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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2S.ClH
Molecular Weight 418.98
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELETRIPTAN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=YPFFNRRUXKXSTA-FSRHSHDFSA-N
InChI=1S/C22H26N2O2S.ClH/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 ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.04086077E12
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
Acute treatment of migraine and the role of triptans.
2001 Mar
Eletriptan.
2001 Oct
Spotlight on rizatriptan in migraine.
2002
Efficacy, tolerability and safety of oral eletriptan and ergotamine plus caffeine (Cafergot) in the acute treatment of migraine: a multicentre, randomised, double-blind, placebo-controlled comparison.
2002
Gateways to Clinical Trials.
2002 Apr
Sumatriptan versus eletriptan: which is best?
2002 Dec
[Migraine has to be treated. Otherwise a stroke threatens].
2002 Feb 14
Tripstar: a comprehensive patient-based approach to compare triptans.
2002 Jan
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
The pharmacokinetics and safety of single escalating oral doses of eletriptan.
2002 May
Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials.
2002 Oct
New medications show promise for migraine sufferers.
2002 Oct
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
Newer formulations of the triptans: advances in migraine management.
2003
Eletriptan (relpax) for migraine.
2003 Apr 28
Eletriptan metabolism by human hepatic CYP450 enzymes and transport by human P-glycoprotein.
2003 Jul
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
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
[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
Migraine: diagnosis and management.
2003 Sep-Oct
Meta-analysis of oral triptans.
2004 Aug
[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
Effect of high-dose intravenous eletriptan on coronary artery diameter.
2004 Jul
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
Gateways to clinical trials.
2004 Jul-Aug
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
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
[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

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 Sun Dec 18 08:32:46 UTC 2022
Edited
by admin
on Sun Dec 18 08:32:46 UTC 2022
Record UNII
OL4Q27AUZF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELETRIPTAN HYDROCHLORIDE
Common Name English
1H-INDOLE, 3-(((2R)-1-METHYL-2-PYRROLIDINYL)METHYL)-5-(2-(PHENYLSULFONYL)ETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
OL4Q27AUZF
Created by admin on Sun Dec 18 08:32:47 UTC 2022 , Edited by admin on Sun Dec 18 08:32:47 UTC 2022
PRIMARY
PUBCHEM
121596618
Created by admin on Sun Dec 18 08:32:47 UTC 2022 , Edited by admin on Sun Dec 18 08:32:47 UTC 2022
PRIMARY
CAS
1163127-11-4
Created by admin on Sun Dec 18 08:32:47 UTC 2022 , Edited by admin on Sun Dec 18 08:32:47 UTC 2022
PRIMARY
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