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
Structure for Isometheptene (DB06706)
- 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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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AAlpha-1A adrenergic receptor agonistHumans ASynaptic vesicular amine transporter inhibitorHumans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Isometheptene can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Isometheptene is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Isometheptene is combined with Acemetacin. Acetaminophen The risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Isometheptene. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Isometheptene. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Isometheptene mucate 8O120FDS6P 7492-31-1 WSXKZIDINJKWPM-IBGZLQDMSA-N - International/Other Brands
- Octanil / Octin
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ANTIALGINA® Isometheptene (50 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg) Solution Oral TECNOFAR TQ S.A.S 2007-03-06 2015-02-27 Colombia 
ANTIALGINA® Isometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg) Tablet, film coated Oral TECNOQUIMICAS S.A. 2007-04-24 Not applicable Colombia CAFETRIN ® Isometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole (300 mg) Tablet, coated Oral LABORATORIOS RICH MONDS S.A.S 2018-05-11 Not applicable Colombia DOSALDIN Isometheptene mucate (30 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg) Tablet Oral SERVICIO TECNICO GONHER FARMACEUTICA LTDA. 2010-01-22 2020-04-16 Colombia DOSALDIN® GOTAS Isometheptene (50 mg) + Caffeine (30 mg) + Metamizole sodium (300 mg) Solution Oral SERVICIO TECNICO GONHER FARMACEUTICA LTDA. 2010-05-10 2021-11-28 Colombia - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Isometheptene Mucate, Caffeine, Acetaminophen Isometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Caffeine (100 mg/1) Capsule Oral River's Edge Pharmaceuticals, LLC 2008-07-01 2010-09-30 US 
Isometheptene Mucate, Caffeine, and Acetaminophen Isometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Caffeine (20 mg/1) Tablet Oral Burel Pharmaceuticals, Llc 2016-04-17 2017-04-30 US Isometheptene Mucate, Caffeine, and Acetaminophen Isometheptene mucate (130 mg/1) + Acetaminophen (500 mg/1) + Caffeine (20 mg/1) Tablet Oral Womens Choice Pharmaceuticals, Llc 2011-10-12 2014-01-14 US Isometheptene Mucate, Caffeine, and Acetaminophen Isometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Caffeine (20 mg/1) Tablet Oral Xspire Pharma 2010-06-01 2018-01-15 US Isometheptene Mucate, Dichloralphenazone, and Acetaminophen Isometheptene mucate (65 mg/1) + Acetaminophen (325 mg/1) + Dichloralphenazone (100 mg/1) Capsule, gelatin coated Oral Vilvet Pharmaceuticals Inc 2011-05-01 2017-10-13 US
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
- External Links
- Human Metabolome Database
- HMDB0015651
- PubChem Compound
- 22297
- PubChem Substance
- 99443258
- ChemSpider
- 21106328
- 27946
- ChEBI
- 134765
- ChEMBL
- CHEMBL1697841
- PharmGKB
- PA165958379
- Wikipedia
- Isometheptene
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Treatment Healthy Volunteers (HV) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral Tablet, film coated Oral Tablet, coated Oral Tablet Oral Capsule, gelatin coated Oral Capsule Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 3.06 mg/mL ALOGPS logP 2.07 ALOGPS logP 2.32 Chemaxon logS -1.7 ALOGPS pKa (Strongest Basic) 10.67 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 47.59 m3·mol-1 Chemaxon Polarizability 18.81 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9876 Blood Brain Barrier + 0.9388 Caco-2 permeable + 0.6722 P-glycoprotein substrate Non-substrate 0.5931 P-glycoprotein inhibitor I Inhibitor 0.5 P-glycoprotein inhibitor II Non-inhibitor 0.7807 Renal organic cation transporter Non-inhibitor 0.7631 CYP450 2C9 substrate Non-substrate 0.8385 CYP450 2D6 substrate Non-substrate 0.5252 CYP450 3A4 substrate Substrate 0.5077 CYP450 1A2 substrate Non-inhibitor 0.8046 CYP450 2C9 inhibitor Non-inhibitor 0.9172 CYP450 2D6 inhibitor Non-inhibitor 0.7719 CYP450 2C19 inhibitor Non-inhibitor 0.9108 CYP450 3A4 inhibitor Non-inhibitor 0.9752 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8181 Ames test Non AMES toxic 0.8476 Carcinogenicity Non-carcinogens 0.7545 Biodegradation Ready biodegradable 0.7933 Rat acute toxicity 2.2809 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9048 hERG inhibition (predictor II) Non-inhibitor 0.8956
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0a4i-9100000000-dd5c87491214e2bb43e8 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0ac9-9000000000-7cd7115d946f605d2a7c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0900000000-378e39a9a4756883ed6c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-2900000000-4b1b1eca9b26a2eb32eb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-066u-9000000000-b43c08e0321ad39237f7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-9100000000-1b47c847cd9c1f4d6bf4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05mo-9000000000-b213273473f295097ce5 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.8593034 predictedDarkChem Lite v0.1.0 [M-H]- 134.95586 predictedDeepCCS 1.0 (2019) [M+H]+ 142.4576034 predictedDarkChem Lite v0.1.0 [M+H]+ 137.56749 predictedDeepCCS 1.0 (2019) [M+Na]+ 142.0165034 predictedDarkChem Lite v0.1.0 [M+Na]+ 146.68707 predictedDeepCCS 1.0 (2019)
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
- 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]
- 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
- 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]
- 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]
- 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]
- 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 February 02, 2024 22:53