기본 정보
- 표준 SMILES
CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1.O=C(O)CCC(=O)O- InChIKey
PORMUFZNYQJOEI-UHFFFAOYSA-N- 분자식
- C18H27N3O6S
- 평균 분자량
- 413.5 g/mol
- 단동위원소 질량
- 413.16205676
이름 및 식별자
- 우선 이름
- Sumatriptan Succinate
- IUPAC
- butanedioic acid;1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide
- 영어명
- Sumatriptan succinate
- 분자식
- C18H27N3O6S
- 분자량
- 413.48848
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
103628-48-4- PubChem CID
- 59772
- DTXSID
DTXSID60145966- ChEMBL
CHEMBL1201150- ChEBI
CHEBI:64359- UNII
- J8BDZ68989
- EC Number
- 600-463-4
물성
구조 계산 물성
- 극성 표면적
- 148 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 8
- 회전 가능 결합 수
- 9
- 무거운 원자 수
- 28
- 형식 전하
- 0
- 복잡도
- 498
물리화학적 성질
- 녹는점
- 165 · 165-166°C
- 저장 조건
- -20 °C · -20°C
- 용해도
- 2 O: · H2O: >20mg/mL
- 물리적 상태
- 고체
- 색상
- 흰색에서 황백색까지
- Merck
- 14 · 14,8997
- BCS Class
- 3 · 3
- 주요 응용
- 의약품(소분자)
- InChI
- 1S/C14H21N3O2S.C4H6O4/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3;5-3(6)1-2-4(7)8/h4-5,8-9,15-16H,6-7,10H2,1-3H3;1-2H2,(H,5,6)(H,7,8)
- InChIKey
- PORMUFZNYQJOEI-UHFFFAOYSA-N
- SMILES
- OC(=O)CCC(O)=O.CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1
화학적 성질
White Crystalline Powder
안전 및 규제
GHS 분류
GHS Classification
Danger
H318 (79.6%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H361 (13%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H412 (16.7%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
P203, P264+P265, P273, P280, P305+P354+P338, P317, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
유해성 정보
독성 정보
Toxicity Summary
The 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors function as autoreceptors, which inhibit the firing of serotonin neurons and a reduction in the synthesis and release of serotonin upon activation. After sumatriptan binds to these receptors, adenylate cyclase activity is inhibited via regulatory G proteins, incrases intracellular calcium, and affects other intracellular events. This results in vasoconstriction and inhibtion of sensory nociceptive (trigeminal) nerve firing and vasoactive neuropeptide release. Sumatriptan stimulates 5-HT receptors of the 1D subtype, most likely presynaptic receptors, resulting in selective vasoconstriction of inflamed and dilated cranial blood vessels in the carotid circulation. Sumatriptan also blocks the release of vasoactive neuropeptides from perivascular trigeminal axons in the dura mater during migraine and may inhibit the release of inflammatory mediators from the trigeminal nerve.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Sumatriptan succinate
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation;Because of the low levels of sumatriptan in breastmilk, amounts ingested by the infant are small. It also has poor oral bioavailability, further decreasing infant exposure to the drug. Some authors have suggested that withholding breastfeeding for 8 hours after a single subcutaneous injection would virtually eliminate infant exposure to the drug. The manufacturer recommends withholding breastfeeding for 12 hours after a dose. Withholding breastfeeding might be helpful in extreme cases, such as in the mother of a preterm infant, but sumatriptan would not be expected to cause any adverse effects in most breastfed infants and has been recommended as a triptan of choice in breastfeeding. Painful, burning nipples and breast pain have been reported after doses of sumatriptan and other triptans. This has occasionally been accompanied by a decrease in milk production.;◉ Effects in Breastfed Infants;One author reported correspondence with the drug's manufacturer stating that of 3 women known to the manufacturer who used sumatriptan (dose and route unspecified) during breastfeeding none reported adverse effects on the infants.;◉ Effects on Lactation and Breastmilk;One author reported correspondence with the drug's manufacturer stating that 1 woman who used a single injection of sumatriptan (dose unspecified) during breastfeeding had a cessation of lactation.;A review of four European adverse reaction databases found 26 reported cases of painful, burning nipples, painful breasts, breast engorgement and/or painful milk ejection in women who took a triptan while nursing. Pain was sometimes intense and occasionally led to decreased milk production. Pain generally subsided with time as the drug was eliminated. The authors proposed that triptans may cause vasoconstriction of the arteries in the breast, nipples, and the arteries surrounding the alveoli and milk ducts, causing a painful sensation and a painful milk ejection reflex.
규제 정보
안전 데이터
- wgk
- 3
- rtecs
- EJ9940000
- ridadr
- 3077
- HS 번호
- 29350090
- risk_code
- 36/37/38-41
- hazard_code
- Xi
- safety_code
- 26-36-39
- Hazard Classifications
- Aquatic Chronic 3Repr. 2
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Metabolism/Metabolites
Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme. Route of Elimination: Only 3% of the dose is excreted in the urine as unchanged sumatriptan; 42% of the dose is excreted as the major metabolite, the indole acetic acid analogue of sumatriptan. Half Life: 2.5 hours
FDA Pharmacological Classification
SUMATRIPTAN SUCCINATE
Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]
MeSH Pharmacological Classification
Drugs used to cause constriction of the blood vessels.
Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes.
용도 및 제조
응용 분야
개요Sumatriptan succinate is a highly selective 5HT1-like receptor agonist introduced as a new treatment for migraine. It is indicated for the acute relief of migraine and cluster headache. Oral administration is reported to be free of substantial side effects. The compound appears to be a significant advance over the use of ergotamine and other agents in the treatment of migraine.
용도Sumatriptan Succinate is a selective 5-HT1B/1D-receptor agonist with anticonvulsant properties (1,2). Sumatriptan Succinate is used for migraine relief (2).
상·하류 제품 정보
상류 원료
하류 제품
공급사50 곳
추가 설명
정의ChEBI: A succinate salt obtained by reaction of sumatriptan with one equivalent of succinic acid. Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). Used for the acute treatm nt of migraine with or without aura in adults.
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