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Details

Stereochemistry ACHIRAL
Molecular Formula C17H25N3O2S
Molecular Weight 335.466
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALMOTRIPTAN

SMILES

CN(C)CCc1c[nH]c2ccc(cc12)CS(=O)(=O)N3CCCC3

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 335.466
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

9.8919357E11
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
Pharmacological characterization of almotriptan: an indolic 5-HT receptor agonist for the treatment of migraine.
2000 Dec 20
Almotriptan: pharmacological differences and clinical results.
2001
Tolerability and efficacy of almotriptan in the long-term treatment of migraine.
2001
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
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
Rizatriptan: an update of its use in the management of migraine.
2002
Almotriptan: a review of its use in migraine.
2002
Use of rescue medication in trials of almotriptan versus placebo in the treatment of acute migraine.
2002 Apr
Gateways to clinical trials.
2002 Dec
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
A long-term open-label study of oral almotriptan 12.5 mg for the treatment of acute migraine.
2002 Jan
Almotriptan increases sustained pain-free outcomes in acute migraine: results from three controlled clinical trials.
2002 Jan
Gateways to clinical trials.
2002 Jan-Feb
New drugs 2002, part III.
2002 Jul
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
Triptan medications to treat acute migraine.
2002 Mar 30
Current perspectives on effective migraine treatments: are small clinical differences important for patients?
2003
A review of the effects of almotriptan and other triptans on clinical trial outcomes that are meaningful to patients with migraine.
2003 Feb
Cost-effectiveness of almotriptan and rizatriptan in the treatment of acute migraine.
2003 Nov
Clinical profile and practice experience of almotriptan.
2004
Almotriptan improves response rates when treatment is within 1 hour of migraine onset.
2004 Apr
Meta-analysis of oral triptans.
2004 Aug
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
Triptans and CNS side-effects: pharmacokinetic and metabolic mechanisms.
2004 Jun
TRIPSTAR: prioritizing oral triptan treatment attributes in migraine management.
2004 Sep
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 Jun 25 22:11:59 UTC 2021
Edited
by admin
on Fri Jun 25 22:11:59 UTC 2021
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
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
LAS 31416
Code English
ALMOTRIPTAN [VANDF]
Common Name English
ALMOTRIPTAN [WHO-DD]
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 Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
NDF-RT N0000175764
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
NCI_THESAURUS C47794
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
LIVERTOX 27
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
NDF-RT N0000175763
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
NDF-RT N0000175765
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
WHO-ATC N02CC05
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
Code System Code Type Description
CAS
154323-57-6
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
DRUG CENTRAL
128
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL1505
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
MERCK INDEX
M1568
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00918
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
IUPHAR
7110
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
RXCUI
279645
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY RxNorm
MESH
C409045
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
EPA CompTox
154323-57-6
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
WIKIPEDIA
ALMOTRIPTAN
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
FDA UNII
1O4XL5SN61
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
NCI_THESAURUS
C65224
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
EVMPD
SUB05350MIG
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
INN
7463
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
LACTMED
Almotriptan
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
PUBCHEM
123606
Created by admin on Fri Jun 25 22:11:59 UTC 2021 , Edited by admin on Fri Jun 25 22:11:59 UTC 2021
PRIMARY
Related Record Type Details
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
METABOLIC ENZYME -> SUBSTRATE
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