ISOMETHEPTENE HYDROCHLORIDE

First approved in 1948

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H19N.ClH
Molecular Weight	177.715
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ISOMETHEPTENE HYDROCHLORIDE

Structure Search

SMILES

Cl.CNC(C)CCC=C(C)C

InChI

InChIKey=AUERTJOCDMCUAL-UHFFFAOYSA-N

InChI=1S/C9H19N.ClH/c1-8(2)6-5-7-9(3)10-4;/h6,9-10H,5,7H2,1-4H3;1H

HIDE SMILES / InChI

Description
Sources: http://araujo.vteximg.com.br/arquivos/ids/2780773/Bula-0000000003528.pdf
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

Targets

Primary Target	Pharmacology	Condition	Potency
Alpha-2a adrenergic receptor 70 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11485035	Agonist 2752
Alpha-2c adrenergic receptor 44 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11485035	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Migraine 107 Sources: http://www.tabletwise.com/brazil/neosaldina-oral-solution	Primary	Approved 8583	Neosaldina Approved Use Unknown
Headache 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22288671	Primary	Approved 8583	Neosaldina Approved Use Unknown
Neuralgia 12 Sources: http://www.tabletwise.com/brazil/neosaldina-oral-solution	Primary	Approved 8583	Neosaldina Approved Use Unknown

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 Sources: https://pubmed.ncbi.nlm.nih.gov/22288671/	unhealthy, 18 to 65 years Health Status: unhealthy Age Group: 18 to 65 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22288671/	Other AEs: Angioneurotic edema, Epigastralgia... Other AEs: Angioneurotic edema (grade 1, 1.3%) Epigastralgia (grade 1, 1.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/22288671/
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: https://pubmed.ncbi.nlm.nih.gov/1100566/	unhealthy, mean age 33 years Health Status: unhealthy Age Group: mean age 33 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1100566/	Other AEs: Dizziness, Numbness... Other AEs: Dizziness (17.1%) Numbness (5.7%) Shortness of breath (2.8%) Chills (2.8%) Nausea (2.8%) Drowsiness (2.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/1100566/
65 mg 1 times / hour multiple, oral Recommended Dose: 65 mg, 1 times / hour Route: oral Route: multiple Dose: 65 mg, 1 times / hour Sources: https://pubmed.ncbi.nlm.nih.gov/11318886/	unhealthy, mean age 40.9 years Health Status: unhealthy Age Group: mean age 40.9 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/11318886/	Other AEs: Abdominal pain, Nausea... Other AEs: Abdominal pain (3.1%) 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%) Sources: https://pubmed.ncbi.nlm.nih.gov/11318886/
325 mg 1 times / episode multiple, oral Recommended Dose: 325 mg, 1 times / episode Route: oral Route: multiple Dose: 325 mg, 1 times / episode Sources: https://pubmed.ncbi.nlm.nih.gov/1107267/	unhealthy, mean age 49 years Health Status: unhealthy Age Group: mean age 49 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/1107267/	Other AEs: Nausea, Vertigo... Other AEs: Nausea (40%) Vertigo (8%) Lump feeling in throat (8%) Drowsiness (4%) Tachycardia (4%) Itching (4%) Dry mouth (4%) Weakness of limbs (4%) Sources: https://pubmed.ncbi.nlm.nih.gov/1107267/

AEs

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY557072	https://www.001chemical.com/chem/503-01-5
AHH Chemical co.,ltd	MR-1008920	http://www.ahhchemical.com/product/MR-1008920.html
Alfa Chemistry	503-01-5	https://www.alfa-chemistry.com/isometheptene-cas-503-01-5-item-292231.htm
Ambinter	Amb17593577	http://www.ambinter.com/reference/17593577
Aurora Fine Chemicals LLC	A06.792.909	http://online.aurorafinechemicals.com/info?ID=A06.792.909
ChemMol	99115822	http://www.chemmol.com/chemmol/99115822.html
Hairui	HR140715	http://www.hairuichem.com/en/product/503-01-5.html
Molcore	MC557072	https://www.molcore.com/product/503-01-5
MuseChem	I007380	https://www.musechem.com/product/I007380.html
Sinfoo Biotech	S010495	http://www.sinfoobiotech.com/product/1013893
Smolecule	S530926	http://www.smolecule.com/products/s530926
THE BioTek	bt-272330	https://www.thebiotek.com/product/inhibitors/bt-272330

PubMed

Title	Date	PubMed
Epidemiological analysis of doping offences in the professional tennis circuit.	2010-12-15	21159201
Managing traumatic brain injury secondary to explosions.	2010-04	20606794
Rizatriptan for the acute treatment of migraine: Consistency, preference, satisfaction, and quality of life.	2009-11-03	19936168
Life threatening intracerebral hemorrhage with isometheptene mucate, dichlorophenazine and acetaminophen combination therapy.	2009-11	19782324
Current and prospective pharmacological targets in relation to antimigraine action.	2008-10	18626630
Acute migraine: Current treatment and emerging therapies.	2007-06	18488069
Effects of current and prospective antimigraine drugs on the porcine isolated meningeal artery.	2006-12	17103145
Intracerebral hemorrhage in postpartum cerebral angiopathy associated with the use of isometheptene.	2006-11	16999965
Time to pain freedom and onset of pain relief with rizatriptan 10 mg and prescription usual-care oral medications in the acute treatment of migraine headaches: a multicenter, prospective, open-label, two-attack, crossover study.	2006-06	16860170
Metabolism of isometheptene in human urine and analysis by gas chromatography-mass spectrometry in doping control.	2005-12-05	16242387
Fixed drug combinations for the acute treatment of migraine : place in therapy.	2005	16142992
Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats.	2004-05-14	15094323
Medication use by persons with chronic fatigue syndrome: results of a randomized telephone survey in Wichita, Kansas.	2003-12-02	14651754
Migraine: diagnosis, management, and new treatment options.	2002-02	11859906
Pharmacological profile of the mechanisms involved in the external carotid vascular effects of the antimigraine agent isometheptene in anaesthetised dogs.	2001-07	11485035
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.	2001-04	11318886

Patents

Sample Use Guides

In Vivo Use Guide

Single dose 1 to 2 tablets/days, Daily Maximum Dose: 8 tablets (4 x 2 dragees). One tablet contains 30 mg of Isometheptene Mucate.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

NSC-13066

Preferred Name

English

ISOMETHEPTENE HYDROCHLORIDE

Common Name

English

5-HEPTEN-2-AMINE, N,6-DIMETHYL-, HYDROCHLORIDE (1:1)

Systematic Name

English

(1,5-DIMETHYLHEX-4-ENYL)METHYLAMMONIUM CHLORIDE

Systematic Name

English

ISOMETHEPTENE HCL

Common Name

English

Isometheptene hydrochloride [WHO-DD]

Common Name

English

ISOMETHEPTENE HYDROCHLORIDE, (±)-

Common Name

English

(±)-ISOMETHEPTENE HYDROCHLORIDE

Common Name

English

ISOMETHEPDRINE CHLORIDE

Common Name

English

ISOMETHEPTENE HYDROCHLORIDE [MI]

Common Name

English

4-HEXENYLAMINE, N,1,5-TRIMETHYL-, HYDROCHLORIDE

Systematic Name

English

ISOMETHEPTENE HYDROCHLORIDE [MART.]

Common Name

English

5-HEPTEN-2-AMINE, N,6-DIMETHYL-, HYDROCHLORIDE

Systematic Name

English

2-METHYLAMINOISOOCTANE HYDROCHLORIDE

Common Name

English

N,1,5-TRIMETHYL-4-HEXENYLAMINE HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709