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セレギリン

Selegiline

HCID 26757
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
14611-51-9
標準SMILES
C#CCN(C)[C@H](C)Cc1ccccc1
InChIKey
MEZLKOACVSPNER-GFCCVEGCSA-N
分子式
C13H17N
平均分子量
187.28 g/mol
単同位体質量
187.13609954

概要

(-)-selegiline is a selegiline and a terminal acetylenic compound. It has a role as a geroprotector. It is a conjugate base of a (-)-selegiline(1+).

名称と識別子

優先名称
Selegiline
IUPAC
(2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
現地名
セレギリン
英語名
Selegiline
分子式
C13H17N
分子量
187.28

名称と別名

selegilineL-Deprenalin(-)-selegiline14611-51-9L-DeprenylSelegilinaSelegilinum(-)-DeprenilL-Selegiline2K1V7GP655N-methyl-N-[(2R)-1-phenylpropan-2-yl]prop-2-yn-1-amineCHEBI:9086
名称をさらに表示
(αR)-N,α-ジメチル-N-(2-プロピニル)ベンゼンエタンアミン(-)-セレギリンセレギリン(R)-セレギリン(αR)-α,N-ジメチル-N-プロパルギルベンゼンエタンアミンN-メチル-N-[(R)-1-メチル-2-フェニルエチル]-2-プロピン-1-アミン(-)-デプレニル(2R)-N-メチル-N-(2-プロピニル)-1-フェニル-2-プロパンアミンN-メチル-N-[(R)-1-ベンジルエチル]-2-プロピン-1-アミンl-デプレニル(R)-(-)-デプレニル(2R)-N-(2-プロピニル)-N-メチル-1-フェニルプロパン-2-アミンメチル[(2R)-1-フェニルプロパン-2-イル](プロパ-2-イン-1-イル)アミンSELEGILINE BASEEmsamBenzeneethanaMine, N,a-diMethyl-N-2-propyn-1-yl-, (aR)-C07245SelgeneZelaparSeleginaSELEGELINEmsam TTS
DTXSID6023575(-)-(N)-Methyl-N-((1R)-1-methyl-2-phenylethyl)prop-2-yn-1-amineSelegylineCHEBI:50217N-methyl-N-((2R)-1-phenylpropan-2-yl)prop-2-yn-1-amineSelegiline, (R)-RefChem:56003DTXCID403575

物性

構造計算による物性

XLogP
2.8
極性表面積
3.2 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
4
重原子数
14
形式電荷
0
複雑度
195

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 5 件

Antidepressants -> Monoamine oxidase inhibitors (MAOI)

Breast Feeding; Lactation; Antiparkinson Agents; Monoamine Oxidase Inhibitors; Neuroprotective Agents

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Animal DrugsPharmaceuticals -> UK Veterinary Medicines Directorate List
Melting Point141-142 °C
Dissociation Constants7.48
Collision Cross Section · 2 件

140.1 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: Antidepressants]

142.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

物理化学的性質

融点
137.5 · 137.5-139 °C
比旋光度
20 · D20 -11.2°
沸点
273 ℃ · 273℃
比重(密度)
0.954 · 0.954
屈折率
20 · nD20 1.5180

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 108 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationStatus: Active Update: 07-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/21229
Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Treatment · 1 件

Treatment of overdose with non-selective MAOIs is symptomatic and supportive. Induction of emesis or gastric lavage with instillation of charcoal slurry may be helpful in early poisoning, provided the airway has been protected against aspiration. Signs and symptoms of central nervous system stimulation, including convulsions, should be treated with diazepam, given slowly intravenously. Phenothiazine derivatives and central nervous system stimulants should be avoided. Hypotension and vascular collapse should be treated with intravenous fluids and, if necessary, blood pressure titration with an intravenous infusion of a dilute pressor agent. It should be noted that adrenergic agents may produce a markedly increased pressor response. Respiration should be supported by appropriate measures, including management of the airway, use of supplemental oxygen, and mechanical ventilatory assistance, as required. Body temperature should be monitored closely. Intensive management of hyperpyrexia may be required. Maintenance of fluid and electrolyte balance is essential. (L1712)

Hepatotoxicity · 1 件

Selegiline has been reported to cause serum enzyme elevations in up to 40% of patients treated long term. Although the abnormalities were usually mild and self-limiting, they were persistent with continuation of treatment in some patients, ultimately requiring drug discointuation. Selegiline has not been implicated in cases of clinically apparent acute liver injury, but such instances have been reported with other less specific MAO inhibitors.

化学と産業

薬理情報

ATC Code · 4 件

N04BD01

N - Nervous system

QN - Nervous system

QN - Nervous system

Protein Binding> 99.5%
Pharmacodynamics · 1 件

Dopamine is an essential chemical that occurs in many parts of the body. It is the premature degradation of dopamine that results in the symptoms of Parkinson's disease. Monoamine oxidase (MAO) is an enzyme which accelerates the breakdown of dopamine. Selegiline can prolong the effects of dopamine in the brain by preventing its breakdown through seletively blocking MAO-B. It also may prevent the removal of dopamine between nerve endings and enhance release of dopamine from nerve cells.

Mechanism of Action · 1 件

Although the mechanisms for selegiline's beneficial action in the treatment of Parkinson's disease are not fully understood, the selective, irreversible inhibition of monoamine oxidase type B (MAO-B) is thought to be of primary importance. MAO-B is involved in the oxidative deamination of dopamine in the brain. Selegiline binds to MAO-B within the nigrostriatal pathways in the central nervous system, thus blocking microsomal metabolism of dopamine and enhancing the dopaminergic activity in the substantial nigra. Selegiline may also increase dopaminergic activity through mechanisms other than inhibition of MAO-B. At higher doses, selegiline can also inhibit monozmine oxidase type A (MAO-A), allowing it to be used for the treatment of depression.

Biological Half-Life1.2-2 hours
Metabolism/Metabolites · 2 件

Selegiline has known human metabolites that include Methamphetamine and Desmethylselegiline.

Half Life: 1.2-2 hours

FDA Pharmacological Classification · 6 件

2K1V7GP655

SELEGILINE

Established Pharmacologic Class [EPC] - Monoamine Oxidase Inhibitor

Mechanisms of Action [MoA] - Monoamine Oxidase Inhibitors

Established Pharmacologic Class [EPC] - Monoamine Oxidase Type B Inhibitor

関連反応

1 件
反応記録を作成
HRID 1740682 の反応式
HRID 1740682反応物としてuspto-grants-1999_10

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

データベース識別子

CAS
14611-51-9
PubChem CID
26757
DTXSID
DTXSID6023575
ChEMBL
CHEMBL972
ChEBI
CHEBI:9086
UNII
2K1V7GP655
EC Number
604-507-3
Nikkaji
J34.132K
闪点
108 ℃ · 108℃
貯蔵温度
-20 °C · -20°C
酸解離定数(Pka)
7.53 · 7.53±0.50(Predicted)
InChI
InChI=1/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/s3
InChIKey
MEZLKOACVSPNER-PLAQIDKDNA-N
SMILES
C1(C=CC=CC=1)C[C@@H](C)N(C)CC#C |&1:7,r|
CAS データベース
14611 · 14611-51-9
Adverse EffectsSelegiline use may lead to the following adverse effects in patients using the medication:
Exposure RoutesOral. Rapidly absorbed from the gastrointestinal tract.
Toxicity Summary · 2 件

A hypertensive crisis caused by selegiline is attributed to the toxic levels of adrenergic metabolites. The recommended treatment options for the crisis include the administration of intravenous phentolamine, labetalol, or nitroprusside, which can rapidly lower elevated blood pressure levels. In such cases, any signs of end-organ damage should be promptly assessed and appropriately treated.

Although the mechanisms for selegiline's beneficial action in the treatment of Parkinson's disease are not fully understood, the selective, irreversible inhibition of monoamine oxidase type B (MAO-B) is thought to be of primary importance. MAO-B is involved in the oxidative deamination of dopamine in the brain. Selegiline binds to MAO-B within the nigrostriatal pathways in the central nervous system, thus blocking microsomal metabolism of dopamine and enhancing the dopaminergic activity in the substantial nigra. Selegiline may also increase dopaminergic activity through mechanisms other than inhibition of MAO-B. At higher doses, selegiline can also inhibit monozmine oxidase type A (MAO-A), allowing it to be used for the treatment of depression. MAO's activity is inhibited when selegiline binds to the isoalloxazine flavin adenine dinucleotide (FAD) at its active center

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

selegiline

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation · 2 件

◉ Summary of Use during Lactation

◈ What is selegiline?

Toxicity DataLD50: 63 mg/kg (Intravenous, Rat) (A308)

安全データ

wgk
1
ridadr
1851
risk_code
11-23/24/25-39/23/24/25
hazard_code
F,T
safety_code
7-16-36/37-45
hazard_class
6.1(b)
packing_group
III

Mechanisms of Action [MoA] - Monoamine Oxidase-B Inhibitors

MeSH Pharmacological Classification · 4 件

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems.

Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.

A chemically heterogeneous group of drugs that have in common the ability to block oxidative deamination of naturally occurring monoamines. (From Gilman, et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p414)

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.

Absorption, Distribution and ExcretionRapidly absorbed from the gastrointestinal tract.

用途と製造

Uses · 2 件

Use (kg; approx.) in Germany (2009): >25

Monotherapy for initial treatment of Parkinson's disease, as well as an adjunct therapy in patients with a decreased response to levodopa/carbadopa. Also used for the palliative treatment of mild to moderate Alzheimer's disease and at higher doses, for the treatment of depression.

Use Classification · 2 件

Pharmaceuticals

Pharmaceuticals -> Antiparkinsons

応用分野 · 2 件

用途モノアミンオキシダーゼB(MAO-B)阻害薬パーキンソン病の治療に併用される

使用This drug is a selective inhibitor of monoaminooxidase B, which suppresses dopamineinactivation processes and facilitates an increase of its level in the brain. In treating Parkinsonism, selegiline is usually used in combination with levodopa.

サプライヤー20 社

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