ethylbis(3-phenylpropyl)amine

• ChemBase编号: 1393
• 分子式: C20H27N
• 平均质量: 281.43508
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: ethylbis(3-phenylpropyl)amine
• IUPAC传统名: alverine
• 商标名: Antispasmin; Dipropylin; Dipropyline; Gamatran citrate; Profenil; Sestron; Spacolin; Spasmaverine
• 别名: 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

登记号

• CAS号: 150-59-4
• PubChem SID: 46506981; 160964853
• PubChem CID: 3678
• CHEBI ID: 518413
• ATC码: A03AX08
• CHEMBL: 253371
• Chemspider ID: 3550
• DrugBank ID: DB01616
• KEGG ID: D07440
• 美国药典/FDA物质标识码: 46TIR1560O
• 维基百科标题: Alverine

理论计算性质

JChem

• 质子受体: 1
• 质子供体: 0
• LogD (pH = 5.5): 1.976472
• LogD (pH = 7.4): 2.54984
• Log P: 5.4623833
• 摩尔折射率: 92.6739 cm^3
• 极化性: 36.165768 Å^3
• 极化表面积: 3.24 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 5.73
• LOG S: -5.47
• 溶解度: 9.60e-04 g/l

详细说明

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

参考文献

• 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/