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a virility drug (trade name Vasomax) to treat erectile dysfunction in men (同)Vasomax

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/06/02 18:47:18」(JST)

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

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 cardiovascular complications, where one would generally avoid Beta-blockers (e.g. metoprolol), as they can cause unopposed alpha-adrenergic mediated coronary vasoconstriction, worsening myocardial ischemia and hypertension. It is important to note that 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. ^[6]^[7]

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 can be synthesized by alkylation of 3-(4-methylanilino)phenol using 2-chloromethylimidazoline:^[12]^[13]

References

^ 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.
^ Phentolamine at the US National Library of Medicine Medical Subject Headings (MeSH)
^ Brock G. Oral phentolamine (Vasomax). Drugs Today (Barcelona). 2000 Feb-Mar;36(2-3):121-4.
^ Shen, Howard (2008). Illustrated Pharmacology Memory Cards: PharMnemonics. Minireview. p. 14. ISBN 1-59541-101-1.
^ Tuncel M, Ram VC. Hypertensive emergencies. Etiology and management. American Journal of Cardiovascular Drugs. 2003;3(1):21-31.
^ Hollander JE, Henry TD. Evaluation and management of the patient who has cocaine-associated chest pain. Cardiology Clinics. 2006 Feb;24(1):103-14.
^ 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.
^ Bella AJ, Brock GB. Intracavernous pharmacotherapy for erectile dysfunction. Endocrine. 2004 Mar-Apr;23(2-3):149-55.
^ Rowbotham MC. Pharmacologic management of complex regional pain syndrome. Clinical Journal of Pain. 2006 Jun;22(5):425-9.
^ http://www.novalar.com/oraverse-dental-specialty-pharmaceutical
^ Malamed S. What's new in local anaesthesia? Society For The Advancement Of Anaesthesia In Dentistry Digest. 2009 Jan;25:4-14.
^ 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)

UpToDate Contents

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1. 高血圧緊急症の治療に用いる薬物 drugs used for the treatment of hypertensive emergencies
2. 昇圧剤および強心剤の使用 use of vasopressors and inotropes
3. コカイン：急性中毒 cocaine acute intoxication
4. 褐色細胞腫を有する成人に対する麻酔 anesthesia for the adult with pheochromocytoma
5. 成人における褐色細胞腫の治療 treatment of pheochromocytoma in adults

English Journal

Alpha2-adrenoceptor-independent inhibition of acetylcholine receptor channel and sodium channel by dexmedetomidine in rat superior cervical ganglion neurons.

Yang L1, Tang J2, Dong J3, Zheng J4.
Neuroscience.Neuroscience.2015 Mar 19;289:9-18. doi: 10.1016/j.neuroscience.2014.12.045. Epub 2015 Jan 9.
Both central and peripheral sympathetic nervous systems contribute to the cardiovascular effects of dexmedetomidine (DMED), a highly selective and widely used a2-adrenoceptor agonist for sedation, analgesia, and stress management. The central sympatholytic effects are augmented by peripheral inhibit
PMID 25583636

Impaired Neuronal Nitric Oxide Synthase-Mediated Vasodilator Responses to Mental Stress in Essential Hypertension.

Khan SG1, Geer A1, Fok HW1, Shabeeh H1, Brett SE1, Shah AM1, Chowienczyk PJ2.
Hypertension.Hypertension.2015 Mar 2. pii: HYPERTENSIONAHA.114.04538. [Epub ahead of print]
Neuronal NO synthase (nNOS) regulates blood flow in resistance vasculature at rest and during mental stress. To investigate whether nNOS signaling is dysfunctional in essential hypertension, forearm blood flow responses to mental stress were examined in 88 subjects: 48 with essential hypertension (4
PMID 25733243

Hyperalgesic effect of subarachnoid administration of phentolamine in mice.

Callegari DC1, Correa JA1, Pires OC2, Braga RB3, Gimbo AF4, de Souza AA5, Pires MH6, Constantino E7, de Paula Posso I7.
Brazilian journal of anesthesiology (Elsevier).Braz J Anesthesiol.2015 Mar-Apr;65(2):111-6. doi: 10.1016/j.bjane.2013.09.013. Epub 2014 Nov 26.
BACKGROUND AND OBJECTIVES: Painful phenomenon is one of the most important and complex experiences. Phentolamine is a non-selective alpha-adrenergic antagonist. The objective of this study was to compare the effect of increasing doses of phentolamine into subarachnoid space in rats in the modulation
PMID 25669863

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★リンクテーブル★

リンク元	「フェントラミン」「α受容体遮断薬」
拡張検索	「phentolamine mesilate」「phentolamine test」

「フェントラミン」

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; category	C (U.S.);
Routes of; administration	Usually IV or IM
Pharmacokinetic data
Metabolism	Hepatic
Half-life	19 minutes
Identifiers
CAS Registry Number	50-60-2
ATC code	C04AB01 V03AB36
PubChem	CID 5775
IUPHAR ligand	502
DrugBank	DB00692
ChemSpider	5571
UNII	Z468598HBV
KEGG	D08362
ChEBI	CHEBI:8081
ChEMBL	CHEMBL597
Chemical data
Formula	C17H19N3O
Molecular mass	281.352 g/mol
	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 ;
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　　[★]

英: phentolamine
化: メシル酸フェントラミン phentolamine mesilate
商: Regitine レギチーン
関: アドレナリン受容体、epinephrine reversal、レギチーン試験

概念

交感神経拮抗薬

α受容体拮抗薬

競合的拮抗薬 (⇔非競合的拮抗薬フェノキシベンザミン)
褐色細胞腫

効能又は効果

レギチーン注射液10mg

褐色細胞腫の手術前・手術中の血圧調整、褐色細胞腫の診断

添付文書

レギチーン注射液10mg

http://www.info.pmda.go.jp/go/pack/7290404A1038_1_02/7290404A1038_1_02?view=body

「α受容体遮断薬」

　　[★]

英: α adrenergic receptor blocker α-adrenergic blocking agent, α-adrenoceptor blocking agent
同: αアドレナリン受容体遮断薬、α遮断薬 α-blocker, α-blockade

非選択的α受容体拮抗薬

選択的α₁受容体拮抗薬

選択的α₂受容体拮抗薬

ヨヒンビン yohimbine

「phentolamine mesilate」

　　[★] メシル酸フェントラミン

関: phentolamine

「phentolamine test」

　　[★] フェントラミンテスト

[isbn0-7817-4266-8-1] 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] Phentolamine at the US National Library of Medicine Medical Subject Headings (MeSH)

[3] Brock G. Oral phentolamine (Vasomax). Drugs Today (Barcelona). 2000 Feb-Mar;36(2-3):121-4.

[pharmnemonics-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] ttp://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.

[12] K. Miescher, A. Marxer, E. Urech, U.S. Patent 2,503,059 (1950)

[13] E. Urech, A. Marxer, K. Miescher, Helv. Chim. Acta, 33, 1386 (1950)

匿名

検索

案内

案内

phentolamine

WordNet

Wikipedia preview

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Contents

Mechanism

Uses

Chemistry

References

UpToDate Contents

English Journal

Related Links

Related Pictures

★リンクテーブル★

「フェントラミン」

概念

効能又は効果

添付文書

「α受容体遮断薬」

非選択的α受容体拮抗薬

選択的α₁受容体拮抗薬

選択的α₂受容体拮抗薬

「phentolamine mesilate」

「phentolamine test」

匿名

検索

案内

phentolamine

WordNet

Wikipedia preview

wiki en

Contents

Mechanism

Uses

Chemistry

References

UpToDate Contents

English Journal

Related Links

Related Pictures

★リンクテーブル★

「フェントラミン」

概念

効能又は効果

添付文書

「α受容体遮断薬」

非選択的α受容体拮抗薬

選択的α1受容体拮抗薬

選択的α2受容体拮抗薬

「phentolamine mesilate」

「phentolamine test」

選択的α₁受容体拮抗薬

選択的α₂受容体拮抗薬