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Phentolamine
Identification
- Name
- Phentolamine
- Accession Number
- DB00692
- Description
A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of raynaud disease and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Phentolamine (DB00692)
- Weight
- Average: 281.3523
Monoisotopic: 281.152812245 - Chemical Formula
- C17H19N3O
- Synonyms
- 2-(N-(m-hydroxyphenyl)-p-toluidinomethyl)imidazoline
- Fentolamina
- Phentolamin
- Phentolamine
- Phentolaminum
- External IDs
- C 7337
- C 7337 Ciba
Pharmacology
- Indication
Used as an aid for the diagnosis of pheochromocytoma, and may be administered immediately prior to or during pheochromocytomectomy to prevent or control paroxysmal hypertension resulting from anesthesia, stress, or operative manipulation of the tumor. Phentolamine has also been used to treat hypertensive crisis caused by sympathomimetic amines or catecholamine excess by certain foods or drugs in patients taking MAO inhibitors, or by clonidine withdrawal syndrome. Other indications include the prevention of dermal necrosis and sloughing following IV administration or extravasation of norepinephrine, decrease in impedance to left ventricular ejection and the infarct size in patients with MI associated with left ventricular failure, treatment of erectile dysfunction through self-injection of small doses combined with papaverine hydrochloride into the corpus cavernosum, and as an adjunct to the management of cocaine overdose to reverse coronary vasoconstriction following use of oxygen, benzodiazepines,and nitroglycerin.
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Phentolamine is indicated for the control of episodes of hypertension and sweating that occur with a disease called pheochromocytoma. If tachycardia is excessive, it may be necessary to use a beta-blocking agent concomitantly. Phentolamine is a long-acting, adrenergic, alpha-receptor blocking agent which 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. Phentolamine works by blocking alpha receptors in certain parts of the body. Alpha receptors are present in the muscle that lines the walls of blood vessels. When the receptors are blocked by Phentolamine, the muscle relaxes and the blood vessels widen. This widening of the blood vessels results in a lowering of blood pressure.
- Mechanism of action
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.
Target Actions Organism AAlpha-2A adrenergic receptor antagonistHumans AAlpha-1A adrenergic receptor antagonistHumans UAlpha-1B adrenergic receptor antagonistHumans UAlpha-1D adrenergic receptor antagonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
10-13% of the drug is excreted unchanged in urine, and the fate of the remainder of the drug is unknown.
- Half-life
19 minutes
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Phentolamine may decrease the excretion rate of Abacavir which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Phentolamine which could result in a higher serum level. Acebutolol Acebutolol may increase the orthostatic hypotensive activities of Phentolamine. Aceclofenac The therapeutic efficacy of Phentolamine can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Phentolamine can be decreased when used in combination with Acemetacin. Acetaminophen Acetaminophen may decrease the excretion rate of Phentolamine which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Phentolamine which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Phentolamine which could result in a higher serum level. Aclidinium Phentolamine may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Phentolamine may decrease the excretion rate of Acrivastine which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Phentolamine mesylate Y7543E5K9T 65-28-1 OGIYDFVHFQEFKQ-UHFFFAOYSA-N - International/Other Brands
- Regitin (Novartis) / Regitina (Novartis) / Vigamed (Grupo Cimed)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataOraverse Injection, solution 0.235 mg/1mL Submucosal Septodont, Inc. 2011-06-01 Not applicable US 
Oraverse Solution 0.4 mg Submucosal Septodont 2014-09-17 Not applicable Canada 
OraVerse Injection, solution 0.4 mg/1.7mL Submucosal Novalar Pharmaceuticals 2008-05-23 Not applicable US Phentolamine Mesylate Injection 5 mg/1mL Intramuscular; Intravenous; Parenteral Sandoz Inc 2012-06-01 2013-07-31 US Phentolamine Mesylate Injection Sandoz Standard Solution Intramuscular; Intravenous Sandoz Canada Incorporated 2001-06-15 Not applicable Canada Regitine Injection, powder, lyophilized, for suspension 5 mg/1mL Intramuscular; Intravenous Novartis Pharmaceuticals Corporation 1952-01-30 2003-12-31 US Rogitine Solution Intramuscular; Intravenous Paladin Labs Inc 2000-12-18 Not applicable Canada Rogitine 5mg/vial Powder, for solution Intramuscular; Intravenous Novartis 1953-12-31 2000-08-02 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataPhentolamine Mesylate Injection, powder, for solution 5 mg/1mL Intramuscular; Intravenous West-Ward Pharmaceuticals Corp 1998-05-15 Not applicable US Phentolamine Mesylate Injection 5 mg/1 Intramuscular; Intravenous Precision Dose Inc. 2017-07-15 Not applicable US Phentolamine Mesylate Injection, powder, for solution 5 mg/1mL Intramuscular; Intravenous Bedford Pharmaceuticals 1998-05-15 2015-09-30 US Phentolamine Mesylate Injection 5 mg/1 Intramuscular; Intravenous TAGI Pharma, Inc. 2017-07-15 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Phentolamine Mesylate Phentolamine mesylate (5 mg/1mL) Injection Intramuscular; Intravenous; Parenteral Sandoz Inc 2012-06-01 2013-07-31 US
Categories
- ATC Codes
- V03AB36 — Phentolamine
- V03AB — Antidotes
- V03A — ALL OTHER THERAPEUTIC PRODUCTS
- V03 — ALL OTHER THERAPEUTIC PRODUCTS
- V — VARIOUS
- Drug Categories
- Adrenergic Agents
- Adrenergic alpha-1 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Agents that produce hypertension
- Antidotes
- Antihypertensive Agents
- Cardiovascular Agents
- Drugs that are Mainly Renally Excreted
- Hypotensive Agents
- Imidazoles
- Imidazoline Derivatives
- Neurotransmitter Agents
- Non-selective Alfa-adrenergic Blocking Agents
- Peripheral alpha-1 blockers
- Peripheral Vasodilators
- Sympatholytic (Adrenergic Blocking) Agents
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Alkyldiarylamines
- Alternative Parents
- m-Aminophenols / Aniline and substituted anilines / Aminotoluenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines show 4 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2-imidazoline / Alkyldiarylamine / Amidine / Aminophenol / Aminotoluene / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary amino compound, substituted aniline, imidazoles, phenols (CHEBI:8081)
Chemical Identifiers
- UNII
- Z468598HBV
- CAS number
- 50-60-2
- InChI Key
- MRBDMNSDAVCSSF-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol
- SMILES
- CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014830
- PubChem Compound
- 5775
- PubChem Substance
- 46506535
- ChemSpider
- 5571
- BindingDB
- 31046
- 8153
- ChEBI
- 8081
- ChEMBL
- CHEMBL597
- ZINC
- ZINC000000020251
- Therapeutic Targets Database
- DAP000299
- PharmGKB
- PA450926
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Phentolamine
- AHFS Codes
- 12:16.04.04 — Non-selective Alfa-adrenergic Blocking Agents
- 12:16.00 — Sympatholytic (Adrenergic Blocking) Agents
- MSDS
- Download (73.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Anesthesia reversal / Anesthesia, Dental / Anesthesia, Reversal / Local Anesthesia 1 4 Completed Treatment Local Anesthesia 1 3 Completed Treatment Anesthesia, Dental 2 2 Completed Supportive Care Prostate Cancer 1 2 Completed Treatment Anesthesia, Dental 1 2 Completed Treatment Decrease in Night Vision / Disturbance; Vision, Loss / Night Vision Complaints 1 2 Completed Treatment Decrease in Night Vision / Disturbance; Vision, Loss / Night Vision Loss 1 2 Completed Treatment Dilation / Mydriasis 1 2 Completed Treatment Ocular Hypertension / Open Angle Glaucoma (OAG) / Open-angle Glaucoma (OAG) 1 2 Completed Treatment Soft Tissue Anesthesia (Numbness) 1
Pharmacoeconomics
- Manufacturers
- Novalar pharmaceuticals inc
- Bedford laboratories div ben venue laboratories inc
- Novartis pharmaceuticals corp
- Sanofi aventis us llc
- Glaxosmithkline
- Perrigo co
- Ranbaxy laboratories ltd
- Mcneil consumer healthcare
- Packagers
- Bedford Labs
- Ben Venue Laboratories Inc.
- Novalar Pharmaceuticals Inc.
- Novartis AG
- Novocol Pharmaceutical Canada
- Dosage Forms
Form Route Strength Injection, solution Submucosal 0.235 mg/1mL Injection, solution Submucosal 0.4 mg/1.7mL Solution Submucosal 0.4 mg Injection Intramuscular; Intravenous 5 mg/1 Injection Intramuscular; Intravenous; Parenteral 5 mg/1mL Injection, powder, for solution Intramuscular; Intravenous 5 mg/1mL Powder Not applicable 1 g/1g Injection, powder, lyophilized, for suspension Intramuscular; Intravenous 5 mg/1mL Solution Intramuscular; Intravenous Powder, for solution Intramuscular; Intravenous - Prices
Unit description Cost Unit Phentolamine 5 mg vial 84.0USD vial DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS6764678 No 2004-07-20 2021-05-11 US US7569230 No 2009-08-04 2023-10-17 US US6872390 No 2005-03-29 2021-05-11 US US7229630 No 2007-06-12 2023-06-20 US US7575757 No 2009-08-18 2025-04-21 US Additional Data Available- Filed On
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 174.5 °C PhysProp logP 3.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.272 mg/mL ALOGPS logP 2.91 ALOGPS logP 2.52 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 9.78 ChemAxon pKa (Strongest Basic) 9.02 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 47.86 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 84.25 m3·mol-1 ChemAxon Polarizability 31.37 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9293 Blood Brain Barrier + 0.838 Caco-2 permeable - 0.6104 P-glycoprotein substrate Substrate 0.772 P-glycoprotein inhibitor I Non-inhibitor 0.9329 P-glycoprotein inhibitor II Inhibitor 0.8031 Renal organic cation transporter Inhibitor 0.7497 CYP450 2C9 substrate Non-substrate 0.6892 CYP450 2D6 substrate Non-substrate 0.5668 CYP450 3A4 substrate Non-substrate 0.6313 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.8454 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7661 Ames test Non AMES toxic 0.6266 Carcinogenicity Non-carcinogens 0.8555 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4366 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6149 hERG inhibition (predictor II) Inhibitor 0.59
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-03di-4890000000-37817fa5f0f18f71350d
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Polak J, Moro C, Klimcakova E, Hejnova J, Majercik M, Viguerie N, Langin D, Lafontan M, Stich V, Berlan M: Dynamic strength training improves insulin sensitivity and functional balance between adrenergic alpha 2A and beta pathways in subcutaneous adipose tissue of obese subjects. Diabetologia. 2005 Dec;48(12):2631-40. Epub 2005 Nov 5. [PubMed:16273345]
- Molderings GJ, Bonisch H, Bruss M, Likungu J, Gothert M: Species-specific pharmacological properties of human alpha(2A)-adrenoceptors. Hypertension. 2000 Sep;36(3):405-10. [PubMed:10988273]
- Vonend O, Habbel S, Stegbauer J, Roth J, Hein L, Rump LC: Alpha(2A)-adrenoceptors regulate sympathetic transmitter release in mice kidneys. Br J Pharmacol. 2007 Jan;150(1):121-7. Epub 2006 Nov 20. [PubMed:17115069]
- Trendelenburg AU, Meyer A, Klebroff W, Guimaraes S, Starke K: Crosstalk between presynaptic angiotensin receptors, bradykinin receptors and alpha 2-autoreceptors in sympathetic neurons: a study in alpha 2-adrenoceptor-deficient mice. Br J Pharmacol. 2003 Apr;138(8):1389-402. [PubMed:12721093]
- Blandizzi C, Fornai M, Colucci R, Baschiera F, Barbara G, De Giorgio R, De Ponti F, Breschi MC, Del Tacca M: Altered prejunctional modulation of intestinal cholinergic and noradrenergic pathways by alpha2-adrenoceptors in the presence of experimental colitis. Br J Pharmacol. 2003 May;139(2):309-20. [PubMed:12770936]
- Giussani DA, Moore PJ, Bennet L, Spencer JA, Hanson MA: Alpha 1- and alpha 2-adrenoreceptor actions of phentolamine and prazosin on breathing movements in fetal sheep in utero. J Physiol. 1995 Jul 1;486 ( Pt 1):249-55. [PubMed:7562640]
- Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768]
- Saeed M, Sommer O, Holtz J, Bassenge E: Alpha-adrenoceptor blockade by phentolamine causes beta-adrenergic vasodilation by increased catecholamine release due to presynaptic alpha-blockade. J Cardiovasc Pharmacol. 1982 Jan-Feb;4(1):44-52. [PubMed:6176798]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1A
- Uniprot ID
- P35348
- Uniprot Name
- Alpha-1A adrenergic receptor
- Molecular Weight
- 51486.005 Da
References
- Giussani DA, Moore PJ, Bennet L, Spencer JA, Hanson MA: Alpha 1- and alpha 2-adrenoreceptor actions of phentolamine and prazosin on breathing movements in fetal sheep in utero. J Physiol. 1995 Jul 1;486 ( Pt 1):249-55. [PubMed:7562640]
- Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768]
- Saeed M, Sommer O, Holtz J, Bassenge E: Alpha-adrenoceptor blockade by phentolamine causes beta-adrenergic vasodilation by increased catecholamine release due to presynaptic alpha-blockade. J Cardiovasc Pharmacol. 1982 Jan-Feb;4(1):44-52. [PubMed:6176798]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
- Gene Name
- ADRA1B
- Uniprot ID
- P35368
- Uniprot Name
- Alpha-1B adrenergic receptor
- Molecular Weight
- 56835.375 Da
References
- Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [PubMed:15306222]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Alpha1-adrenergic receptor activity
- Specific Function
- This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
- Gene Name
- ADRA1D
- Uniprot ID
- P25100
- Uniprot Name
- Alpha-1D adrenergic receptor
- Molecular Weight
- 60462.205 Da
References
- Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [PubMed:15306222]
- Zhang D, Yuan B, Deng X, Yang G, He L, Zhang Y, Han Q: Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane. Sci China C Life Sci. 2004 Aug;47(4):376-81. [PubMed:15493479]
Drug created on June 13, 2005 07:24 / Updated on September 27, 2020 08:17
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