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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 582
실험 및 물리화학적 성질
Solubility
Readily soluble as hydrobromide formulation
1.18e-03 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Serotonin Receptor Agonists; Serotonin 5-HT1 Receptor Agonists; Triptans; Vasoconstrictor Agents
Pharmaceuticals
Collision Cross Section
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
- 산도 계수 (pKa)
- 17.14 · 17.14±0.30(Predicted)
- 색상
- 연한 노란색에서 진한 노란색까지
- 안정성
- 흡습성
- InChI
- InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1
- InChIKey
- PWVXXGRKLHYWKM-LJQANCHMSA-N
- SMILES
- N1C2=C(C=C(CCS(C3=CC=CC=C3)(=O)=O)C=C2)C(C[C@H]2CCCN2C)=C1
화학적 성질
Yellow Foam
안전 및 규제
GHS 분류
GHS Classification
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
독성 정보
Adverse Effects
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%.
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
eletriptan
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
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
N02CC06
N - Nervous system
QN - Nervous system
Pharmacodynamics
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
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.
FDA Pharmacological Classification
22QOO9B8KI
ELETRIPTAN
Mechanisms of Action [MoA] - Serotonin 1b Receptor Agonists
Mechanisms of Action [MoA] - Serotonin 1d Receptor Agonists
Established Pharmacologic Class [EPC] - Serotonin-1b and Serotonin-1d Receptor Agonist
Eletriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist. The mechanism of action of eletriptan is as a Serotonin 1b Receptor Agonist and Serotonin 1d Receptor Agonist.
Absorption, Distribution and Excretion
Well absorbed after oral administration with a mean absolute bioavailability of approximately 50%.
138 L
Renal cl=3.9 L/h
용도 및 제조
응용 분야
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.
상·하류 제품 정보
상류 원료
하류 제품
공급사83 곳
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.
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