desipramine

デシプラミン 　

WordNet

1. a tricyclic antidepressant drug that activates the psychomotor system

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/01/18 21:11:46」(JST)

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Not to be confused with depramine.

Desipramine

Systematic (IUPAC) name
3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N-methylpropan-1-amine
Clinical data
Trade names	Norpramin
AHFS/Drugs.com	monograph
MedlinePlus	a682387
Pregnancy cat.	C (US)
Legal status	℞-only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	73-92%
Metabolism	Hepatic (CYP2D6)
Half-life	15-24 hours
Excretion	Urine (70%)
Identifiers
CAS number	50-47-5 Y
ATC code	N06AA01
PubChem	CID 2995
IUPHAR ligand	2399
DrugBank	DB01151
ChemSpider	2888 Y
UNII	TG537D343B Y
KEGG	D07791 Y
ChEBI	CHEBI:47781 Y
ChEMBL	CHEMBL72 Y
Chemical data
Formula	C18H22N2
Mol. mass	266.381 g/mol
SMILES c1cc3c(cc1)CCc2c(cccc2)N3CCCNC
InChI InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3 Y Key:HCYAFALTSJYZDH-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant (TCA). It inhibits the reuptake of norepinephrine and to a minor extent serotonin. It is used to treat depression, but not considered a first line treatment since the introduction of SSRI antidepressants. Desipramine is an active metabolite of imipramine. It is sold under the brand names Norpramin and Pertofrane.

Along with other tricyclics, desipramine has found use in treating neuropathic pain. The mechanism of action seems to involve the activation, through norepinephrine reuptake inhibition, of descending pathways in the spinal cord that block pain signals from ascending to the brain. Desipramine is one of the most potent and selective medications in this respect. It may also be used to treat symptoms of Attention Deficit Hyperactivity Disorder, as the underproduction of norepinephrine has been increasingly linked to symptoms associated with Attention Deficit Disorder^{[citation needed]}. It may also be used to treat symptoms of cocaine withdrawal.^{[citation needed]}

Cardiac arrhythmia

On December 2, 2009, the US Food and Drug Administration (FDA) and Sanofi-Aventis are warning healthcare professionals to use caution when prescribing the antidepressant desipramine hydrochloride (Norpramin) in patients with a family history of dysrhythmias or sudden cardiac death.

"The new safety information states that extreme caution should be used when this drug is given to patients who have a family history of sudden death, cardiac dysrhythmias, and cardiac conduction disturbances," according to an alert sent today from MedWatch, the FDA's safety information and adverse event reporting program.

The FDA and the manufacturer also warn that some patients may have seizures before cardiac dysrhythmias and death. Desipramine overdose is more likely to result in death than overdose with other tricyclic antidepressants, notes a company letter sent to healthcare professionals.

The "warnings" and "overdosage" sections of the drug's labeling are being changed to reflect these potential adverse events.

Genotoxicity

Desipramine has been shown to be genotoxic in fruit flies and associated with an increased risk of breast cancer in women.

Overdose

As tricyclic antidepressants have a relatively narrow therapeutic index, the likelihood of overdose (both accidental and intentional) is fairly high and should be considered carefully by the prescribing physician prior to patient use. Symptoms of overdose are similar to those of other tricyclic antidepressants, with cardiac toxicity (due to inhibition of sodium and calcium channels) generally occurring before the threshold for serotonin syndrome is reached. Due to this risk, tricyclic antidepressants are rarely selected as the first line treatment for depression. Desipramine overdose should always be considered a medical emergency. In the event of a suspected or known overdose, a poison control center (in the U.S. 1-800-222-1222), or 911 (999 in the UK) should be contacted immediately. The victim should be brought to the nearest hospital when/where phone services are not available.

See also

• Tricyclic antidepressant

References

External links

• Desipramine - medicinenet.com
• Desipramine - medlineplus.org
• Desipramine - mentalhealth.com
• Desipramine - medscape.com

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 三環系抗うつ剤および四環系抗うつ剤：薬理学、投与、および副作用 tricyclic and tetracyclic drugs pharmacology administration and side effects
• 2. 糖尿病性神経障害の治療 treatment of diabetic neuropathy
• 3. 成人における過敏性腸症候群の治療 treatment of irritable bowel syndrome in adults
• 4. 癌疼痛のマネージメント：鎮痛補助剤（鎮痛剤） cancer pain management adjuvant analgesics coanalgesics
• 5. 身体化：治療および予後 somatization treatment and prognosis

English Journal

• Effects of desvenlafaxine on the pharmacokinetics of desipramine in healthy adults.

• Nichols AI, Madelyn A, Chen Y, Behrle JA, Frick G, Paul J.SourceaPfizer Inc., formerly Wyeth Research, Collegeville, Pennsylvania bDepartment of Pharmaceutical Sciences, University at Buffalo, The State University of New York, Buffalo, New York, USA.
• International clinical psychopharmacology.Int Clin Psychopharmacol.2013 Mar;28(2):99-105. doi: 10.1097/YIC.0b013e32835c1f49.
• The results of two single-center, two-period, open-label trials that evaluated the effects of multiple doses of desvenlafaxine on the pharmacokinetics of desipramine, a cytochrome P450 (CYP) 2D6 enzyme substrate, are presented. Healthy individuals aged 18-45 years were administered a single oral dos
• PMID 23221858

• Active behaviours produced by antidepressants and opioids in the mouse tail suspension test.

• Berrocoso E, Ikeda K, Sora I, Uhl GR, Sánchez-Blázquez P, Mico JA.SourceNeuropsychopharmacology Research Group, Psychobiology Area, Department of Psychology, University of Cadiz, Cadiz, Spain.
• The international journal of neuropsychopharmacology / official scientific journal of the Collegium Internationale Neuropsychopharmacologicum (CINP).Int J Neuropsychopharmacol.2013 Feb;16(1):151-62. doi: 10.1017/S1461145711001842. Epub 2012 Jan 5.
• Most classical preclinical tests to predict antidepressant activity were initially developed to detect compounds that influenced noradrenergic and/or serotonergic activity, in accordance with the monoaminergic hypothesis of depression. However, central opioid systems are also known to influence the
• PMID 22217458

Japanese Journal

• Pharmacological Interaction With the Sigma1 (σ1)-Receptor in the Acute Behavioral Effects of Antidepressants

• Villard Vanessa,Meunier Johann,Chevallier Nathalie,Maurice Tangui
• Journal of Pharmacological Sciences 115(3), 279-292, 2011
• … The SSRI fluoxetine and sertraline, but not fluvoxamine, and the tricyclic antidepressants imipramine, desipramine, and amitriptyline were also effective. …
• NAID 130000663391

• A Novel Approach to the Prediction of Drug-Drug Interactions in Humans Based on the Serum Incubation Method

• SHIBATA Yoshihiro,TAKAHASHI Hiroyuki,CHIBA Masato,ISHII Yasuyuki
• Drug metabolism and pharmacokinetics 23(5), 328-339, 2008-10-25
• NAID 10024384558

Related Links

• Desipramine - Wikipedia, the free encyclopedia

Desipramine (also known as desmethylimipramine) is a tricyclic antidepressant ( TCA). It inhibits the reuptake of norepinephrine and to a lesser extent serotonin. It is used to treat depression, but not considered a first line treatment since the ...

• Desipramine - Internet Mental Health

The anticholinergic actions of desipramine are responsible for many of the commonly observed side effects of the drug. Desipramine causes ECG changes such as prolongation of the P-R interval and a decreased magnitude with an increased ...

Related Pictures

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★リンクテーブル★

リンク元	「抗うつ薬」「三環系抗うつ薬」「デシプラミン」

「抗うつ薬」

　　[★]

英

antidepressant, antidepressants

関

薬理学、そううつ病、精神疾患

作用機序

三環系抗うつ薬 tricyclic antidepressant

• ２つの説がある。

• 1. (急性作用)シナプス前膜におけるノルアドレナリン、セロトニンの再取り込み↓→シナプス間隙における薬剤濃度↑
• 2. (慢性作用)(2週間後)シナプス後膜における受容体の数↓

• 慢性作用はシナプス間隙のノルアドレナリン、セロトニン濃度が上昇した結果、シナプス後膜の受容体が減少したために出現すると考えられる。

抗うつ薬

• 三環系

• イミプラミン imipramine
• アミトリプチリン amitriptyline
• デシプラミン desipramine
• クロミプラミン clomipramine

• 四環系

• マプロチリン maprotiline
• ミアンセリン mianserin

• 選択的セロトニン再取り込み阻害薬 selective serotonin reuptake inhibitor SSRI

• フルボキサミン fluvoxamine
• パロキセチン paroxetine
• フルオキセチン fluoxetine

• セロトニン・ノルアドレナリン再取り込み阻害薬 serotonin noradrenaline reuptake inhibitor SNRI

ミルナシプラン milnacipran

• 非定型抗うつ薬 atypical agent

• トラゾドン trazodone

副作用

Adams and s Principles of Neurology, Ninth Edition Allan Ropper p.1474

		不眠、焦燥	鎮静	低血圧	抗コリン作用	消化管症状(嘔吐等)	性機能低下	体重増加
三環系	アミトリプチリン	±	2+	2+	3+	±	＋	2+
三環系	ドスレピン	±	2+	2+	2+	±	＋	2+
三環系	イミプラミン	2+	＋	2+	2+	±	＋	2+
SSRI	フルオキセチン	2+	±	±	＋	2+	2+	＋
SSRI	パロキセチン	2+	±	±	±	2+	2+	＋
SSRI	セルトラリン	2+	±	±	±	2+	2+	＋
SSRI	フルボキサミン	2+	＋	±	±	2+	2+	＋
SSRI	シタロプラム	2+	±	±	±	2+	2+	＋
SSRI	エスシタロプラム	2+	±	±	±	2+	2+	＋
SNRI	デシプラミン	＋	±	2+	＋	±	＋	＋
SNRI	ノルトリプチリン	＋	＋	＋	＋	±	＋	＋
SNRI	マプロチリン	＋	±	＋	＋	±	＋	2+
SNRI	ベンラファキシン	2+	±	±	±	2+	2+	±
SNRI	デュロキセチン	±	＋	±	＋	＋	±	±
NDRI	ブプロピオン	2+	±	±	＋	＋	±	±
MAOI	フェネルジン	2+	＋	2+	＋	＋	2+	＋
MAOI	トラニルシプロミン	2+	＋	2+	＋	＋	2+	＋
MAOI	イソカルボキサジド	2+	±	2+	＋	＋	2+	2+
MAOI	セレギリン	＋	±	＋	＋	＋	＋	＋
NaSSA	ミルタザピン	±	3+	＋	±	±	±	3+
非定型	ネファゾドン	±	2+	＋	＋	＋	±	＋
非定型	トラゾドン	±	3+	＋	±	＋	2+	＋

「三環系抗うつ薬」

　　[★]

英

tricyclic antidepressant, tricyclic anti-depressant agent

関

抗うつ薬、四環系抗うつ薬

イミプラミン

概念

• 環状の構造を三つ持つ抗うつ薬
• 治療効果発現には2-3週間必要

種類

• イミプラミン imipramine
• アミトリプチリン amitriptyline
• デシプラミン desipramine
• クロミプラミン clomipramine

作用機序

• ノルアドレナリン、セロトニンのシナプス前ニューロンへの再取り込みを抑制
• シナプス前膜のα₂受容体の脱感作。ネガティブフィードバックが解除され、モノアミンの放出が促進される

副作用

• 抗コリン作用

視力障害、口渇、便秘、尿閉

頻脈

• α₁ブロック作用

起立性低血圧

血中ノルアドレナリンの上昇

• 抗ヒスタミン作用

鎮静、眠気

「デシプラミン」

　　[★]

英

desipramine

化

塩酸デシプラミン desipramine hydrochloride

同

デスメチルイミプラミン desmethylimipramine

商

Norpramin, Pertofrane

関

抗うつ薬