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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2S.BrH
Molecular Weight 463.4324
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELETRIPTAN HYDROBROMIDE

SMILES

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

InChI

InChIKey=UTINOWOSWSPFLJ-FSRHSHDFSA-N
InChI=1S/C22H26N2O2S.BrH/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 C22H26N2O2S
Molecular Weight 382.521
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula BrH
Molecular Weight 80.9115
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain.
2001 Aug 17
Establishing a standard of speed for assessing the efficacy of the serotonin(1B/1D) agonists (triptans).
2001 Jul
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
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
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
Eletriptan vs sumatriptan: a double-blind, placebo-controlled, multiple migraine attack study.
2002 Oct 22
Gateways to Clinical Trials.
2002 Sep
Current perspectives on effective migraine treatments: are small clinical differences important for patients?
2003
[Pharmacological, pharmacokinetic and clinical profile of eletriptan (Relpax), a new triptan for migraine].
2003 Jul
Eletriptan for the treatment of migraine in patients with previous poor response or tolerance to oral sumatriptan.
2003 Jul
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
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
The 40-mg dose of eletriptan: comparative efficacy and tolerability versus sumatriptan 100 mg.
2004 Feb
[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
Double-blind clinical trials of oral triptans vs other classes of acute migraine medication - a review.
2004 May
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: a comparative review of pharmacology, pharmacokinetics].
2004 Sep
TRIPSTAR: prioritizing oral triptan treatment attributes in migraine management.
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 Fri Jun 25 21:38:58 UTC 2021
Edited
by admin
on Fri Jun 25 21:38:58 UTC 2021
Record UNII
M41W832TA3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELETRIPTAN HYDROBROMIDE
JAN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
USAN  
Official Name English
ELETRIPTAN HYDROBROMIDE [ORANGE BOOK]
Common Name English
RELPAX
Brand Name English
3-(((R)-1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)INDOLE, MONOHYDROBROMIDE
Common Name English
ELETRIPTAN HYDROBROMIDE [JAN]
Common Name English
ELETRIPTAN HYDROBROMIDE [MART.]
Common Name English
UK-116,044-04
Code English
(R)-3-((1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)-1H-INDOLE MONOHYDROBROMIDE
Systematic Name English
ELETRIPTAN HYDROBROMIDE [WHO-DD]
Common Name English
ELETRIPTAN HBR
Common Name English
ELETRIPTAN HYDROBROMIDE [USP-RS]
Common Name English
ELETRIPTAN HYDROBROMIDE [MI]
Common Name English
UK-116044-04
Code English
NSC-759258
Code English
ELETRIPTAN HYDROBROMIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
Code System Code Type Description
EVMPD
SUB26382
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
RXCUI
360288
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY RxNorm
CAS
177834-92-3
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
PUBCHEM
656631
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL1510
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
MERCK INDEX
M4867
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1234453
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY USP-RS
FDA UNII
M41W832TA3
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
NCI_THESAURUS
C47508
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
DRUG BANK
DBSALT000884
Created by admin on Fri Jun 25 21:38:58 UTC 2021 , Edited by admin on Fri Jun 25 21:38:58 UTC 2021
PRIMARY
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