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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2S.ClH
Molecular Weight 418.98
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELETRIPTAN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=YPFFNRRUXKXSTA-FSRHSHDFSA-N
InChI=1S/C22H26N2O2S.ClH/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;1H/t19-;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
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
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples.
2001 Jan
Safety and rational use of the triptans.
2001 Jul
[New potent serotonin receptor agonist. Helps migraine patients even when other triptans fail].
2001 Jul 5
Pharmacology and efficacy of eletriptan for the treatment of migraine attacks.
2001 Jun
Functional immunohistochemistry of neuropeptides and nitric oxide synthase in the nerve fibers of the supratentorial dura mater in an experimental migraine model.
2001 May 1
Advances in pharmacological treatment of migraine.
2001 Oct
Spotlight on rizatriptan in migraine.
2002
Sumatriptan versus eletriptan: which is best?
2002 Dec
Efficacy and safety of eletriptan 20 mg, 40 mg and 80 mg in Japanese migraineurs.
2002 Jul
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
Gateways to Clinical Trials. June 2002.
2002 Jun
Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials.
2002 Oct
New medications show promise for migraine sufferers.
2002 Oct
Suppression by eletriptan of the activation of trigeminovascular sensory neurons by glyceryl trinitrate.
2002 Oct 25
Gateways to Clinical Trials.
2002 Sep
[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
Efficacy, safety, and tolerability of oral eletriptan for treatment of acute migraine: a multicenter, double-blind, placebo-controlled study conducted in the United States.
2003 Mar
Efficacy of eletriptan in migraineurs with persistent poor response to nonsteroidal anti-inflammatory drugs.
2003 Oct
The 40-mg dose of eletriptan: comparative efficacy and tolerability versus sumatriptan 100 mg.
2004 Feb
[Recent progress in therapy for migraine headache].
2004 Feb 10
Cardiovascular safety of triptans.
2004 Jul
Triptans and CNS side-effects: pharmacokinetic and metabolic mechanisms.
2004 Jun
Effectiveness of eletriptan in acute migraine: primary care for Excedrin nonresponders.
2004 Mar
Cost effectiveness of oral triptan therapy: a trans-national comparison based on a meta-analysis of randomised controlled trials.
2004 May
[Triptans in migraine: from clinical view].
2004 Sep
Gateways to clinical trials.
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 16:44:20 UTC 2019
Edited
by admin
on Tue Oct 22 16:44:20 UTC 2019
Record UNII
OL4Q27AUZF
Record Status Validated (UNII)
Record Version
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Name Type Language
ELETRIPTAN HYDROCHLORIDE
Common Name English
1H-INDOLE, 3-(((2R)-1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
121596618
Created by admin on Tue Oct 22 16:44:21 UTC 2019 , Edited by admin on Tue Oct 22 16:44:21 UTC 2019
PRIMARY
CAS
1163127-11-4
Created by admin on Tue Oct 22 16:44:21 UTC 2019 , Edited by admin on Tue Oct 22 16:44:21 UTC 2019
PRIMARY
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