4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1H-imidazol-2-one

• ChemBase编号: 4395
• 分子式: C12H12N2O2S
• 平均质量: 248.30088
• 单一同位素质量: 248.06194863
• SMILES: S(c1ccc(C(=O)c2[nH]c(=O)[nH]c2C)cc1)C
• Canonical SMILES: CSc1ccc(cc1)C(=O)c1[nH]c(=O)[nH]c1C
• InChI: InChI=1S/C12H12N2O2S/c1-7-10(14-12(16)13-7)11(15)8-3-5-9(17-2)6-4-8/h3-6H,1-2H3,(H2,13,14,16)
• InChIKey: ZJKNESGOIKRXQY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1H-imidazol-2-one
• IUPAC传统名: 4-methyl-5-[4-(methylsulfanyl)benzoyl]-1,3-dihydroimidazol-2-one; enoximone
• 商标名: Perfan
• 别名: enoximone; Enoximone; 1,3-Dihydro-4-methyl-5-(4-methylthiobenzoyl)-2H-imidazol-2-one; Enoximone

登记号

• CAS号: 77671-31-9
• MDL号: MFCD00867130
• PubChem SID: 24278408; 160967827; 46505575
• PubChem CID: 53708

理论计算性质

JChem

• Acid pKa: 9.681237
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 1.8442538
• LogD (pH = 7.4): 1.8421843
• Log P: 1.8442802
• 摩尔折射率: 70.045 cm^3
• 极化性: 25.852839 Å^3
• 极化表面积: 58.2 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.97
• LOG S: -3.56
• 溶解度: 6.82e-02 g/l

分子性质

理化性质

• 溶解度: DMSO: soluble28 mg/mL
• 外观: light yellow solid

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

药理学性质

• 相关基因信息: human ... PDE3A(5139), PDE3B(5140)

产品相关信息

• Empirical Formula (Hill Notation): C12H12N2O2S

详细说明

DrugBank - DB04880

• Drug Groups: approved; investigational
• Description: Enoximone is a selective phosphodiesterase inhibitor with vasodilating and positive inotropic activity that does not cause changes in myocardial oxygen consumption. It is used in patients with congestive heart failure. Trials were halted in the U.S., but the drug is used in various countries.
• Indication: For the treatment of congestive heart failure.
• Pharmacology: Enoximone is a phosphodiesterase inhibitor (type III) that increases the force of contraction of the heart and dilates blood vessels. In June 2005, Myogen announced that they were discontinuing development of enoximone due to negative results. The drug is approved for use in the UK.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic oxidation
• Absorption: Bioavailabvility is 50% following oral administration.
• Half Life: 4-10 hours
• Protein Binding: 85%
• References: Sandroni C, Cavallaro F, Caricato A, Scapigliati A, Fenici P, Antonelli M: Enoximone in cardiac arrest caused by propranolol: two case reports. Acta Anaesthesiol Scand. 2006 Jul;50(6):759-61. [Pubmed] ; van der Maaten JM, de Vries AJ, Rietman GW, Gallandat Huet RC, De Hert SG: Effects of preemptive enoximone on left ventricular diastolic function after valve replacement for aortic stenosis. J Cardiothorac Vasc Anesth. 2007 Jun;21(3):357-66. Epub 2006 May 4. [Pubmed] ; Schauvliege S, Van den Eede A, Duchateau L, Gasthuys F: Cardiovascular effects of enoximone in isoflurane anaesthetized ponies. Vet Anaesth Analg. 2007 Aug 13;. [Pubmed] ; Boldt J, Suttner S: Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone. Expert Opin Pharmacother. 2007 Sep;8(13):2135-47. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - E1279

Biochem/physiol Actions
Selective phosphodiesterase III (PDE3) inhibitor. Prevents the degradation of cAMP by PDE. Increased cAMP results in enhanced contractility of the heart.

参考文献

• Schauvliege S, Van den Eede A, Duchateau L, Gasthuys F: Cardiovascular effects of enoximone in isoflurane anaesthetized ponies. Vet Anaesth Analg. 2007 Aug 13;. Pubmed
• Boldt J, Suttner S: Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone. Expert Opin Pharmacother. 2007 Sep;8(13):2135-47. Pubmed
• Sandroni C, Cavallaro F, Caricato A, Scapigliati A, Fenici P, Antonelli M: Enoximone in cardiac arrest caused by propranolol: two case reports. Acta Anaesthesiol Scand. 2006 Jul;50(6):759-61. Pubmed
• van der Maaten JM, de Vries AJ, Rietman GW, Gallandat Huet RC, De Hert SG: Effects of preemptive enoximone on left ventricular diastolic function after valve replacement for aortic stenosis. J Cardiothorac Vasc Anesth. 2007 Jun;21(3):357-66. Epub 2006 May 4. Pubmed