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Details

Stereochemistry RACEMIC
Molecular Formula C17H25N3O2S.C4H6O5
Molecular Weight 469.552
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0
Stereo Comments MALATE

SHOW SMILES / InChI
Structure of ALMOTRIPTAN MALATE

SMILES

OC(CC(O)=O)C(O)=O.CN(C)CCC1=CNC2=CC=C(CS(=O)(=O)N3CCCC3)C=C12

InChI

InChIKey=QHATUKWEVNMHRY-UHFFFAOYSA-N
InChI=1S/C17H25N3O2S.C4H6O5/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;5-2(4(8)9)1-3(6)7/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3;2,5H,1H2,(H,6,7)(H,8,9)

HIDE SMILES / InChI

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

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
Almotriptan: pharmacological differences and clinical results.
2001
Spotlight on rizatriptan in migraine.
2002
Rizatriptan: an update of its use in the management of migraine.
2002
Spotlight on almotriptan in migraine.
2002
Gateways to clinical trials.
2002 Dec
Absolute bioavailability, pharmacokinetics, and urinary excretion of the novel antimigraine agent almotriptan in healthy male volunteers.
2002 Dec
Almotriptan, a new anti-migraine agent: a review.
2002 Fall
[Treatment of migraine in patients with hypertension and ischemic heart disease].
2002 Jan 20
New drugs 2002, part III.
2002 Jul
Almotriptan is an effective and well-tolerated treatment for migraine pain: results of a randomized, double-blind, placebo-controlled clinical trial.
2002 Jul
Mechanisms of action of the 5-HT1B/1D receptor agonists.
2002 Jul
Gateways to Clinical Trials. June 2002.
2002 Jun
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
Current perspectives on effective migraine treatments: are small clinical differences important for patients?
2003
Almotriptan: an effective and well-tolerated treatment for migraine pain.
2003
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
[Almotriptan in the treatment of migraine attacks in clinical practice: results of the TEA 2000 observational study].
2003 Jan-Feb
Safety profile of the triptans.
2003 Mar
A case of carotidynia with response to almotriptan.
2003 Mar
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
Clinical profile and practice experience of almotriptan.
2004
What do patients want from acute migraine treatment?
2004
Migraine pathophysiology and its clinical implications.
2004
Almotriptan improves response rates when treatment is within 1 hour of migraine onset.
2004 Apr
Triptans and chest symptoms: the role of pulmonary vasoconstriction.
2004 Apr
A comparison of the pharmacokinetics and tolerability of the anti-migraine compound almotriptan in healthy adolescents and adults.
2004 Apr
Meta-analysis of oral triptans.
2004 Aug
Evaluating triptan usage.
2004 Feb
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
Gateways to clinical trials.
2004 Jan-Feb
Involvement of 5-HT1B receptors in triptan-induced contractile responses in guinea-pig isolated iliac artery.
2004 Jul
Patterns of use of triptans and reasons for switching them in a tertiary care migraine population.
2004 Jul-Aug
Triptans and CNS side-effects: pharmacokinetic and metabolic mechanisms.
2004 Jun
Cost considerations of acute migraine treatment.
2004 Mar
A comparison of the cost-effectiveness of almotriptan and sumatriptan in the treatment of acute migraine using a composite efficacy/tolerability end point.
2004 May-Jun
Evaluating triptan usage: a rebuttal.
2004 Oct
Pharmacokinetics and safety of oral almotriptan in healthy male volunteers.
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
TRIPSTAR: prioritizing oral triptan treatment attributes in migraine management.
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 15:55:03 UTC 2023
Edited
by admin
on Fri Dec 15 15:55:03 UTC 2023
Record UNII
PJP312605E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALMOTRIPTAN MALATE
MART.   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
LAS-31416 D,L-MALATE ACID
Code English
ALMOTRIPTAN MALATE [ORANGE BOOK]
Common Name English
ALMOTRIPTAN MALATE [EP MONOGRAPH]
Common Name English
LAS-31416-D,L-MALATE-ACID
Code English
1-(((3-(2-(DIMETHYLAMINO)ETHYL)-1H-INDOL-5-YL)METHYL)SULFONYL)PYRROLIDINE, HYDROXYBUTANEDIOATE (1:1)
Systematic Name English
ALMOTRIPTAN MALEATE [MI]
Common Name English
ALMOTRIPTAN MALATE [USAN]
Common Name English
ALMOTRIPTAN MALEATE
MI  
Common Name English
Almotriptan malate [WHO-DD]
Common Name English
ALMOTRIPTAN D,L-HYDROGENMALATE
Common Name English
ALMOTRIPTAN MALATE [USP-RS]
Common Name English
1-[({3-[2-(Dimethylamino)ethyl]indol-5-yl}methyl)sulfonyl]pyrrolidine malate (1:1)
Systematic Name English
ALMOTRIPTAN MALATE [VANDF]
Common Name English
ALMOGRAN
Common Name English
ALMOTRIPTAN MALATE [USP MONOGRAPH]
Common Name English
LAS 31416 D,L-MALATE ACID
Code English
AXERT
Brand Name English
PNU-180638E
Code English
ALMOTRIPTAN MALATE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47794
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1505
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
SMS_ID
100000090447
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
MERCK INDEX
m1568
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY Merck Index
CAS
181183-52-8
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
RXCUI
283792
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00918
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
NCI_THESAURUS
C61628
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
USAN
KK-101
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
WIKIPEDIA
Almotriptan malate
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
PUBCHEM
123607
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID1044225
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
EVMPD
SUB20534
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
DAILYMED
PJP312605E
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
RS_ITEM_NUM
1013512
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
FDA UNII
PJP312605E
Created by admin on Fri Dec 15 15:55:04 UTC 2023 , Edited by admin on Fri Dec 15 15:55:04 UTC 2023
PRIMARY
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