홈MCP워크벤치Skills
홈워크벤치알림마이페이지
Huagongshe 오픈 프로젝트:[email protected]AI 접속: llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.7.8
  1. 홈
  2. /화합물

Zolmitriptan

HCID 60857
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
139264-17-8
표준 SMILES
CN(C)CCc1c[nH]c2ccc(C[C@H]3COC(=O)N3)cc12
InChIKey
ULSDMUVEXKOYBU-ZDUSSCGKSA-N
분자식
C16H21N3O2
평균 분자량
287.36 g/mol
단동위원소 질량
287.16337691

개요

Zolmitriptan is a member of the class of tryptamines that is N,N-dimethyltryptamine in which the hydrogen at position 5 of the indole ring has been replaced by a [(4S)-2-oxo-1,3-oxazolidin-4-yl]methyl group. A serotonin 5-HT1 B and D receptor agonist, it is used for the treatment of migraine. It has a role as an anti-inflammatory drug, a serotonergic agonist and a vasoconstrictor agent. It is a member of tryptamines and an oxazolidinone. It is functionally related to a N,N-dimethyltryptamine.

이름 및 식별자

우선 이름
Zolmitriptan
IUPAC
(4S)-4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one
영어명
Zolmitriptan
분자식
C16H21N3O2
분자량
287.36

이름 및 동의어

zolmitriptan139264-17-8ZomigZomigoroZomig-ZMT311C90AscoTopzolmitriptanumDTXSID8045933Cvt-4272FS66TH3YWNSC-760383
이름 더 보기
Zomibw311c90ZolmitrptanzolmitripanZOLMITRIPTANEZOLIMITRIPTANZuomi quputan
(4S)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one(4S)-4-[[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone(S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinoneDTXCID6025933CHEBI:10124311-C-902-Oxazolidinone, 4-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-, (S)-

데이터베이스 식별자

CAS
139264-17-8
PubChem CID
60857
DTXSID
DTXSID8045933
ChEMBL
CHEMBL1185
ChEBI
CHEBI:10124
UNII
2FS66TH3YW
EC Number
629-919-0
Nikkaji
J694.097H

물성

구조 계산 물성

XLogP
2.2
극성 표면적
57.4 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
3
회전 가능 결합 수
5
무거운 원자 수
21
형식 전하
0
복잡도
375

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2건

1.6

0.79

Solubility1.90e-01 g/L
Human Drugs · 3건

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

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physical DescriptionSolid
Dissociation Constants9.64
Collision Cross Section · 3건

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

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

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

물리화학적 성질

녹는점
136 · 136-141°C
끓는 점
563.3 · 563.3±38.0 °C(Predicted)

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 4건

Warning

H302 (95.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P308+P316, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 21 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

유해성 정보

Hazard Classes and CategoriesAcute Tox. 4 (95.2%)

독성 정보

Treatment · 1건

There is no specific antidote to zolmitriptan. In cases of severe intoxication, intensive care procedures are recommended, including establishing and maintaining a patent airway, ensuring adequate oxygenation and ventilation, and monitoring and support of the cardiovascular system. (L1712)

Health EffectsSerious cardiac events, including myocardial infarction migth occur. [Wikipedia]
Adverse Effects · 1건

Dysgeusia is the most commonly observed adverse effect of zolmitriptan in healthy individuals, with the nasal spray causing a more significant impact. This phenomenon is likely attributed to the method of drug administration through the nasal route. Additional minor adverse events reported with intranasal zolmitriptan usage include nasal passage irritation, dizziness, throat irritation, and fatigue. Furthermore, phase 1 trials of the Real Life Intranasal Zolmitriptan Exposure (REALIZE) study revealed that the encountered adverse effects did not result in participants discontinuing the medication.

Exposure Routes

화학 및 산업

약리 정보

ATC Code · 3건

N02CC03

N - Nervous system

QN - Nervous system

Protein BindingZolmitriptan and its active N-desmethyl metabolite remain approximately 25% bound to plasma proteins over a concentration range of 10-1000 ng/mL.
Pharmacodynamics · 1건

Zolmitriptan, like other triptans, is a serotonin (5-hydroxytryptamine; 5-HT) receptor agonist, with enhanced specificity for the 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptor subtypes. It is through the downstream effects of 5-HT<sub>1B/1D</sub> activation that triptans are proposed to provide acute relief of migraines. Zolmitriptan is also a vasoconstrictor, leading to possible adverse cardiovascular effects such as myocardial ischemia/infarction, arrhythmias, cerebral and subarachnoid hemorrhage, stroke, gastrointestinal ischemia, and peripheral vasospastic reactions. In addition, chest/throat/neck/jaw pain, tightness, and/or pressure has been reported, along with the possibility of medication overuse headaches and serotonin syndrome. Patients with phenylketonuria should be advised that ZOMIG-ZMT contains phenylalanine.

Mechanism of Action · 1건

Migraines are complex physiological events characterized by unilateral throbbing headaches combined with photophobia and other aversions to sensory input. Migraine attacks are generally divided into phases: the premonitory phase, which typically involves irritability, fatigue, yawning, and stiff neck; the headache phase, which lasts for between four and 72 hours; and the postdrome phase, which lasts for up to a day following resolution of pain and whose symptoms are similar to those of the premonitory phase. In addition, neurological deficits, collectively termed migraine aura, may precede the headache phase. The underlying pathophysiology of migraines is a matter of active research but involves both neurological and vascular components. The head pain associated with migraine is thought to be a consequence of activation of the nociceptive nerves comprising the trigeminocervical complex (TCC). Terminals of nociceptive nerves that innervate the dura matter release vasoactive peptides, such as calcitonin gene-related peptide (CGRP), resulting in cranial vasodilation. Finally, when present, migraine aura appears to correlate with a transient wave(s) of cortical depolarization, termed cortical spreading depression (CSD). Triptans, including zolmitriptan, are proposed to act in three ways. The main mechanism is through modulation of nociceptive nerve signalling in the central nervous system through 5-HT<sub>1B/1D</sub> receptors throughout the TCC and associated areas of the brain. In addition, triptans can enhance vasoconstriction, both through direct 5-HT<sub>1B</sub>-mediated dilation of cranial blood vessels, as well as through 5-HT<sub>1D</sub>-mediated suppression of CGRP release. Although triptans are classically described solely in terms of their effects on 5-HT<sub>1B/1D</sub> receptors, they also act as 5-HT<sub>1F</sub> agonists as well. This 5-HT subtype is also found throughout the TCC, but is not present appreciably in cerebral vasculature; the significance of triptan-mediated 5-HT<sub>1F</sub> activation is currently not well described. Additionally, CSD that initiates in the ipsilateral parietal region may exert its effects in a manner that relies on 5-HT<sub>1B/1D</sub> receptor activation, suggesting that triptans may have some effect on CSD-mediated symptoms.

관련 반응

9건
반응 기록 만들기
HRID 128986 반응식
HRID 128986생성물로uspto-grants-1995_11
HRID 128989 반응식
HRID 128989생성물로uspto-grants-1995_11
HRID 229756 반응식
HRID 229756생성물로uspto-grants-2009_07
HRID 343916 반응식
HRID 343916반응물로uspto-grants-1999_01
HRID 343917 반응식
HRID 343917생성물로uspto-grants-1999_01
HRID 1392220 반응식
HRID 1392220생성물로uspto-grants-2008_03
HRID 1470540 반응식
HRID 1470540반응물로uspto-grants-2015_04
HRID 1608997 반응식
HRID 1608997생성물로uspto-grants-1995_03
1 / 2 페이지

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
밀도
1.217 · 1.217±0.06 g/cm3(Predicted)
저장 조건
15 · 15-25°C
용해도
5 mg/ml의 · 5mg/ml의 DMSO에 용해됨
산도 계수 (pKa)
9.64 · 9.64(at 25℃)
물리적 상태
가루
색상
흰색에서 베이지색
Merck
14 · 14,10189
안정성
2 · 제공된 대로 구매일로부터 2년 동안 안정적입니다. DMSO 용액은 -20°C에서 최대 3개월 동안 보관할 수 있습니다.
InChI
1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
InChIKey
ULSDMUVEXKOYBU-ZDUSSCGKSA-N
SMILES
CN(C)CCc1c[nH]c2ccc(C[C@H]3COC(=O)N3)cc12

화학적 성질

White Crystalline Powder

Topical(nasal); Oral. Mean absolute oral bioavailability is approximately 40%. Food has no affect on the rate and extent of absorption.
Toxicity Summary · 2건

In pediatric cases, zolmitriptan toxicity did not result in life-threatening complications; however, the common signs of toxicity included tachycardia, dyspnea, and vomiting. Zolmitriptan overdoses have been linked to hypertension, tachycardia, and drowsiness in adults. Furthermore, there have been 2 documented cases of hepatotoxicity associated with zolmitriptan use.

Zolmitriptan binds with high affinity to human 5-HT<sub>1B</sub> and 5-HT<sub>1D</sub> receptors leading to cranial blood vessel constriction. Current theories proposed to explain the etiology of migraine headache suggest that symptoms are due to local cranial vasodilatation and/or to the release of sensory neuropeptides (vasoactive intestinal peptide, substance P and calcitonin gene-related peptide) through nerve endings in the trigeminal system. The therapeutic activity of zolmitriptan for the treatment of migraine headache can most likely be attributed to the agonist effects at the 5HT1B/1D receptors on intracranial blood vessels (including the arterio-venous anastomoses) and sensory nerves of the trigeminal system which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Zolmitriptan

Ambiguous-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

안전 데이터

wgk
3
rtecs
RQ2707000
독성
women,TDLo,oral,6mg/kg/43W-I (6mg/kg),BEHAVIORAL: HEADACHE,Lancet. Vol. 353, Pg. 378, 1999.
HS 번호
29349990
risk_code
36/37/38-22
hazard_code
Xi,Xn
safety_code
26-36
스토리지 클래스
11 - Combustible Solids
Biological Half-LifeZolmitriptan has a mean elimination half-life of approximately three hours following oral or nasal administration. Its active N-desmethyl metabolite has a slightly longer (approximately 3.5 hours) half-life.
Metabolism/Metabolites · 3건

Zolmitriptan is metabolized in the liver, and studies using cytochrome P450 inhibitors like [cimetidine] suggest that it is likely metabolized by CYP1A2, as well as by monoamine oxidase (MAO). Zolmitriptan metabolism results in three major metabolites: an active N-desmethyl metabolite (183C91) as well as inactive N-oxide (1652W92) and indole acetic acid (2161W92) metabolites.

Zolmitriptan has known human metabolites that include N-Desmethylzolmitriptan and Zolmitriptan N-oxide.

Hepatic. There have been three metabolites identified: indole acetic acid, N -oxide, and N-desmethyl metabolites. However, the N-desmethyl is the only active metabolite. Half Life: The mean elimination half-life of zolmitriptan and of the active N-desmethyl metabolite is 3 hours.

FDA Pharmacological Classification · 6건

2FS66TH3YW

ZOLMITRIPTAN

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

Zolmitriptan is a Serotonin-1b and Serotonin-1d Receptor Agonist. The mechanism of action of zolmitriptan is as a Serotonin 1b Receptor Agonist and Serotonin 1d Receptor Agonist.

MeSH Pharmacological ClassificationEndogenous 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.
Absorption, Distribution and Excretion · 4건

Zolmitriptan tablets have a mean absolute oral bioavailability of approximately 40%, with food having no effect on the rate or extent of absorption. The dosing kinetics are linear over a range of 2.5 to 50 mg with 75% of the eventual Cmax being attained within 1 hour of dosing. The median Tmax for the tablet form is 1.5 hours, while for the orally disintegrating tablet form, it is 3 hours. The AUC across studies was in the range of 84.4-173.8 ng/mL*h while the Cmax was between 16 and 25.2 ng/mL. Zolmitriptan administered as a nasal spray is detected in the plasma within 2-5 minutes, compared to 10-15 minutes for the tablet form; the faster kinetics likely reflect fast absorption across the nasal mucosa. The bioavailability compared to the tablet is 102%, and plasma zolmitriptan concentration is maintained for 4-6 hours after intranasal delivery. The active N-desmethyl metabolite of zolmitriptan has a mean plasma concentration that is roughly two-thirds of zolmitriptan, regardless of dosage route or concentration.

Zolmitriptan is primarily excreted in urine (approximately 65%) and feces (approximately 30%). Within urine, the most common form is the indole acetic acid metabolite (31%), followed by the N-oxide (7%), and N-desmethyl (4%) metabolites; the majority of zolmitriptan recovered in feces remains unchanged.

Zolmitriptan has a volume of distribution between 7 and 8.4 L/kg.

Zolmitriptan has a clearance of 31.5 mL/min/kg for oral tablets and 25.9 mL/min/kg for nasal administration; one-sixth of the clearance is renal.

Cellular LocationsCytoplasm

용도 및 제조

Uses · 2건

Use (kg; approx.) in Germany (2009): ?10

Used in the acute treatment of migraine attacks with or without aura and cluster headaches.

응용 분야 · 3건

개요Zolmitriptan is a selective serotonin receptor agonist of the 1B and 1D subtypes. It is mainly used in the acute treatment of migraine attacks with or without aura and cluster headaches. Zolmitriptan takes effect through binding to human 5-HT1Band 5-HT1Dreceptors, leading to cranial blood vessel constriction and the release of sensory neuropeptides through nerve endings in the trigeminal system.

용도Zolmitriptan is a serotonin 5HTID-receptor agonist and used to treat migraine (1,2,3).

일반 설명Zolmitriptan, the second triptan marketed (approved in1997), has a much better bioavailability (40%–48%) thansumatriptan. It is rapidly absorbed after oral or nasal sprayadministration. It also has an orally disintegrating tablet formulation(Zomig ZMT), which can be taken without water.Zolmitriptan undergoes rapid N-demethylation via CYP1A2to a more potent, active metabolite, N-desmethylzolmitriptan,which is 2 to 6 times more potent than the parentdrug. This active metabolite was detected 5 minutesafter dosing and accounts for about two thirds of the plasmaconcentration of the administered dose of the parent drug.284Thus, it is reasonable to assume that the therapeutic effectsand especially the CNS side effects of zolmitriptan must bein part attributed to the plasma levels of this active metabolite,at least until it is further degraded by hepatic MAO-Ato its inactive indole acetic acid derivatives.

상·하류 제품 정보

상류 원료

디메틸아민Copper(II) oxide메탄술폰산퀴놀린6-디메틸아미노퓨린

공급사100 곳

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
Wuhan EnTai Technology Development Co,.Ltd86-27-82330560 · [email protected]
芷威(上海)化学科技有限公司021-20221225 13917446399 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
太原市瑞和丰科贸有限公司+86 351 7031519 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
武汉凯威斯科技有限公司86-027-67849912 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
武汉海正工贸发展有限公司027-8866 0053/88660577/88660578
上海源叶生物科技有限公司18916372613 · [email protected]
成都宇洋高科技发展有限责任公司+86-28-61777709 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
北京清露源科技有限公司+86 (10) 6333-0989 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
卡迪亚医药科技有限公司0371-86615086 18203638366 0371-86159066 13526786601
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
上海睿升化工科技有限公司+86-021-50935922
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18602735115 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海御略医药科技有限公司021-60345187 13671753212 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
台州市科德化工有限公司0576-84613060 13093829633;13736603231 · [email protected]
湖北巨胜科技有限公司027-59599241 18871490274 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
南京励合化学新材料有限公司025-87787262