Avanafil

Names

[ Name ]:
Avanafil

[Synonym ]:
(S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2pyrimidinylmethyl)-5-pyrimidinecarboxamide
Stendra
4-[(3-Chloro-4-methoxybenzyl)amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide
5-Pyrimidinecarboxamide, 4-[[(3-chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-
Avanafil
TA-1790

Biological Activity

[Description]:

Avanafil(TA-1790) is a potent and highly selective phosphodiesterase-5(PDE-5) inhibitor(IC50=5.2 nM) for erectile dysfunction; lower selectivity against PDE1, PDE6, and PDE11.IC50 value: 5.2 nM [1]Target: PDE5Avanafil is highly selective toward PDE5 and against all other PDE isozymes tested. Lower selectivity against PDE1, PDE6, and PDE11 is consistent with results from randomized, placebo-controlled, phase 3 trials in which musculoskeletal and hemodynamic adverse events were reported in <2% of patients and no color vision-related abnormalities were reported with avanafil doses up to 200mg once daily [2]. Intraduodenal doses of avanafil or sildenafil (0.1 and 1 mg/kg) potentiated the AUC of nitroglycerin induced hypotension. However, the potentiating effect of avanafil at 1 mg/kg was significantly weaker than that of sildenafil (p <0.05) [3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Cardiovascular Disease

[References]

[1]. Kotera J, et al. Avanafil, a potent and highly selective phosphodiesterase-5 inhibitor for erectile dysfunction. J Urol. 2012 Aug;188(2):668-74.

[2]. Wang R, et al. Selectivity of avanafil, a PDE5 inhibitor for the treatment of erectile dysfunction: implications for clinical safety and improved tolerability. J Sex Med. 2012 Aug;9(8):2122-9.

[3]. Mochida H, et al. Avanafil, a highly selective phosphodiesterase type 5 inhibitor for erectile dysfunction, shows good safety profiles for retinal function and hemodynamics in anesthetized dogs. J Urol. 2013 Aug;190(2):799-806.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
150-152ºC

[ Molecular Formula ]:
C₂₃H₂₆ClN₇O₃

[ Molecular Weight ]:
483.951

[ Exact Mass ]:
483.178558

[ PSA ]:
125.39000

[ LogP ]:
3.52

[ Index of Refraction ]:
1.651

[ Storage condition ]:
Refrigerator

Safety Information

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%