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

• ChemBase ID: 4395
• Molecular Formular: C12H12N2O2S
• Molecular Mass: 248.30088
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1H-imidazol-2-one
• IUPAC Traditional name: 4-methyl-5-[4-(methylsulfanyl)benzoyl]-1,3-dihydroimidazol-2-one; enoximone
• Brand Name: Perfan
• Synonyms: enoximone; Enoximone; 1,3-Dihydro-4-methyl-5-(4-methylthiobenzoyl)-2H-imidazol-2-one; Enoximone

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.681237
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.8442538
• LogD (pH = 7.4): 1.8421843
• Log P: 1.8442802
• Molar Refractivity: 70.045 cm^3
• Polarizability: 25.852839 Å^3
• Polar Surface Area: 58.2 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.97
• LOG S: -3.56
• Solubility (Water): 6.82e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble28 mg/mL
• Apperance: light yellow solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Pharmacology Properties

• Gene Information: human ... PDE3A(5139), PDE3B(5140)

Product Information

• Empirical Formula (Hill Notation): C12H12N2O2S

DETAILS

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.

REFERENCES

• 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