10214. Udenafil

Nomenclature

CAS number: 268203-93-6
3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-4-propoxybenzenesulfonamide; 5-[2-propyloxy-5-(1-methyl-2-pyrrolidinylethylamidosulfonyl)phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one; DA-8159; Zydena (Dong-A).
C25H36N6O4S; mol wt 516.66.
C 58.12%, H 7.02%, N 16.27%, O 12.39%, S 6.21%.

Description and references

Selective phosphodiesterase type 5 (PDE5) inhibitor. Prepn: M. Yoo et al., WO 0027848; eidem, US 6583147 (2000, 2003 both to Dong A). Erectogenic potential: T. Y. Oh et al., Arch. Pharmacal Res. 23, 471 (2000). Inhibition of PDE5: H. Doh et al., ibid. 25, 873 (2002). HPLC determn in plasma and urine: H. J. Shim et al., J. Pharm. Biomed. Anal. 30, 527 (2002) DOI PubMed. Review of pharmacology and clinical experience: E. A. Salem et al., Curr. Opin. Investig. Drugs 7, 661-669 (2006) PubMed.

Chemical structure

Properties

mp 162-164°. pKa1 6.5; pKa2 12.5. Log P (octanol/buffer): 0.76 (pH 1); 0.75 (pH 3); 0.81 (pH 5); 1.85 (pH 7). Soly in water (mg/ml): 27.4 (pH 2); 12.5 (pH 5); 0.82 (pH 7); 0.033 (pH 10); 0.019 (distilled H2O). LD50 in rats (g/kg): >1 orally (Yoo).

Therapeutic Category

In treatment of erectile dysfunction.

Keywords

Impotence Therapy