ISOMETHEPTENE MUCATE

First approved in 1948

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

Structure Search

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-

HIDE SMILES / InChI

Molecular Formula	C6H10O8
Molecular Weight	210.1388
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C9H19N
Molecular Weight	141.2539
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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 63 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11485035	Agonist 2678
Alpha-2c adrenergic receptor 37 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11485035	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Migraine 103 Sources: http://www.tabletwise.com/brazil/neosaldina-oral-solution	Primary	Approved 8429	Neosaldina Approved Use Unknown
Headache 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22288671	Primary	Approved 8429	Neosaldina Approved Use Unknown
Neuralgia 12 Sources: http://www.tabletwise.com/brazil/neosaldina-oral-solution	Primary	Approved 8429	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 Co-administed with:: dipyrone(1200 mg) caffeine(120 mg) Sources: https://pubmed.ncbi.nlm.nih.gov/22288671/	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: 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 n = 36 Health Status: unhealthy Condition: migraine Age Group: mean age 33 years Sex: M+F Population Size: 36 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 Co-administed with:: dichloralphenazone(500 mg per 12 h) acetaminophen(1625 mg per 12 h) Sources: https://pubmed.ncbi.nlm.nih.gov/11318886/	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: 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 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: https://pubmed.ncbi.nlm.nih.gov/1107267/	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: 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
Comparative study of a combination of isometheptene mucate, dichloralphenazone with acetaminophen and sumatriptan succinate in the treatment of migraine.	2001 Apr	11318886
Pharmacological profile of the mechanisms involved in the external carotid vascular effects of the antimigraine agent isometheptene in anaesthetised dogs.	2001 Jul	11485035
Fixed drug combinations for the acute treatment of migraine : place in therapy.	2005	16142992
Metabolism of isometheptene in human urine and analysis by gas chromatography-mass spectrometry in doping control.	2005 Dec 5	16242387
Effects of current and prospective antimigraine drugs on the porcine isolated meningeal artery.	2006 Dec	17103145
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 Jun	16860170
Intracerebral hemorrhage in postpartum cerebral angiopathy associated with the use of isometheptene.	2006 Nov	16999965
Acute migraine: Current treatment and emerging therapies.	2007 Jun	18488069
Current and prospective pharmacological targets in relation to antimigraine action.	2008 Oct	18626630
Life threatening intracerebral hemorrhage with isometheptene mucate, dichlorophenazine and acetaminophen combination therapy.	2009 Nov	19782324
Rizatriptan for the acute treatment of migraine: Consistency, preference, satisfaction, and quality of life.	2009 Nov 3	19936168

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:09:38 GMT 2023` Edited by `admin` on `Fri Dec 15 15:09:38 GMT 2023`
Record UNII	8O120FDS6P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOMETHEPTENE MUCATE

Common Name

English

4-HEXENYLAMINE, N,1,5-TRIMETHYL-, MUCATE (2:1)

Common Name

English

4-HEXENYLAMINE, N,1,5-TRIMETHYL-, COMPD. WITH GALACTARIC ACID (2:1)

Common Name

English

GALACTARIC ACID, COMPOUND WITH N,1,5-TRIMETHYLHEX-4-EN-1-YLAMINE (1:2)

Common Name

English

6-Methylamino-2-methylheptene, tetrahydroxyadipic acid (2:1) (salt)

Common Name

English

ISOMETHEPTENE MUCATE [MI]

Common Name

English

OCTIN MUCATE

Common Name

English

ISOMETHEPTENE MUCATE [USP-RS]

Common Name

English

ISOMETHEPTENE MUCATE [MART.]

Common Name

English

ISOMETHEPTENE MUCATE [USP MONOGRAPH]

Common Name

English

ISOMETHEPTENE MUCATE [VANDF]

Common Name

English

Isometheptene mucate [WHO-DD]

Common Name

English

ISOMETHEPTENE, GALACTARATE (2:1) (SALT)

Common Name

English

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

Common Name

English

4-HEXENYLAMINE, N,1,5-TRIMETHYL-, GALACTARATE (2:1)

Common Name

English

GALACTARIC ACID, COMPD. WITH N,1,5-TRIMETHYL-4-HEXENYLAMINE (1:2)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29709