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
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
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.
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 |
---|---|---|---|---|
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 Date2001 |
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 |
---|---|---|---|---|
3.5 h |
unknown, oral |
ALMOTRIPTAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
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 |
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 |
|
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%) 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 Health Status: unhealthy Age Group: adult Sources: |
|
200 mg single, oral Highest studied dose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
healthy, adult Health Status: healthy Age Group: adult 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) 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
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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Comparative aspects of triptans in treating migraine. | 2001 |
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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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Almotriptan: a balanced approach to migraine. | 2001 Feb |
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Establishing a standard of speed for assessing the efficacy of the serotonin(1B/1D) agonists (triptans). | 2001 Jul |
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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 |
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Efficacy and tolerability of subcutaneous almotriptan for the treatment of acute migraine: a randomized, double-blind, parallel-group, dose-finding study. | 2001 Nov |
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Oral triptans (serotonin 5-HT(1B/1D) agonists) in acute migraine treatment: a meta-analysis of 53 trials. | 2001 Nov 17 |
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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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Almotriptan versus sumatriptan in migraine treatment: direct medical costs of managing adverse chest symptoms. | 2002 Feb |
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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 |
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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 |
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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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Newer formulations of the triptans: advances in migraine management. | 2003 |
|
Interaction between ketoconazole and almotriptan in healthy volunteers. | 2003 Apr |
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A review of the effects of almotriptan and other triptans on clinical trial outcomes that are meaningful to patients with migraine. | 2003 Feb |
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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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[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
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
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by
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on
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Record UNII |
1O4XL5SN61
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Record Status |
Validated (UNII)
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Record Version |
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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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N0000175763
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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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ALMOTRIPTAN
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Almotriptan
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100000087462
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
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BINDER->LIGAND |
BINDING
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EXCRETED UNCHANGED |
AMOUNT EXCRETED
URINE
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EXCRETED UNCHANGED |
Approximately 3% of the administered dose is excreted via feces, both unchanged and metabolized.
FECAL
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METABOLIC ENZYME -> SUBSTRATE |
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TARGET -> AGONIST |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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