U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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
Structure of ALMOTRIPTAN

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AXERT

Approved Use

Almotriptan tablets, USP are a 5HT1B/1D receptor agonist (triptan) indicated for: •Acute treatment of migraine attacks in adults with a history of migraine with or without aura (1.1) •Acute treatment of migraine headache pain in adolescents age 12 to 17 years with a history of migraine with or without aura, and who have migraine attacks usually lasting 4 hours or more (1.1) Important Limitations: •Use only after a clear diagnosis of migraine has been established (1.2) •In adolescents age 12 to 17 years, efficacy of almotriptan tablets on migraine-associated symptoms was not established (1.2) •Not intended for the prophylactic therapy of migraine (1.2) •Not indicated for the treatment of cluster headache (1.2) 1.1 Acute Treatment of Migraine Attacks Adults Almotriptan tablets, USP are indicated for the acute treatment of migraine attacks in patients with a history of migraine with or without aura. Adolescents Age 12 to 17 Years Almotriptan tablets are indicated for the acute treatment of migraine headache pain in patients with a history of migraine attacks with or without aura usually lasting 4 hours or more (when untreated). 1.2 Important Limitations Almotriptan tablets should only be used where a clear diagnosis of migraine has been established. If a patient has no response for the first migraine attack treated with almotriptan tablets, the diagnosis of migraine should be reconsidered before almotriptan tablets are administered to treat any subsequent attacks. In adolescents age 12 to 17 years, efficacy of almotriptan tablets on migraine-associated symptoms (nausea, photophobia, and phonophobia) was not established. Almotriptan tablets are not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine [see Contraindications (4.7)

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
52.6 ng/mL
12.5 mg single, oral
dose: 12.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALMOTRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
312 ng × h/mL
12.5 mg single, oral
dose: 12.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALMOTRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.5 h
unknown, oral
ALMOTRIPTAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
6.1 h
12.5 mg single, oral
dose: 12.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALMOTRIPTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
65%
unknown, oral
ALMOTRIPTAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3 mg single, intravenous
Dose: 3 mg
Route: intravenous
Route: single
Dose: 3 mg
Sources:
healthy, 19-33 years
Health Status: healthy
Age Group: 19-33 years
Sex: M
Sources:
10 mg single, subcutaneous
Highest studied dose
Dose: 10 mg
Route: subcutaneous
Route: single
Dose: 10 mg
Sources:
unhealthy, 42 years (range: 18-72 years)
Health Status: unhealthy
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Sources:
12.5 mg multiple, oral
Recommended
Dose: 12.5 mg
Route: oral
Route: multiple
Dose: 12.5 mg
Sources:
unhealthy, 42 years (range: 18-72 years)
Health Status: unhealthy
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Sources:
Disc. AE: Chest pain, Electrocardiogram QTc interval prolonged...
AEs leading to
discontinuation/dose reduction:
Chest pain (0.9%)
Electrocardiogram QTc interval prolonged (0.7%)
Sources:
100 mg multiple, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: multiple
Dose: 100 mg
Sources:
unhealthy, adult
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
healthy, adult
AEs

AEs

AESignificanceDosePopulation
Electrocardiogram QTc interval prolonged 0.7%
Disc. AE
12.5 mg multiple, oral
Recommended
Dose: 12.5 mg
Route: oral
Route: multiple
Dose: 12.5 mg
Sources:
unhealthy, 42 years (range: 18-72 years)
Health Status: unhealthy
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Sources:
Chest pain 0.9%
Disc. AE
12.5 mg multiple, oral
Recommended
Dose: 12.5 mg
Route: oral
Route: multiple
Dose: 12.5 mg
Sources:
unhealthy, 42 years (range: 18-72 years)
Health Status: unhealthy
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Sources:
Overview

Overview

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Cardiovascular safety profile of almotriptan, a new indolic derivative for the treatment of migraine.
2000 Dec 20
Comparative aspects of triptans in treating migraine.
2001
Tolerability and efficacy of almotriptan in the long-term treatment of migraine.
2001
[Current topics: expectation for new triptans].
2001 Apr 10
Almotriptan: a balanced approach to migraine.
2001 Feb
Establishing a standard of speed for assessing the efficacy of the serotonin(1B/1D) agonists (triptans).
2001 Jul
Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison.
2001 Jun
Acute treatment of migraine and the role of triptans.
2001 Mar
Effect of MAO-A inhibition on the pharmacokinetics of almotriptan, an antimigraine agent in humans.
2001 May
Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study.
2001 Nov
Oral triptans (serotonin 5-HT(1B/1D) agonists) in acute migraine treatment: a meta-analysis of 53 trials.
2001 Nov 17
How does almotriptan compare with other triptans? A review of data from placebo-controlled clinical trials.
2002 Feb
[Profile of the antimigraine drug almotriptan].
2002 Feb
Almotriptan versus sumatriptan in migraine treatment: direct medical costs of managing adverse chest symptoms.
2002 Feb
Health outcomes evaluations: estimating the impact of almotriptan in managed care settings.
2002 Feb
Migraine: diagnosis, management, and new treatment options.
2002 Feb
[Treatment of migraine in patients with hypertension and ischemic heart disease].
2002 Jan 20
New drugs 2002, part III.
2002 Jul
Gateways to Clinical Trials. June 2002.
2002 Jun
Cardiovascular effect of almotriptan in treated hypertensive patients.
2002 Mar
Efficacy and safety of almotriptan malate for migraine.
2002 Nov 15
Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials.
2002 Oct
Newer formulations of the triptans: advances in migraine management.
2003
Interaction between ketoconazole and almotriptan in healthy volunteers.
2003 Apr
A review of the effects of almotriptan and other triptans on clinical trial outcomes that are meaningful to patients with migraine.
2003 Feb
Meta-analysis of oral triptan therapy for migraine: number needed to treat and relative cost to achieve relief within 2 hours.
2003 Jan-Feb
[Almotriptan in the treatment of migraine attacks in clinical practice: results of the TEA 2000 observational study].
2003 Jan-Feb
A review of the clinical efficacy and tolerability of almotriptan in acute migraine.
2003 Jul
Almotriptan versus rizatriptan in patients with migraine in Spain.
2003 Jul-Aug
Safety profile of the triptans.
2003 Mar
Gateways to clinical trials. March 2003.
2003 Mar
Validation of a general measure of treatment satisfaction, the Treatment Satisfaction Questionnaire for Medication (TSQM), using a national panel study of chronic disease.
2004 Feb 26
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
Correlation between lipophilicity and triptan outcomes.
2005 Jan
Patents

Patents

Sample Use Guides

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 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
Created
by admin
on Mon Mar 31 18:07:05 GMT 2025
Edited
by admin
on Mon Mar 31 18:07:05 GMT 2025
Record UNII
1O4XL5SN61
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALMOTRIPTAN
INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
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
almotriptan [INN]
Common Name English
LAS31416
Code English
ALMOTRIPTAN [VANDF]
Common Name English
ALMOTRIPTAN [MI]
Common Name English
PYRROLIDINE, 1-(((3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-5-YL)METHYL)SULFONYL)-
Systematic Name English
NSC-760092
Code English
Classification Tree Code System Code
WHO-VATC QN02CC05
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
NDF-RT N0000175764
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
NCI_THESAURUS C47794
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
LIVERTOX 27
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
NDF-RT N0000175763
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
NDF-RT N0000175765
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
WHO-ATC N02CC05
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
Code System Code Type Description
CAS
154323-57-6
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
DRUG CENTRAL
128
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL1505
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
MERCK INDEX
m1568
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY Merck Index
DRUG BANK
DB00918
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
IUPHAR
7110
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
RXCUI
279645
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY RxNorm
MESH
C409045
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID5044289
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
WIKIPEDIA
ALMOTRIPTAN
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
FDA UNII
1O4XL5SN61
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
USAN
JJ-24
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
NCI_THESAURUS
C65224
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
EVMPD
SUB05350MIG
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
DAILYMED
1O4XL5SN61
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
NSC
760092
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
INN
7463
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
LACTMED
Almotriptan
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
PUBCHEM
123606
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
CHEBI
520985
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
SMS_ID
100000087462
Created by admin on Mon Mar 31 18:07:05 GMT 2025 , Edited by admin on Mon Mar 31 18:07:05 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDER->LIGAND
BINDING
EXCRETED UNCHANGED
AMOUNT EXCRETED
URINE
EXCRETED UNCHANGED
Approximately 3% of the administered dose is excreted via feces, both unchanged and metabolized.
FECAL
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC