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SML2799

Sigma-Aldrich

Avanafil

≥98% (HPLC)

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Synonym(s):
(S)-2-(2-Hydroxymethyl-1-pyrrolidinyl)-4-(3-chloro-4-methoxybenzylamino)-5-[N-(2-pyrimidinylmethyl)carbamoyl]pyrimidine, (S)-4-[(3-Chloro-4-methoxybenzyl)amino]-2-[2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide, 4-[[(3-Chloro-4-methoxyphenyl)methyl]amino]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]-N-(2-pyrimidinylmethyl)-5-pyrimidinecarboxamide, TA 1790, TA-1790, TA1790
Empirical Formula (Hill Notation):
C23H26ClN7O3
CAS Number:
330784-47-9
Molecular Weight:
483.95
MDL number:
MFCD11977961
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1

InChI key

WEAJZXNPAWBCOA-INIZCTEOSA-N

Biochem/physiol Actions

Avanafil is an orally active, potent and selective phosphodiesterase-5 (PDE5) inhibitor (IC50 = 5.2 nM) with superior PDE5 selectivity (19,000-, >10,000-, 121-fold over PDE1, PDE11, PDE6, respectively) when compared with tadalafil (25-fold over PDE11), sildenafil and vardenafil (375-fold over PDE1 & 16 to 21-fold over PDE6).

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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S Gur et al.
Andrologia, 47(8), 897-903 (2014-09-23)
We compared the activity of a new phosphodiesterase-5 inhibitor (PDE5i) avanafil with sildenafil and tadalafil in human and rat corpus cavernosum (CC) tissues. The effect of avanafil with several inhibitors and electrical field stimulation (EFS) was evaluated on CC after
Effects of the Phosphodiesterase-5 (PDE-5) Inhibitors, Avanafil and Zaprinast, on Bone Remodeling and Oxidative Damage in a Rat Model of Glucocorticoid-Induced Osteoporosis.
Zübeyir Huyut et al.
Medical science monitor basic research, 24, 47-58 (2018-03-21)
Didem Yilmaz et al.
Urology, 83(2), 508-508 (2013-12-18)
To determine the effect of avanafil, a novel phosphodiesterase-5 inhibitor, on the treatment of erectile dysfunction associated with type 2 diabetes mellitus (T2DM). In 2-day-old rats, T2DM was induced by single intraperitoneal injection of 90 mg/kg of streptozotocin (STZ; i.p.).
Jun Kotera et al.
The Journal of urology, 188(2), 668-674 (2012-06-19)
We investigated the in vitro inhibitory effects of avanafil, a novel, potent inhibitor of phosphodiesterase-5, on 11 phosphodiesterases. We also studied its potentiation of penile tumescence in dogs. Phosphodiesterase assay was done with the 4 phosphodiesterase-5 inhibitors avanafil, sildenafil, vardenafil
Carmen Lorenz et al.
Cell stem cell, 20(5), 659-674 (2017-01-31)
Mitochondrial DNA (mtDNA) mutations frequently cause neurological diseases. Modeling of these defects has been difficult because of the challenges associated with engineering mtDNA. We show here that neural progenitor cells (NPCs) derived from human induced pluripotent stem cells (iPSCs) retain

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