Eletriptan

HCID 77993

기본 정보

CAS
143322-58-1
표준 SMILES
CN1CCC[C@@H]1Cc1c[nH]c2ccc(CCS(=O)(=O)c3ccccc3)cc12
InChIKey
PWVXXGRKLHYWKM-LJQANCHMSA-N
분자식
C22H26N2O2S
평균 분자량
382.5 g/mol
단동위원소 질량
382.17149907

개요

Eletriptan is an N-alkylpyrrolidine, that is N-methylpyrrolidine in which the pro-R hydrogen at position 2 is replaced by a {5-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl}methyl group. It has a role as a non-steroidal anti-inflammatory drug, a serotonergic agonist and a vasoconstrictor agent. It is a member of indoles, a sulfone and a N-alkylpyrrolidine. It is a conjugate base of an eletriptan(1+).

이름 및 식별자

우선 이름
Eletriptan
IUPAC
5-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indole
영어명
Eletriptan
분자식
C22H26N2O2S
분자량
382.52

이름 및 동의어

Eletriptan143322-58-1eletriptanumUK 116044UK-116044DTXSID9046861UK-116,04422QOO9B8KICHEBI:509225-[2-(benzenesulfonyl)ethyl]-3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-1H-indoleUK-116044-04 FREE BASEUK-116,044-04 FREE BASE
이름 더 보기
RelpaxRelpax free aMine(R)-EletriptanUnii-22qoo9B8kiEletriptan Free BaseEletriptan USP/EP/BPEletriptan Impurity 6According to triptans
5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indoleDTXCID7026861(R)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole3-(((2R)-1-methylpyrrolidin-2-yl)methyl)-5-(2-phenylsulfonylethyl)-1H-indole3-[[(2R)-1-methylpyrrolidin-2-yl]methyl]-5-(2-phenylsulfonylethyl)-1H-indole5-(2-(benzenesulfonyl)ethyl)-3-(((2R)-1-methylpyrrolidin-2-yl)methyl)-1H-indoleRefChem:57394N02CC06

데이터베이스 식별자

CAS
143322-58-1
PubChem CID
77993
DTXSID
DTXSID9046861
ChEMBL
CHEMBL1510
ChEBI
CHEBI:50922
UNII
22QOO9B8KI
EC Number
640-088-3
Nikkaji
J979.643F

물성

구조 계산 물성

XLogP
4.1
극성 표면적
61.6 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
27

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP3.9
Solubility · 2건

Readily soluble as hydrobromide formulation

1.18e-03 g/L

Human Drugs · 2건

Breast Feeding; Lactation; Milk, Human; Serotonin Receptor Agonists; Serotonin 5-HT1 Receptor Agonists; Triptans; Vasoconstrictor Agents

Pharmaceuticals

Physical DescriptionSolid
Collision Cross Section · 2건

189.45 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

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

물리화학적 성질

녹는점
168 · 168-170C
끓는 점
613.4 · 613.4±55.0 °C(Predicted)
밀도
1.235 · 1.235±0.06 g/cm3(Predicted)
저장 조건
Sealed in dry,Room Temperature
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체

화학적 성질

Yellow Foam

안전 및 규제

GHS 분류

GHS Classification · 4건

Danger

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

P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 29 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (100%)

독성 정보

Adverse Effects · 1건

Adverse events reported from eletriptan use are mostly mild, moderate, and transient. Although eletriptan is associated with nausea, dizziness, drowsiness, and coronary vasoconstriction, the most common adverse effects include a group of sensations referred to as "triptan sensations," including paresthesia, flushing, tingling, chest tightness, and neck pain. Additional effects, such as palpitations, headaches, chills, pain, hypertonia, hypoesthesia, diaphoresis, abdominal pain, including cramps, discomfort, and pressure, xerostomia, dysphagia, dyspepsia, pharyngitis, back pain, and generalized weakness, have been reported, albeit at a much lower incidence ranging from 1% to 7%.

Toxicity SummarySigns and Symptoms of Overdose
Drug Induced Liver Injury · 5건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

eletriptan

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

신호 어
Danger
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302

화학 및 산업

약리 정보

ATC Code · 3건

N02CC06

N - Nervous system

QN - Nervous system

Protein BindingPlasma protein binding is moderate and approximately 85%.
Pharmacodynamics · 1건

Eletriptan is a selective 5-hydroxytryptamine 1B/1D receptor agonist. In the anesthetized dog, eletriptan has been shown to reduce carotid arterial blood flow, with only a small increase in arterial blood pressure at high doses. While the effect on blood flow was selective for the carotid arterial bed, decreases in coronary artery diameter were observed. Eletriptan has also been shown to inhibit trigeminal nerve activity in the rat.

Mechanism of Action · 1건

Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors, and little or no affinity for 5-HT2A, 5-HT2C, 5-HT3, 5-HT4, 5-HT5A and 5-HT6 receptors. In contrast, eletriptan displays insignificant pharmacological activity at adrenergic alpha1, alpha2, or beta; dopaminergic D1 or D2; muscarinic; or opioid receptors. While the full mechanism of action of 5-HT receptor agonists in relieving migrains is not fully elucidated, it is proposed that the activation of 5-HT1 receptors located on intracranial blood vessels leads to vasoconstriction that correlates with the relief of migraine headaches. It is also proposed that the activation of 5-HT1 receptors on sensory nerve endings in the trigeminal system leads to the inhibition of release of pro-inflammatory neuropeptides.

Biological Half-LifeThe terminal elimination half-life of eletriptan is approximately 4 hours.
Metabolism/MetabolitesIn vitro studies indicate that eletriptan is primarily metabolized by cytochrome P-450 enzyme CYP3A4. The N-demethylated metabolite of eletriptan is the only known active metabolite.

용도 및 제조

UsesUse (kg; approx.) in Germany (2009): >25
Use ClassificationPharmaceuticals
응용 분야 · 2건

용도Eletriptan is a selective serotonin 5-HT1B and 5-HT1D receptor agonist and used to treat migraines (1,2,3).

일반 설명Eletriptan, introduced into the market in 2002, is the newesttriptan with highest affinity for 5-HT1B, 5-HT1D, and 5-HT1Freceptors. It is one of the most lipophilic triptans marketedto date and is well tolerated and safe across its dosing rangeof 20 to 80 mg. However, it is metabolized primarily(>90%) by CYP3A4 isozyme to its active metabolite, theN-desmethyleletriptan, which accounts for approximately10% to 20% of the plasma concentration of that observedfor parent drug. Thus, coadministration of eletriptan withpotent CYP3A4 inhibitors such as ketoconazole, itraconazole,nefazodone, troleandomycin, clarithromycin, ritonavir,and nelfinavir may require dose reduction and closer monitoringfor CNS side effects. Furthermore, becauseeletriptan and its active metabolite, N-desmethyleletriptan,are also substrates for the P-glycoprotein efflux pumps thatare responsible for their removal from the brain, coadministrationof eletriptan with a known P-glycoprotein inhibitorand/or inducer such as digoxin, diltiazem, verapamil, or St.John’s Worth would result in higher brain levels of its activemetabolite, and thus a higher rate of the CNS side effectsreported for this drug.

공급사83 곳

北京华美互利生物化工010-56205725 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
武汉布林科技有限公司3456065315 13260619011 · [email protected]
Henan Rane Chemical Co., Ltd.+86-18738066252 · [email protected]

추가 설명

정의ChEBI: Eletriptan is an N-alkylpyrrolidine, being N-methylpyrrolidine in which the pro-R hydrogen at position 2 is substituted by a {5-[2-(phenylsulfonyl)ethyl]-1H-indol-3-yl}m thyl group.

관련 반응

21건

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