Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C9H19N.C6H10O8 |
| Molecular Weight | 492.6465 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 4 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(C)CCC=C(C)C.CNC(C)CCC=C(C)C.O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O
InChI
InChIKey=WSXKZIDINJKWPM-IBGZLQDMSA-N
InChI=1S/2C9H19N.C6H10O8/c2*1-8(2)6-5-7-9(3)10-4;7-1(3(9)5(11)12)2(8)4(10)6(13)14/h2*6,9-10H,5,7H2,1-4H3;1-4,7-10H,(H,11,12)(H,13,14)/t;;1-,2+,3+,4-
DescriptionCurator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02290379 | https://www.ncbi.nlm.nih.gov/pubmed/22288671 | https://clinicaltrials.gov/ct2/show/NCT02706015 | https://www.drugbank.ca/drugs/DB06706
Curator's Comment: description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02290379 | https://www.ncbi.nlm.nih.gov/pubmed/22288671 | https://clinicaltrials.gov/ct2/show/NCT02706015 | https://www.drugbank.ca/drugs/DB06706
Isometheptene (usually as isometheptene mucate) is a sympathomimetic amine sometimes used in the treatment of migraines and tension headaches due to its vasoconstricting properties. Isometheptene's vasoconstricting properties arise through activation of the sympathetic nervous system via epinephrine and norepinephrine. These compounds elicit smooth muscle activation leading to vasoconstriction by interacting with cell surface adrenergic receptors.
Originator
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
120 mg 1 times / episode multiple, oral Studied dose Dose: 120 mg, 1 times / episode Route: oral Route: multiple Dose: 120 mg, 1 times / episode Co-administed with:: dipyrone(1200 mg) Sources: caffeine(120 mg) |
unhealthy, 18 to 65 years n = 76 Health Status: unhealthy Condition: primary headache Age Group: 18 to 65 years Sex: M+F Population Size: 76 Sources: |
Other AEs: Angioneurotic edema, Epigastralgia... Other AEs: Angioneurotic edema (grade 1, 1.3%) Sources: Epigastralgia (grade 1, 1.3%) |
780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
Other AEs: Dizziness, Numbness... Other AEs: Dizziness (17.1%) Sources: Numbness (5.7%) Shortness of breath (2.8%) Chills (2.8%) Nausea (2.8%) Drowsiness (2.8%) |
65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
Other AEs: Abdominal pain, Nausea... Other AEs: Abdominal pain (3.1%) Sources: Nausea (3.1%) Lightheadedness (6.1%) Sleepiness (3.1%) Dry mouth (1.5%) Hot flashes (1.5%) Palpitations (1.5%) Enlarged thyroid (1.5%) Confusion (1.5%) |
325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
Other AEs: Nausea, Vertigo... Other AEs: Nausea (40%) Sources: Vertigo (8%) Lump feeling in throat (8%) Drowsiness (4%) Tachycardia (4%) Itching (4%) Dry mouth (4%) Weakness of limbs (4%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Angioneurotic edema | grade 1, 1.3% | 120 mg 1 times / episode multiple, oral Studied dose Dose: 120 mg, 1 times / episode Route: oral Route: multiple Dose: 120 mg, 1 times / episode Co-administed with:: dipyrone(1200 mg) Sources: caffeine(120 mg) |
unhealthy, 18 to 65 years n = 76 Health Status: unhealthy Condition: primary headache Age Group: 18 to 65 years Sex: M+F Population Size: 76 Sources: |
| Epigastralgia | grade 1, 1.3% | 120 mg 1 times / episode multiple, oral Studied dose Dose: 120 mg, 1 times / episode Route: oral Route: multiple Dose: 120 mg, 1 times / episode Co-administed with:: dipyrone(1200 mg) Sources: caffeine(120 mg) |
unhealthy, 18 to 65 years n = 76 Health Status: unhealthy Condition: primary headache Age Group: 18 to 65 years Sex: M+F Population Size: 76 Sources: |
| Dizziness | 17.1% | 780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
| Chills | 2.8% | 780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
| Drowsiness | 2.8% | 780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
| Nausea | 2.8% | 780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
| Shortness of breath | 2.8% | 780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
| Numbness | 5.7% | 780 mg 1 times / episode multiple, oral Studied dose Dose: 780 mg, 1 times / episode Route: oral Route: multiple Dose: 780 mg, 1 times / episode Sources: |
unhealthy, mean age 33 years n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 Sources: |
| Confusion | 1.5% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Dry mouth | 1.5% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Enlarged thyroid | 1.5% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Hot flashes | 1.5% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Palpitations | 1.5% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Abdominal pain | 3.1% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Nausea | 3.1% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Sleepiness | 3.1% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Lightheadedness | 6.1% | 65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Co-administed with:: dichloralphenazone(500 mg per 12 h) Sources: acetaminophen(1625 mg per 12 h) |
unhealthy, mean age 40.9 years n = 65 Health Status: unhealthy Condition: migraine Age Group: mean age 40.9 years Sex: M+F Population Size: 65 Sources: |
| Drowsiness | 4% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Dry mouth | 4% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Itching | 4% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Tachycardia | 4% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Weakness of limbs | 4% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Nausea | 40% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Lump feeling in throat | 8% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
| Vertigo | 8% | 325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Co-administed with:: acetaminophen(325 mg; two capsules at once, followed by one capsule every hour until relieved, up to 5 capsules in four hours; during 2 weeks to 2 months) Sources: |
unhealthy, mean age 49 years n = 25 Health Status: unhealthy Condition: migraine Age Group: mean age 49 years Sex: M+F Population Size: 25 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolism of isometheptene in human urine and analysis by gas chromatography-mass spectrometry in doping control. | 2005 Dec 5 |
|
| Effects of current and prospective antimigraine drugs on the porcine isolated meningeal artery. | 2006 Dec |
|
| Rizatriptan for the acute treatment of migraine: Consistency, preference, satisfaction, and quality of life. | 2009 Nov 3 |
|
| Managing traumatic brain injury secondary to explosions. | 2010 Apr |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29709
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100000086457
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m6501
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8O120FDS6P
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DBSALT001313
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C87577
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104994
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7492-31-1
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1349659
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231-315-3
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CHEMBL1697841
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ACTIVE MOIETY
SUBSTANCE RECORD
