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

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=CC=C(CS(=O)(=O)N3CCCC3)C=C12

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
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
3.5 h
unknown, oral
ALMOTRIPTAN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
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
n = 24
Health Status: healthy
Age Group: 19-33 years
Sex: M
Population Size: 24
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)
n = 31
Health Status: unhealthy
Condition: acute migraine
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Population Size: 31
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)
n = 582
Health Status: unhealthy
Condition: acute migraine
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Population Size: 582
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
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
200 mg single, oral
Highest studied dose
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
healthy, adult
n = 6
Health Status: healthy
Age Group: adult
Population Size: 6
Sources:
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)
n = 582
Health Status: unhealthy
Condition: acute migraine
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Population Size: 582
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)
n = 582
Health Status: unhealthy
Condition: acute migraine
Age Group: 42 years (range: 18-72 years)
Sex: M+F
Population Size: 582
Sources:
Overview

Overview

Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Almotriptan: pharmacological differences and clinical results.
2001
Tolerability and efficacy of almotriptan in the long-term treatment of migraine.
2001
Lack of pharmacokinetic interaction between the antimigraine compound, almotriptan, and propranolol in healthy volunteers.
2001 Feb
[Migraine headache. Severe attacks: triptans are essential].
2001 Jul 19
Acute treatment of migraine and the role of triptans.
2001 Mar
Safety profile of almotriptan, a new antimigraine agent. Effects on central nervous system, renal function and respiratory dynamics.
2001 Sep
Almotriptan: a review of its use in migraine.
2002
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
Health outcomes evaluations: estimating the impact of almotriptan in managed care settings.
2002 Feb
Economic comparison of oral triptans for management of acute migraine: implications for managed care.
2002 Feb
Almotriptan: a review of pharmacology, clinical efficacy, and tolerability.
2002 Feb
Within-patient early versus delayed treatment of migraine attacks with almotriptan: the sooner the better.
2002 Jan
Impact of chest pain on cost of migraine treatment with almotriptan and sumatriptan.
2002 Jan
Gateways to clinical trials.
2002 Jan-Feb
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
Gateways to Clinical Trials. June 2002.
2002 Jun
Cardiovascular effect of almotriptan in treated hypertensive patients.
2002 Mar
Triptan medications to treat acute migraine.
2002 Mar 30
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
New medications show promise for migraine sufferers.
2002 Oct
Newer formulations of the triptans: advances in migraine management.
2003
Interaction between ketoconazole and almotriptan in healthy volunteers.
2003 Apr
Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan.
2003 Apr
Gateways to clinical trials.
2003 Dec
Meta-analysis of oral triptan therapy for migraine: number needed to treat and relative cost to achieve relief within 2 hours.
2003 Jan-Feb
Cost-effectiveness of almotriptan and rizatriptan in the treatment of acute migraine.
2003 Nov
Early intervention with almotriptan improves sustained pain-free response in acute migraine.
2003 Nov-Dec
Migraine: diagnosis and management.
2003 Sep-Oct
Clinical benefits of early triptan therapy for migraine.
2004
A comparison of the pharmacokinetics and tolerability of the anti-migraine compound almotriptan in healthy adolescents and adults.
2004 Apr
Gateways to clinical trials.
2004 Jan-Feb
Cost considerations of acute migraine treatment.
2004 Mar
Evaluating triptan usage: a rebuttal.
2004 Oct
[Meta-analysis of triptan treatment in migraine].
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
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 Fri Dec 15 15:44:06 GMT 2023
Edited
by admin
on Fri Dec 15 15:44:06 GMT 2023
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
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
LAS-31416
Code 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 Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
NDF-RT N0000175764
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
LIVERTOX 27
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
NDF-RT N0000175763
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
NDF-RT N0000175765
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
WHO-ATC N02CC05
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
Code System Code Type Description
CAS
154323-57-6
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
DRUG CENTRAL
128
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL1505
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PRIMARY
MERCK INDEX
m1568
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB00918
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
IUPHAR
7110
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PRIMARY
RXCUI
279645
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PRIMARY RxNorm
MESH
C409045
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PRIMARY
EPA CompTox
DTXSID5044289
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
WIKIPEDIA
ALMOTRIPTAN
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
FDA UNII
1O4XL5SN61
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
USAN
JJ-24
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
NCI_THESAURUS
C65224
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
EVMPD
SUB05350MIG
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
DAILYMED
1O4XL5SN61
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
NSC
760092
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
INN
7463
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
LACTMED
Almotriptan
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
PUBCHEM
123606
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
CHEBI
520985
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
PRIMARY
SMS_ID
100000087462
Created by admin on Fri Dec 15 15:44:06 GMT 2023 , Edited by admin on Fri Dec 15 15:44:06 GMT 2023
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