エレトリプタン
エレトリプタン · 3-[[(2R)-1-メチル-2-ピロリジニル]メチル]-5-[2-(フェニルスルホニル)エチル]-1H-インドール · 5-[2-(ベンゼンスルホニル)エチル]-3-{[(2R)-1-メチルピロリジン-2-イル]メチル}-1H-インドール · 3-[[(2R)-1-メチルピロリジン-2-イル]メチル]-5-[2-(フェニルスルホニル)エチル]-1H-インドール · Relpax · Relpax free aMine · UK-116044 · ELETRIPTAN
識別子と物理属性
| CAS No. | 143322-58-1 |
|---|---|
| 分子式 | C22H26N2O2S |
| 平均分子量 | 382.5 g/mol |
| 単同位体質量 | 382.17149925 g/mol |
| SMILES | CN1CCC[C@@H]1Cc1c[nH]c2ccc(CCS(=O)(=O)c3ccccc3)cc12 |
| InChIKey | PWVXXGRKLHYWKM-LJQANCHMSA-N |
| PubChem CID | 77993 |
| ChEMBL | CHEMBL1510 |
| ChEBI | CHEBI:50922 |
| EC No. | 640-088-3 |
| DTXSID | DTXSID9046861 |
| 現地名 | エレトリプタン |
化学・物理的性質
| XLogP | 4.1 |
|---|---|
| 極性表面積 | 61.6 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 6 |
| 重原子数 | 27 |
| 形式電荷 | 0 |
| 複雑度 | 582 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | 3.9 |
| 溶解度 | Readily soluble as hydrobromide formulation1.18e-03 g/LDMSO（微量）、メタノール（微量） |
| Human Drugs | Breast FeedingLactationMilk, HumanSerotonin Receptor AgonistsSerotonin 5-HT1 Receptor AgonistsTriptansVasoconstrictor AgentsPharmaceuticalsMedicines for acute migraine attacks |
| Physical Description | Solid |
| Collision Cross Section | 189.45 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]186.1 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| 融点 | 168-170C |
| 沸点 | 613.4±55.0 °C(Predicted) |
| 密度 | 1.235±0.06 g/cm3(Predicted) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | 17.14±0.30(Predicted) |
| 色 | 淡い黄色から濃い黄色 |
| 安定性 | 吸湿性 |
| 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 |
| CAS データベース | 143322-58-1(CAS DataBase Reference) |
化学的特性
Yellow Foam
安全性と法規制
| GHS 分類 | DangerH302 (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. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| 有害作用 | 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%. |
| 毒性の概要 | Signs and Symptoms of Overdose |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)eletriptanDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| 危険有害性情報 | コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302 |
用途
使用
Eletriptan is a selective serotonin 5-HT1B and 5-HT1D receptor agonist and used to treat migraines (1,2,3).
一般的な説明
Eletriptan, 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.