ethylbis(3-phenylpropyl)amine

• ChemBase ID: 1393
• Molecular Formular: C20H27N
• Molecular Mass: 281.43508
• Monoisotopic Mass: 281.21434987
• SMILES: N(CCCc1ccccc1)(CCCc1ccccc1)CC
• Canonical SMILES: CCN(CCCc1ccccc1)CCCc1ccccc1
• 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
• InChIKey: ZPFXAOWNKLFJDN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethylbis(3-phenylpropyl)amine
• IUPAC Traditional name: alverine
• Brand Name: Antispasmin; Dipropylin; Dipropyline; Gamatran citrate; Profenil; Sestron; Spacolin; Spasmaverine
• Synonyms: Alverina [inn-spanish]; Alverine citrate; Alverinum [inn-latin]; Bis(gamma-phenylpropyl)ethylamine; Di(phenylpropyl)ethylamine; N,N-Bis(3-phenylpropyl)ethylamine; N-Ethyl-3,3'-diphenyldipropylamine; N-Ethyl-3-phenyl-N-(3-phenylpropyl)-1-propanamine; N-Ethyl-bis(3-phenylpropyl)amin; N-Ethyl-N-(3-phenylpropyl)benzenepropanamine; Phenopropamine; Phenpropamine; Alverine

Database IDs

• CAS Number: 150-59-4
• PubChem SID: 46506981; 160964853
• PubChem CID: 3678
• CHEBI ID: 518413
• ATC CODE: A03AX08
• CHEMBL: 253371
• Chemspider ID: 3550
• DrugBank ID: DB01616
• KEGG ID: D07440
• Unique Ingredient Identifier: 46TIR1560O
• Wikipedia Title: Alverine

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.976472
• LogD (pH = 7.4): 2.54984
• Log P: 5.4623833
• Molar Refractivity: 92.6739 cm^3
• Polarizability: 36.165768 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.73
• LOG S: -5.47
• Solubility (Water): 9.60e-04 g/l

DETAILS

DrugBank - DB01616

• Drug Groups: approved
• Description: 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. It is 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 is formulated as the citrate salt (5982-87-6).
• 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.
• Pharmacology: 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).
• Toxicity: Can produce hypotension and atropine-like toxic effects. Fatality has occurred following overdose with very high doses.
• Affected Organisms: Humans and other mammals
• Biotransformation: Rapidly converted to its primary active metabolite, which is then further converted to two secondary metabolites.
• Half Life: The plasma half-life averages 0.8 hours for alverine and 5.7 hours for the active primary metabolite.
• Elimination: High renal clearance of all metabolites indicating that they are eliminated by active renal secretion.
• 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] ; 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. Epub 2009 Dec 10. [Pubmed] ; 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] ; "Spasmonal Package Insert":http://www.medicines.org.uk/EMC/medicine/24562/SPC/
• External Links: Wikipedia

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
• 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. Epub 2009 Dec 10. Pubmed
• 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
• Spasmonal Package Insert
• "Spasmonal Package Insert":http://www.medicines.org.uk/EMC/medicine/24562/SPC/