Identification

Summary

Isometheptene is a sympathomimetic used to relieve painful spasms in combination with other agents such as caffeine and metamizole.

Generic Name
Isometheptene
DrugBank Accession Number
DB06706
Background

Isometheptene is a sympathomimetic drug that causes vasoconstriction. It is used for treating migraines and tension headaches.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 141.2539
Monoisotopic: 141.151749613
Chemical Formula
C9H19N
Synonyms
  • Isometepteno
  • Isometheptene
  • Isometheptenum

Pharmacology

Indication

Isometheptene is a sympathomimetic drug which causes vasoconstriction. It is used for treating migraines and tension headaches.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Isometheptene Mucate is an indirect-acting sympathomimetic. Due to its vasoconstricting properties, Isometheptene Mucate is used for the treatment of acute migraine attacks, usually in combination with other analgeics. It can also displace catecholamines from vesicles inside the neuron leading to the sympathetic responses it is known for.

Mechanism of action

Isometheptene's vasoconstricting properties arise through activation of the sympathetic nervous system via epinephrine and norepinephrine (or their molecular analogues as is the case with this drug). These compounds elicites smooth muscle activation leading to vasoconstriction. These compounds interact with cell surface adrenergic receptors. Such stimuli result in a signal transduction cascade that leads to increased intracellular calcium from the sarcoplasmic reticulum through IP3 mediated calcium release, as well as enhanced calcium entry across the sarcolemma through calcium channels. The rise in intracellular calcium complexes with calmodulin, which in turn activates myosin light chain kinase. This enzyme is responsible for phosphorylating the light chain of myosin to stimulate cross bridge cycling.

Once elevated, the intracellular calcium concentration is returned to its basal level through a variety of protein pumps and calcium exchangers located on the plasma membrane and sarcoplasmic reticulum. This reduction in calcium removes the stimulus necessary for contraction allowing for a return to baseline. The drug can also cause vesicular displacement of noradrenaline from the neuron into the synapse with a similar effect as tyramine.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Humans
ASynaptic vesicular amine transporter
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe therapeutic efficacy of Isometheptene can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Isometheptene is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Isometheptene is combined with Acemetacin.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Isometheptene.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Isometheptene.
AclidiniumThe risk or severity of Tachycardia can be increased when Isometheptene is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Isometheptene.
AlclofenacThe risk or severity of hypertension can be increased when Isometheptene is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Isometheptene.
AlfuzosinThe therapeutic efficacy of Isometheptene can be decreased when used in combination with Alfuzosin.
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Isometheptene mucate8O120FDS6P7492-31-1WSXKZIDINJKWPM-IBGZLQDMSA-N
International/Other Brands
Octanil / Octin
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ANTIALGINA®Isometheptene (50 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg)SolutionOralTECNOFAR TQ S.A.S2007-03-062015-02-27Colombia flag
ANTIALGINA®Isometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg)Tablet, film coatedOralTECNOQUIMICAS S.A.2007-04-24Not applicableColombia flag
CAFETRIN ®Isometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole (300 mg)Tablet, coatedOralLABORATORIOS RICH MONDS S.A.S2018-05-11Not applicableColombia flag
DIPIRONA 300 MG + ISOMETEPTENO 50 MG + CAFEINA 30 MG GOTASIsometheptene (50 mg) + Caffeine (30 mg) + Metamizole sodium monohydrate (300 mg)SolutionOralSANOFI-AVENTIS DE COLOMBIA S.A.2018-07-062019-04-22Colombia flag
DIPIRONA 300 MG + ISOMETEPTENO MUCATO 30 MG + CAFEINA 30 MGIsometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole sodium monohydrate (300 mg)Tablet, coatedOralSANOFI - AVENTIS DE COLOMBIA S.A.2006-11-102020-10-20Colombia flag
DIPIRONA SODICA / ISOMETEPTENO MUCATO/CAFEINA 300 MG / 30 MG/30MG TABLETA RECUBIERTAIsometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg)Tablet, coatedOralLABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S.2013-07-09Not applicableColombia flag
DIPIRONA SODICA 300 MG/ ISOMETEPTENO CLORHIDRATO 50 MG / CAFEINA 30 MG GOTASIsometheptene (50 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg)SolutionOralLABORATORIO FRANCO COLOMBIANO - LAFRANCOL S.A.S.2013-08-30Not applicableColombia flag
MIGRINON® TABLETAS RECUBIERTASIsometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole (300 mg)Tablet, coatedOralFAREVA VILLA RICA S.A.S.2009-11-19Not applicableColombia flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Isometheptene Mucate, Caffeine, AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Caffeine (100 mg/1)CapsuleOralRiver's Edge Pharmaceuticals, LLC2008-07-012010-09-30US flag
Isometheptene Mucate, Caffeine, and AcetaminophenIsometheptene mucate (130 mg/1) + Acetaminophen (500 mg/1) + Caffeine (20 mg/1)TabletOralWomens Choice Pharmaceuticals, Llc2011-10-122014-01-14US flag
Isometheptene Mucate, Caffeine, and AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Caffeine (20 mg/1)TabletOralXspire Pharma2010-06-012018-01-15US flag
Isometheptene Mucate, Caffeine, and AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Caffeine (20 mg/1)TabletOralBurel Pharmaceuticals, Llc2016-04-172017-04-30US flag
Isometheptene Mucate, Dichloralphenazone, and AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1)Capsule, gelatin coatedOralVilvet Pharmaceuticals Inc2011-05-012017-10-13US flag
Isometheptene Mucate, Dichloralphenazone, and AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1)CapsuleOralBurel Pharmaceuticals, Llc2016-04-162016-11-10US flag
Isometheptene Mucate, Dichloralphenazone, and AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1)CapsuleOralMacoven Pharmaceuticals2011-06-282017-12-20US flag
Isometheptene Mucate/Dichloralphenazone/AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1)CapsuleOralPhysicians Total Care, Inc.2007-12-042012-06-30US flag
Isometheptene Mucate/Dichloralphenazone/AcetaminophenIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1)CapsuleOralEci Pharmaceuticals Llc2011-02-152018-03-31US flag
Isometheptene-Dichloral-APAP OralIsometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1)CapsuleOralMethod Pharmaceuticals2014-09-042017-11-20US flag

Categories

ATC Codes
A03AX10 — Isometheptene
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dialkylamines. These are organic compounds containing a dialkylamine group, characterized by two alkyl groups bonded to the amino nitrogen.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Dialkylamines
Alternative Parents
Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aliphatic acyclic compound / Hydrocarbon derivative / Organopnictogen compound / Secondary aliphatic amine
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Y7L24THH6T
CAS number
503-01-5
InChI Key
XVQUOJBERHHONY-UHFFFAOYSA-N
InChI
InChI=1S/C9H19N/c1-8(2)6-5-7-9(3)10-4/h6,9-10H,5,7H2,1-4H3
IUPAC Name
methyl(6-methylhept-5-en-2-yl)amine
SMILES
CNC(C)CCC=C(C)C

References

Synthesis Reference

U.S. Patent 2,230,753 U.S. Patent 2,230,754

General References
Not Available
Human Metabolome Database
HMDB0015651
PubChem Compound
22297
PubChem Substance
99443258
ChemSpider
21106328
RxNav
27946
ChEBI
134765
ChEMBL
CHEMBL1697841
PharmGKB
PA165958379
Wikipedia
Isometheptene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Subjects (HS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, coatedOral
Tablet, coatedOral30 mg
TabletOral30 mg
SolutionOral
Tablet, film coatedOral
TabletOral
Capsule, gelatin coatedOral
CapsuleOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility3.06 mg/mLALOGPS
logP2.07ALOGPS
logP2.32ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)10.67ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity47.59 m3·mol-1ChemAxon
Polarizability18.81 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9876
Blood Brain Barrier+0.9388
Caco-2 permeable+0.6722
P-glycoprotein substrateNon-substrate0.5931
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.7807
Renal organic cation transporterNon-inhibitor0.7631
CYP450 2C9 substrateNon-substrate0.8385
CYP450 2D6 substrateNon-substrate0.5252
CYP450 3A4 substrateSubstrate0.5077
CYP450 1A2 substrateNon-inhibitor0.8046
CYP450 2C9 inhibitorNon-inhibitor0.9172
CYP450 2D6 inhibitorNon-inhibitor0.7719
CYP450 2C19 inhibitorNon-inhibitor0.9108
CYP450 3A4 inhibitorNon-inhibitor0.9752
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8181
Ames testNon AMES toxic0.8476
CarcinogenicityNon-carcinogens0.7545
BiodegradationReady biodegradable0.7933
Rat acute toxicity2.2809 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9048
hERG inhibition (predictor II)Non-inhibitor0.8956
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Valdivia LF, Centurion D, Perusquia M, Arulmani U, Saxena PR, Villalon CM: Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. Life Sci. 2004 May 14;74(26):3223-34. [Article]
  2. Parker EM, Cubeddu LX: Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding. J Pharmacol Exp Ther. 1988 Apr;245(1):199-210. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Valdivia LF, Centurion D, Perusquia M, Arulmani U, Saxena PR, Villalon CM: Pharmacological analysis of the mechanisms involved in the tachycardic and vasopressor responses to the antimigraine agent, isometheptene, in pithed rats. Life Sci. 2004 May 14;74(26):3223-34. [Article]
  2. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [Article]
  3. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [Article]
  4. Parker EM, Cubeddu LX: Comparative effects of amphetamine, phenylethylamine and related drugs on dopamine efflux, dopamine uptake and mazindol binding. J Pharmacol Exp Ther. 1988 Apr;245(1):199-210. [Article]

Drug created at May 16, 2010 00:52 / Updated at June 19, 2021 00:26