Title: Tadalafil
CAS Registry Number: 171596-29-5
CAS Name: (6
R,12a
R)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1￠,2￠:1,6]pyrido[3,4-
b]indole-1,4-dione
Synonyms: (6
R,12a
R)-2,3,6,7,12,12a-hexahydro-2-methyl-6-[3,4-(methylenedioxy)phenyl]pyrazino[1￠,2￠:1,6]pyrido[3,4-
b]indole-1,4-dione
Manufacturers' Codes: GF-196960; IC-351
Trademarks: Cialis (Lilly)
Molecular Formula: C22H19N3O4
Molecular Weight: 389.40
Percent Composition: C 67.86%, H 4.92%, N 10.79%, O 16.43%
Literature References: Selective type 5 cGMP phosphodiesterase (PDE-5) inhibitor. Prepn: A. C. Daugan,
WO 9519978 (1995 to Glaxo);
eidem,
US 5859006 (1999 to ICOS); and PDE-5 inhibition:
idem et al., J. Med. Chem. 46, 4525, 4533 (2003). HPLC determn in plasma: C.-L. Cheng, C.-H. Chou,
J. Chromatogr. B 822, 278 (2005). Clinical pharmacokinetics: S. T. Forgue
et al., Br. J. Clin. Pharmacol. 61, 280 (2005). Clinical trial in erectile dysfunction: G. B. Brock
et al., J. Urol. 168, 1332 (2002); in comparison with sildenafil: I. Eardley
et al., BJU Int. 96, 1323 (2005). Review of pharmacology and clinical experience: H. Porst,
Int. J. Impotence Res. 14, Suppl. 1, S57-S64 (2002); in comparison with other phosphodiesterase inhibitors: S. A. Doggrell,
Expert Opin. Pharmacother. 6, 75-84 (2005).
Properties: White crystals from 2-propanol, mp 302-303°. [a]D20 +71.0° (c = 1.00 in CHCl3). Very slightly sol in ethanol. Practically insol in water.
Melting point: mp 302-303°
Optical Rotation: [a]D20 +71.0°
Therap-Cat: In treatment of male erectile dysfunction.
Keywords: Impotence Therapy; Phosphodiesterase Inhibitor.
