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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2S.CH4O3S
Molecular Weight 478.625
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELETRIPTAN MESYLATE

SMILES

CS(O)(=O)=O.CN1CCC[C@@H]1CC2=CNC3=C2C=C(CCS(=O)(=O)C4=CC=CC=C4)C=C3

InChI

InChIKey=ONTTXXMBZRRMPL-FSRHSHDFSA-N
InChI=1S/C22H26N2O2S.CH4O3S/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;1-5(2,3)4/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3;1H3,(H,2,3,4)/t19-;/m1./s1

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C22H26N2O2S
Molecular Weight 382.519
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Eletriptan (eletriptan hydrobromide, trade name Relpax) is a selective 5-hydroxytryptamine (5-HT1B/1D) serotonin receptor agonist (triptan) indicated for the acute treatment of migraine with or without aura in adults. Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, and has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors. The therapeutic activity of eletriptan for the treatment of migraine headache is thought to be due to the agonist effects at the 5-HT1B/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. Eletriptan (Relpax) has been approved for use in the acute treatment of migraine in 51 countries and has been introduced in 17 countries including Mexico, Italy, France and Japan.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Profiles of 5-HT 1B/1D agonists in acute migraine with special reference to second generation agents.
1999 Jun
Comparative aspects of triptans in treating migraine.
2001
Pharmacokinetics and safety of oral eletriptan during different phases of the menstrual cycle in healthy volunteers.
2001 Dec
Safety and rational use of the triptans.
2001 Jul
Pharmacology and efficacy of eletriptan for the treatment of migraine attacks.
2001 Jun
Acute treatment of migraine and the role of triptans.
2001 Mar
Efficacy, tolerability and safety of oral eletriptan and ergotamine plus caffeine (Cafergot) in the acute treatment of migraine: a multicentre, randomised, double-blind, placebo-controlled comparison.
2002
Sumatriptan versus eletriptan: which is best?
2002 Dec
Efficacy, safety and tolerability of oral eletriptan in the acute treatment of migraine: results of a phase III, multicentre, placebo-controlled study across three attacks.
2002 Feb
[New triptanes in control of migraine attacks. More rapid onset of action--more efficient reduction of pain].
2002 Jan 24
Efficacy and safety of eletriptan 20 mg, 40 mg and 80 mg in Japanese migraineurs.
2002 Jul
Gateways to Clinical Trials. June 2002.
2002 Jun
Pharmacokinetics, pharmacodynamics, and safety of the 5-HT(1B/1D) agonist eletriptan following intravenous and oral administration.
2002 May
The pharmacokinetics and safety of single escalating oral doses of eletriptan.
2002 May
Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials.
2002 Oct
Newer formulations of the triptans: advances in migraine management.
2003
Pharmacological approaches to migraine.
2003
Eletriptan (relpax) for migraine.
2003 Apr 28
Eletriptan vs sumatriptan: a double-blind, placebo-controlled, multiple migraine attack study.
2003 Apr 8
[Pharmacological, pharmacokinetic and clinical profile of eletriptan (Relpax), a new triptan for migraine].
2003 Jul
Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein.
2003 Jul
Eletriptan for the treatment of migraine in patients with previous poor response or tolerance to oral sumatriptan.
2003 Jul
A cost-effectiveness analysis of eletriptan 40 and 80 mg versus sumatriptan 50 and 100 mg in the acute treatment of migraine.
2003 Jul-Aug
Cost-effectiveness of migraine treatment: a commentary.
2003 Jul-Aug
The evolving management of migraine.
2003 Jun
[Improved pharmacokinetics. Fast tryptan with sustained response].
2003 May 26
Comparative efficacy of eletriptan vs. naratriptan in the acute treatment of migraine.
2003 Nov
Efficacy of eletriptan in migraineurs with persistent poor response to nonsteroidal anti-inflammatory drugs.
2003 Oct
Musing on Mathew et al.
2003 Sep
Encapsulated sumatriptan is not bioequivalent to commercial sumatriptan.
2003 Sep
Unilateral time-delayed encapsulation does not make for a fair race.
2003 Sep
Migraine: diagnosis and management.
2003 Sep-Oct
New drugs 04, part 1.
2004 Feb
The 40-mg dose of eletriptan: comparative efficacy and tolerability versus sumatriptan 100 mg.
2004 Feb
The 5-hydroxytryptamine1B/1D/1F receptor agonists eletriptan and naratriptan inhibit trigeminovascular input to the nucleus tractus solitarius in the cat.
2004 Feb 13
Neuronal expression and regulation of CGRP promoter activity following viral gene transfer into cultured trigeminal ganglia neurons.
2004 Jan 30
Gateways to clinical trials.
2004 Jan-Feb
Nitrergic and glutamatergic neuronal mechanisms at the trigeminovascular first-order synapse.
2004 Jul
Gateways to clinical trials.
2004 Mar
Effectiveness of eletriptan in acute migraine: primary care for Excedrin nonresponders.
2004 Mar
Double-blind clinical trials of oral triptans vs other classes of acute migraine medication - a review.
2004 May
[Triptans in migraine: from clinical view].
2004 Sep
Gateways to clinical trials.
2004 Sep
TRIPSTAR: prioritizing oral triptan treatment attributes in migraine management.
2004 Sep
Patents

Sample Use Guides

In Vivo Use Guide
The maximum recommended single dose of Relpax (eletriptan hydrobromide) is 40 mg. If after the initial dose, headache improves but then returns, a repeat dose may be beneficial. If a second dose is required, it should be taken at least 2 hours after the initial dose. If the initial dose is ineffective, controlled clinical trials have not shown a benefit of a second dose to treat the same attack. The maximum daily dose should not exceed 80 mg.
Route of Administration: Oral
In Vitro Use Guide
The 5-hydroxytryptamine (5-HT) receptor mediation of the contraction in guinea-pig iliac arteries moderately precontracted by prostaglandin F2alpha (PGF2alpha) was characterized in vitro using eletriptan. Eletriptan contracted guinea-pig iliac arteries and the concentration-response curve for eletriptan was biphasic (first phase: 0.01-3 uM, pD2 approximately 6.6; second phase: greater or equal 10 uM).
Substance Class Chemical
Created
by admin
on Tue Oct 22 16:44:19 UTC 2019
Edited
by admin
on Tue Oct 22 16:44:19 UTC 2019
Record UNII
607KP935Y1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELETRIPTAN MESYLATE
Common Name English
1H-INDOLE, 3-(((2R)-1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)-, METHANESULFONATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
1261286-61-6
Created by admin on Tue Oct 22 16:44:20 UTC 2019 , Edited by admin on Tue Oct 22 16:44:20 UTC 2019
PRIMARY
PUBCHEM
49857984
Created by admin on Tue Oct 22 16:44:20 UTC 2019 , Edited by admin on Tue Oct 22 16:44:20 UTC 2019
PRIMARY
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