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{{Short description|An α-adrenergic antagonist medication}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 418037369 | verifiedrevid = 464200826
⚫ | image = Phentolamine.svg
⚫ | IUPAC_name = 3-phenol
| width = 150
⚫ | image = Phentolamine Structural Formulae.svg
| image2 = Phentolamine-space-filling.png | image2 = Phentolamine-space-filling.png


<!--Clinical data--> <!--Clinical data-->
| tradename = Regitine | tradename = Regitine, Oraverse
| Drugs.com = {{drugs.com|CONS|phentolamine}} | Drugs.com = {{drugs.com|monograph|phentolamine-mesylate}}
| legal_US = Rx-only
| pregnancy_category = C <small>(])
| routes_of_administration = ], ], ]
| legal_status =
⚫ | ATC_prefix = C04
| routes_of_administration = Usually IV or IM
⚫ | ATC_suffix = AB01
⚫ | ATC_supplemental = {{ATC|V03|AB36}}, {{ATC|G04|BE05}}


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = | protein_bound =
| metabolism = Hepatic | metabolism = ]
| elimination_half-life = 19 minutes | elimination_half-life = 19 minutes


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 50-60-2 | CAS_number = 50-60-2
⚫ | ATC_prefix = C04
⚫ | ATC_suffix = AB01
⚫ | ATC_supplemental = {{ATC|V03|AB36}}
| PubChem = 5775 | PubChem = 5775
| IUPHAR_ligand = 502 | IUPHAR_ligand = 502
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = APRD00615 | DrugBank = DB00692
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5571 | ChemSpiderID = 5571
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z468598HBV | UNII = Z468598HBV
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 8081
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08362 | KEGG = D08362
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<!--Chemical data--> <!--Chemical data-->
⚫ | IUPAC_name = 3-phenol
| C=17 | H=19 | N=3 | O=1 | C=17 | H=19 | N=3 | O=1
| molecular_weight = 281.352 g/mol
| smiles = Oc3cc(N(c1ccc(cc1)C)CC/2=N/CCN\2)ccc3 | smiles = Oc3cc(N(c1ccc(cc1)C)CC/2=N/CCN\2)ccc3
| InChI = 1/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)
| InChIKey = MRBDMNSDAVCSSF-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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) | StdInChI = 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)
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| StdInChIKey = MRBDMNSDAVCSSF-UHFFFAOYSA-N | StdInChIKey = MRBDMNSDAVCSSF-UHFFFAOYSA-N
}} }}

'''Phentolamine''' (Regitine) is a reversible<ref name="isbn0-7817-4266-8">{{cite book |author=Jewell, John R.; Longworth, David L.; Stoller, James K.; Casey, David |title=The Cleveland Clinic internal medicine case reviews |publisher=Lippincott Williams & Wilkins |location=Hagerstown, MD |year=2003 |isbn=0-7817-4266-8 |oclc= |doi= |accessdate= |page=32}}</ref> nonselective alpha-]. <ref>{{MeshName|Phentolamine}}</ref> '''Phentolamine''', sold under the brand name '''Regitine''' among others, is a reversible<ref name="isbn0-7817-4266-8">{{cite book | vauthors = Jewell JR, Longworth DL, Stoller JK, Casey D |title=The Cleveland Clinic internal medicine case reviews |publisher=Lippincott Williams & Wilkins |location=Hagerstown, MD |year=2003 |isbn=0-7817-4266-8 |page=32}}</ref> nonselective α-].<ref>{{MeshName|Phentolamine}}</ref>


==Mechanism== ==Mechanism==
Its primary action is ] due to α<sub>1</sub> blockade.<ref>Brock G. Oral phentolamine (Vasomax). ''Drugs Today (Barcelona)''. 2000 Feb-Mar;36(2-3):121-4.</ref> Its primary action is ] due to α<sub>1</sub> blockade.<ref name="pmid12879109">{{cite journal | vauthors = Brock G | title = Oral phentolamine (Vasomax) | journal = Drugs of Today | location = Barcelona, Spain | volume = 36 | issue = 2–3 | pages = 121–4 | date = 2000 | pmid = 12879109 | doi = 10.1358/dot.2000.36.2-3.568785 }}</ref>


Non-selective α-blockers can cause a much more pronounced reflex ] than the selective ]. Like the selective α<sub>1</sub> blockers, phentolamine causes a relaxation of systemic vasculature, leading to ]. This hypotension is sensed by the ], which results in increased sympathetic nerve firing on the heart, releasing ]. In response, the ] on the heart increase their ], ], and ], which help to offset the decrease in systemic blood pressure. Unlike the α<sub>1</sub> selective blockers, phentolamine also inhibits the α<sub>2</sub> receptors, which function predominantly as ] ] for norepinephrine release. By abolishing this negative feedback phentolamine leads to even less regulated norepinephrine release, which results in a more drastic increase in heart rate.<ref name=pharmnemonics>{{cite book | vauthors = Shen H | title=Illustrated Pharmacology Memory Cards: PharMnemonics | year=2008 | publisher=Minireview | isbn=978-1-59541-101-3 | page=14}}</ref>
It also can lead to reflex ] because of hypotension and α<sub>2</sub> inhibition, which increases sympathetic tone.<ref name=pharmnemonics>{{Cite book | author=Shen, Howard | title=Illustrated Pharmacology Memory Cards: PharMnemonics | date=2008 | publisher=Minireview | isbn=1-59541-101-1 | page=14}}</ref>


==Uses== ==Uses==
The primary application for phentolamine is for the control of ], most notably due to ].<ref>Tuncel M, Ram VC. Hypertensive emergencies. Etiology and management. ''American Journal of Cardiovascular Drugs''. 2003;3(1):21-31.</ref> The primary application for phentolamine is for the control of ], most notably due to ].<ref name="pmid14727943">{{cite journal | vauthors = Tuncel M, Ram VC | s2cid = 1993954 | title = Hypertensive emergencies. Etiology and management | journal = American Journal of Cardiovascular Drugs: Drugs, Devices, and Other Interventions | volume = 3 | issue = 1 | pages = 21–31 | date = 2003 | pmid = 14727943 | doi = 10.2165/00129784-200303010-00003 }}</ref>


It also has usefulness in the treatment of ]-induced cardiovascular complications, where one would generally avoid ]s (e.g. ]), as they can cause unopposed α-adrenergic mediated ], worsening myocardial ischemia and hypertension.<ref>{{cite journal | vauthors = Schurr JW, Gitman B, Belchikov Y | title = Controversial therapeutics: the β-adrenergic antagonist and cocaine-associated cardiovascular complications dilemma | journal = Pharmacotherapy | volume = 34 | issue = 12 | pages = 1269–1281 | date = December 2014 | pmid = 25224512 | doi = 10.1002/phar.1486 | s2cid = 5282953 }}</ref><ref>{{cite journal | vauthors = Freeman K, Feldman JA | title = Cocaine, myocardial infarction, and beta-blockers: time to rethink the equation? | journal = Annals of Emergency Medicine | volume = 51 | issue = 2 | pages = 130–134 | date = February 2008 | pmid = 17933425 | doi = 10.1016/j.annemergmed.2007.08.020 }}</ref> Phentolamine is not a first-line agent for this indication. Phentolamine should only be given to patients who do not fully respond to ]s, ], and ]s.<ref name="pmid16326260">{{cite journal | vauthors = Hollander JE, Henry TD | title = Evaluation and management of the patient who has cocaine-associated chest pain | journal = Cardiology Clinics | volume = 24 | issue = 1 | pages = 103–114 | date = February 2006 | pmid = 16326260 | doi = 10.1016/j.ccl.2005.09.003 }}</ref><ref name="pmid18072128">{{cite journal | vauthors = Chan GM, Sharma R, Price D, Hoffman RS, Nelson LS | title = Phentolamine therapy for cocaine-association acute coronary syndrome (CAACS) | journal = Journal of Medical Toxicology | volume = 2 | issue = 3 | pages = 108–111 | date = September 2006 | pmid = 18072128 | pmc = 3550159 | doi = 10.1007/BF03161019 }}</ref>
It also has usefulness in the treatment of ] induced hypertension, where one would generally avoid ] and where ] 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.


⚫ When given by injection it causes blood vessels to ], thereby increasing blood flow. When injected into the penis (intracavernosal), it increases blood flow to the penis, which results in an erection.<ref name="pmid15146094">{{cite journal | vauthors = Bella AJ, Brock GB | s2cid = 13056029 | title = Intracavernous pharmacotherapy for erectile dysfunction | journal = Endocrine | volume = 23 | issue = 2–3 | pages = 149–55 | date = 2004 | pmid = 15146094 | doi = 10.1385/ENDO:23:2-3:149 }}</ref>
<ref>Hollander JE, Henry TD. Evaluation and management of the patient who has cocaine-associated chest pain. ''Cardiology Clinics''. 2006 Feb;24(1):103-14.</ref><ref>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.</ref> In this context it is probably most safely given by infusion since ] doses have a propensity towards causing precipitous falls in blood pressure.


⚫ It may be stored in ]s to counteract severe peripheral vasoconstriction secondary to ] of peripherally placed ] infusions, typically of ]. ] infusions are less vasoconstrictive than norepinephrine as they primarily stimulate β receptor more than α receptors, but the effect remains dose-dependent.
⚫ 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.<ref>Bella AJ, Brock GB. Intracavernous pharmacotherapy for erectile dysfunction. ''Endocrine''. 2004 Mar-Apr;23(2-3):149-55.</ref>


⚫ Phentolamine also has diagnostic and therapeutic roles in ] (reflex sympathetic dystrophy).<ref name="pmid16772796">{{cite journal | vauthors = Rowbotham MC | s2cid = 17837280 | title = Pharmacologic management of complex regional pain syndrome | journal = The Clinical Journal of Pain | volume = 22 | issue = 5 | pages = 425–9 | date = June 2006 | pmid = 16772796 | doi = 10.1097/01.ajp.0000194281.74379.01 }}</ref>
⚫ It may be stored in ]s to counteract severe peripheral vasoconstriction secondary to ] of peripherally placed ] infusions, typically of ]. ] infusions are less vasoconstrictive than norepinephrine as they primarily stimulate beta receptor more than alpha receptors, but the effect remains dose dependent.


Phentolamine is marketed in the dental field as a local anesthetic reversal agent. Branded as OraVerse, it is a phentolamine mesylate injection designed to reverse the local vasoconstrictor properties used in many local anesthetics to prolong anesthesia.<ref name="pmid19267135">{{cite journal | vauthors = Malamed S | title = What's new in local anaesthesia? | journal = SAAD Digest | volume = 25 | pages = 4–14 | date = January 2009 | pmid = 19267135 }}</ref>
⚫ Phentolamine also has diagnostic and therapeutic roles in ] (reflex sympathetic dystrophy).<ref>Rowbotham MC. Pharmacologic management of complex regional pain syndrome. ''Clinical Journal of Pain''. 2006 Jun;22(5):425-9.</ref>

Phentolamine has recently been introduced in the dental field as a local anesthetic reversal agent. Distributed by Septodont, ] is a Phentolamine Mesylate injection designed to reverse the local vasoconstrictor properties used in many local anesthetics to prolong anesthesia.<ref> http://www.novalar.com/oraverse-dental-specialty-pharmaceutical</ref> OraVerse has been shown to accelerate the reversal of the lingering soft-tissue numbness associated with the widely used anesthetic-vasoconstrictor combinations.<ref>Malamed S. What's new in local anaesthesia? ''Society For The Advancement Of Anaesthesia In Dentistry Digest''. 2009 Jan;25:4-14.</ref>


==Chemistry== ==Chemistry==
Phentolamine can be synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline:<ref>{{cite patent | inventor = Miescher K, Marxer A, Urech E | assign1 = Ciba Pharmaceuticals Products, Inc. | country = US | number = 2503059 | title = 2-(N:N-diphenyl-aminomethyl) imidazolines | gdate = 1950 }}</ref><ref>{{cite journal | vauthors = Urech E, Marxer A, Miescher K | title = 2-Aminoalkylimidazoline. | journal = Helv. Chim. Acta | date = 1950 | volume = 33 | issue = 5 | pages = 1386–407 | doi = 10.1002/hlca.19500330539 }}</ref>
Phentolamine, 2-methyl]-2-imidazoline, is synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline.

] :]{{clear left}}
*K. Miescher, A. Marxer, E. Urech, {{US Patent|2503059}} (1950).

*E. Urech, A. Marxer, K. Miescher, Helv. Chim. Acta, 33, 1386 (1950).
== Adverse effects ==
* ].<ref>{{cite web|url=http://www.rxlist.com/phentolamine-mesylate-for-injection-side-effects-drug-center.htm|title=Common Side Effects of Phentolamine Mesylate for Injection (Phentolamine Mesylate) | work = Drug Center - RxList }}</ref>


==References== ==References==
{{reflist|2}} {{reflist}}


{{Antihypertensives and diuretics}} {{Antihypertensives and diuretics}}
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{{Drugs for erectile dysfunction and PE}} {{Drugs for erectile dysfunction and PE}}
{{Alpha blockers}} {{Alpha blockers}}
{{Portal bar | Medicine}}


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Latest revision as of 18:12, 21 October 2024

An α-adrenergic antagonist medication Pharmaceutical compound
Phentolamine
Clinical data
Trade namesRegitine, Oraverse
AHFS/Drugs.comMonograph
Routes of
administration		intravenous, intramuscular, eye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life19 minutes
Identifiers
IUPAC name
  • 3-phenol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.049 Edit this at Wikidata
Chemical and physical data
FormulaC17H19N3O
Molar mass281.359 g·mol
3D model (JSmol)
SMILES
  • Oc3cc(N(c1ccc(cc1)C)CC/2=N/CCN\2)ccc3
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)
  • Key:MRBDMNSDAVCSSF-UHFFFAOYSA-N
  (what is this?)  (verify)

Phentolamine, sold under the brand name Regitine among others, is a reversible nonselective α-adrenergic antagonist.

Mechanism

Its primary action is vasodilation due to α1 blockade.

Non-selective α-blockers can cause a much more pronounced reflex tachycardia than the selective α1 blockers. Like the selective α1 blockers, phentolamine causes a relaxation of systemic vasculature, leading to hypotension. This hypotension is sensed by the baroreceptor reflex, which results in increased sympathetic nerve firing on the heart, releasing norepinephrine. In response, the β1 adrenergic receptors on the heart increase their rate, contractility, and dromotropy, which help to offset the decrease in systemic blood pressure. Unlike the α1 selective blockers, phentolamine also inhibits the α2 receptors, which function predominantly as presynaptic negative feedback for norepinephrine release. By abolishing this negative feedback phentolamine leads to even less regulated norepinephrine release, which results in a more drastic increase in heart rate.

Uses

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

It also has usefulness in the treatment of cocaine-induced cardiovascular complications, where one would generally avoid β-blockers (e.g. metoprolol), as they can cause unopposed α-adrenergic mediated coronary vasoconstriction, worsening myocardial ischemia and hypertension. Phentolamine is not a first-line agent for this indication. Phentolamine should only be given to patients who do not fully respond to benzodiazepines, nitroglycerin, and calcium channel blockers.

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

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 β receptor more than α receptors, but the effect remains dose-dependent.

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

Phentolamine is marketed in the dental field as a local anesthetic reversal agent. Branded as OraVerse, it is a phentolamine mesylate injection designed to reverse the local vasoconstrictor properties used in many local anesthetics to prolong anesthesia.

Chemistry

Phentolamine can be synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline:

Adverse effects

References

  1. Jewell JR, Longworth DL, Stoller JK, Casey D (2003). The Cleveland Clinic internal medicine case reviews. Hagerstown, MD: Lippincott Williams & Wilkins. p. 32. ISBN 0-7817-4266-8.
  2. Phentolamine at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  3. Brock G (2000). "Oral phentolamine (Vasomax)". Drugs of Today. 36 (2–3). Barcelona, Spain: 121–4. doi:10.1358/dot.2000.36.2-3.568785. PMID 12879109.
  4. Shen H (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 14. ISBN 978-1-59541-101-3.
  5. Tuncel M, Ram VC (2003). "Hypertensive emergencies. Etiology and management". American Journal of Cardiovascular Drugs: Drugs, Devices, and Other Interventions. 3 (1): 21–31. doi:10.2165/00129784-200303010-00003. PMID 14727943. S2CID 1993954.
  6. Schurr JW, Gitman B, Belchikov Y (December 2014). "Controversial therapeutics: the β-adrenergic antagonist and cocaine-associated cardiovascular complications dilemma". Pharmacotherapy. 34 (12): 1269–1281. doi:10.1002/phar.1486. PMID 25224512. S2CID 5282953.
  7. Freeman K, Feldman JA (February 2008). "Cocaine, myocardial infarction, and beta-blockers: time to rethink the equation?". Annals of Emergency Medicine. 51 (2): 130–134. doi:10.1016/j.annemergmed.2007.08.020. PMID 17933425.
  8. Hollander JE, Henry TD (February 2006). "Evaluation and management of the patient who has cocaine-associated chest pain". Cardiology Clinics. 24 (1): 103–114. doi:10.1016/j.ccl.2005.09.003. PMID 16326260.
  9. Chan GM, Sharma R, Price D, Hoffman RS, Nelson LS (September 2006). "Phentolamine therapy for cocaine-association acute coronary syndrome (CAACS)". Journal of Medical Toxicology. 2 (3): 108–111. doi:10.1007/BF03161019. PMC 3550159. PMID 18072128.
  10. Bella AJ, Brock GB (2004). "Intracavernous pharmacotherapy for erectile dysfunction". Endocrine. 23 (2–3): 149–55. doi:10.1385/ENDO:23:2-3:149. PMID 15146094. S2CID 13056029.
  11. Rowbotham MC (June 2006). "Pharmacologic management of complex regional pain syndrome". The Clinical Journal of Pain. 22 (5): 425–9. doi:10.1097/01.ajp.0000194281.74379.01. PMID 16772796. S2CID 17837280.
  12. Malamed S (January 2009). "What's new in local anaesthesia?". SAAD Digest. 25: 4–14. PMID 19267135.
  13. US 2503059, Miescher K, Marxer A, Urech E, "2-(N:N-diphenyl-aminomethyl) imidazolines", issued 1950, assigned to Ciba Pharmaceuticals Products, Inc. 
  14. Urech E, Marxer A, Miescher K (1950). "2-Aminoalkylimidazoline". Helv. Chim. Acta. 33 (5): 1386–407. doi:10.1002/hlca.19500330539.
  15. "Common Side Effects of Phentolamine Mesylate for Injection (Phentolamine Mesylate)". Drug Center - RxList.
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