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

• ChemBase ID: 4423
• Molecular Formular: C25H36N6O4S
• Molecular Mass: 516.65614
• Monoisotopic Mass: 516.25187466
• SMILES: S(=O)(=O)(NCCC1N(CCC1)C)c1cc(c2[nH]c3c(nn(c3c(=O)n2)C)CCC)c(OCCC)cc1
• Canonical SMILES: CCCOc1ccc(cc1c1nc(=O)c2c([nH]1)c(CCC)nn2C)S(=O)(=O)NCCC1CCCN1C
• 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)
• InChIKey: IYFNEFQTYQPVOC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: @udenafil; udenafil
• Brand Name: Zydena
• Synonyms: Udenafil

Database IDs

• CAS Number: 268203-93-6
• PubChem SID: 99443240; 160967855
• PubChem CID: 6918523
• Chemspider ID: 5293720
• DrugBank ID: DB06267
• KEGG ID: D10027
• Unique Ingredient Identifier: L5IB4XLY36
• Wikipedia Title: Udenafil

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.2116613
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.11699866
• LogD (pH = 7.4): 1.5393687
• Log P: 1.6629407
• Molar Refractivity: 153.1134 cm^3
• Polarizability: 53.998516 Å^3
• Polar Surface Area: 117.92 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 3.2
• LOG S: -3.81
• Solubility (Water): 7.98e-02 g/l

PROPERTIES

Pharmacology Properties

• Half Life: 7.3–12.1 hours

DETAILS

DrugBank - DB06267

• Drug 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.
• Indication: Investigated for use/treatment in erectile dysfunction and hypertension.
• Pharmacology: Udenafil is a potent selective phosphodiesterase type 5 (PDE5) inhibitor.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Metabolized by CYP3A4 and CYP3A5.
• References: 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] ; 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. Epub 2008 Feb 28. [Pubmed]
• External Links: Wikipedia

REFERENCES

• 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
• 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. Epub 2008 Feb 28. Pubmed