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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/08/21 13:58:36」(JST)

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

Mechanism[edit source | edit]

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[edit source | edit]

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 (e.g. metoprolol) or combined alpha and beta adrenergic blocking agents (e.g. 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. It is also used in the treatment of pheochromocytoma prior to the administration of beta blockers to avoid unopposed alpha-stimulation.

^[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[edit source | edit]

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

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[edit source | edit]

^ 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.

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. 成人における褐色細胞腫の治療 treatment of pheochromocytoma in adults
5. フェニレフリンおよび類似構造のうっ血除去薬：小児の中毒 phenylephrine and related decongestants pediatric poisoning

English Journal

Biological effects of α-adrenergic phentolamine on erythrocyte hemeprotein: Molecular insights from biorecognition behavior, protein dynamics and flexibility.

Peng W1, Ding F2, Peng YK3, Xie Y4.
Journal of photochemistry and photobiology. B, Biology.J Photochem Photobiol B.2017 Jun;171:75-84. doi: 10.1016/j.jphotobiol.2017.04.035. Epub 2017 Apr 28.
PMID 28482223

Nerve-induced responses of mouse vaginal smooth muscle.

van Helden DF1, Kamiya A2, Kelsey S3, Laver DR3, Jobling P3, Mitsui R2, Hashitani H2.
Pflugers Archiv : European journal of physiology.Pflugers Arch.2017 May 27. doi: 10.1007/s00424-017-1995-x. [Epub ahead of print]
PMID 28551705

Octopamine and tyramine regulate the activity of reproductive visceral muscles in the adult female blood-feeding bug, Rhodnius prolixus.

Hana S1, Lange AB2.
The Journal of experimental biology.J Exp Biol.2017 May 15;220(Pt 10):1830-1836. doi: 10.1242/jeb.156307. Epub 2017 Feb 24.
PMID 28235907

Japanese Journal

Severe hypertension and tachycardia associated with pancuronium bromide in a patient with asymptomatic pheochromocytoma

HIRANO Shoji,UEKI Osamu,MISAKI Toshimitsu,HISAZUMI Haruo,HAMATANI Kazuo,MATSUBARA Fujitsugu,MIWA Umeo
泌尿器科紀要 30(5), 709-713, 1984-05
… 入院し,同19日左副腎摘除術を受けた.エトレンおよび笑気で十分な全身麻酔をおこなった後,pancuronium7.5mgを筋弛緩を得るため投与したところ急激な血圧上昇(220mmHg),2段脈,心室性頻脈を認めた.Lidocain(R),Inderal(R),Regitine(のR)投与にて症状は消失した.手術中に特記すべき血圧の変動は認められなかった.腫瘍の重さは33.69で,組織所見は褐色細胞腫であった.福色細胞腫における高血圧の発症機序についてはいまだ不明な点が多い. …
NAID 120002158708

16)Regitine投与後著明な血圧上昇を認めβ-受容体機能亢進状態を呈した低レニン性本態性高血圧症の1例 : 日本循環器学会第76回東北地方会

重富秀一,橋本重厚,福地総逸
Japanese circulation journal 46(SupplementIII), 552, 1982-11-01
NAID 110002648869

Related Pictures

brand names regitine Usermeds › Medications › Regitine Regitine, phentolamine mesylate B.P; CIBA Phentolamine Mesylate for Injection Regitin, Regitine, Regitina; CIBA; T153 Queen Nefertiti used aloe vera for skin (not including cloth > REGITINE

★リンクテーブル★

リンク元

「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 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	DB00692
ChemSpider	5571
UNII	Z468598HBV
KEGG	D08362
ChEMBL	CHEMBL597
Chemical data
Formula	C17H19N3O
Mol. 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

[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.

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案内

案内

Regitine