U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

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

SHOW SMILES / InChI
Structure of ELETRIPTAN

SMILES

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

InChI

InChIKey=PWVXXGRKLHYWKM-LJQANCHMSA-N
InChI=1S/C22H26N2O2S/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/t19-/m1/s1

HIDE SMILES / InChI

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
Sumatriptan versus eletriptan: which is best?
2002 Dec
Current perspectives on effective migraine treatments: are small clinical differences important for patients?
2003
Newer formulations of the triptans: advances in migraine management.
2003
[Strong and sustained-acting triptan. Therewith migraine does not return soon].
2003 Aug 7
Comparative efficacy of eletriptan and zolmitriptan in the acute treatment of migraine.
2003 Dec
[Treatment of migraine: an update].
2003 Jan
Eletriptan issues.
2003 Jul-Aug
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
Safety profile of the triptans.
2003 Mar
[Highly selective beginning. Associated symptoms and side effects in retrospect].
2003 May 26
[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
Tolerability and safety of eletriptan in the treatment of migraine: a comprehensive review.
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
Eletriptan for the short-term prophylaxis of cluster headache.
2004 Apr
Meta-analysis of oral triptans.
2004 Aug
New drugs 04, part 1.
2004 Feb
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
[Use of triptanes according to indications. Risk of infarct is not increased].
2004 Feb 12
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
Effect of high-dose intravenous eletriptan on coronary artery diameter.
2004 Jul
Cardiovascular safety of triptans.
2004 Jul
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
Nitrergic and glutamatergic neuronal mechanisms at the trigeminovascular first-order synapse.
2004 Jul
Gateways to clinical trials.
2004 Jul-Aug
Triptans and CNS side-effects: pharmacokinetic and metabolic mechanisms.
2004 Jun
Gateways to clinical trials.
2004 Mar
Eletriptan for the acute treatment of migraine: results of bridging a Japanese study to Western clinical trials.
2004 Mar
Cost considerations of acute migraine treatment.
2004 Mar
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
Double-blind clinical trials of oral triptans vs other classes of acute migraine medication - a review.
2004 May
[A case of the usefulness of MR angiography and diffusion weighted image to evaluate migraine].
2004 Oct
[Spanish contribution to the clinical development of eletriptan: an analysis of controlled studies].
2004 Oct
No effect of eletriptan administration during the aura phase of migraine.
2004 Oct
[Meta-analysis of triptan treatment in migraine].
2004 Sep
[Triptans in migraine: from clinical view].
2004 Sep
[Triptans in migraine: a comparative review of pharmacology, pharmacokinetics].
2004 Sep
Gateways to clinical trials.
2004 Sep
Priorities for triptan treatment attributes and the implications for selecting an oral triptan for acute migraine: a study of US primary care physicians (the TRIPSTAR Project).
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 00:06:41 UTC 2019
Edited
by admin
on Tue Oct 22 00:06:41 UTC 2019
Record UNII
22QOO9B8KI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELETRIPTAN
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
UK-116,044
Code English
UK-116044
Code English
UK-116,044-04 FREE BASE
Code English
ELETRIPTAN [VANDF]
Common Name English
ELETRIPTAN [INN]
Common Name English
ELETRIPTAN [MI]
Common Name English
3-(((R)-1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)INDOLE
Systematic Name English
UK-116044-04 FREE BASE
Code English
ELETRIPTAN [WHO-DD]
Common Name English
(R)-3-((1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)-1H-INDOLE
Systematic Name English
Classification Tree Code System Code
LIVERTOX 343
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
NCI_THESAURUS C47794
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
WHO-ATC N02CC06
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
NDF-RT N0000175764
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
WHO-VATC QN02CC06
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
NDF-RT N0000175763
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
NDF-RT N0000175765
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
Code System Code Type Description
EPA CompTox
143322-58-1
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
EVMPD
SUB06482MIG
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
DRUG BANK
DB00216
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
ChEMBL
CHEMBL1510
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
NCI_THESAURUS
C65509
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
CAS
143322-58-1
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
MESH
C115647
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
INN
7426
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
WIKIPEDIA
ELETRIPTAN
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
MERCK INDEX
M4867
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY Merck Index
RXCUI
231049
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY RxNorm
IUPHAR
40
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
PUBCHEM
77993
Created by admin on Tue Oct 22 00:06:41 UTC 2019 , Edited by admin on Tue Oct 22 00:06:41 UTC 2019
PRIMARY
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