Identification

Name
Udenafil
Accession Number
DB06267
Type
Small Molecule
Groups
Approved, Investigational
Description

Udenafil is a new phosphodiesterase type 5 (PDE5) inhibitor used to treat erectile dysfunction (ED). It has been approved in South Korea and will be marketed under the brand name Zydena. It is not yet approved for use in the U.S., E.U., or Canada.

Structure
Thumb
Synonyms
  • DA-8159
  • Udenafil
International/Other Brands
Zydena
Categories
UNII
L5IB4XLY36
CAS number
268203-93-6
Weight
Average: 516.656
Monoisotopic: 516.25187436
Chemical Formula
C25H36N6O4S
InChI Key
IYFNEFQTYQPVOC-UHFFFAOYSA-N
InChI
InChI=1S/C25H36N6O4S/c1-5-8-20-22-23(31(4)29-20)25(32)28-24(27-22)19-16-18(10-11-21(19)35-15-6-2)36(33,34)26-13-12-17-9-7-14-30(17)3/h10-11,16-17,26H,5-9,12-15H2,1-4H3,(H,27,28,32)
IUPAC Name
3-{1-methyl-7-oxo-3-propyl-1H,4H,7H-pyrazolo[4,3-d]pyrimidin-5-yl}-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzene-1-sulfonamide
SMILES
CCCOC1=C(C=C(C=C1)S(=O)(=O)NCCC1CCCN1C)C1=NC(=O)C2=C(N1)C(CCC)=NN2C

Pharmacology

Indication

Investigated for use/treatment in erectile dysfunction and hypertension.

Structured Indications
Not Available
Pharmacodynamics

Udenafil is a potent selective phosphodiesterase type 5 (PDE5) inhibitor.

Mechanism of action

Udenafil inhibits the cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cGMP in smooth muscle cells. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. The inhibition of phosphodiesterase type 5 (PDE5) by udenafil enhances erectile function by increasing the amount of cGMP.

TargetActionsOrganism
AcGMP-specific 3',5'-cyclic phosphodiesterase
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic. Metabolized by CYP3A4 and CYP3A5.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcebutololUdenafil may increase the antihypertensive activities of Acebutolol.Approved
AlfuzosinUdenafil may increase the hypotensive activities of Alfuzosin.Approved, Investigational
AliskirenUdenafil may increase the antihypertensive activities of Aliskiren.Approved, Investigational
AlprenololUdenafil may increase the antihypertensive activities of Alprenolol.Approved, Withdrawn
AlprostadilThe risk or severity of adverse effects can be increased when Udenafil is combined with Alprostadil.Approved, Investigational
AmbrisentanUdenafil may increase the antihypertensive activities of Ambrisentan.Approved, Investigational
AmiodaroneThe metabolism of Udenafil can be decreased when combined with Amiodarone.Approved, Investigational
AmlodipineUdenafil may increase the antihypertensive activities of Amlodipine.Approved
Amyl NitriteUdenafil may increase the vasodilatory activities of Amyl Nitrite.Approved
AprepitantThe serum concentration of Udenafil can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Udenafil can be decreased when combined with Atazanavir.Approved, Investigational
AtenololUdenafil may increase the antihypertensive activities of Atenolol.Approved
AtomoxetineThe metabolism of Udenafil can be decreased when combined with Atomoxetine.Approved
BenazeprilUdenafil may increase the antihypertensive activities of Benazepril.Approved, Investigational
BendroflumethiazideUdenafil may increase the antihypertensive activities of Bendroflumethiazide.Approved
BepridilUdenafil may increase the antihypertensive activities of Bepridil.Approved, Withdrawn
BetaxololUdenafil may increase the antihypertensive activities of Betaxolol.Approved
BethanidineUdenafil may increase the antihypertensive activities of Bethanidine.Approved
BietaserpineUdenafil may increase the antihypertensive activities of Bietaserpine.Experimental
BimatoprostUdenafil may increase the antihypertensive activities of Bimatoprost.Approved, Investigational
BisoprololUdenafil may increase the antihypertensive activities of Bisoprolol.Approved
BoceprevirThe metabolism of Udenafil can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Udenafil can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Udenafil can be decreased when it is combined with Bosentan.Approved, Investigational
BQ-123Udenafil may increase the antihypertensive activities of BQ-123.Investigational
BretyliumUdenafil may increase the antihypertensive activities of Bretylium.Approved
BrimonidineUdenafil may increase the antihypertensive activities of Brimonidine.Approved
BucindololUdenafil may increase the hypotensive activities of Bucindolol.Investigational
BunazosinUdenafil may increase the hypotensive activities of Bunazosin.Investigational
BupranololUdenafil may increase the antihypertensive activities of Bupranolol.Approved
CadralazineUdenafil may increase the antihypertensive activities of Cadralazine.Experimental
CafedrineUdenafil may increase the antihypertensive activities of Cafedrine.Investigational
Candesartan cilexetilUdenafil may increase the antihypertensive activities of Candesartan.Approved
CandoxatrilUdenafil may increase the antihypertensive activities of Candoxatril.Experimental
CaptoprilUdenafil may increase the antihypertensive activities of Captopril.Approved
CarbamazepineThe metabolism of Udenafil can be increased when combined with Carbamazepine.Approved, Investigational
CarteololUdenafil may increase the antihypertensive activities of Carteolol.Approved
CarvedilolUdenafil may increase the hypotensive activities of Carvedilol.Approved, Investigational
CeliprololUdenafil may increase the antihypertensive activities of Celiprolol.Approved, Investigational
CeritinibThe serum concentration of Udenafil can be increased when it is combined with Ceritinib.Approved
ChlorothiazideUdenafil may increase the antihypertensive activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidoneUdenafil may increase the antihypertensive activities of Chlorthalidone.Approved
CicletanineUdenafil may increase the antihypertensive activities of Cicletanine.Investigational
CilazaprilUdenafil may increase the antihypertensive activities of Cilazapril.Approved
ClarithromycinThe metabolism of Udenafil can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Udenafil can be decreased when combined with Clemastine.Approved
ClonidineUdenafil may increase the antihypertensive activities of Clonidine.Approved
CloranololUdenafil may increase the antihypertensive activities of Cloranolol.Experimental
ClotrimazoleThe metabolism of Udenafil can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Udenafil can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Udenafil can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Udenafil can be decreased when combined with Crizotinib.Approved
CryptenamineUdenafil may increase the antihypertensive activities of Cryptenamine.Approved
CyclopenthiazideUdenafil may increase the antihypertensive activities of Cyclopenthiazide.Experimental
CyclosporineThe metabolism of Udenafil can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CyclothiazideUdenafil may increase the antihypertensive activities of Cyclothiazide.Approved
DabrafenibThe serum concentration of Udenafil can be decreased when it is combined with Dabrafenib.Approved
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Udenafil.Investigational
DarunavirThe metabolism of Udenafil can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Udenafil can be increased when it is combined with Dasatinib.Approved, Investigational
DebrisoquinUdenafil may increase the antihypertensive activities of Debrisoquin.Approved, Investigational
DeferasiroxThe serum concentration of Udenafil can be decreased when it is combined with Deferasirox.Approved, Investigational
DelaprilUdenafil may increase the antihypertensive activities of Delapril.Experimental
DelavirdineThe metabolism of Udenafil can be decreased when combined with Delavirdine.Approved
DeserpidineUdenafil may increase the antihypertensive activities of Deserpidine.Approved
DiazoxideUdenafil may increase the antihypertensive activities of Diazoxide.Approved
diethylnorspermineUdenafil may increase the antihypertensive activities of diethylnorspermine.Investigational
DihydralazineUdenafil may increase the antihypertensive activities of Dihydralazine.Investigational
DihydroergotamineThe metabolism of Udenafil can be decreased when combined with Dihydroergotamine.Approved
DiltiazemUdenafil may increase the antihypertensive activities of Diltiazem.Approved
DorzolamideUdenafil may increase the antihypertensive activities of Dorzolamide.Approved
DoxazosinUdenafil may increase the hypotensive activities of Doxazosin.Approved
DoxycyclineThe metabolism of Udenafil can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Udenafil can be decreased when combined with Dronedarone.Approved
EfonidipineUdenafil may increase the antihypertensive activities of Efonidipine.Approved
EnalaprilUdenafil may increase the antihypertensive activities of Enalapril.Approved, Vet Approved
EnalaprilatUdenafil may increase the antihypertensive activities of Enalaprilat.Approved
EndralazineUdenafil may increase the antihypertensive activities of Endralazine.Experimental
EnzalutamideThe serum concentration of Udenafil can be decreased when it is combined with Enzalutamide.Approved
EpanololUdenafil may increase the antihypertensive activities of Epanolol.Experimental
EpoprostenolUdenafil may increase the antihypertensive activities of Epoprostenol.Approved
EprosartanUdenafil may increase the antihypertensive activities of Eprosartan.Approved
Erythrityl TetranitrateUdenafil may increase the vasodilatory activities of Erythrityl Tetranitrate.Approved, Investigational
ErythromycinThe metabolism of Udenafil can be decreased when combined with Erythromycin.Approved, Vet Approved
EthanolEthanol may increase the hypotensive activities of Udenafil.Approved
EtravirineThe serum concentration of Udenafil can be decreased when it is combined with Etravirine.Approved
FelodipineUdenafil may increase the antihypertensive activities of Felodipine.Approved, Investigational
FenoldopamUdenafil may increase the antihypertensive activities of Fenoldopam.Approved
Ferulic acidUdenafil may increase the antihypertensive activities of Ferulic acid.Experimental
FluconazoleThe metabolism of Udenafil can be decreased when combined with Fluconazole.Approved
FluvoxamineThe metabolism of Udenafil can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Udenafil can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Udenafil can be increased when it is combined with Fosaprepitant.Approved
FosinoprilUdenafil may increase the antihypertensive activities of Fosinopril.Approved
FosphenytoinThe metabolism of Udenafil can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Udenafil can be increased when it is combined with Fusidic Acid.Approved
GuanabenzUdenafil may increase the antihypertensive activities of Guanabenz.Approved, Investigational
GuanadrelUdenafil may increase the antihypertensive activities of Guanadrel.Approved
GuanazodineUdenafil may increase the antihypertensive activities of Guanazodine.Experimental
GuanethidineUdenafil may increase the antihypertensive activities of Guanethidine.Approved
GuanfacineUdenafil may increase the antihypertensive activities of Guanfacine.Approved, Investigational
GuanoclorUdenafil may increase the antihypertensive activities of Guanoclor.Experimental
GuanoxabenzUdenafil may increase the antihypertensive activities of Guanoxabenz.Experimental
GuanoxanUdenafil may increase the antihypertensive activities of Guanoxan.Experimental
HexamethoniumUdenafil may increase the antihypertensive activities of Hexamethonium.Experimental
HydralazineUdenafil may increase the antihypertensive activities of Hydralazine.Approved
HydrochlorothiazideUdenafil may increase the antihypertensive activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideUdenafil may increase the antihypertensive activities of Hydroflumethiazide.Approved, Investigational
IdelalisibThe serum concentration of Udenafil can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Udenafil can be decreased when combined with Imatinib.Approved
ImidaprilUdenafil may increase the antihypertensive activities of Imidapril.Investigational
IndapamideUdenafil may increase the antihypertensive activities of Indapamide.Approved
IndenololUdenafil may increase the antihypertensive activities of Indenolol.Withdrawn
IndinavirThe metabolism of Udenafil can be decreased when combined with Indinavir.Approved
IndoraminUdenafil may increase the hypotensive activities of Indoramin.Withdrawn
IrbesartanUdenafil may increase the antihypertensive activities of Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Udenafil can be decreased when combined with Isavuconazonium.Approved, Investigational
Isosorbide DinitrateUdenafil may increase the vasodilatory activities of Isosorbide Dinitrate.Approved
Isosorbide MononitrateUdenafil may increase the vasodilatory activities of Isosorbide Mononitrate.Approved
IsradipineUdenafil may increase the antihypertensive activities of Isradipine.Approved
ItraconazoleThe metabolism of Udenafil can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Udenafil can be increased when it is combined with Ivacaftor.Approved
KetanserinUdenafil may increase the antihypertensive activities of Ketanserin.Investigational
KetoconazoleThe metabolism of Udenafil can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolUdenafil may increase the hypotensive activities of Labetalol.Approved
LacidipineUdenafil may increase the antihypertensive activities of Lacidipine.Approved, Investigational
LatanoprostUdenafil may increase the antihypertensive activities of Latanoprost.Approved, Investigational
LercanidipineUdenafil may increase the antihypertensive activities of Lercanidipine.Approved, Investigational
LinsidomineUdenafil may increase the antihypertensive activities of Linsidomine.Experimental
LisinoprilUdenafil may increase the antihypertensive activities of Lisinopril.Approved, Investigational
LofexidineUdenafil may increase the antihypertensive activities of Lofexidine.Approved, Investigational
LopinavirThe metabolism of Udenafil can be decreased when combined with Lopinavir.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Udenafil.Approved
LosartanUdenafil may increase the antihypertensive activities of Losartan.Approved
LovastatinThe metabolism of Udenafil can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Udenafil can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Udenafil can be increased when combined with Lumacaftor.Approved
MacitentanUdenafil may increase the antihypertensive activities of Macitentan.Approved
ManidipineUdenafil may increase the antihypertensive activities of Manidipine.Approved, Investigational
MecamylamineUdenafil may increase the antihypertensive activities of Mecamylamine.Approved
MethoserpidineUdenafil may increase the antihypertensive activities of Methoserpidine.Experimental
MethyldopaUdenafil may increase the antihypertensive activities of Methyldopa.Approved
Methylpropylpropanediol dinitrateUdenafil may increase the vasodilatory activities of Methylpropylpropanediol dinitrate.Experimental
MetipranololUdenafil may increase the antihypertensive activities of Metipranolol.Approved
MetolazoneUdenafil may increase the antihypertensive activities of Metolazone.Approved
MetoprololUdenafil may increase the antihypertensive activities of Metoprolol.Approved, Investigational
MetyrosineUdenafil may increase the antihypertensive activities of Metyrosine.Approved
MibefradilUdenafil may increase the antihypertensive activities of Mibefradil.Investigational, Withdrawn
MifepristoneThe serum concentration of Udenafil can be increased when it is combined with Mifepristone.Approved, Investigational
MinoxidilUdenafil may increase the antihypertensive activities of Minoxidil.Approved
MirodenafilThe risk or severity of adverse effects can be increased when Udenafil is combined with Mirodenafil.Investigational
MitotaneThe serum concentration of Udenafil can be decreased when it is combined with Mitotane.Approved
MoexiprilUdenafil may increase the antihypertensive activities of Moexipril.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Udenafil.Approved, Investigational
MoxonidineUdenafil may increase the antihypertensive activities of Moxonidine.Approved, Investigational
MuzolimineUdenafil may increase the antihypertensive activities of Muzolimine.Experimental
NadololUdenafil may increase the antihypertensive activities of Nadolol.Approved
NaftopidilUdenafil may increase the antihypertensive activities of Naftopidil.Investigational
NebivololUdenafil may increase the antihypertensive activities of Nebivolol.Approved, Investigational
NefazodoneThe metabolism of Udenafil can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Udenafil can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Udenafil can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Udenafil can be increased when combined with Nevirapine.Approved
NicardipineUdenafil may increase the antihypertensive activities of Nicardipine.Approved
NicorandilUdenafil may increase the antihypertensive activities of Nicorandil.Approved, Investigational
NiguldipineUdenafil may increase the antihypertensive activities of Niguldipine.Experimental
NilotinibThe metabolism of Udenafil can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipineUdenafil may increase the antihypertensive activities of Nilvadipine.Approved, Investigational
NimodipineUdenafil may increase the antihypertensive activities of Nimodipine.Approved
NisoldipineUdenafil may increase the antihypertensive activities of Nisoldipine.Approved
NitrendipineUdenafil may increase the antihypertensive activities of Nitrendipine.Approved, Investigational
NitroglycerinUdenafil may increase the vasodilatory activities of Nitroglycerin.Approved, Investigational
NitroprussideUdenafil may increase the antihypertensive activities of Nitroprusside.Approved
OlaparibThe metabolism of Udenafil can be decreased when combined with Olaparib.Approved
OlmesartanUdenafil may increase the antihypertensive activities of Olmesartan.Approved, Investigational
OmapatrilatUdenafil may increase the antihypertensive activities of Omapatrilat.Investigational
OsimertinibThe serum concentration of Udenafil can be increased when it is combined with Osimertinib.Approved
OxprenololUdenafil may increase the antihypertensive activities of Oxprenolol.Approved
PalbociclibThe serum concentration of Udenafil can be increased when it is combined with Palbociclib.Approved
PargylineUdenafil may increase the antihypertensive activities of Pargyline.Approved
PenbutololUdenafil may increase the antihypertensive activities of Penbutolol.Approved, Investigational
Pentaerythritol TetranitrateUdenafil may increase the vasodilatory activities of Pentaerythritol Tetranitrate.Approved
PentobarbitalThe metabolism of Udenafil can be increased when combined with Pentobarbital.Approved, Vet Approved
PentoliniumUdenafil may increase the antihypertensive activities of Pentolinium.Approved
PerindoprilUdenafil may increase the antihypertensive activities of Perindopril.Approved
PhenobarbitalThe metabolism of Udenafil can be increased when combined with Phenobarbital.Approved
PhenoxybenzamineUdenafil may increase the antihypertensive activities of Phenoxybenzamine.Approved
PhentolamineUdenafil may increase the antihypertensive activities of Phentolamine.Approved
PhenytoinThe metabolism of Udenafil can be increased when combined with Phenytoin.Approved, Vet Approved
PinacidilUdenafil may increase the antihypertensive activities of Pinacidil.Withdrawn
PindololUdenafil may increase the antihypertensive activities of Pindolol.Approved
PolythiazideUdenafil may increase the antihypertensive activities of Polythiazide.Approved
PosaconazoleThe metabolism of Udenafil can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrazosinUdenafil may increase the hypotensive activities of Prazosin.Approved
PrimidoneThe metabolism of Udenafil can be increased when combined with Primidone.Approved, Vet Approved
PropatylnitrateUdenafil may increase the vasodilatory activities of Propatylnitrate.Experimental, Investigational
PropranololUdenafil may increase the antihypertensive activities of Propranolol.Approved, Investigational
QuinaprilUdenafil may increase the antihypertensive activities of Quinapril.Approved, Investigational
RamiprilUdenafil may increase the antihypertensive activities of Ramipril.Approved
RanolazineThe metabolism of Udenafil can be decreased when combined with Ranolazine.Approved, Investigational
RemikirenUdenafil may increase the antihypertensive activities of Remikiren.Approved
RescinnamineUdenafil may increase the antihypertensive activities of Rescinnamine.Approved
ReserpineUdenafil may increase the antihypertensive activities of Reserpine.Approved, Investigational
RifabutinThe metabolism of Udenafil can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Udenafil can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Udenafil can be increased when combined with Rifapentine.Approved
RilmenidineUdenafil may increase the antihypertensive activities of Rilmenidine.Investigational
RiociguatUdenafil may increase the hypotensive activities of Riociguat.Approved
RitonavirThe metabolism of Udenafil can be decreased when combined with Ritonavir.Approved, Investigational
SaprisartanUdenafil may increase the antihypertensive activities of Saprisartan.Experimental
SapropterinSapropterin may increase the hypotensive activities of Udenafil.Approved, Investigational
SaquinavirThe metabolism of Udenafil can be decreased when combined with Saquinavir.Approved, Investigational
SelexipagUdenafil may increase the antihypertensive activities of Selexipag.Approved
SildenafilThe metabolism of Udenafil can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinUdenafil may increase the hypotensive activities of Silodosin.Approved
SiltuximabThe serum concentration of Udenafil can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Udenafil can be increased when it is combined with Simeprevir.Approved
SitaxentanUdenafil may increase the antihypertensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SpiraprilUdenafil may increase the antihypertensive activities of Spirapril.Approved
St. John's WortThe serum concentration of Udenafil can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Udenafil can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Udenafil can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TadalafilThe risk or severity of adverse effects can be increased when Tadalafil is combined with Udenafil.Approved, Investigational
TalinololUdenafil may increase the antihypertensive activities of Talinolol.Investigational
TamsulosinUdenafil may increase the hypotensive activities of Tamsulosin.Approved, Investigational
TelaprevirThe metabolism of Udenafil can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Udenafil can be decreased when combined with Telithromycin.Approved
TelmisartanUdenafil may increase the antihypertensive activities of Telmisartan.Approved, Investigational
TemocaprilUdenafil may increase the antihypertensive activities of Temocapril.Experimental, Investigational
TenitramineUdenafil may increase the vasodilatory activities of Tenitramine.Experimental
TerazosinUdenafil may increase the hypotensive activities of Terazosin.Approved
TerlipressinUdenafil may increase the antihypertensive activities of Terlipressin.Approved, Investigational
TetrahydropalmatineUdenafil may increase the antihypertensive activities of Tetrahydropalmatine.Investigational
TheodrenalineUdenafil may increase the antihypertensive activities of Theodrenaline.Investigational
TiboloneUdenafil may increase the antihypertensive activities of Tibolone.Approved, Investigational
TiclopidineThe metabolism of Udenafil can be decreased when combined with Ticlopidine.Approved
TicrynafenUdenafil may increase the antihypertensive activities of Ticrynafen.Withdrawn
TimololUdenafil may increase the antihypertensive activities of Timolol.Approved
TocilizumabThe serum concentration of Udenafil can be decreased when it is combined with Tocilizumab.Approved
TolazolineUdenafil may increase the antihypertensive activities of Tolazoline.Approved, Vet Approved
TolonidineUdenafil may increase the antihypertensive activities of Tolonidine.Experimental
TorasemideUdenafil may increase the antihypertensive activities of Torasemide.Approved
TrandolaprilUdenafil may increase the antihypertensive activities of Trandolapril.Approved
TravoprostUdenafil may increase the antihypertensive activities of Travoprost.Approved
TreprostinilUdenafil may increase the antihypertensive activities of Treprostinil.Approved, Investigational
TrichlormethiazideUdenafil may increase the antihypertensive activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinUdenafil may increase the hypotensive activities of Trimazosin.Experimental
TrimethaphanUdenafil may increase the antihypertensive activities of Trimethaphan.Approved, Investigational
TrolnitrateUdenafil may increase the vasodilatory activities of Trolnitrate.Experimental
UnoprostoneUdenafil may increase the antihypertensive activities of Unoprostone.Approved
UrapidilUdenafil may increase the hypotensive activities of Urapidil.Investigational
ValsartanUdenafil may increase the antihypertensive activities of Valsartan.Approved, Investigational
VardenafilThe risk or severity of adverse effects can be increased when Vardenafil is combined with Udenafil.Approved
VenlafaxineThe metabolism of Udenafil can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Udenafil can be decreased when combined with Verapamil.Approved
VincamineUdenafil may increase the antihypertensive activities of Vincamine.Experimental
VinpocetineUdenafil may increase the antihypertensive activities of Vinpocetine.Investigational
VoriconazoleThe metabolism of Udenafil can be decreased when combined with Voriconazole.Approved, Investigational
XipamideUdenafil may increase the antihypertensive activities of Xipamide.Experimental
XylometazolineUdenafil may increase the antihypertensive activities of Xylometazoline.Approved
ZiprasidoneThe metabolism of Udenafil can be decreased when combined with Ziprasidone.Approved
ZofenoprilUdenafil may increase the antihypertensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Chan-Ho Lee, Chang-Yong Shin, Seul-Min Choi, Kyung-Koo Kang, Dong-Seong Kim, Byoung-Ok Ahn, Moo-Hi Yoo, "ACID ADDITION SALT OF UDENAFIL, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME." U.S. Patent US20110306762, issued December 15, 2011.

US20110306762
General References
  1. Ji HY, Shim HJ, Yoo M, Park ES, Lee HS: Transport of a new erectogenic udenafil in Caco-2 cells. Arch Pharm Res. 2007 Sep;30(9):1168-73. [PubMed:17958337]
  2. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836]
External Links
Human Metabolome Database
HMDB15628
KEGG Drug
D10027
PubChem Compound
6918523
PubChem Substance
99443240
ChemSpider
5293720
ChEBI
135926
ChEMBL
CHEMBL2103849
Therapeutic Targets Database
DAP000960
PharmGKB
PA164776753
Wikipedia
Udenafil
ATC Codes
G04BE11 — Udenafil

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableErectile Dysfunction (ED) / Phosphodiesterase 5 Inhibitor1
1CompletedNot AvailableErectile Dysfunction (ED) / Spermatogenesis1
1CompletedBasic ScienceGenetic Polymorphic CYP3A5 / Healthy Volunteers / Pharmacokinetics of Three PDE5Is1
1CompletedSupportive CareErectile Dysfunction (ED) / Healthy Volunteers1
1CompletedSupportive CareHepatic Impairment1
1CompletedSupportive CareImpaired Renal Function / Kidney Diseases / Urologic Diseases1
1Unknown StatusTreatmentHealthy Male Subjects1
1Unknown StatusTreatmentHealthy Volunteers1
1, 2CompletedTreatmentSingle Ventricle Heart Disease After Fontan Surgery1
2CompletedTreatmentErectile Dysfunction (ED)1
2CompletedTreatmentErectile Dysfunction (ED) / Rectal Carcinoma / Sigmoid Colon Cancer1
2CompletedTreatmentPulmonary Arterial Hypertension (PAH)1
2Unknown StatusTreatmentDementia, Vascular / Subcortical Vascular Dementia1
2WithdrawnTreatmentBenign Prostatic Hyperplasia (BPH) / Erectile Dysfunction (ED)1
2, 3CompletedTreatmentPulmonary Arterial Hypertension (PAH)1
3CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD) / Dyspnea / Pulmonary Hypertension (PH)1
3CompletedTreatmentErectile Dysfunction (ED)6
3Not Yet RecruitingTreatmentFunctional Single Ventricle Heart Disease1
3RecruitingTreatmentSingle Ventricle Heart Disease1
3TerminatedTreatmentHeart Failure With Reduced Ejection Fraction (HFrEF)1
3Unknown StatusTreatmentAlzheimer's Disease (AD)1
3Unknown StatusTreatmentDiastolic Heart Failure1
3Unknown StatusTreatmentMild Pulmonary Hypertension1
4CompletedSupportive CareRectal Carcinoma1
4Not Yet RecruitingTreatmentProstate Cancer With Radical Prostatectomy1
4Unknown StatusTreatmentMicrovascular Angina1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0798 mg/mLALOGPS
logP3.2ALOGPS
logP1.66ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)7.21ChemAxon
pKa (Strongest Basic)8.48ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area117.92 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity153.11 m3·mol-1ChemAxon
Polarizability56.34 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.8093
P-glycoprotein inhibitor IInhibitor0.6138
P-glycoprotein inhibitor IIInhibitor0.658
Renal organic cation transporterNon-inhibitor0.784
CYP450 2C9 substrateNon-substrate0.6694
CYP450 2D6 substrateSubstrate0.6391
CYP450 3A4 substrateSubstrate0.721
CYP450 1A2 substrateNon-inhibitor0.8355
CYP450 2C9 inhibitorInhibitor0.5391
CYP450 2D6 inhibitorNon-inhibitor0.8885
CYP450 2C19 inhibitorNon-inhibitor0.8588
CYP450 3A4 inhibitorInhibitor0.8863
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5793
Ames testNon AMES toxic0.5747
CarcinogenicityNon-carcinogens0.5502
BiodegradationNot ready biodegradable0.8961
Rat acute toxicity2.6102 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8455
hERG inhibition (predictor II)Inhibitor0.805
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Pyrazolopyrimidines / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Pyrimidones / N-alkylpyrrolidines / Organosulfonamides / Vinylogous amides / Aminosulfonyl compounds
show 7 more
Substituents
Benzenesulfonamide / Benzenesulfonyl group / Pyrazolopyrimidine / Phenoxy compound / Phenol ether / Alkyl aryl ether / Pyrimidone / Organosulfonic acid amide / N-alkylpyrrolidine / Pyrimidine
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:9714779, ...
Gene Name
PDE5A
Uniprot ID
O76074
Uniprot Name
cGMP-specific 3',5'-cyclic phosphodiesterase
Molecular Weight
99984.14 Da
References
  1. Gur S, Sikka SC, Hellstrom WJ: Novel phosphodiesterase-5 (PDE5) inhibitors in the alleviation of erectile dysfunction due to diabetes and ageing-induced oxidative stress. Expert Opin Investig Drugs. 2008 Jun;17(6):855-64. doi: 10.1517/13543784.17.6.855 . [PubMed:18491987]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  3. Ahn GJ, Chung HK, Lee CH, Kang KK, Ahn BO: Increased expression of the nitric oxide synthase gene and protein in corpus cavernosum by repeated dosing of udenafil in a rat model of chemical diabetogenesis. Asian J Androl. 2009 Jul;11(4):435-42. doi: 10.1038/aja.2009.27. Epub 2009 May 25. [PubMed:19465935]
  4. Zhao C, Kim SH, Lee SW, Jeon JH, Kang KK, Choi SB, Park JK: Activity of phosphodiesterase type 5 inhibitors in patients with lower urinary tract symptoms due to benign prostatic hyperplasia. BJU Int. 2011 Jun;107(12):1943-7. doi: 10.1111/j.1464-410X.2010.09759.x. Epub 2010 Nov 5. [PubMed:21054754]
  5. Kouvelas D, Goulas A, Papazisis G, Sardeli C, Pourzitaki C: PDE5 inhibitors: in vitro and in vivo pharmacological profile. Curr Pharm Des. 2009;15(30):3464-75. [PubMed:19860692]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Ji HY, Lee HW, Kim HH, Kim DS, Yoo M, Kim WB, Lee HS: Role of human cytochrome P450 3A4 in the metabolism of DA-8159, a new erectogenic. Xenobiotica. 2004 Nov-Dec;34(11-12):973-82. [PubMed:15801542]
  2. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Ku HY, Ahn HJ, Seo KA, Kim H, Oh M, Bae SK, Shin JG, Shon JH, Liu KH: The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil. Drug Metab Dispos. 2008 Jun;36(6):986-90. doi: 10.1124/dmd.107.020099. Epub 2008 Feb 28. [PubMed:18308836]

Drug created on March 19, 2008 10:20 / Updated on November 09, 2017 03:53