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Selegiline

HCID 26757
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
14611-51-9
표준 SMILES
C#CCN(C)[C@H](C)Cc1ccccc1
InChIKey
MEZLKOACVSPNER-GFCCVEGCSA-N
분자식
C13H17N
평균 분자량
187.28 g/mol
단동위원소 질량
187.13609954

개요

(-)-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+).

이름 및 식별자

우선 이름
Selegiline
IUPAC
(2R)-N-methyl-1-phenyl-N-prop-2-ynylpropan-2-amine
영어명
Selegiline
분자식
C13H17N
분자량
187.28

이름 및 동의어

selegilineL-Deprenalin(-)-selegiline14611-51-9L-DeprenylSelegilinaSelegilinum(-)-DeprenilL-Selegiline2K1V7GP655N-methyl-N-[(2R)-1-phenylpropan-2-yl]prop-2-yn-1-amineCHEBI:9086
이름 더 보기
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

데이터베이스 식별자

CAS
14611-51-9
PubChem CID
26757
DTXSID
DTXSID6023575
ChEMBL
CHEMBL972
ChEBI
CHEBI:9086
UNII
2K1V7GP655
EC Number
604-507-3
Nikkaji
J34.132K

물성

구조 계산 물성

XLogP
2.8
극성 표면적
3.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
1
회전 가능 결합 수
4
무거운 원자 수
14
형식 전하
0
복잡도
195

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 5건

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 · 2건

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)]

물리화학적 성질

녹는점
137.5 · 137.5-139 °C
끓는 점
273 ℃ · 273℃
밀도
0.954 · 0.954
굴절률
20 · nD20 1.5180
인화점
108 ℃ · 108℃

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

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.

유해성 정보

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

독성 정보

Treatment · 1건

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 · 1건

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.

화학 및 산업

약리 정보

ATC Code · 4건

N04BD01

N - Nervous system

QN - Nervous system

QN - Nervous system

Protein Binding> 99.5%
Pharmacodynamics · 1건

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 · 1건

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 · 2건

Selegiline has known human metabolites that include Methamphetamine and Desmethylselegiline.

Half Life: 1.2-2 hours

FDA Pharmacological Classification · 6건

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

관련 반응

1건
반응 기록 만들기
HRID 1740682 반응식
HRID 1740682반응물로uspto-grants-1999_10

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
저장 조건
-20 °C · -20°C
산도 계수 (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|
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 · 2건

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 · 5건

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 · 2건

◉ Summary of Use during Lactation

◈ What is selegiline?

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

안전 데이터

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
포장분류
III
위험 등급
6.1(b)

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

MeSH Pharmacological Classification · 4건

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.

용도 및 제조

Uses · 2건

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 · 2건

Pharmaceuticals

Pharmaceuticals -> Antiparkinsons

응용 분야 · 1건

용도This 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.

공급사20 곳

北京华美互利生物化工010-56205725 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
深圳法默科技有限公司0755-86648230 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
武汉德拜技术有限公司18086626237 18086626237 · [email protected]
上海昕凯医药科技有限公司21-619849051-1 18521059765 · [email protected]
西安美川生物科技有限公司029-89275612 +8618991951683 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 13028896684 · [email protected]
南昌朗纳化工有限公司15079032866 · [email protected]
湖北摩科化学有限公司18627753421; 18627756402 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
重庆卡兰医药有限公司[email protected]
Wuhan Han Sheng New Material Technology Co.,Ltd+86-17798174412 · [email protected]
Henan Lavoisier Chemical Products Co.Ltd+86-86-37163682289 +8615981966935 · [email protected]
Golden Pharma Co., Limited+86-18958062155 · [email protected]
Wuhan Fortuna Chemical Co., Ltd+86-27-59207850 · [email protected]