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Synopsis

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Chemistry

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Also known as: 77671-31-9, Perfan, Fenoximone, Mdl-17043, Mdl 17,043, 4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one

Molecular Formula

C₁₂H₁₂N₂O₂S

Molecular Weight

248.30 g/mol

InChI Key

ZJKNESGOIKRXQY-UHFFFAOYSA-N

FDA UNII

C7Z4ITI7L7

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.

1 2D Structure

Enoximone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one

2.1.2 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)

2.1.3 InChI Key

ZJKNESGOIKRXQY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(NC(=O)N1)C(=O)C2=CC=C(C=C2)SC

2.2 Other Identifiers

2.2.1 UNII

C7Z4ITI7L7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fenoximone

2. Mdl 17,043

3. Mdl 17043

4. Mdl 19,438

5. Mdl 19438

6. Mdl-17,043

7. Mdl-17043

8. Mdl-19,438

9. Mdl17,043

10. Mdl17043

11. Mdl19,438

12. Perfan

2.3.2 Depositor-Supplied Synonyms

1. 77671-31-9

2. Perfan

3. Fenoximone

4. Mdl-17043

5. Mdl 17,043

6. 4-methyl-5-(4-methylsulfanylbenzoyl)-1,3-dihydroimidazol-2-one

7. 4-methyl-5-(p-(methylthio)benzoyl)-4-imidazolin-2-one

8. Rmi-17043

9. 2h-imidazol-2-one, 1,3-dihydro-4-methyl-5-(4-(methylthio)benzoyl)-

10. C7z4iti7l7

11. Chembl249856

12. Enoximonum [latin]

13. Ncgc00015400-02

14. Enoximona [spanish]

15. Enoximona

16. Enoximonum

17. 1,3-dihydro-4-methyl-5-[4-(methylthio)benzoyl]-2h-imidazol-2-one

18. 1,3-dihydro-4-methyl-5-[4-methylthiobenzoyl]-2h-imidazol-2-one

19. Dsstox_cid_25147

20. Dsstox_rid_80702

21. Dsstox_gsid_45147

22. Perfane

23. 2h-imidazol-2-one, 1,3-dihydro-4-methyl-5-[4-(methylthio)benzoyl]-

24. Smr000857318

25. Mdl-17,043

26. Cas-77671-31-9

27. Perfan (tn)

28. Enoximone (usan/inn)

29. Unii-c7z4iti7l7

30. Enoximone [usan:inn:ban]

31. Enoximone, Solid

32. Enoximone [inn]

33. Enoximone [jan]

34. Enoximone [mi]

35. Enoximone [usan]

36. Lopac-e-1279

37. Enoximone [mart.]

38. E 1279

39. Enoximone [who-dd]

40. Lopac0_000410

41. Schembl44049

42. Mls001335963

43. Mls001335964

44. Mls002172494

45. Gtpl9063

46. Schembl5702510

47. Dtxsid8045147

48. Chebi:135010

49. Hms2234c20

50. Hms3261a22

51. Hms3369o01

52. Bcp04265

53. Ex-a3632

54. Hy-b1639

55. Zinc9225358

56. Tox21_110137

57. Tox21_500410

58. Bdbm50241379

59. Akos005145769

60. Tox21_110137_1

61. Ac-3396

62. Ccg-204503

63. Db04880

64. Lp00410

65. Sdccgsbi-0050396.p002

66. Ncgc00015400-01

67. Ncgc00015400-03

68. Ncgc00015400-04

69. Ncgc00015400-05

70. Ncgc00015400-10

71. Ncgc00093835-01

72. Ncgc00093835-02

73. Ncgc00261095-01

74. As-81876

75. Db-056240

76. B6833

77. Cs-0013589

78. E1370

79. Eu-0100410

80. Ft-0630855

81. D04004

82. 671e319

83. A848234

84. Sr-01000075850

85. Q5379471

86. Sr-01000075850-1

87. 4-methyl-5-(4-(methylthio)benzoyl)-1h-imidazol-2(3h)-one

88. 5-methyl-4-(4-(methylthio)benzoyl)-1h-imidazol-2(3h)-one

89. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one

90. 4-methyl-5-[4-(methylsulfanyl)benzoyl]-1,3-dihydro-2h-imidazol-2-one

91. 4-methyl-5-[4-(methylsulfanyl)benzoyl]-2,3-dihydro-1h-imidazol-2-one

92. (enoximone)4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one

93. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one (enoximone)

94. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one(enoximone)

95. 4-methyl-5-(4-methylsulfanyl-benzoyl)-1,3-dihydro-imidazol-2-one(fenoximone, Mdl-17043)

96. 4-methyl-5-{[4-(methylsulfanyl)phenyl]carbonyl}-2,3-dihydro-1h-imidazol-2-one

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₂N₂O₂S
Molecular Weight	248.30 g/mol
XLogP3	1.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	248.06194880 g/mol
Monoisotopic Mass	248.06194880 g/mol
Topological Polar Surface Area	83.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	371
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of congestive heart failure.

5 Pharmacology and Biochemistry

5.1 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.

5.2 MeSH Pharmacological Classification

Cardiotonic Agents

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)

Phosphodiesterase 3 Inhibitors

Compounds that specifically inhibit PHOSPHODIESTERASE 3. (See all compounds classified as Phosphodiesterase 3 Inhibitors.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.3 ATC Code

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CE - Phosphodiesterase inhibitors

C01CE03 - Enoximone

5.4 Absorption, Distribution and Excretion

Absorption

Bioavailabvility is 50% following oral administration.

5.5 Metabolism/Metabolites

Hepatic oxidation

5.6 Biological Half-Life

4-10 hours

5.7 Mechanism of Action

Further research is required to determine accurately the mechanism of action of drugs with phosphodiesterase inhibitory activity, however, inhibition of PDE3 inhibits degredation of cGMP. This allows for increased NO release and vascular relaxation.

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