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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H26N2O2S.BrH
Molecular Weight 463.431
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELETRIPTAN HYDROBROMIDE

SMILES

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

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 BrH
Molecular Weight 80.912
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
Eletriptan: pharmacological differences and clinical results.
2001
Eletriptan for acute migraine.
2001
Acute treatment of migraine and the role of triptans.
2001 Mar
[Eletriptan shortly before drug approval. Fewer problems in migraine therapy].
2001 May 28
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
[Migraine has to be treated. Otherwise a stroke threatens].
2002 Feb 14
Gateways to clinical trials.
2002 Oct
Eletriptan vs sumatriptan: a double-blind, placebo-controlled, multiple migraine attack study.
2002 Oct 22
Suppression by eletriptan of the activation of trigeminovascular sensory neurons by glyceryl trinitrate.
2002 Oct 25
Eletriptan Pfizer.
2002 Sep
Comparative efficacy of eletriptan and zolmitriptan in the acute treatment of migraine.
2003 Dec
[Recent progress in therapy for migraine headache].
2004 Feb 10
Gateways to clinical trials.
2004 Jan-Feb
Gateways to clinical trials.
2004 Jul-Aug
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
[Meta-analysis of triptan treatment in migraine].
2004 Sep
[Triptans in migraine: from clinical view].
2004 Sep
[Triptans in migraine: a comparative review of pharmacology, pharmacokinetics].
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 Fri Dec 15 16:35:39 UTC 2023
Edited
by admin
on Fri Dec 15 16:35:39 UTC 2023
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 HBR
Common Name English
Eletriptan hydrobromide [WHO-DD]
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 Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
Code System Code Type Description
EVMPD
SUB26382
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
RXCUI
360288
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY RxNorm
USAN
JJ-101
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
CAS
177834-92-3
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
NSC
759258
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
PUBCHEM
656631
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
ChEMBL
CHEMBL1510
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
RS_ITEM_NUM
1234453
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
SMS_ID
100000091986
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
CHEBI
61176
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
MERCK INDEX
m4867
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY Merck Index
FDA UNII
M41W832TA3
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
NCI_THESAURUS
C47508
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID001016113
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
DAILYMED
M41W832TA3
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
DRUG BANK
DBSALT000884
Created by admin on Fri Dec 15 16:35:39 UTC 2023 , Edited by admin on Fri Dec 15 16:35:39 UTC 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY