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
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
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 |
---|---|---|---|
Target ID: CHEMBL1898 |
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Target ID: CHEMBL1983 |
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Target ID: CHEMBL1805 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | AXERT Approved UseAlmotriptan 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 Date9.8919357E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
52.6 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12723463 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
312 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12723463 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12723463 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65% |
unknown, oral |
ALMOTRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse 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%) Sources: Electrocardiogram QTc interval prolonged (0.7%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
no | |||
Page: 49.0 |
weak [Ki 87 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 27.0 |
yes | |||
Page: 27.0 |
yes | |||
Page: 27.0 |
yes | |||
Page: 27.0 |
yes | |||
Page: 27, 49 |
yes | |||
Page: 27.0 |
yes | |||
Page: 27.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Cardiovascular safety profile of almotriptan, a new indolic derivative for the treatment of migraine. | 2000 Dec 20 |
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Pharmacological characterization of almotriptan: an indolic 5-HT receptor agonist 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 |
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[Current topics: expectation for new triptans]. | 2001 Apr 10 |
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Evaluation of the potential pharmacokinetic interaction between almotriptan and fluoxetine in healthy volunteers. | 2001 Feb |
|
Treatment satisfaction, functional status, and health-related quality of life of migraine patients treated with almotriptan or sumatriptan. | 2001 Jan |
|
Long-term efficacy and safety of oral almotriptan: interim analysis of a 1-year open study. | 2001 Jan |
|
[Migraine headache. Severe attacks: triptans are essential]. | 2001 Jul 19 |
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Oral almotriptan vs. oral sumatriptan in the abortive treatment of migraine: a double-blind, randomized, parallel-group, optimum-dose comparison. | 2001 Jun |
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Acute treatment of migraine and the role of triptans. | 2001 Mar |
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Effect of MAO-A inhibition on the pharmacokinetics of almotriptan, an antimigraine agent in humans. | 2001 May |
|
Oral almotriptan in the treatment of migraine: safety and tolerability. | 2001 May |
|
Rizatriptan: an update of its use in the management of migraine. | 2002 |
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Spotlight on almotriptan in migraine. | 2002 |
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How does almotriptan compare with other triptans? A review of data from placebo-controlled clinical trials. | 2002 Feb |
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[Profile of the antimigraine drug almotriptan]. | 2002 Feb |
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Health outcomes evaluations: estimating the impact of almotriptan in managed care settings. | 2002 Feb |
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Economic comparison of oral triptans for management of acute migraine: implications for managed care. | 2002 Feb |
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Almotriptan: a review of pharmacology, clinical efficacy, and tolerability. | 2002 Feb |
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Migraine: diagnosis, management, and new treatment options. | 2002 Feb |
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Almotriptan (Axert) and frovatriptan (Frova) for migrane. | 2002 Feb 18 |
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New drugs 2002, part III. | 2002 Jul |
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Mechanisms of action of the 5-HT1B/1D receptor agonists. | 2002 Jul |
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Triptans (serotonin, 5-HT1B/1D agonists) in migraine: detailed results and methods of a meta-analysis of 53 trials. | 2002 Oct |
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Almotriptan: an effective and well-tolerated treatment for migraine pain. | 2003 |
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Newer formulations of the triptans: advances in migraine management. | 2003 |
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Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. | 2003 Apr |
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Gateways to clinical trials. | 2003 Dec |
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Meta-analysis of oral triptan therapy for migraine: number needed to treat and relative cost to achieve relief within 2 hours. | 2003 Jan-Feb |
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A review of the clinical efficacy and tolerability of almotriptan in acute migraine. | 2003 Jul |
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Almotriptan versus rizatriptan in patients with migraine in Spain. | 2003 Jul-Aug |
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Safety profile of the triptans. | 2003 Mar |
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A case of carotidynia with response to almotriptan. | 2003 Mar |
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Cost-effectiveness of almotriptan and rizatriptan in the treatment of acute migraine. | 2003 Nov |
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Clinical benefits of early triptan therapy for migraine. | 2004 |
|
Clinical profile and practice experience of almotriptan. | 2004 |
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What do patients want from acute migraine treatment? | 2004 |
|
Migraine pathophysiology and its clinical implications. | 2004 |
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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 |
|
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 |
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 Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11737005
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.
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WHO-VATC |
QN02CC05
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NDF-RT |
N0000175764
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NCI_THESAURUS |
C47794
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LIVERTOX |
27
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NDF-RT |
N0000175763
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NDF-RT |
N0000175765
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WHO-ATC |
N02CC05
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154323-57-6
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128
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CHEMBL1505
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M1568
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DB00918
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7110
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279645
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C409045
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154323-57-6
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ALMOTRIPTAN
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1O4XL5SN61
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C65224
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SUB05350MIG
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7463
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Almotriptan
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123606
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ACTIVE MOIETY
METABOLITE (PARENT)