ALMOTRIPTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H25N3O2S
Molecular Weight	335.464
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N3CCCC3)C=C2

InChI

InChIKey=WKEMJKQOLOHJLZ-UHFFFAOYSA-N

InChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C17H25N3O2S
Molecular Weight	335.464
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Almotriptan is a triptan drug for the treatment of migraine headaches. Almotriptan is marketed under the trade name Axert. Almotriptan is used for treating acute migraine headaches with or without aura (eg, dark spots, flashing lights, wavy lines). Almotriptan binds with high affinity to 5-HT1D, 5-HT1B, and 5-HT1F receptors. Almotriptan has weak affinity for 5-HT1A and 5-HT7 receptors, but has no significant affinity or pharmacological activity at 5-HT2, 5-HT3, 5-HT4, 5-HT6; alpha or beta adrenergic; adenosine (A1, A2); angiotensin (AT1, AT2); dopamine (D1, D2); endothelin (ETA, ETB); or tachykinin (NK1, NK2, NK3) binding sites.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1b (5-HT1b) receptor 45	Agonist 2,752
Serotonin 1d (5-HT1d) receptor 53	Agonist 2,752
Serotonin 1f (5-HT1f) receptor 15	Agonist 2,752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 107	Primary		Approved 8,583	AXERT

C_max

Value	Dose	Co-administered	Analyte	Population
52.6 ng/mL	12.5 mg single, oral		ALMOTRIPTAN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
312 ng × h/mL	12.5 mg single, oral		ALMOTRIPTAN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.5 h	unknown, oral		ALMOTRIPTAN plasma	Homo sapiens
6.1 h	12.5 mg single, oral		ALMOTRIPTAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
65%	unknown, oral		ALMOTRIPTAN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
3 mg single, intravenous	healthy, 19-33 years
10 mg single, subcutaneous Highest studied dose	unhealthy, 42 years (range: 18-72 years)
12.5 mg multiple, oral Recommended	unhealthy, 42 years (range: 18-72 years)	Disc. AE: Chest pain, Electrocardiogram QTc interval prolonged...
100 mg multiple, oral Highest studied dose	unhealthy, adult
200 mg single, oral Highest studied dose	healthy, adult

Showing 1 to 5 of 5 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Electrocardiogram QTc interval prolonged	0.7% Disc. AE	12.5 mg multiple, oral Recommended	unhealthy, 42 years (range: 18-72 years)
Chest pain	0.9% Disc. AE	12.5 mg multiple, oral Recommended	unhealthy, 42 years (range: 18-72 years)

Showing 1 to 2 of 2 entries

Previous1Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946	inhibitor 2,438	substrate 1,388 inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2A6 879 CYP2B6 926 CYP2C19 2,057 CYP2E1 1,060 CYP3A4/5 296 CYP4A9/11 35	FMO3 77 CYP3A4/5 91 CYP1A2 1,197 CYP2C8 810 CYP2C19 1,119

Drug as perpetrator

Show entries

Target	Modality	Activity
CYP1A2 2,333	inhibitor 4,027	no
CYP2A6 911	inhibitor 4,027	no
CYP2B6 1,160	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no

Showing 1 to 5 of 9 entries

Previous1 2Next

Drug as victim

Show entries

Target	Modality	Activity
CYP1A2 1,197	substrate 4,014	yes
CYP2C19 1,119	substrate 4,014	yes
CYP2C8 810	substrate 4,014	yes
CYP2D6 1,388	substrate 4,014	yes
CYP3A4 1,946	substrate 4,014	yes

Showing 1 to 5 of 7 entries

Previous1 2Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:520985	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:520985
ChemicalBook	CB7716603	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7716603
eMolecules	5852303	https://www.emolecules.com/cgi-bin/more?vid=5852303
ZINC	ZINC000000018087	http://zinc15.docking.org/substances/ZINC000000018087

Showing 1 to 4 of 4 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Comparative aspects of triptans in treating migraine.	2001	12739316
Spotlight on rizatriptan in migraine.	2002	12269863
Rizatriptan: an update of its use in the management of migraine.	2002	12093318
Gateways to clinical trials.	2002 Dec	12616965
Absolute bioavailability, pharmacokinetics, and urinary excretion of the novel antimigraine agent almotriptan in healthy male volunteers.	2002 Dec	12463724

Showing 1 to 5 of 50 entries

Previous1 2 3 4 5…10Next

Patents

Sample Use Guides

In Vivo Use Guide

Adults and adolescents age 12 to 17 years: 6.25 mg or 12.5 mg single dose; may repeat after 2 hours if headache returns; benefit of second dose in patients who have failed to respond to first dose has not been established; maximum daily dose 25 mg Patients with hepatic or severe renal impairment: 6.25 mg starting dose; maximum daily dose 12.5 mg

Route of Administration: Oral

In Vitro Use Guide

In vitro Almotriptan showed selectivity of action for migraine-related human arteries (i.e. contractile EC(50) of 30 and 700 nm for meningeal and temporal arteries, respectively), whereas the effect on arteries supplying blood to the brain was lower.

Substance Class	Chemical
Record UNII	1O4XL5SN61
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ALMOTRIPTAN

Official Name

English

LAS-31416

Preferred Name

English

Almotriptan [WHO-DD]

Common Name

English

1-[[[3-[2-(Dimethylamino)ethyl]indol-5-yl]methyl]sulfonyl]pyrrolidine

Systematic Name

English

ALMOTRIPTAN [USAN]

Common Name

English

Showing 1 to 5 of 11 entries

Previous1 2 3Next

Show entries

Classification Tree

Code System

Code

Selective serotonin (5HT1) agonists

WHO-VATC

QN02CC05

Serotonin Agonists

NDF-RT

N0000175764

Agent Affecting Nervous System

NCI_THESAURUS

C47794

Migraine

LIVERTOX

27

Serotonin Agonists

NDF-RT

N0000175763

Showing 1 to 5 of 7 entries

Previous1 2Next

Show entries

Code System

Code

Type

Description

CAS

154323-57-6

PRIMARY

DRUG CENTRAL

128

PRIMARY

ChEMBL

CHEMBL1505

PRIMARY

MERCK INDEX

m1568

PRIMARY

Merck Index

DRUG BANK

DB00918

PRIMARY

Showing 1 to 5 of 21 entries

Previous1 2 3 4 5Next

Show entries

Related Record

Type

Details


					ZI18M2JAY5

5-HYDROXYTRYPTAMINE RECEPTOR 1D

TARGET -> AGONIST

Amount:


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

35 % (average)


					1O4XL5SN61

ALMOTRIPTAN

EXCRETED UNCHANGED

Interaction Type:

AMOUNT EXCRETED

Qualification:

URINE

Amount:

40 % (average)
of administered dose


					1O4XL5SN61

ALMOTRIPTAN

EXCRETED UNCHANGED

Comments:

Approximately 3% of the administered dose is excreted via feces, both unchanged and metabolized.

Qualification:

FECAL

Amount:


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> SUBSTRATE

Amount:

Showing 1 to 5 of 8 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					N6TR3763RN

1-(((3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-5-YL)METHYL)SULFONYL)-2-PYRROLIDINOL

METABOLITE -> PARENT

Amount:


					9LX8M2H6V5

N-Desmethyl almotriptan

METABOLITE -> PARENT

Amount:

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Related Record

Type

Details


					2EU666P9ND

4-((1-PYRROLIDINYLSULFONYL)METHYL)BENZENAMINE

IMPURITY -> PARENT

Amount:


					7X93GAN4WT

1-[[(4-Hydrazinylphenyl)methyl]sulfonyl]pyrrolidine

IMPURITY -> PARENT

Amount:


					4R9ZF5AV6Y

5-HYDROXYMETHYL-N,N-DIMETHYLTRYPTAMINE

IMPURITY -> PARENT

Amount:

Showing 1 to 3 of 3 entries

Previous1Next

Show entries

Related Record

Type

Details


					1O4XL5SN61

ALMOTRIPTAN

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Name	Property Type	Amount	Parameters
Tmax	PHARMACOKINETIC	[1 to 3] hours (average)	ORAL ADMINISTRATION

Biological Half-life	PHARMACOKINETIC	[3 to 5] hours (average)

Volume of Distribution	PHARMACOKINETIC	[2.57 to 2.86] Liters/Kilogram (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