comparison of a mixture of papaverine, phentolamine and prostaglandin E1 with other intracavernous injections. | 1994 |
|
| The involvement of noradrenaline, 5-hydroxytryptamine and acetylcholine in imipramine-induced seizures in mice. | 1993-10-15 |
|
| Presynaptic alpha 2-autoreceptors in brain cortex: alpha 2D in the rat and alpha 2A in the rabbit. | 1993-07 |
|
| Sodium bicarbonate alleviates penile pain induced by intracavernous injections for erectile dysfunction. | 1993-05 |
|
| Treatment of peripheral ischemia secondary to lidocaine containing epinephrine. | 1989-07 |
|
| Complications of phenylpropanolamine. | 1989-04 |
|
| Propranolol antagonizes hypotension induced by alpha-blockers but not by sodium nitroprusside or methacholine. | 1989-02 |
|
| Prostaglandins inhibit endogenous pain control mechanisms by blocking transmission at spinal noradrenergic synapses. | 1988-04 |
|
| 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. | 1988-01 |
|
| Antagonism of cocaine-induced hepatotoxicity by the alpha adrenergic antagonists phentolamine and yohimbine. | 1987-08 |
|
| Cardiac myonecrosis in hypertensive crisis associated with monoamine oxidase inhibitor therapy. | 1987-05 |
|
| Sympathetic mechanisms in poststenotic myocardial ischemia. | 1986 |
|
| Hypertension after epidural meperidine. | 1985-11 |
|
| Ventricular tachycardia induced by clonidine withdrawal. | 1985-06 |
|
| Dissociation of epinephrine's hyperglycemic and anorectic effect. | 1985-03 |
|
| [Hemodynamic and respiratory effects of phentolamine in pulmonary hypertension secondary to chronic obstructive syndrome]. | 1985-01-19 |
|
| Pharmacological, hemodynamic and autonomic nervous system mechanisms responsible for the blood pressure and heart rate lowering effects of pergolide in rats. | 1984-03 |
|
| Involvement of adenosine receptor activities in aggressive responses produced by clonidine in mice. | 1984 |
|
| A nonhuman primate model for evaluating the potential of antihypertensive drugs to cause orthostatic hypotension. | 1983-05 |
|
| Contribution of alpha-adrenoceptor activation to the pathogenesis of norepinephrine cardiomyopathy. | 1983-04 |
|
| Role of autonomic nervous system in the pathogenesis of angina pectoris. | 1983-02 |
|
| Some functional changes in experimentally induced cardiac overload. | 1983 |
|
| The effects of cigarette smoke and nicotine on platelet thrombus formation in stenosed dog coronary arteries: inhibition with phentolamine. | 1982-03 |
|
| [Acute and chronic cardiac decompensation: is vasodilator therapy useful?]. | 1982-01-14 |
|
| Alpha-adrenoceptor blockade by phentolamine causes beta-adrenergic vasodilation by increased catecholamine release due to presynaptic alpha-blockade. | 1982-01-01 |
|
| Mediation of renin release in essential hypertension by alpha-adrenoreceptors. | 1981-11-01 |
|
| Hypertensive crisis resulting from avocados and a MAO inhibitor. | 1981-11 |
|
| Pharmacological characterisation of the alpha-adrenoceptors responsible for a decrease of blood pressure in the nucleus tractus solitarii of the rat. | 1981-09 |
|
| Noninvasive assessment of load reduction in chronic congestive heart failure patients. | 1981-08 |
|
| Effects of clonidine on canine cardiac neuroeffector structures controlling heart rate. | 1980-10 |
|
| Electrophysiologic properties of hydralazine in man. | 1980-09 |
|
| Noradrenergic influences on sound-induced seizures. | 1980-08 |
|
| Effects of pretreatment with 6-hydroxydopamine or noradrenergic receptor blockers on the clonidine-induced distruption of conditioned avoidance responding. | 1979-09-01 |
|
| Chronic treatment with antidepressant drugs: potentiation of apomorphine-induced aggressive behaviour in rats. | 1979-08 |
|
| Oral therapy with phentolamine in chronic congestive heart failure. | 1979-04 |
|
| DDT-induced myoclonus: serotonin and alpha noradrenergic interaction. | 1979-02 |
|
| Three cases of sinoatrial block induced by anticonvulsants. | 1978-07 |
|
| A study of the sympathomimetic action of guanethidine on the isolated anococcygeus muscle of the rat. | 1978-02 |
|
| Effects of phentolamine, dihydroergocristine and isoxsuprine on the blood pressure and heart rate in normotensive, hypotensive and hypertensive rats. | 1975 |
|
| Use of phentolamine in acute myocardial infarction associated with hypertension and left ventricular failure. | 1973-04 |
|
| Positive phentolamine test in hypertension induced by a nasal decongestant. | 1969-04-17 |
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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C29713
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100000086574
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CHEMBL597
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200-793-5
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DTXSID40223271
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86DRW83R1H
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C80007
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SUB22729
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m8646
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PRIMARY | Merck Index |
ACTIVE MOIETY
SUBSTANCE RECORD
