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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2S
Molecular Weight 382.521
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELETRIPTAN

SMILES

CN1CCC[C@]1([H])Cc2c[nH]c3ccc(CCS(=O)(=O)c4ccccc4)cc23

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 382.521
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/10193663 | http://www.migraines.org/treatment/pro_rlpx.htm

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

Curator's Comment:: Known to be CNS penetrant in rats. Human data not available. It was concluded that eletriptan, acting on perikarya and both the peripheral and the central axon terminals of primary sensory neurons, exerts its antimigraine effect by an agonist action on 5-HT1B/1D receptors throughout the entire trigeminal system, probably by passing the blood-brain-barrier because of its lipophilic character.

Originator

Curator's Comment:: # Pfizer

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P28221
Gene ID: 3352
Gene Symbol: HTR1D
Target Organism: Homo sapiens (Human)
0.92000000000000004 nM [Kd]
Target ID: P28222
Gene ID: 3351
Gene Symbol: HTR1B
Target Organism: Homo sapiens (Human)
3.14000000000000012 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RELPAX

Approved Use

RELPAX is indicated for the acute treatment of migraine with or without aura in adults. RELPAX is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. Safety and effectiveness of RELPAX Tablets have not been established for cluster headache, which is present in an older, predominantly male population.

Launch Date

1040860800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
183.6 ng/mL
40 mg 2 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
200.1 ng/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
46.5 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
94.72 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1278 ng × h/mL
40 mg 2 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
1282 ng × h/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
291.3 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
575.6 ng × h/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.75 h
40 mg 2 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
4.58 h
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
4.92 h
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
4.63 h
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ELETRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
15%
ELETRIPTAN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Disc. AE: Nausea, Dizziness...
AEs leading to
discontinuation/dose reduction:
Nausea (0.4%)
Dizziness (0.4%)
Asthenia (0.3%)
Chest pain (0.3%)
Headache (0.2%)
Vomiting (0.2%)
Hypertonia (0.2%)
Paresthesia (0.2%)
Somnolence (0.2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Headache 0.2%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Hypertonia 0.2%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Paresthesia 0.2%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Somnolence 0.2%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Vomiting 0.2%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Asthenia 0.3%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Chest pain 0.3%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Dizziness 0.4%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Nausea 0.4%
Disc. AE
80 mg 1 times / day single, oral
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 41.9
Health Status: unhealthy
Age Group: 41.9
Sex: M+F
Sources:
Overview

OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
little
little
no
no
no
no
no
no
no
no
no
yes [IC50 41 uM]
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
inconclusive
major
yes (co-administration study)
Comment: when administered with ketoconazole, Cmax and AUC increased by 2.7-fold and 5.9-fold, respectively; when administered with verapamil, Cmax and AUC increased by 2.2-fold and 2.7-fold, respectively; when administered with fluconazole, Cmax and AUC increased by 1.4-fold and 2-fold, respectively;
Page: 9
minor
minor
PubMed

PubMed

TitleDatePubMed
Comparative aspects of triptans in treating migraine.
2001
Eletriptan for acute migraine.
2001
Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain.
2001 Aug 17
Safety and rational use of the triptans.
2001 Jul
Craniovascular selectivity of eletriptan and sumatriptan in human isolated blood vessels.
2001 Jul 10
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
Advances in pharmacological treatment of migraine.
2001 Oct
Gateways to Clinical Trials.
2002 Apr
Sumatriptan versus eletriptan: which is best?
2002 Dec
Tripstar: a comprehensive patient-based approach to compare triptans.
2002 Jan
[New triptanes in control of migraine attacks. More rapid onset of action--more efficient reduction of pain].
2002 Jan 24
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
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
Comparative efficacy of eletriptan and zolmitriptan in the acute treatment of migraine.
2003 Dec
Eletriptan for the treatment of migraine in patients with previous poor response or tolerance to oral sumatriptan.
2003 Jul
Cost-effectiveness of migraine treatment: a commentary.
2003 Jul-Aug
Comparative efficacy of eletriptan 40 mg versus sumatriptan 100 mg.
2003 Mar
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
Comparative efficacy of eletriptan vs. naratriptan in the acute treatment of migraine.
2003 Nov
Tolerability and safety of eletriptan in the treatment of migraine: a comprehensive review.
2003 Oct
Unilateral time-delayed encapsulation does not make for a fair race.
2003 Sep
Meta-analysis of oral triptans.
2004 Aug
New drugs 04, part 1.
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
Cardiovascular safety of triptans.
2004 Jul
Gateways to clinical trials.
2004 Jul-Aug
Gateways to clinical trials.
2004 Mar
Cost considerations of acute migraine treatment.
2004 Mar
[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
[Triptans in migraine: from clinical view].
2004 Sep
Patents

Sample Use Guides

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
Route of Administration: Oral
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 Sat Jun 26 05:22:48 UTC 2021
Edited
by admin
on Sat Jun 26 05:22:48 UTC 2021
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 Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
NCI_THESAURUS C47794
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
WHO-ATC N02CC06
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
NDF-RT N0000175764
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
WHO-VATC QN02CC06
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
NDF-RT N0000175763
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
NDF-RT N0000175765
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
Code System Code Type Description
LACTMED
Eletriptan
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
EPA CompTox
143322-58-1
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
EVMPD
SUB06482MIG
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
DRUG BANK
DB00216
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL1510
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
NCI_THESAURUS
C65509
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
CAS
143322-58-1
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
DRUG CENTRAL
995
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
MESH
C115647
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
INN
7426
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
WIKIPEDIA
ELETRIPTAN
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
FDA UNII
22QOO9B8KI
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
MERCK INDEX
M4867
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY Merck Index
RXCUI
231049
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY RxNorm
IUPHAR
40
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
PUBCHEM
77993
Created by admin on Sat Jun 26 05:22:49 UTC 2021 , Edited by admin on Sat Jun 26 05:22:49 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors
BINDING
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors
METABOLIC ENZYME -> SUBSTRATE
MINOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors
TARGET -> AGONIST
Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
Eletriptan binds with high affinity to 5-HT1B, 5-HT1D and 5-HT1F receptors, has modest affinity for 5-HT1A, 5-HT1E, 5-HT2B and 5-HT7 receptors
BINDING
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE ACTIVE -> PARENT
PLASMA
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC