ELETRIPTAN

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
5-hydroxytryptamine receptor 1D 17	Agonist 2,678	0.92 nM [Kd]
5-hydroxytryptamine receptor 1B 21	Agonist 2,678	3.14 nM [Kd]
5-hydroxytryptamine receptor 1F 8	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 103	Primary		Approved 8,429	RELPAX

C_max

Value	Dose	Analyte	Population
183.6 ng/mL	40 mg 2 times / day multiple, oral	ELETRIPTAN plasma	Homo sapiens
200.1 ng/mL	80 mg single, oral	ELETRIPTAN plasma	Homo sapiens
46.5 ng/mL	20 mg single, oral	ELETRIPTAN plasma	Homo sapiens
94.72 ng/mL	40 mg single, oral	ELETRIPTAN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1278 ng × h/mL	40 mg 2 times / day multiple, oral	ELETRIPTAN plasma	Homo sapiens
1282 ng × h/mL	80 mg single, oral	ELETRIPTAN plasma	Homo sapiens
291.3 ng × h/mL	20 mg single, oral	ELETRIPTAN plasma	Homo sapiens
575.6 ng × h/mL	40 mg single, oral	ELETRIPTAN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.75 h	40 mg 2 times / day multiple, oral	ELETRIPTAN plasma	Homo sapiens
4.58 h	80 mg single, oral	ELETRIPTAN plasma	Homo sapiens
4.92 h	20 mg single, oral	ELETRIPTAN plasma	Homo sapiens
4.63 h	40 mg single, oral	ELETRIPTAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
15%			ELETRIPTAN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
80 mg 1 times / day single, oral (typical) Recommended	unhealthy, 41.9 n = 312	Disc. AE: Nausea, Dizziness...

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AEs

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AE	Significance	Dose	Population
Headache	0.2% Disc. AE	80 mg 1 times / day single, oral (typical) Recommended	unhealthy, 41.9 n = 312
Hypertonia	0.2% Disc. AE	80 mg 1 times / day single, oral (typical) Recommended	unhealthy, 41.9 n = 312
Paresthesia	0.2% Disc. AE	80 mg 1 times / day single, oral (typical) Recommended	unhealthy, 41.9 n = 312
Somnolence	0.2% Disc. AE	80 mg 1 times / day single, oral (typical) Recommended	unhealthy, 41.9 n = 312
Vomiting	0.2% Disc. AE	80 mg 1 times / day single, oral (typical) Recommended	unhealthy, 41.9 n = 312

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inhibitor 1,587 inducer 781	inhibitor 1,767 inducer 389	substrate 1,217 inhibitor 1,852 inducer 97

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C19 1,478 CYP1A2 1,524 CYP2B6 810 CYP2E1 882	CYP1A 22 P-gp 1,537	CYP2A6 79 CYP1A2 701 CYP2C19 293 CYP2E1 128

Drug as perpetrator

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Target	Modality	Activity
CYP2A6 739	inducer 1,573	likely
CYP2B6 1,001	inhibitor 3,277	little
CYP2C19 1,553	inhibitor 3,277	little
CYP1A2 1,692	inducer 1,573	no
CYP1A2 1,692	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
P-gp 1,537	substrate 3,367	inconclusive
CYP3A4 1,737	substrate 3,367	major	yes (co-administration study)
CYP1A 22	substrate 3,367	minor
CYP2D6 1,217	substrate 3,367	minor

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50922	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50922
ChemicalBook	CB1404591	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1404591
MolPort	MolPort-005-940-717	https://www.molport.com/shop/molecule-link/MolPort-005-940-717
ZINC	ZINC000003823475	http://zinc15.docking.org/substances/ZINC000003823475
eMolecules	30512783	https://www.emolecules.com/cgi-bin/more?vid=30512783

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PubMed

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Title	Date	PubMed
Eletriptan: pharmacological differences and clinical results.	2001	12463280
Serotonergic effects and extracellular brain levels of eletriptan, zolmitriptan and sumatriptan in rat brain.	2001 Aug 17	11513839
Triptans are all different.	2001 Sep	11559322
Spotlight on rizatriptan in migraine.	2002	12269863
Gateways to Clinical Trials.	2002 Apr	12087878

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Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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
Record UNII	22QOO9B8KI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELETRIPTAN

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

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Classification Tree

Code System

Code

Migraine

LIVERTOX

343

Agent Affecting Nervous System

NCI_THESAURUS

C47794

Selective serotonin (5HT1) agonists

WHO-ATC

N02CC06

Serotonin Agonists

NDF-RT

N0000175764

Selective serotonin (5HT1) agonists

WHO-VATC

QN02CC06

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Code System

Code

Type

Description

LACTMED

Eletriptan

PRIMARY

EPA CompTox

DTXSID9046861

PRIMARY

SMS_ID

100000080522

PRIMARY

EVMPD

SUB06482MIG

PRIMARY

DRUG BANK

DB00216

PRIMARY

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Related Record

Type

Details


					ZI18M2JAY5

5-HYDROXYTRYPTAMINE RECEPTOR 1D

TARGET -> AGONIST

Comments:

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

Interaction Type:

BINDING

Amount:


					92AD31CQ59

ELETRIPTAN SUCCINATE

SALT/SOLVATE -> PARENT

Amount:


					1AG1A6ENX6

5-HYDROXYTRYPTAMINE RECEPTOR 7

TARGET -> AGONIST

Comments:

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

Amount:


					9DX651UO0D

CYTOCHROME P450 1A1

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

MINOR

Amount:


					M41W832TA3

ELETRIPTAN HYDROBROMIDE

SALT/SOLVATE -> PARENT

Amount:

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Related Record

Type

Details


					6MOZ326Q5L

N-DESMETHYL ELETRIPTAN

METABOLITE ACTIVE -> PARENT

Qualification:

PLASMA

Amount:

[10 to 20] % (average)
of parent drug

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Related Record

Type

Details


					22QOO9B8KI

ELETRIPTAN

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount
Volume of Distribution	PHARMACOKINETIC	1.97 Liters/Kilogram (average)

Tmax	PHARMACOKINETIC	[1 to 2] hours (average)

Biological Half-life	PHARMACOKINETIC	13 hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator