Identification

Name
Phentolamine
Accession Number
DB00692  (APRD00615)
Type
Small Molecule
Groups
Approved
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. [PubChem]

Structure
Thumb
Synonyms
  • 2-(N-(m-Hydroxyphenyl)-P-toluidinomethyl)imidazoline
  • Fentolamina
  • Phentolamin
  • Phentolamine
  • Phentolamine mesylate
  • Phentolaminum
  • Regitina
  • Vesomax
Product Ingredients
IngredientUNIICASInChI Key
Phentolamine MesylateNot AvailableNot AvailableNot applicable
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OraverseInjection, solution.235 mg/mLSubmucosalSeptodont2011-06-01Not applicableUs
OraverseSolution0.4 mgSubmucosalSeptodont2014-09-17Not applicableCanada
Phentolamine Mesylate Injection Sandoz StandardSolution5 mgIntramuscular; IntravenousSandoz Canada Incorporated2001-06-15Not applicableCanada
RogitineSolution10 mgIntramuscular; IntravenousPaladin Labs Inc2000-12-18Not applicableCanada
Rogitine 5mg/vialPowder, for solution5 mgIntramuscular; IntravenousNovartis1953-12-312000-08-02Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Phentolamine MesylateInjection5 mg/1Intramuscular; IntravenousPrecision Dose, Inc.2017-07-15Not applicableUs
Phentolamine MesylateInjection, powder, for solution5 mg/mLIntramuscular; IntravenousWest Ward Pharmaceutical1998-05-15Not applicableUs
International/Other Brands
Regitin (Novartis) / Regitina (Novartis) / Regitine (Novartis) / Rogitine / Vigamed (Grupo Cimed)
Categories
UNII
Z468598HBV
CAS number
50-60-2
Weight
Average: 281.3523
Monoisotopic: 281.152812245
Chemical Formula
C17H19N3O
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

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.

Structured Indications
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.

TargetActionsOrganism
AAlpha-2A adrenergic receptor
antagonist
Human
AAlpha-1A adrenergic receptor
antagonist
Human
UAlpha-1B adrenergic receptor
antagonist
Human
UAlpha-1D adrenergic receptor
antagonist
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Phentolamine.Experimental
AcebutololPhentolamine may increase the hypotensive activities of Acebutolol.Approved
AldesleukinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Aldesleukin.Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Phentolamine.Approved, Investigational
AliskirenPhentolamine may increase the hypotensive activities of Aliskiren.Approved, Investigational
AlprenololPhentolamine may increase the hypotensive activities of Alprenolol.Approved, Withdrawn
AmbrisentanPhentolamine may increase the hypotensive activities of Ambrisentan.Approved, Investigational
AmifostinePhentolamine may increase the hypotensive activities of Amifostine.Approved, Investigational
AmilorideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Amiloride.Approved
AmiodaroneThe risk or severity of adverse effects can be increased when Amiodarone is combined with Phentolamine.Approved, Investigational
AmlodipineAmlodipine may increase the hypotensive activities of Phentolamine.Approved
AmobarbitalAmobarbital may increase the hypotensive activities of Phentolamine.Approved, Illicit
AmphetamineAmphetamine may increase the hypotensive activities of Phentolamine.Approved, Illicit
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Phentolamine.Approved, Investigational
Amyl NitriteThe risk or severity of adverse effects can be increased when Phentolamine is combined with Amyl Nitrite.Approved
ApomorphineThe risk or severity of adverse effects can be increased when Apomorphine is combined with Phentolamine.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Apraclonidine.Approved
AripiprazoleAripiprazole may increase the hypotensive activities of Phentolamine.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Phentolamine.Approved, Investigational
Arsenic trioxideThe risk or severity of adverse effects can be increased when Arsenic trioxide is combined with Phentolamine.Approved, Investigational
AtenololAtenolol may increase the hypotensive activities of Phentolamine.Approved
AvanafilAvanafil may increase the antihypertensive activities of Phentolamine.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Phentolamine is combined with Azilsartan medoxomil.Approved
BarbexacloneBarbexaclone may increase the hypotensive activities of Phentolamine.Experimental
BarbitalBarbital may increase the hypotensive activities of Phentolamine.Illicit
BarnidipineThe risk or severity of adverse effects can be increased when Barnidipine is combined with Phentolamine.Approved
BenazeprilBenazepril may increase the hypotensive activities of Phentolamine.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Phentolamine.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Phentolamine.Withdrawn
BepridilPhentolamine may increase the hypotensive activities of Bepridil.Approved, Withdrawn
BetaxololBetaxolol may increase the hypotensive activities of Phentolamine.Approved
BethanidineBethanidine may increase the hypotensive activities of Phentolamine.Approved
BietaserpineBietaserpine may increase the hypotensive activities of Phentolamine.Experimental
BimatoprostPhentolamine may increase the hypotensive activities of Bimatoprost.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Phentolamine.Approved
BortezomibThe risk or severity of adverse effects can be increased when Bortezomib is combined with Phentolamine.Approved, Investigational
BosentanBosentan may increase the hypotensive activities of Phentolamine.Approved, Investigational
BQ-123Phentolamine may increase the hypotensive activities of BQ-123.Investigational
BretyliumPhentolamine may increase the hypotensive activities of Bretylium.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Phentolamine.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Phentolamine.Experimental
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Phentolamine.Approved, Investigational
BumetanideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Bumetanide.Approved
BupivacaineThe risk or severity of adverse effects can be increased when Bupivacaine is combined with Phentolamine.Approved, Investigational
BupranololPhentolamine may increase the hypotensive activities of Bupranolol.Approved
CadralazineCadralazine may increase the hypotensive activities of Phentolamine.Experimental
CafedrinePhentolamine may increase the hypotensive activities of Cafedrine.Investigational
CanagliflozinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Canagliflozin.Approved
CandesartanPhentolamine may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilPhentolamine may increase the hypotensive activities of Candesartan cilexetil.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Phentolamine.Experimental
CaptoprilPhentolamine may increase the hypotensive activities of Captopril.Approved
CarbetocinThe risk or severity of adverse effects can be increased when Carbetocin is combined with Phentolamine.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Phentolamine.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Phentolamine.Approved
CarvedilolPhentolamine may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololPhentolamine may increase the hypotensive activities of Celiprolol.Approved, Investigational
ChlorothiazidePhentolamine may increase the hypotensive activities of Chlorothiazide.Approved, Vet Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Chlorpromazine is combined with Phentolamine.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Phentolamine.Approved
CicletaninePhentolamine may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilPhentolamine may increase the hypotensive activities of Cilazapril.Approved
CilnidipineThe risk or severity of adverse effects can be increased when Cilnidipine is combined with Phentolamine.Approved, Investigational
ClevidipineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Clevidipine.Approved
ClofarabineThe risk or severity of adverse effects can be increased when Clofarabine is combined with Phentolamine.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Phentolamine.Approved, Vet Approved
ClonidineClonidine may increase the hypotensive activities of Phentolamine.Approved
CloranololPhentolamine may increase the hypotensive activities of Cloranolol.Experimental
ClozapineThe risk or severity of adverse effects can be increased when Clozapine is combined with Phentolamine.Approved
ConivaptanThe risk or severity of adverse effects can be increased when Conivaptan is combined with Phentolamine.Approved, Investigational
CryptenaminePhentolamine may increase the hypotensive activities of Cryptenamine.Approved
CyclopenthiazidePhentolamine may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclothiazideCyclothiazide may increase the hypotensive activities of Phentolamine.Approved
DapagliflozinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Dapagliflozin.Approved
DebrisoquinDebrisoquin may increase the hypotensive activities of Phentolamine.Approved, Investigational
DelaprilPhentolamine may increase the hypotensive activities of Delapril.Experimental
DeserpidinePhentolamine may increase the hypotensive activities of Deserpidine.Approved
DesfluraneThe risk or severity of adverse effects can be increased when Desflurane is combined with Phentolamine.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Dexmedetomidine.Approved, Vet Approved
DiazoxideDiazoxide may increase the hypotensive activities of Phentolamine.Approved
DiclofenamideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Diclofenamide.Approved
diethylnorsperminePhentolamine may increase the hypotensive activities of diethylnorspermine.Investigational
DihydralazineDihydralazine may increase the hypotensive activities of Phentolamine.Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Phentolamine.Approved
DinutuximabThe risk or severity of adverse effects can be increased when Phentolamine is combined with Dinutuximab.Approved
DipyridamoleThe risk or severity of adverse effects can be increased when Phentolamine is combined with Dipyridamole.Approved
DorzolamidePhentolamine may increase the hypotensive activities of Dorzolamide.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Phentolamine.Approved
DuloxetinePhentolamine may increase the orthostatic hypotensive activities of Duloxetine.Approved
EfonidipinePhentolamine may increase the hypotensive activities of Efonidipine.Approved, Investigational
EmpagliflozinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Empagliflozin.Approved
EnalaprilEnalapril may increase the hypotensive activities of Phentolamine.Approved, Vet Approved
EnalaprilatPhentolamine may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Phentolamine.Experimental
EpanololPhentolamine may increase the hypotensive activities of Epanolol.Experimental
EplerenoneThe risk or severity of adverse effects can be increased when Phentolamine is combined with Eplerenone.Approved
EpoprostenolPhentolamine may increase the hypotensive activities of Epoprostenol.Approved
EprosartanPhentolamine may increase the hypotensive activities of Eprosartan.Approved
EsmololThe risk or severity of adverse effects can be increased when Phentolamine is combined with Esmolol.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Phentolamine is combined with Etacrynic acid.Approved
FelodipinePhentolamine may increase the hypotensive activities of Felodipine.Approved, Investigational
FenoldopamPhentolamine may increase the hypotensive activities of Fenoldopam.Approved
Ferulic acidPhentolamine may increase the hypotensive activities of Ferulic acid.Experimental
FimasartanThe risk or severity of adverse effects can be increased when Fimasartan is combined with Phentolamine.Approved, Investigational
FosinoprilFosinopril may increase the hypotensive activities of Phentolamine.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Phentolamine.Approved, Investigational, Vet Approved
FurosemideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Furosemide.Approved, Vet Approved
GuanabenzGuanabenz may increase the hypotensive activities of Phentolamine.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Phentolamine.Approved
GuanazodinePhentolamine may increase the hypotensive activities of Guanazodine.Experimental
GuanethidinePhentolamine may increase the hypotensive activities of Guanethidine.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Phentolamine.Approved, Investigational
GuanoclorPhentolamine may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzPhentolamine may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanPhentolamine may increase the hypotensive activities of Guanoxan.Experimental
HalothaneThe risk or severity of adverse effects can be increased when Halothane is combined with Phentolamine.Approved, Vet Approved
HarmalineHarmaline may increase the hypotensive activities of Phentolamine.Experimental
HexamethoniumPhentolamine may increase the hypotensive activities of Hexamethonium.Experimental
HexobarbitalHexobarbital may increase the hypotensive activities of Phentolamine.Approved
HydracarbazineHydracarbazine may increase the hypotensive activities of Phentolamine.Experimental
HydralazineHydralazine may increase the hypotensive activities of Phentolamine.Approved
HydrochlorothiazidePhentolamine may increase the hypotensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazidePhentolamine may increase the hypotensive activities of Hydroflumethiazide.Approved, Investigational
IloprostIloprost may increase the hypotensive activities of Phentolamine.Approved, Investigational
ImidaprilThe risk or severity of adverse effects can be increased when Imidapril is combined with Phentolamine.Investigational
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Phentolamine.Approved
IndapamidePhentolamine may increase the hypotensive activities of Indapamide.Approved
IndenololPhentolamine may increase the hypotensive activities of Indenolol.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Phentolamine.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Phentolamine.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Phentolamine.Withdrawn
IrbesartanPhentolamine may increase the hypotensive activities of Irbesartan.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Phentolamine.Approved
IsofluraneThe risk or severity of adverse effects can be increased when Isoflurane is combined with Phentolamine.Approved, Vet Approved
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Phentolamine is combined with Isosorbide Dinitrate.Approved
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Phentolamine is combined with Isosorbide Mononitrate.Approved
IsoxsuprineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Isoxsuprine.Approved, Withdrawn
IsradipineIsradipine may increase the hypotensive activities of Phentolamine.Approved
KetanserinKetanserin may increase the hypotensive activities of Phentolamine.Investigational
LabetalolLabetalol may increase the hypotensive activities of Phentolamine.Approved
LacidipinePhentolamine may increase the hypotensive activities of Lacidipine.Approved, Investigational
LatanoprostLatanoprost may increase the hypotensive activities of Phentolamine.Approved, Investigational
LercanidipineLercanidipine may increase the hypotensive activities of Phentolamine.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Phentolamine is combined with Levobunolol.Approved
LevobupivacaineThe risk or severity of adverse effects can be increased when Levobupivacaine is combined with Phentolamine.Approved, Investigational
LevodopaPhentolamine may increase the orthostatic hypotensive activities of Levodopa.Approved
LevosimendanThe risk or severity of adverse effects can be increased when Levosimendan is combined with Phentolamine.Approved, Investigational
LinsidominePhentolamine may increase the hypotensive activities of Linsidomine.Experimental
LisinoprilPhentolamine may increase the hypotensive activities of Lisinopril.Approved, Investigational
LofexidinePhentolamine may increase the hypotensive activities of Lofexidine.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Phentolamine.Approved
MacitentanPhentolamine may increase the hypotensive activities of Macitentan.Approved
ManidipinePhentolamine may increase the hypotensive activities of Manidipine.Approved, Investigational
MannitolThe risk or severity of adverse effects can be increased when Phentolamine is combined with Mannitol.Approved, Investigational
MebanazineMebanazine may increase the hypotensive activities of Phentolamine.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Phentolamine.Approved
MethazolamideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Methazolamide.Approved
MethohexitalMethohexital may increase the hypotensive activities of Phentolamine.Approved
MethoserpidinePhentolamine may increase the hypotensive activities of Methoserpidine.Experimental
MethyclothiazideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Methyclothiazide.Approved
MethyldopaPhentolamine may increase the hypotensive activities of Methyldopa.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Phentolamine.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Phentolamine.Approved, Investigational
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Phentolamine.Approved
MetipranololPhentolamine may increase the hypotensive activities of Metipranolol.Approved
MetolazoneMetolazone may increase the hypotensive activities of Phentolamine.Approved
MetoprololMetoprolol may increase the hypotensive activities of Phentolamine.Approved, Investigational
MetyrosinePhentolamine may increase the hypotensive activities of Metyrosine.Approved
MibefradilPhentolamine may increase the hypotensive activities of Mibefradil.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Phentolamine.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Phentolamine.Approved
MirodenafilMirodenafil may increase the antihypertensive activities of Phentolamine.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Phentolamine.Approved
MoexiprilMoexipril may increase the hypotensive activities of Phentolamine.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Phentolamine.Approved, Investigational
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Phentolamine.Approved, Investigational
MoxonidineMoxonidine may increase the hypotensive activities of Phentolamine.Approved, Investigational
MuzoliminePhentolamine may increase the hypotensive activities of Muzolimine.Experimental
NabiloneThe risk or severity of adverse effects can be increased when Nabilone is combined with Phentolamine.Approved, Investigational
NadololPhentolamine may increase the hypotensive activities of Nadolol.Approved
NaftopidilPhentolamine may increase the hypotensive activities of Naftopidil.Investigational
NebivololPhentolamine may increase the hypotensive activities of Nebivolol.Approved, Investigational
NesiritideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Nesiritide.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Phentolamine.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Phentolamine.Approved
NicorandilNicorandil may increase the hypotensive activities of Phentolamine.Approved, Investigational
NifedipineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Nifedipine.Approved
NiguldipinePhentolamine may increase the hypotensive activities of Niguldipine.Experimental
NilvadipinePhentolamine may increase the hypotensive activities of Nilvadipine.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Phentolamine.Approved
NisoldipineNisoldipine may increase the hypotensive activities of Phentolamine.Approved
NitrendipinePhentolamine may increase the hypotensive activities of Nitrendipine.Approved, Investigational
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Phentolamine.Approved
NitroglycerinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Nitroglycerin.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Phentolamine.Approved
ObinutuzumabPhentolamine may increase the hypotensive activities of Obinutuzumab.Approved
OctamoxinOctamoxin may increase the hypotensive activities of Phentolamine.Withdrawn
OlmesartanOlmesartan may increase the hypotensive activities of Phentolamine.Approved, Investigational
OmapatrilatPhentolamine may increase the hypotensive activities of Omapatrilat.Investigational
OxprenololPhentolamine may increase the hypotensive activities of Oxprenolol.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Phentolamine.Approved, Vet Approved
PapaverineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Papaverine.Approved
PargylinePargyline may increase the hypotensive activities of Phentolamine.Approved
PenbutololPhentolamine may increase the hypotensive activities of Penbutolol.Approved, Investigational
PentobarbitalPentobarbital may increase the hypotensive activities of Phentolamine.Approved, Vet Approved
PentoliniumPhentolamine may increase the hypotensive activities of Pentolinium.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Phentolamine.Approved, Investigational
PerindoprilPhentolamine may increase the hypotensive activities of Perindopril.Approved
PhenelzinePhenelzine may increase the hypotensive activities of Phentolamine.Approved
PheniprazinePheniprazine may increase the hypotensive activities of Phentolamine.Withdrawn
PhenobarbitalPhenobarbital may increase the hypotensive activities of Phentolamine.Approved
PhenoxybenzaminePhentolamine may increase the hypotensive activities of Phenoxybenzamine.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Phentolamine.Withdrawn
PinacidilPinacidil may increase the hypotensive activities of Phentolamine.Withdrawn
PindololPhentolamine may increase the hypotensive activities of Pindolol.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Phentolamine is combined with Pipamperone.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Phentolamine.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Phentolamine.Withdrawn
Platelet Activating FactorPhentolamine may increase the hypotensive activities of Platelet Activating Factor.Experimental
PolythiazidePhentolamine may increase the hypotensive activities of Polythiazide.Approved
PramipexoleThe risk or severity of adverse effects can be increased when Phentolamine is combined with Pramipexole.Approved, Investigational
PrazosinPrazosin may increase the hypotensive activities of Phentolamine.Approved
PrimidonePrimidone may increase the hypotensive activities of Phentolamine.Approved, Vet Approved
ProcarbazineProcarbazine may increase the hypotensive activities of Phentolamine.Approved
PropofolThe risk or severity of adverse effects can be increased when Phentolamine is combined with Propofol.Approved, Investigational, Vet Approved
PropranololPropranolol may increase the hypotensive activities of Phentolamine.Approved, Investigational
QuetiapineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Quetiapine.Approved
QuinaprilPhentolamine may increase the hypotensive activities of Quinapril.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Phentolamine.Approved
RamiprilRamipril may increase the hypotensive activities of Phentolamine.Approved
RasagilineRasagiline may increase the hypotensive activities of Phentolamine.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Phentolamine is combined with Remifentanil.Approved
RemikirenRemikiren may increase the hypotensive activities of Phentolamine.Approved
RescinnaminePhentolamine may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Phentolamine.Approved, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Phentolamine.Investigational
RiociguatPhentolamine may increase the hypotensive activities of Riociguat.Approved
RisperidonePhentolamine may increase the hypotensive activities of Risperidone.Approved, Investigational
RituximabPhentolamine may increase the hypotensive activities of Rituximab.Approved
RopiniroleThe risk or severity of adverse effects can be increased when Phentolamine is combined with Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Ropivacaine.Approved
RotigotineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Rotigotine.Approved
SacubitrilThe risk or severity of adverse effects can be increased when Phentolamine is combined with Sacubitril.Approved
SafrazineSafrazine may increase the hypotensive activities of Phentolamine.Withdrawn
SaprisartanPhentolamine may increase the hypotensive activities of Saprisartan.Experimental
SecobarbitalSecobarbital may increase the hypotensive activities of Phentolamine.Approved, Vet Approved
SelegilineSelegiline may increase the hypotensive activities of Phentolamine.Approved, Investigational, Vet Approved
SelexipagPhentolamine may increase the hypotensive activities of Selexipag.Approved
SevofluraneThe risk or severity of adverse effects can be increased when Phentolamine is combined with Sevoflurane.Approved, Vet Approved
SildenafilSildenafil may increase the antihypertensive activities of Phentolamine.Approved, Investigational
SitaxentanPhentolamine may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
Sodium NitriteThe risk or severity of adverse effects can be increased when Phentolamine is combined with Sodium Nitrite.Approved
SotalolThe risk or severity of adverse effects can be increased when Phentolamine is combined with Sotalol.Approved
SpiraprilPhentolamine may increase the hypotensive activities of Spirapril.Approved
SpironolactoneThe risk or severity of adverse effects can be increased when Phentolamine is combined with Spironolactone.Approved
StreptokinaseThe risk or severity of adverse effects can be increased when Phentolamine is combined with Streptokinase.Approved, Investigational
SufentanilThe risk or severity of adverse effects can be increased when Phentolamine is combined with Sufentanil.Approved, Investigational
TadalafilTadalafil may increase the antihypertensive activities of Phentolamine.Approved, Investigational
TalinololPhentolamine may increase the hypotensive activities of Talinolol.Investigational
TamsulosinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Tamsulosin.Approved, Investigational
TelmisartanPhentolamine may increase the hypotensive activities of Telmisartan.Approved, Investigational
TemocaprilPhentolamine may increase the hypotensive activities of Temocapril.Experimental, Investigational
TerazosinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Terazosin.Approved
TerlipressinPhentolamine may increase the hypotensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatinePhentolamine may increase the hypotensive activities of Tetrahydropalmatine.Investigational
ThalidomideThe risk or severity of adverse effects can be increased when Phentolamine is combined with Thalidomide.Approved, Investigational, Withdrawn
TheodrenalinePhentolamine may increase the hypotensive activities of Theodrenaline.Investigational
ThiamylalThiamylal may increase the hypotensive activities of Phentolamine.Approved, Vet Approved
ThiopentalThiopental may increase the hypotensive activities of Phentolamine.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Thioridazine.Approved, Withdrawn
TibolonePhentolamine may increase the hypotensive activities of Tibolone.Approved, Investigational
TicrynafenPhentolamine may increase the hypotensive activities of Ticrynafen.Withdrawn
TimololTimolol may increase the hypotensive activities of Phentolamine.Approved
TizanidineThe risk or severity of adverse effects can be increased when Phentolamine is combined with Tizanidine.Approved
TolazolinePhentolamine may increase the hypotensive activities of Tolazoline.Approved, Vet Approved
TolcaponeThe risk or severity of adverse effects can be increased when Phentolamine is combined with Tolcapone.Approved, Withdrawn
TolonidinePhentolamine may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Phentolamine.Approved
TorasemideTorasemide may increase the hypotensive activities of Phentolamine.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Phentolamine.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the hypotensive activities of Phentolamine.Experimental
TranylcypromineTranylcypromine may increase the hypotensive activities of Phentolamine.Approved
TravoprostTravoprost may increase the hypotensive activities of Phentolamine.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Phentolamine.Approved, Investigational
TretinoinThe risk or severity of adverse effects can be increased when Phentolamine is combined with Tretinoin.Approved, Investigational, Nutraceutical
TriamtereneThe risk or severity of adverse effects can be increased when Phentolamine is combined with Triamterene.Approved
TrichlormethiazidePhentolamine may increase the hypotensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Phentolamine.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Phentolamine.Approved, Investigational
UdenafilUdenafil may increase the antihypertensive activities of Phentolamine.Approved, Investigational
UnoprostonePhentolamine may increase the hypotensive activities of Unoprostone.Approved
UrapidilUrapidil may increase the hypotensive activities of Phentolamine.Investigational
ValsartanValsartan may increase the hypotensive activities of Phentolamine.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Phentolamine.Approved
VerapamilThe risk or severity of adverse effects can be increased when Phentolamine is combined with Verapamil.Approved
VincaminePhentolamine may increase the hypotensive activities of Vincamine.Experimental
VinpocetinePhentolamine may increase the hypotensive activities of Vinpocetine.Investigational
XipamidePhentolamine may increase the hypotensive activities of Xipamide.Experimental
XylometazolinePhentolamine may increase the hypotensive activities of Xylometazoline.Approved
YohimbineYohimbine may decrease the antihypertensive activities of Phentolamine.Approved, Vet Approved
ZofenoprilPhentolamine may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14830
PubChem Compound
5775
PubChem Substance
46506535
ChemSpider
5571
BindingDB
31046
ChEBI
8081
ChEMBL
CHEMBL597
Therapeutic Targets Database
DAP000299
PharmGKB
PA450926
IUPHAR
502
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phentolamine
ATC Codes
V03AB36 — PhentolamineC04AB01 — 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
PhaseStatusPurposeConditionsCount
1RecruitingBasic ScienceBMI >30 kg/m2 / Healthy Volunteers / Insulin Resistance1
1RecruitingBasic ScienceCardiovascular System Disease / Drug-Related Side Effects and Adverse Reactions1
1RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Heart Failure, Unspecified / High Blood Pressure (Hypertension) / Pulmonary Arterial Hypertension (PAH)1
2CompletedSupportive CareProstate Cancer1
2CompletedTreatmentAnesthesia, Dental1
2CompletedTreatmentNight Vision Complaints1
2CompletedTreatmentSoft Tissue Anesthesia (Numbness)1
3CompletedTreatmentAnesthesia, Dental2
4CompletedTreatmentAnesthesia, Dental / Anesthesia, Reversal / Local Anesthesia1
4RecruitingTreatmentLocal Anesthesia1
Not AvailableCompletedTreatmentCVA (Cerebrovascular Accident) / Intracerebral Hemorrhage / Intracranial Hemorrhages1
Not AvailableCompletedTreatmentSoft Tissue Anaesthesia1
Not AvailableRecruitingBasic ScienceHypoglycemia / Type1diabetes1
Not AvailableUnknown StatusNot AvailableCongestive Heart Failure (CHF)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
Dosage forms
FormRouteStrength
Injection, solutionSubmucosal.235 mg/mL
SolutionSubmucosal0.4 mg
InjectionIntramuscular; Intravenous5 mg/1
Injection, powder, for solutionIntramuscular; Intravenous5 mg/mL
SolutionIntramuscular; Intravenous5 mg
SolutionIntramuscular; Intravenous10 mg
Powder, for solutionIntramuscular; Intravenous5 mg
Prices
Unit descriptionCostUnit
Phentolamine 5 mg vial84.0USD vial
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6764678No2001-05-112021-05-11Us
US7569230No2003-10-172023-10-17Us
US6872390No2001-05-112021-05-11Us
US7229630No2003-06-202023-06-20Us
US7575757No2005-04-212025-04-21Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)174.5 °CPhysProp
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.272 mg/mLALOGPS
logP2.91ALOGPS
logP2.52ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.78ChemAxon
pKa (Strongest Basic)9.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area47.86 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.25 m3·mol-1ChemAxon
Polarizability31.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9293
Blood Brain Barrier+0.838
Caco-2 permeable-0.6104
P-glycoprotein substrateSubstrate0.772
P-glycoprotein inhibitor INon-inhibitor0.9329
P-glycoprotein inhibitor IIInhibitor0.8031
Renal organic cation transporterInhibitor0.7497
CYP450 2C9 substrateNon-substrate0.6892
CYP450 2D6 substrateNon-substrate0.5668
CYP450 3A4 substrateNon-substrate0.6313
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.8454
CYP450 3A4 inhibitorNon-inhibitor0.831
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7661
Ames testNon AMES toxic0.6266
CarcinogenicityNon-carcinogens0.8555
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4366 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6149
hERG inhibition (predictor II)Inhibitor0.59
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-4890000000-37817fa5f0f18f71350d

Taxonomy

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
Alkyldiarylamine / M-aminophenol / Aminophenol / Aminotoluene / Aniline or substituted anilines / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Toluene / Monocyclic benzene moiety
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary amino compound, substituted aniline, imidazoles, phenols (CHEBI:8081)

Targets

Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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]
  7. Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768]
  8. 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
Human
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
  1. 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]
  2. Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768]
  3. 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
Human
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
  1. 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
Human
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
  1. 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]
  2. 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 December 10, 2017 17:18