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Details

Stereochemistry RACEMIC
Molecular Formula C25H36N6O4S
Molecular Weight 516.656
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UDENAFIL

SMILES

CCCOC1=CC=C(C=C1C2=NC(=O)C3=C(N2)C(CCC)=NN3C)S(=O)(=O)NCCC4CCCN4C

InChI

InChIKey=IYFNEFQTYQPVOC-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Udenafil is a new phosphodiesterase type 5 (PDE5) inhibitor used to treat erectile dysfunction. Udenafil inhibits the cyclic GMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of Cyclic GMP in the corpus cavernosum located around the penis. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. So the inhibition of phosphodiesterase type 5 (PDE5) by Udenafil enhances erectile function by increasing the amount of Cyclic GMP. Udenafil has proven to have high efficacy and a favorable safety profile for a broad spectrum of erectile dysfunction patients, which are comparable to those of other PDE5Is. Due to the clinical properties of relatively rapid onset and long duration of action, Udenafil may be a better option for erectile dysfunction treatment according to patient-specific sex-life patterns. Udenafil is as effective in the treatment of diabetes mellitus-associated erectile dysfunction as other PDE5Is. Recent data suggest that the concomitant use of anti-hypertensive drugs does not significantly affect the efficacy and safety profile. Also, due to its clinical properties, Udenafil can be a daily-dosing option for the treatment of erectile dysfunction, as suggested by its favorable efficacy and safety profile. Udenafil has been approved in South Korea and will be marketed under the brand name Zydena.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.25 nM [IC50]
PubMed

PubMed

TitleDatePubMed
DA-8159 reverses selective serotonin reuptake inhibitor-induced erectile dysfunction in rats.
2005 Jan
Transport of a new erectogenic udenafil in Caco-2 cells.
2007 Sep
The contributions of cytochromes P450 3A4 and 3A5 to the metabolism of the phosphodiesterase type 5 inhibitors sildenafil, udenafil, and vardenafil.
2008 Jun
Chronic administration of udenafil, a selective phosphodiesterase type 5 inhibitor, promotes erectile function recovery in an animal model of bilateral cavernous nerve crush injury.
2011 May
Patents
Name Type Language
UDENAFIL
DASH   INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
3-(1-METHYL-7-OXO-3-PROPOXY-4,7-DIHYDRO-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-N-(2-(1-METHYLPYRROLIDIN-2-YL)ETHYL)-4-PROPOXYBENZENESULFONAMIDE
Systematic Name English
BENZENESULFONAMIDE, 3-(4,7-DIHYDRO-1-METHYL-7-OXO-3-PROPOXY-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-N-(2-(1-METHYL-2-PYRROLIDINYL)ETHYL)-4-PROPOXY-
Systematic Name English
Udenafil [WHO-DD]
Common Name English
UDENAFIL [USAN]
Common Name English
3-(1-METHYL-7-OXO-3-PROPYL-4,7-DIHYDRO-1H-PYRAZOLO(4,3-D)PYRIMIDIN-5-YL)-N-(2-((2RS)- 1-METHYLPYRROLIDIN-2-YL)ETHYL)-4-PROPOXYBENZENESULFONAMIDE
Systematic Name English
ZYDENA
Brand Name English
udenafil [INN]
Common Name English
UDENAFIL [MI]
Common Name English
DA-8159
Code English
UDENAFIL [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2127
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
EU-Orphan Drug EU/3/16/1807
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
FDA ORPHAN DRUG 449714
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
WHO-ATC G04BE11
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C74086
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
DRUG BANK
DB06267
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL2103849
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
USAN
XX-10
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
PUBCHEM
135413547
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
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WIKIPEDIA
UDENAFIL
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
INN
8551
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
FDA UNII
L5IB4XLY36
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
MERCK INDEX
m11297
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY Merck Index
CAS
268203-93-6
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
SMS_ID
100000124303
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
EPA CompTox
DTXSID00870301
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
MESH
C419664
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
DRUG CENTRAL
4141
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY
EVMPD
SUB32099
Created by admin on Fri Dec 15 16:42:41 UTC 2023 , Edited by admin on Fri Dec 15 16:42:41 UTC 2023
PRIMARY