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 No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created using several sources including: 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: 3352.0
Gene Symbol: HTR1D
Target Organism: Homo sapiens (Human)
0.92 nM [Kd]
Target ID: P28222
Gene ID: 3351.0
Gene Symbol: HTR1B
Target Organism: Homo sapiens (Human)
3.14 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

2002
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 (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
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: Page: Study 102
AEs

AEs

AESignificanceDosePopulation
Headache 0.2%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Hypertonia 0.2%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Paresthesia 0.2%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Somnolence 0.2%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Vomiting 0.2%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Asthenia 0.3%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Chest pain 0.3%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Dizziness 0.4%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
Nausea 0.4%
Disc. AE
80 mg 1 times / day single, oral (typical)
Recommended
Dose: 80 mg, 1 times / day
Route: oral
Route: single
Dose: 80 mg, 1 times / day
Sources: Page: Study 102
unhealthy, 41.9
n = 312
Health Status: unhealthy
Condition: migraine
Age Group: 41.9
Sex: M+F
Population Size: 312
Sources: Page: Study 102
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: 9.0
minor
minor
PubMed

PubMed

TitleDatePubMed
Comparative aspects of triptans in treating migraine.
2001
Eletriptan for acute migraine.
2001
Pharmacokinetics and safety of oral eletriptan during different phases of the menstrual cycle in healthy volunteers.
2001 Dec
Establishing a standard of speed for assessing the efficacy of the serotonin(1B/1D) agonists (triptans).
2001 Jul
Craniovascular selectivity of eletriptan and sumatriptan in human isolated blood vessels.
2001 Jul 10
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
Advances in pharmacological treatment of migraine.
2001 Oct
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
[Migraine has to be treated. Otherwise a stroke threatens].
2002 Feb 14
Tripstar: a comprehensive patient-based approach to compare triptans.
2002 Jan
Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials.
2002 Oct
Suppression by eletriptan of the activation of trigeminovascular sensory neurons by glyceryl trinitrate.
2002 Oct 25
Eletriptan Pfizer.
2002 Sep
Eletriptan (relpax) for migraine.
2003 Apr 28
Eletriptan for the treatment of migraine in patients with previous poor response or tolerance to oral sumatriptan.
2003 Jul
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
Gateways to clinical trials.
2004 Jan-Feb
Gateways to clinical trials.
2004 Jul-Aug
Gateways to 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
[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
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 of a second dose to treat the same attack. The maximum daily dose should not exceed 80 mg.
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 Fri Dec 15 16:17:27 GMT 2023
Edited
by admin
on Fri Dec 15 16:17:27 GMT 2023
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 [WHO-DD]
Common Name 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
(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 Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
WHO-ATC N02CC06
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
NDF-RT N0000175764
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
WHO-VATC QN02CC06
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
NDF-RT N0000175763
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
NDF-RT N0000175765
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
Code System Code Type Description
LACTMED
Eletriptan
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046861
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
SMS_ID
100000080522
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
EVMPD
SUB06482MIG
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
DRUG BANK
DB00216
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL1510
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
DAILYMED
22QOO9B8KI
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
NCI_THESAURUS
C65509
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
CAS
143322-58-1
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
DRUG CENTRAL
995
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
MESH
C115647
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
INN
7426
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
CHEBI
50922
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
WIKIPEDIA
ELETRIPTAN
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
FDA UNII
22QOO9B8KI
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
MERCK INDEX
m4867
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY Merck Index
RXCUI
231049
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY RxNorm
IUPHAR
40
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
PRIMARY
PUBCHEM
77993
Created by admin on Fri Dec 15 16:17:27 GMT 2023 , Edited by admin on Fri Dec 15 16:17:27 GMT 2023
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
METABOLIC ENZYME -> SUBSTRATE
MINOR
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
TRANSPORTER -> SUBSTRATE
EFFLUX RATIO
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