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
Comparative aspects of triptans in treating migraine.
2001
[Current topics: expectation for new triptans].
2001 Apr 10
pH-mediated field-amplified sample stacking of pharmaceutical cations in high-ionic strength samples.
2001 Jan
[New potent serotonin receptor agonist. Helps migraine patients even when other triptans fail].
2001 Jul 5
Acute treatment of migraine and the role of triptans.
2001 Mar
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
[Eletriptan shortly before drug approval. Fewer problems in migraine therapy].
2001 May 28
Oral triptans (serotonin 5-HT(1B/1D) agonists) in acute migraine treatment: a meta-analysis of 53 trials.
2001 Nov 17
Eletriptan.
2001 Oct
Advances in pharmacological treatment of migraine.
2001 Oct
Rizatriptan: an update of its use in the management of migraine.
2002
Gateways to Clinical Trials.
2002 Apr
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
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
Suppression by eletriptan of the activation of trigeminovascular sensory neurons by glyceryl trinitrate.
2002 Oct 25
Eletriptan Pfizer.
2002 Sep
Gateways to Clinical Trials.
2002 Sep
Pharmacological approaches to migraine.
2003
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 issues.
2003 Jul-Aug
The evolving management of migraine.
2003 Jun
Safety profile of the triptans.
2003 Mar
Comparative efficacy of eletriptan 40 mg versus sumatriptan 100 mg.
2003 Mar
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
Migraine: diagnosis and management.
2003 Sep-Oct
New drugs 04, part 1.
2004 Feb
[Use of triptanes according to indications. Risk of infarct is not increased].
2004 Feb 12
Gateways to clinical trials.
2004 Jul-Aug
Cost considerations of acute migraine treatment.
2004 Mar
Double-blind clinical trials of oral triptans vs other classes of acute migraine medication - a review.
2004 May
[Triptans in migraine: a comparative review of pharmacology, pharmacokinetics].
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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