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Alverine
Identification
- Name
- Alverine
- Accession Number
- DB01616
- Description
Alverine is a smooth muscle relaxant used to relieve cramps or spasms of the stomach and intestines. It is therefore useful in treating irritable bowel syndrome (IBS) and similar conditions. It can also be used to help relieve period pain.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Alverine (DB01616)
- Weight
- Average: 281.4351
Monoisotopic: 281.214349869 - Chemical Formula
- C20H27N
- Synonyms
- Alverina
- Alverine
- Alverinum
- Bis(gamma-phenylpropyl)ethylamine
- Di(phenylpropyl)ethylamine
- N-Ethyl-3-phenyl-N-(3-phenylpropyl)-1-propanamine
- N-Ethyl-3,3'-diphenyldipropylamine
- N-Ethyl-N-(3-phenylpropyl)benzenepropanamine
- N,N-Bis(3-phenylpropyl)ethylamine
- Phenopropamine
- Phenpropamine
Pharmacology
- Indication
Used to relieve cramps or spasms of the stomach and intestines. It is also useful in treating irritable bowel syndrome (IBS) and similar conditions. It can also be used to help relieve period pain. Alverine citrate is also under investigation to increase the cytotoxic effects of the proteasome inhibitor MG132 on breast cancer cells.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Alverine is a smooth muscle relaxant. Smooth muscle is a type of muscle that is not under voluntary control; it is the muscle present in places such as the gut and uterus. Alverine acts directly on the muscle in the gut, causing it to relax. This prevents the muscle spasms which occur in the gut in conditions such as irritable bowel syndrome and diverticular disease. Diverticular disease is a condition in which small pouches form in the gut lining. These pouches can trap particles of food and become inflamed and painful. In irritable bowel syndrome the normal activity of the gut muscle is lost. The muscle spasms result in symptoms such as heartburn, abdominal pain and bloating, constipation or diarrhoea. By relaxing the gut muscle, alverine citrate relieves the symptoms of this condition. Alverine also relaxes the smooth muscle in the womb (uterus). It is therefore also used to treat painful menstruation, which is caused by muscle spasms in the uterus (dysmenorrhea).
- Mechanism of action
Target Actions Organism A5-hydroxytryptamine receptor 1A antagonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Rapidly converted to its primary active metabolite, which is then further converted to two secondary metabolites.
- Route of elimination
High renal clearance of all metabolites indicating that they are eliminated by active renal secretion.
- Half-life
The plasma half-life averages 0.8 hours for alverine and 5.7 hours for the active primary metabolite.
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Can produce hypotension and atropine-like toxic effects. Fatality has occurred following overdose with very high doses.
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAcenocoumarol The risk or severity of adverse effects can be increased when Alverine is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Alverine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Alverine. Aclidinium Alverine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Alverine is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Alverine. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Alverine. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Alverine. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Alverine. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Alverine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Alverine citrate 9JFB58YK1E 5560-59-8 RYHCACJBKCOBTJ-UHFFFAOYSA-N - International/Other Brands
- Audmonal / Profenil / Spasmaverine / Spasmonal
Categories
- ATC Codes
- A03AX08 — Alverine
- A03AX — Other drugs for functional gastrointestinal disorders
- A03A — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A03 — DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Alimentary Tract and Metabolism
- Amines
- Antidepressive Agents
- Autonomic Agents
- Central Nervous System Depressants
- Drugs for Functional Gastrointestinal Disorders
- Parasympatholytics
- Peripheral Nervous System Agents
- Serotonin 5-HT1 Receptor Antagonists
- Serotonin 5-HT1A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylpropylamines
- Direct Parent
- Phenylpropylamines
- Alternative Parents
- Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropylamine / Tertiary aliphatic amine / Tertiary amine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- tertiary amine (CHEBI:518413)
Chemical Identifiers
- UNII
- 46TIR1560O
- CAS number
- 150-59-4
- InChI Key
- ZPFXAOWNKLFJDN-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H27N/c1-2-21(17-9-15-19-11-5-3-6-12-19)18-10-16-20-13-7-4-8-14-20/h3-8,11-14H,2,9-10,15-18H2,1H3
- IUPAC Name
- ethylbis(3-phenylpropyl)amine
- SMILES
- CCN(CCCC1=CC=CC=C1)CCCC1=CC=CC=C1
References
- General References
- Hayase M, Hashitani H, Suzuki H, Kohri K, Brading AF: Evolving mechanisms of action of alverine citrate on phasic smooth muscles. Br J Pharmacol. 2007 Dec;152(8):1228-38. Epub 2007 Oct 15. [PubMed:17934514]
- Wittmann T, Paradowski L, Ducrotte P, Bueno L, Andro Delestrain MC: Clinical trial: the efficacy of alverine citrate/simeticone combination on abdominal pain/discomfort in irritable bowel syndrome--a randomized, double-blind, placebo-controlled study. Aliment Pharmacol Ther. 2010 Mar;31(6):615-24. doi: 10.1111/j.1365-2036.2009.04216.x. Epub 2009 Dec 10. [PubMed:20003095]
- Ju D, Wang X, Xie Y: Dyclonine and alverine citrate enhance the cytotoxic effects of proteasome inhibitor MG132 on breast cancer cells. Int J Mol Med. 2009 Feb;23(2):205-9. [PubMed:19148544]
- Spasmonal Package Insert [Link]
- External Links
- Human Metabolome Database
- HMDB0015554
- KEGG Drug
- D07440
- PubChem Compound
- 3678
- PubChem Substance
- 46506981
- ChemSpider
- 3550
- BindingDB
- 37636
- 17627
- ChEBI
- 518413
- ChEMBL
- CHEMBL253371
- ZINC
- ZINC000001481966
- PharmGKB
- PA164764505
- Wikipedia
- Alverine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Irritable Bowel Syndrome (IBS) 3
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule, liquid filled Oral 60 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp boiling point (°C) 212.5 °C at 1.30E+01 mm Hg PhysProp - Predicted Properties
Property Value Source Water Solubility 0.00096 mg/mL ALOGPS logP 5.73 ALOGPS logP 5.46 ChemAxon logS -5.5 ALOGPS pKa (Strongest Basic) 10.44 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 3.24 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 92.67 m3·mol-1 ChemAxon Polarizability 35.42 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9482 Caco-2 permeable + 0.8219 P-glycoprotein substrate Substrate 0.6368 P-glycoprotein inhibitor I Non-inhibitor 0.6741 P-glycoprotein inhibitor II Non-inhibitor 0.853 Renal organic cation transporter Inhibitor 0.7848 CYP450 2C9 substrate Non-substrate 0.7873 CYP450 2D6 substrate Substrate 0.5452 CYP450 3A4 substrate Non-substrate 0.6521 CYP450 1A2 substrate Inhibitor 0.6458 CYP450 2C9 inhibitor Non-inhibitor 0.9308 CYP450 2D6 inhibitor Inhibitor 0.8368 CYP450 2C19 inhibitor Inhibitor 0.5919 CYP450 3A4 inhibitor Non-inhibitor 0.8074 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5739 Ames test Non AMES toxic 0.9653 Carcinogenicity Non-carcinogens 0.6473 Biodegradation Not ready biodegradable 0.9649 Rat acute toxicity 2.6539 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6077 hERG inhibition (predictor II) Inhibitor 0.7442
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Coelho AM, Jacob L, Fioramonti J, Bueno L: Rectal antinociceptive properties of alverine citrate are linked to antagonism at the 5-HT1A receptor subtype. J Pharm Pharmacol. 2001 Oct;53(10):1419-26. [PubMed:11697552]
Drug created on August 29, 2007 14:13 / Updated on June 12, 2020 10:51
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