Enoximone

Enoximone
Systematic (IUPAC) name

4-methyl-5-{[4-(methylsulfanyl)phenyl]carbonyl}-2,3-dihydro-1H-imidazol-2-one
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous
Legal status
Legal status	UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	50% (oral)
Protein binding	85%
Metabolism	Hepatic oxidation
Biological half-life	4 to 10 hours
Excretion	Renal (60 to 70%)
Identifiers
CAS Number	77671-31-9^Y
ATC code	C01CE03 (WHO)
PubChem	CID 53708
DrugBank	DB04880^Y
ChemSpider	48492^Y
UNII	C7Z4ITI7L7^Y
KEGG	D04004^Y
ChEMBL	CHEMBL249856^Y
Chemical data
Formula	C₁₂H₁₂N₂O₂S
Molar mass	248.302 g/mol
SMILES O=C(/C1=C(/NC(=O)N1)C)c2ccc(SC)cc2
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)^Y Key:ZJKNESGOIKRXQY-UHFFFAOYSA-N^Y
Physical data
Melting point	255 to 258 °C (491 to 496 °F) (decomposes)
(verify)

Enoximone (INN, trade name Perfan) is an imidazole phosphodiesterase inhibitor. It is used in the treatment of congestive heart failure and is selective for phosphodiesterase 3.^[1]

Synthesis

^[2]

Prepn: BE 883856 (1980 to Richardson-Merrell); R. A. Schnettler et al., U.S. Patent 4,405,635 (1983 to Merrell-Dow)

References

↑ Boldt J, Suttner S (September 2007). "Combined use of ultra-short acting beta-blocker esmolol and intravenous phosphodiesterase 3 inhibitor enoximone". Expert Opin Pharmacother 8 (13): 2135–47. doi:10.1517/14656566.8.13.2135. PMID 17714066.
↑ Schnettler, Richard A.; Dage, Richard C.; Grisar, J. Martin (1982). "4-Aroyl-1,3-dihydro-2H-imidazol-2-ones, a new class of cardiotonic agents". Journal of Medicinal Chemistry 25 (12): 1477–1481. doi:10.1021/jm00354a017. ISSN 0022-2623.

PDE inhibitors

PDE1	MMPX SCH-51866 Vinpocetine

PDE2	BAY 60-7550 EHNA Oxindole PDP

PDE3	Adibendan Amrinone (inamrinone) Anagrelide Bucladesine Cilostamide Cilostazol Enoximone Imazodan KMUP-1 Meribendan Milrinone Olprinone Pimobendan Quazinone RPL-554 Siguazodan Tetomilast Tofimilast Trequinsin Vesnarinone

PDE4	AN2728 Apremilast Arofylline Atizoram Catramilast CC-1088 CDP-840 CGH-2466 Cilomilast Cipamfylline CP-80633 Crisaborole Denbutylline Drotaverine Etazolate Filaminast Glaucine HT-0712 ICI-63197 Indimilast Irsogladine Lavamilast Lirimilast Luteolin Mesembrenone Mesembrine Mesopram Oglemilast Piclamilast Revamilast Ro 20-1724 Roflumilast Rolipram Ronomilast RPL-554 RS-25344 YM-976

PDE5	Acetildenafil Aildenafil Avanafil Beminafil Benzamidenafil Dasantafil Icariin Gisadenafil Homosildenafil Lodenafil Mirodenafil MY-5445 Nitrosoprodenafil Sildenafil Sulfoaildenafil T-0156 Tadalafil Udenafil Vardenafil

PDE7	BRL-50481

PDE9	BAY 73-6691 PF-04447943

PDE10	Papaverine PF-2545920 TC-E 5005 Tofisopam

PDE11	BC11-38

Nonselective	Aminophylline Caffeine Choline theophyllinate CPX Dipyridamole Doxofylline Enprofylline Ibudilast IBMX Luteolin Paraxanthine Pentoxifylline Propentofylline SCH-51866 Theobromine Theophylline Zaprinast Zardaverine

Unknown/unsorted	Benafentrine Carbazeran Diazepam Diphylline Doxofylline DPCPX Furafylline Lisofylline MDL-12330A Moxaverine Oxagrelate Parogrelil Pentifylline Proxyphylline Pumafentrine Quercetin Tolafentrine Trapidil

Cardiac stimulants excluding cardiac glycosides (C01C)

Adrenergic and
dopaminergic agents

Adrenergic agonists

α	Metaraminol Phenylephrine Methoxamine Norfenefrine Oxedrine Midodrine Mephentermine

β	Dobutamine Arbutamine Isoprenaline Prenalterol

mixed	Amezinium metilsulfate Droxidopa Epinephrine # Norepinephrine Etilefrine

Dopamine agonists

Fenoldopam

Both

Unknown/ungrouped

Phosphodiesterase inhibitors (PDE3I)

Other cardiac stimulants

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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