スマトリプタン
3-[2-(ジメチルアミノ)エチル]-5-[(メチルアミノスルホニル)メチル]-1H-インドール · [3-(2-ジメチルアミノエチル)-1H-インドール-5-イル]-N-メチルメタンスルホンアミド · スマトリプタン · 3-[2-(ジメチルアミノ)エチル]-N-メチル-1H-インドール-5-メタンスルホンアミド · N-メチル-[3-[2-(ジメチルアミノ)エチル]-1H-インドール-5-イル]メタンスルホンアミド · スマトリプタン (JAN) · N-メチル-3-[2-(ジメチルアミノ)エチル]-1H-インドール-5-メタンスルホンアミド · 1-{3-[2-(ジメチルアミノ)エチル]-1H-インドール-5-イル}-N-メチルメタンスルホンアミド
識別子と物理属性
| CAS No. | 103628-46-2 |
|---|---|
| 分子式 | C14H21N3O2S |
| 平均分子量 | 295.4 g/mol |
| 単同位体質量 | 295.13544791 g/mol |
| SMILES | CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1 |
| InChIKey | KQKPFRSPSRPDEB-UHFFFAOYSA-N |
| PubChem CID | 5358 |
| ChEMBL | CHEMBL128 |
| ChEBI | CHEBI:10650 |
| EC No. | 600-462-9 |
| DTXSID | DTXSID4023628 |
| 現地名 | スマトリプタン |
化学・物理的性質
| XLogP | 0.9 |
|---|---|
| 極性表面積 | 73.6 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 6 |
| 重原子数 | 20 |
| 形式電荷 | 0 |
| 複雑度 | 405 |
| 医薬品 | PharmaceuticalsPharmaceuticals -> Listed in ZINC15 |
| LogP（分配係数） | log Kow = 0.93 |
| 溶解度 | 54mg/mL40.3 [ug/mL] (The mean of the results at pH 7.4)DMSO（微量）、メタノール（微量）21.4mg/mL |
| Human Drugs | Breast FeedingLactationMilk, HumanSerotonin Receptor AgonistsSerotonin 5-HT1 Receptor AgonistsTriptansVasoconstrictor AgentsFDA approved drugs -> Active ingredientPharmaceuticalsMedicines for acute migraine attacks |
| 融点 | 169-170169-171 °C169 - 171 °C169-171°C |
| Physical Description | Solid |
| Dissociation Constants | 9.54.9 |
| Collision Cross Section | 162.1 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Other Experimental Properties | MW: 413.49mp 165-166 °C /Sumatriptan succinate/ |
| 沸点 | 497.7±55.0 °C(Predicted) |
| 密度 | 1.1778 (rough estimate) |
| 屈折率 | 1.6740 (estimate) |
| 貯蔵条件 | Refrigerator |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | pKa 9.5 (Uncertain) |
| 色 | オフホワイトからペールイエロー |
| ヘンリー定数 | 2.2×108 mol/(m3Pa) at 25℃, HSDB (2015) |
| 主な用途 | 医薬品 |
| InChI | InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3 |
| InChIKey | KQKPFRSPSRPDEB-UHFFFAOYSA-N |
| SMILES | N1C2=C(C=C(CS(NC)(=O)=O)C=C2)C(CCN(C)C)=C1 |
| CAS データベース | 103628-46-2(CAS DataBase Reference) |
| NISTの化学物質情報 | Sumatriptan(103628-46-2) |
| EPAの化学物質情報 | 1H-Indole-5-methanesulfonamide, 3-[2-(dimethylamino)ethyl]-N-methyl- (103628-46-2) |
安全性と法規制
| GHS 分類 | WarningH319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]P203, P264+P265, P273, P280, P305+P351+P338, P318, P337+P317, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 6 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Sumatriptan: Does not have an individual approval but may be used under an appropriate group standard |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl sumatriptan, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl sumatriptan succinate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Sumatriptan succinate/ |
| Hazard Classes and Categories | Eye Irrit. 2 (33.3%) |
| 保管条件 | Sumatriptan succinate injection and tablets and sumatriptan nasal spray should be protected from light and stored at 2-30 °C. |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 相互作用 | Alcohol consumed 30 minutes prior to sumatriptan ingestion had no effect on the pharmacokinetics of sumatriptan.Due to gut and hepatic metabolic first-pass effects, the increase of systemic exposure after coadministration of an MAO-A inhibitor with oral sumatriptan is greater than after coadministration of the monoamine oxidase inhibitors (MAOI) with subcutaneous sumatriptan. In a study of 14 healthy females, pretreatment with an MAO-A inhibitor decreased the clearance of subcutaneous sumatriptan. Under the conditions of this experiment, the result was a 2-fold increase in the area under the sumatriptan plasma concentration x time curve (AUC), corresponding to a 40% increase in elimination half-life. This interaction was not evident with an MAO-B inhibitor. A small study evaluating the effect of pretreatment with an MAO-A inhibitor on the bioavailability from a 25-mg oral sumatriptan tablet resulted in an approximately 7-fold increase in systemic exposure. |
用途
使用
Sumatriptan is a serotonin 5HT1-receptor agonist.
一般的な説明
Sumatriptan was the first triptan approved (1991) for theacute treatment of migraine headaches. It has the lowestoral bioavailability among all triptans because of its lowlipophilicity. The availability of many different dosageforms (i.e., an oral tablet, a SC injection, a nasal spray formulation,and a suppository) allows the flexibility of tailoringtherapy to the needs of the individual patients, thusmaking sumatriptans a very useful drug for an acute treatmentof migraine headaches. It also has a very fastonset of action via SC injection or nasal spray administration.However, sumatriptan is contraindicated withmonoamine oxidase inhibitors because it is primarily degradedby hepatic MAO-A. Thus, it may require frequentdosing as a result of its short duration of action to preventmigraine recurrence.