Phentolamine


Phentolamine
Phentolamine
Systematic (IUPAC) name
3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol
Clinical data
Trade names Regitine
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. C (U.S.)
Legal status  ?
Routes Usually IV or IM
Pharmacokinetic data
Metabolism Hepatic
Half-life 19 minutes
Identifiers
CAS number 50-60-2
ATC code C04AB01 V03AB36
PubChem CID 5775
IUPHAR ligand 502
DrugBank APRD00615
ChemSpider 5571 YesY
UNII Z468598HBV YesY
KEGG D08362 YesY
ChEMBL CHEMBL597 YesY
Chemical data
Formula C17H19N3O 
Mol. mass 281.352 g/mol
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

Phentolamine (Regitine) is a reversible[1] nonselective alpha-adrenergic antagonist. [2]

Contents

Mechanism

Its primary action is vasodilation due to α1 blockade.[3]

It also can lead to reflex tachycardia because of hypotension and α2 inhibition, which increases sympathetic tone.[4]

Uses

The primary application for phentolamine is for the control of hypertensive emergencies, most notably due to pheochromocytoma.[5]

It also has usefulness in the treatment of cocaine induced hypertension, where one would generally avoid beta blockers and where calcium channel blockers are not effective. Beta-blockers (i.e. metoprolol) or combined alpha and beta adrenergic blocking agents (i.e. labetalol) should be avoided in patients with a history of cocaine abuse. They can cause an unopposed alpha-adrenergic mediated coronary vasoconstriction, causing the worsening of myocardial ischemia and hypertension.

[6][7] In this context it is probably most safely given by infusion since bolus doses have a propensity towards causing precipitous falls in blood pressure.

When given by injection it causes blood vessels to expand, thereby increasing blood flow. When injected into the penis (intracavernosal), it increases blood flow to the penis, which results in an erection.[8]

It may be stored in crash carts to counteract severe peripheral vasoconstriction secondary to extravasation of peripherally placed vasopressor infusions, typically of norepinephrine. Epinephrine infusions are less vasoconstrictive than norepinephrine as they primarily stimulate beta receptor more than alpha receptors, but the effect remains dose dependent.

Phentolamine also has diagnostic and therapeutic roles in complex regional pain syndrome (reflex sympathetic dystrophy).[9]

Phentolamine has recently been introduced in the dental field as a local anesthetic reversal agent. Distributed by Septodont, OraVerse is a Phentolamine Mesylate injection designed to reverse the local vasoconstrictor properties used in many local anesthetics to prolong anesthesia.[10] OraVerse has been shown to accelerate the reversal of the lingering soft-tissue numbness associated with the widely used anesthetic-vasoconstrictor combinations.[11]

Chemistry

Phentolamine, 2-[[N-(3′-hydroxyphenyl)-para-toluidion]methyl]-2-imidazoline, is synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline.

Phentolamine synthesis.png
  • K. Miescher, A. Marxer, E. Urech, U.S. Patent 2,503,059 (1950).
  • E. Urech, A. Marxer, K. Miescher, Helv. Chim. Acta, 33, 1386 (1950).

References

  1. ^ Jewell, John R.; Longworth, David L.; Stoller, James K.; Casey, David (2003). The Cleveland Clinic internal medicine case reviews. Hagerstown, MD: Lippincott Williams & Wilkins. p. 32. ISBN 0-7817-4266-8. 
  2. ^ MeSH Phentolamine
  3. ^ Brock G. Oral phentolamine (Vasomax). Drugs Today (Barcelona). 2000 Feb-Mar;36(2-3):121-4.
  4. ^ Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 14. ISBN 1-59541-101-1. 
  5. ^ Tuncel M, Ram VC. Hypertensive emergencies. Etiology and management. American Journal of Cardiovascular Drugs. 2003;3(1):21-31.
  6. ^ Hollander JE, Henry TD. Evaluation and management of the patient who has cocaine-associated chest pain. Cardiology Clinics. 2006 Feb;24(1):103-14.
  7. ^ Chan GM, Sharma R, Price D, Hoffman RS, Nelson LS. Phentolamine Therapy for Cocaine-Association Acute Coronary Syndrome (CAACS). Journal of Medical Toxicology. 2006 Sep;2(3):108-11.
  8. ^ Bella AJ, Brock GB. Intracavernous pharmacotherapy for erectile dysfunction. Endocrine. 2004 Mar-Apr;23(2-3):149-55.
  9. ^ Rowbotham MC. Pharmacologic management of complex regional pain syndrome. Clinical Journal of Pain. 2006 Jun;22(5):425-9.
  10. ^ http://www.novalar.com/oraverse-dental-specialty-pharmaceutical
  11. ^ Malamed S. What's new in local anaesthesia? Society For The Advancement Of Anaesthesia In Dentistry Digest. 2009 Jan;25:4-14.

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Look at other dictionaries:

  • phentolamine — noun Etymology: phen + toluidine + amine Date: 1952 an adrenergic blocking agent C17H19N3O used especially in the diagnosis and treatment of hypertension due to pheochromocytoma …   New Collegiate Dictionary

  • phentolamine — /fen tol euh meen , min/, n. Pharm. an alpha blocker, C17H19N3O, used to reduce hypertensive states caused by a catecholamine excess, as in the treatment of pheochromocytoma. [1950 55; PHEN + TOL(UIDINE) + AMINE; see TOLU] * * * …   Universalium

  • phentolamine — noun A drug, injected into the penis, to treat erectile dysfunction …   Wiktionary

  • phentolamine — phen·tol·amine fen täl ə .mēn, mən n an adrenergic blocking agent that is administered by injection in the form of its mesylate C17H19N3O·CH4O3S esp. in the diagnosis and treatment of hypertension due to pheochromocytoma see REGITINE * * * n. a… …   Medical dictionary

  • phentolamine — phen·tol·amine …   English syllables

  • phentolamine — n. a drug that dilates blood vessels (see alpha blocker) and is used to reduce high blood pressure in patients with phaeochromocytoma. It is administered by mouth or injection; side effects include fast heartbeat and digestive upsets. Trade names …   The new mediacal dictionary

  • phentolamine — noun a virility drug (trade name Vasomax) to treat erectile dysfunction in men • Syn: ↑Vasomax • Usage Domain: ↑trade name (for: ↑Vasomax) • Hypernyms: ↑virility drug, ↑ …   Useful english dictionary

  • phentolamine mesylate — The same actions as phentolamine hydrochloride, for intravenous use only. * * * [USP] the methanesulfonate salt of phentolamine, having the same antiadrenergic actions as the base; administered intramuscularly or intravenously in the prophylaxis… …   Medical dictionary

  • phentolamine hydrochloride — A nonselective adrenergic (α receptor) blocking agent …   Medical dictionary

  • Фентоламин (Phentolamine) — лекарственное вещество, которое расширяет кровеносные сосуды (см. Альфа блокатор); применяется для снижения повышенного кровяного давления у больных с феохромоцитомой, а также для лечения заболеваний, сопровождающихся нарушением кровообращения… …   Медицинские термины


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