HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
Huagongshe Open Program:[email protected]AI access: llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.7.8
  1. Home
  2. /Compound

Phentolamine

HCID 5775
NotesReactions

Completing data — refresh the page later to see the latest

Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
50-60-2
Standard SMILES
Cc1ccc(N(CC2=NCCN2)c2cccc(O)c2)cc1
InChIKey
MRBDMNSDAVCSSF-UHFFFAOYSA-N
Molecular formula
C17H19N3O
Average molar mass
281.35 g/mol
Monoisotopic mass
281.15281224

Names & identifiers

Preferred name
Phentolamine
IUPAC
3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol
English name
Phentolamine
Molecular formula
C17H19N3O
Molecular weight
281.35

Names & synonyms

phentolamine50-60-2RegitinDibasinFentolaminFentolaminaRogitinePhentolaminumC 7337 CibaPhentolamin2-(N-(m-Hydroxyphenyl)-p-toluidinomethyl)imidazolineC 7337
Show more names
Fentolamineregitine3-(((4,5-Dihydro-1H-imidazol-2-yl)methyl)(p-tolyl)amino)phenolregitipec7337cibaphentalamine
DTXSID40234622-(m-Hydroxy-N-p-tolylanilinomethyl)-2-imidazoline3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol2-((N-(m-Hydroxyphenyl)-p-toluidino)methyl)-2-imidazoline2-(N'-p-Tolyl-N'-m-hydroxyphenylaminomethyl)-2-imidazolineZ468598HBVPhenol, m-(N-(2-imidazolin-2-ylmethyl)-p-toluidino)-CHEBI:8081

Database identifiers

CAS
50-60-2
PubChem CID
5775
DTXSID
DTXSID4023462
ChEMBL
CHEMBL597
ChEBI
CHEBI:8081
UNII
Z468598HBV
EC Number
200-053-1
Nikkaji
J4.105J

Properties

Computed structural propertiesFilling in

XLogP
2.6
Topological polar surface area
47.9 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
21
Formal charge
0
Complexity
363

Experimental & physicochemical properties

LogP · 2 items

3.3

3.3

Color/FormCrystals
Solubility2.72e-01 g/L
Melting Point · 4 items

181

175 °C

Bitter crystals; MP: 239-240 °C. One gram dissolves in 50 mL water, in 70 mL alcohol. Very slightly soluble in chloroform. Practically insoluble in acetone, ethyl acetate. pH of 1% aqueous solution 4.5 to 5.5. Aqueous solutions cannot be stored. /Phentolamin hydrochloride/

174.5 °C

Physical DescriptionSolid
Stability/Shelf Life · 1 item

Following reconstitution of the commercially available lyophilized powder with sterile water for injection to a concentration of 5 mg/mL, phentolamine mesylate injection is stable for 48 hours at room temperature or 1 week at 2-8 °C; however, the manufacturer recommends that the reconstituted injection be used immediately and not stored.

Collision Cross Section · 1 item

166.27 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];156.25 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];170.52 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];174.26 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including phentolamine mesylate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Phentolamine mesylate/

Hazard Classes and CategoriesAcute Tox. 4 (100%);Skin Irrit. 2 (100%);Eye Irrit. 2 (100%)
Skin, Eye, and Respiratory IrritationsPossible eye, skin, gastrointestinal, and/or respiratory tract irritation.

Safety & protection

Fire Fighting Procedures · 2 items

Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials.

As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.

Storage Conditions · 2 items

Chemistry & industry

Pharmacology

ATC Code · 4 items

V - Various;V03 - All other therapeutic products;V03A - All other therapeutic products;V03AB - Antidotes;V03AB36 - Phentolamine

C - Cardiovascular system;C04 - Peripheral vasodilators;C04A - Peripheral vasodilators;C04AB - Imidazoline derivatives;C04AB01 - Phentolamine

QC - Cardiovascular system;QC04 - Peripheral vasodilators;QC04A - Peripheral vasodilators;QC04AB - Imidazoline derivatives;QC04AB01 - Phentolamine

QV - Various;QV03 - All other therapeutic products;QV03A - All other therapeutic products;QV03AB - Antidotes;QV03AB36 - Phentolamin

Pharmacodynamics · 1 item

Phentolamine produces an alpha-adrenergic block of a relatively short duration. Phentolamine induces vasodilatation of vascular smooth muscle and pupils. When used in an ophthalmic solution, the onset of pupil dilation generally occurred in 30 minutes, with the maximal effect seen in 60 to 90 minutes. Pupil dilation lasted for at least 24 hours. Phentolamine also has direct but less marked positive inotropic and chronotropic effects on cardiac muscle and vasodilator effects on vascular smooth muscle; however, phentolamine is not believed to affect contractile or adenyl cyclase function. Large doses can lead to a mild sympatholytic action. Some evidence suggests that phentolamine also stimulates beta-adrenergic receptors, thereby causing peripheral vasodilation. Phentolamine was shown to stimulate insulin secretion, possibly related to its blocking actions on ATP-sensitive K<sup>+</sup> channels.

Mechanism of Action · 6 items

Phentolamine is a reversible, competitive antagonist at alpha-1 and alpha-2 adrenergic receptors. It causes vasodilation of vascular smooth muscles. Pupil dilation is primarily controlled by the radial iris dilator muscles surrounding the pupil, which are activated by the alpha-1 adrenergic receptors. Phentolamine reversibly binds to these receptors and reduces pupil diameter. By blocking alpha-1 adrenergic receptors, phentolamine can also be used to reverse mydriasis induced by muscarinic antagonists.

Phentolamine inhibits responses to adrenergic stimuli by competitively blocking a-adrenergic receptors (primarily excitatory responses of smooth muscle and exocrine glands), but the action of the drug is relatively transient and a-adrenergic blockade is incomplete. Phentolamine has greater a-adrenergic blocking effects than does tolazoline. Phentolamine is more effective in antagonizing responses to circulating epinephrine and/or norepinephrine than in antagonizing responses to mediator released at the adrenergic nerve ending. The drug causes peripheral vasodilation and decreases peripheral resistance, primarily by direct relaxation of vascular smooth muscle, but a-adrenergic blockade also contributes to vasodilation. Phentolamine also stimulates beta-adrenergic receptors and produces a positive inotropic and chronotropic effect on the heart and increases cardiac output.

Related reactions

2 records
New reaction record
HRID 979728 reaction equation
HRID 979728As reactantuspto-grants-1987_05
HRID 2231343 reaction equation
HRID 2231343As reactantuspto-grants-1988_11

Compound notes

Loading…

On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Other Experimental Properties · 4 items

log Kow = 0.31 at pH 7.5

White or slightly grayish, crystalline powder /Perphanzine hydrochloride/

Crystals; MP 177-181 °C. One gram dissolves in 50 mL water, 23 mL alcohol, 660 mL chloroform. pH of 1% aqueous solution 4.5 to 5.5. Aqueous solutions cannot be stored. /Phentolamine methanesulfonate/

White crystalline powder /Mesylate/

Physicochemical properties

Melting point
174 · 174-175°
Boiling point
424.02 °C · 424.02°C (rough estimate)
Density
1.051 · 1.0510 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility
DMSO (Slightly), Methanol (Slightly)
form
Solid
pka
7.7 · pKa 7.7 (Uncertain)
color
Crystals
Stability
Hygroscopic
CAS DataBase Reference
50 · 50-60-2(CAS DataBase Reference)
FDA UNII
468598 HBV · Z468598HBV
NCI Drug Dictionary
Regitine
ATC code
4 AB01,V03AB36 · C04AB01,V03AB36
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302-H314
Precautionary statements
501 · P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Hazardous Substances Data
50 · 50-60-2(Hazardous Substances Data)
Toxicity
50 orl-rat: · LD50 orl-rat: 1250 mg/kg PSEBAA 71,70,49

Phentolamine mesylate powder for injection should be stored at 15 - 30 °C.

Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity.

Cleanup MethodsWipe up spillage or collect spillage using a high- efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.
Disposal Methods · 2 items

SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.

SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.

Preventive Measures · 5 items

Engineering controls such as exhaust ventilation are recommended.

This material is assumed to be combustible. As with all dry powders, it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.

As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

For more Preventive Measures (Complete) data for Phentolamine (7 total), please visit the HSDB record page.

Personal Protective Equipment (PPE) · 2 items

Use a NIOSH-approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.

Wear approved respiratory protection, chemically compatible gloves, and protective clothing.

Toxicology

InteractionsPIMOZIDE WAS A POTENT ANTAGONIST OF (+)AMPHETAMINE, DIETHYLPROPION, MAZINDOL & PHENTERMINE ANOREXIA IN MOUSE. PHENTOLAMINE & PROPRANOLOL PRODUCED NO SUCH ANTAGONISM, BUT EITHER POTENTIATED OR HAD NO EFFECT ON DRUG-INDUCED ANOREXIA.
Food Survey ValuesExamples of tyramine-containing food includes aged cheese, red wine, avocados, bananas, chocolate, prepared meats and sauerkraut /Tyramine/
Human Toxicity Excerpts · 4 items

/SIGNS AND SYMPTOMS/ Phentolamine may cause acute and prolonged hypotension, tachycardia, cardiac arrhythmias, and angina, especially after parenteral administration. Myocardial infarction and cerebrovascular spasm or occlusion, usually in association with marked hypotension and a shock-like state, have been reported occasionally following parenteral administration of phentolamine. Deaths have occurred after IV administration of phentolamine for the diagnosis of pheochromocytoma.

/SIGNS AND SYMPTOMS/ Overdosage with Regitine is characterized chiefly by cardiovascular disturbances, such as arrhythmias, tachycardia, hypotension, and possibly shock. In addition, the following might occur: excitation, headache, sweating, pupillary contraction, visual disturbances; nausea, vomiting, diarrhea; hypoglycemia.

/SIGNS AND SYMPTOMS/ Phentolamine may cause acute and prolonged hypotension, tachycardia, cardiac arrhythmias, and angina, especially after parenteral administration. Myocardial infarction and cerebrovascular spasm or occlusion, usually in association with marked hypotension and a shock-like state, have been reported occasionally following parenteral administration of phentolamine. Deaths have occurred after IV administration of phentolamine for the diagnosis of pheochromocytoma.

/SIGNS AND SYMPTOMS/ Intracavernous injection /not approved in the US/ of combined phentolamine and papaverine for the treatment of impotence occasionally has caused priapism. Priapism is a medical emergency that could result in penile tissue damage and permanent loss of potency if not treated immediately, and therefore, patients should be advised to report promptly to their physician or, if unavailable, to seek alternative immediate medical attention if an erection that persists longer than 4 hours or that is extremely painful occurs. ...

Drug Induced Liver Injury · 6 items

Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)

phentolamine

Regitine®

Vasodilators

Not Applicable

no-DILI-concern

Non-Human Toxicity Excerpts · 3 items

/LABORATORY ANIMALS: Acute Exposure/ OraVerse, an injectable formulation of phentolamine mesylate), was recently approved by the U.S. Food and Drug Administration (FDA) for reversal of anesthesia of the lip and tongue and associated functional deficits resulting from an intraoral submucosal injection of a local anesthetic containing a vasoconstrictor. Because phentolamine mesylate had not been approved previously for submucosal administration, 2 Good Laboratory Practices (GLP) studies in dogs designed to investigate systemic toxicity and the local effects of single and repeated dosing of OraVerse on the inferior alveolar nerve and branches of the superior alveolar nerve and adjacent soft tissues after local administration were conducted. Systemic toxicity was measured by preinjection and postinjection clinical examinations, clinical chemistry, and gross and microscopic examinations of major organs after necropsy. No evidence of systemic toxicity was detected. Local nerve and adjacent tissue damage was assessed by conventional histopathology. Nerve degeneration was evident in 1 animal. Mild perineural inflammation adjacent to the inferior alveolar nerve and inflammatory exudates were observed in submucosal tissues in several animals. No changes were observed in the nerves at injection sites of dogs from any dose group that were considered directly related to the test articles.

/LABORATORY ANIMALS: Acute Exposure/ The aim of this study was to assess the effects of acute systemic, nonselective alpha-adrenergic blockade on aqueous flow. This study used pentobarbital-anesthetized rabbits (n=7), in which the following parameters were measured: mean arterial pressure, carotid blood flow, heart rate, intraocular pressure (IOP), orbital venous pressure (OVP), ciliary blood flow, and aqueous flow (AqFlow). Measurements were made before and after an intravenous administration of phentolamine (0.1 mg/kg). Phentolamine caused significant decreases in IOP -23%+/-2%; P<0.01), OVP (-28%+/-12%; P<0.05), and AqFlow (-33%+/-6%; P<0.01). The other parameters were not significantly altered. The rapidity of the OVP and IOP responses were noteworthy, being essentially complete 60 s after the phentolamine injection. A subpressor dose of phentolamine has complex effects on ocular hydrodynamics. The initial IOP decrease is too fast to be explained by aqueous dynamics or ocular rigidity, and so is most likely a result of the disgorgement of choroidal blood volume caused by decreased venous pressure outside the eye. The more prolonged ocular hypotensive effect is explained by the decrease in AqFlow, and perhaps a decrease in episcleral venous pressure or increase in uveoscleral outflow. However, the inhibition of aqueous production is odd, as lost prejunctional inhibition of norepinephrine release and unopposed beta-receptor activation should have increased aqueous production.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ ... Phentolamine mesylate was administered to rats by oral gavage at daily doses of 10, 50, and 150 mg/kg for 24 months. A dose-related increase in mortality, ascribed to an exaggerated pharmacologic effect, was seen at high doses. Systemic exposure as measured by plasma drug concentration increased with dose and duration of dosing and slight drug accumulation occurred, particularly in high-dose males. In the treated groups, 10 males and 1 female were diagnosed with hibernomas, neoplasms of brown adipose tissue, which appeared in the thoracic cavity or retroperitoneal area as circumscribed, tan to reddish-brown lobulated masses. Histologically, the masses were well circumscribed with variably sized lobules defined by a rich capillary network and consisted of closely apposed oval to polygonal cells with large amounts of cytoplasm and a centrally located nucleus. The cytoplasm's appearance varied from multivacuolated to univacuolated to granular eosinophilic. In a few cases, neoplastic emboli were observed in capsular vessels. Ultrastructurally, the neoplastic cells contained numerous mitochondria with transverse parallel cristae that occupied over 60% of the cytoplasm and lipid droplets.

Antidote and Emergency Treatment · 4 items

Treatment. There is no specific antidote. A decrease in blood pressure to dangerous levels or other evidence of shocklike conditions should be treated vigorously and promptly. The patient's legs should be kept raised and a plasma expander should be administered. If necessary, intravenous infusion of norepinephrine, titrated to maintain blood pressure at the normotensive level, and all available supportive measures should be included. Epinephrine should not be used, since it may cause a paradoxical reduction in blood pressure.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

Non-Human Toxicity Values · 2 items

LD50 Rat oral 1250 mg/kg

LD50 Mouse oral 1000 mg/kg

Regulatory information

FDA Requirements · 1 item

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including phentolamine mesylate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Phentolamine mesylate/

Safety data

Toxicity
LD50 orl-rat: 1250 mg/kg PSEBAA 71,70,49
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
Hazard statements
H302-H314
Precautionary statements
P501-P260-P270-P264-P280-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405
Hazardous Substances Data
50-60-2(Hazardous Substances Data)

DIFFERENCES IN PLASMA GLUCOSE & LACTOSE OBSERVED SUGGEST PROTECTION OF HEPATIC METABOLISM IN PHENTOLAMINE-TREATED ENDOTOXIC RATS (FASTED MALE RATS ADMIN E COLI ENDOTOXIN 25 MG/KG/IP) BY PREVENTION OF EXCESSIVE HEPATIC HYPOXIA.

INFUSION OF PHENTOLAMINE AUGMENTED ACUTE INSULIN RESPONSE & GLUCOSE TOLERANCE.

COMPARISON OF CARDIOVASCULAR ACTIONS OF DIHYDRALAZINE, PHENTOLAMINE, & PRAZOSIN IN SPONTANEOUSLY HYPERTENSIVE RATS IS DISCUSSED.

For more Mechanism of Action (Complete) data for Phentolamine (8 total), please visit the HSDB record page.

Biological Half-Life · 2 items

Phentolamine has a half-life of 19 minutes following intravenous administration. The terminal elimination half-life of phentolamine was approximately two to three hours following submucosal administration.

The elimination half life /of phentolamine/ is 19 minutes after intravenous administration, 5 to 7 hours after oral administration.

Metabolism/MetabolitesPhentolamine has known human metabolites that include [3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenyl] hydrogen sulfate.
FDA Pharmacological Classification · 5 items

Z468598HBV

PHENTOLAMINE

Mechanisms of Action [MoA] - Adrenergic alpha-Antagonists

Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker

Phentolamine is an alpha-Adrenergic Blocker. The mechanism of action of phentolamine is as an Adrenergic alpha-Antagonist.

MeSH Pharmacological Classification · 2 items

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Absorption, Distribution and Excretion · 5 items

The peak concentrations of phentolamine are achieved within 10 to 20 minutes following submucosal administration. The Cmax was higher in children with greater weights. Following topical ocular administration of phentolamine ophthalmic solution 0.75%, the peak concentration levels were achieved between 15 minutes and one hour after dosing with the median value of 0.45 ng/mL.

Approximately 13% of a single intravenous dose appears in the urine as unchanged drug.

While there is limited information on phentolamine distribution, the drug is reported to cross the blood-brain barrier.

The Tmax is 30 to 60 minutes. Protein binding is less than 72%. It undergoes extensive hepatic metabolism, 80% renal excretion (10% to 13% excreted as unchanged drug) and 20% fecal excretion.

Phentolamine is only about 20% as active after oral administration as after parenteral administration. About 10% of a parenteral dose can be recovered in the urine as active drug; the fate of the remainder is not known. It is not known whether the drug crosses the placenta or appears in milk.

Cellular LocationsMembrane

Uses & manufacturing

Uses · 4 items

Treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of Raynaud disease and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease

To relieve pseudo-obstruction of the bowel in patients with pheochromocytoma; to prevent dermal necrosis after inadvertent extravasation of an alpha-receptor antagonist; for treatment of hypertensive crisis that follow the abrupt withdrawal of clonidine or that may result from the ingestion of tyramine-containing food during the use of nonselective MAO inhibitors.

THERAPEUTIC CATEGORY: Antihypertensive in treatment of pheochromocytoma; diagnostic aid (pheochromocytoma). In treatment of male erectile dysfunction.

MEDICATION

Methods of Manufacturingm-(p-Toluidino)phenol is refluxed with 2-chloromethylimidazoline hydrochloride and the resulting phentolamine base treated with an equimolar protion of methanesulfonic acid. /Phentolamine mesylate/
Formulations/Preparations · 3 items

For injection, powder, lyophilized, for suspension: vials each containing 5 mg of phentolamine mesylate for injection, USP, and 25 mg of mannitol, USP, inlyophilized form, Regitine (Novartis).

For injection, solution for submucosal use: 0.4 mg/1.7 mL solution per cartridge, OraVerse (Novalar).

Parenteral: For injection: 5 mg Phentolamine Mesylate for Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name). /Phentolamine mesylate/

Use ClassificationPharmaceuticals
General Manufacturing InformationNo longer widely used because of its side effects /which include arrhythmia and tachycardia/.
Applications · 5 items

UsesPhentolamine is a synthetic imidazoline with alpha-adrenergic antagonist activity. As a competitive alpha-adrenergic antagonist, phentolamine binds to alpha-1 and alpha-2 receptors, resulting in a decrease in peripheral vascular resistance and vasodilatation. This agent also may block 5-hydroxytryptamine (5-HT) receptors and stimulate release of histamine from mast cells. Phentolamine is used mainly in the diagnosis of pheochromocytoma and to control or prevent paroxysmal hypertension immediately prior to or during pheochromocytomectomy. Phentolamine has been used to treat hypertensive crises secondary to MAO inhibitor/sympathomimetic amine interactions and rebound hypertension on withdrawal of clonidine, propranolol or other antihypertensive agents.

DescriptionPhentolamine is also a derivative of imidazoline that exhibits a direct α-adrenoblocking, muscle-relaxant effect on smooth muscle as well as cholinomimetic, histamine, and sympathomimetic effects. The chemical variation of its structure permits a few of its properties to be more expressed. For example, the aforementioned tolazoline, 2-benzyl-2-imidazoline, a structural analog of phentolamine, has more of an expressed muscle-relaxant effect on smooth muscle than an α-adrenoblocking effect.

UsesPhentolamine is used for peripheral blood circulation disorders, in particular in the beginning stages of gangrene, for treatment of trophic ulcers of the extremities, bedsores, and frostbite.

UsesAnti-adrenergic. Phentolamine is used to prevent or control hypertensive episodes that occurin patients with pheochromocytoma. It also has been used incombination with papaverine to treat impotence.

General DescriptionPhentolamine isthe more effectiveα -blocker.

Upstream & downstream products

Upstream raw materials

Hydrochloric acidN-(3-Hydroxyphenyl)-4-toluidine2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride2-(Chloromethyl)-2-imidazolineEthylenediaminep-Cresol4-Methylcyclohexanone3-Nitrophenol

Downstream products

Phentolamine mesilate

Suppliers62 total

北京华美互利生物化工010-56205725 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Sinoway Industrial co., ltd.+86-0592-5800732 +86-13806035118 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海康恩博科技有限公司(科小研试剂)400-1388-521 17673770086 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
XI'AN TIANGUANGYUAN BIOTECH CO., LTD.—
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
西安泽邦生物科技有限公司[email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
深圳菲斯生物科技有限公司0755-83725681-603
武汉鹏胤药业有限公司13163333255 · [email protected]
HAINAN POLY PHARMCEUTICAL CO. LTD+86-0571-89385087 +8613616530509 · [email protected]
上海丽康新材料有限公司+86-16631818819 +86-17736933208 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
许昌峰飞新材料科技有限公司19713077352; 19713077352 · [email protected]
深圳卓越生物医药科技有限公司26050679 18318671572 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
风咏生物(AbMole)021-10000000 13000000000 · [email protected]
Nantong Guangyuan Chemicl Co,Ltd+86-17331189928 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
安泰精细化工技术有限公司18503026267 · [email protected]
广东翁江化学试剂有限公司0751-2886750 13927877953 · [email protected]
山东小野化学股份有限公司0539-6362799 20)
陕西爱施达尔生物科技有限公司18682931470; 18682931470 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
嘉兴市德亿化工有限公司86-0573-85866609 18367600069 · [email protected]
珠海嘉亿生物科技有限公司18578209868 2355327026 · [email protected]
河南天孚化工有限公司+86-0371-55170693 +86-19937530512 · [email protected]
厦门盈融达化工有限公司+86-0592-6210733 · [email protected]
成都圣美凯生物科技有限公司028-85157043 15882256948 · [email protected]
career henan chemical co+86-0371-86658258 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
深圳大力水手生物科技有限公司0755-86320212 · [email protected]
Aladdin Scientific[email protected]
爆牛贸易重庆有限公司+86-023-6139-8061 +86-86-13650506873 · [email protected]
陕西缔都医药化工有限公司029-029-029-81148696 18161915376 · [email protected]
青岛浩海安杰医药科技有限公司156-6622-8711 18639325623 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
Guangzhou Tengyue Chemical Co., Ltd.+86-86-18148706580 +86-18826483838 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A substituted aniline that is 3-aminophenol in which the hydrogens of the amino group are replaced by 4-methylphenyl and 4,5-dihydro-1H-imidazol-2-ylmethyl groups respectively. An alpha-adrenergic antagonist, it is used fo the treatment of hypertension.