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Vardenafil (Standard)

CAT: 0804-HY-B0442R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0442R-01Size:5 mg
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Description
Vardenafil (Standard) is the analytical standard of Vardenafil. This product is intended for research and analytical applications. Vardenafil is a selective and orally active inhibitor of phosphodiesterase-5 (PDE5), with an IC50 of 0.7 nM. Vardenafil shows inhibitory towards PDE1, PDE6 with IC50s of 180 nM, and 11 nM, while IC50s are >1000 nM for PDE3 and PDE4[1]. Vardenafil competitively inhibits cyclic guanosine monophosphate (cGMP) hydrolysis and thus increases cGMP levels[2]. Vardenafil can be used for the research of erectile dysfunction, hepatitis, diabetes[1]-[6].
CAS Number
224785-90-4
UNSPSC
12352005
Target
Endogenous Metabolite; Phosphodiesterase (PDE) ; Reference Standards
Type
Reference Standards
Related Pathways
Metabolic Enzyme/Protease; Others
Field of Research
Endocrinology; Metabolic Disease; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/vardenafil-standard.html
Smiles
CCCC1=NC(C)=C2N1N=C(C(C=C(S(=O)(N3CCN(CC)CC3)=O)C=C4)=C4OCC)NC2=O
Molecular Formula
C23H32N6O4S
Molecular Weight
488.60
References & Citations
[1]Ashour AE, et al. Vardenafil dihydrochloride. Profiles Drug Subst Excip Relat Methodol. 2014;39:515-544.|[2]Saenz de Tejada I, et al. The phosphodiesterase inhibitory selectivity and the in vitro and in vivo potency of the new PDE5 inhibitor vardenafil. Int J Impot Res. 2001;13 (5) :282-290.|[3]Gresser U, et al. Erectile dysfunction: comparison of efficacy and side effects of the PDE-5 inhibitors sildenafil, vardenafil and tadalafil--review of the literature. Eur J Med Res. 2002 Oct 29. 7 (10) :435-46. |[4]Oudot A, et al. Combination of BAY 60-4552 and vardenafil exerts proerectile facilitator effects in rats with cavernous nerve injury: a proof of concept study for the treatment of phosphodiesterase type 5 inhibitor failure. Eur Urol. 2011 Nov. 60 (5) :1020-6. |[5]Ahmed N, et al. Hepatoprotective role of vardenafil against experimentally induced hepatitis in mice. J Biochem Mol Toxicol. 2017 Mar. 31 (3) . |[6]Bódi B, et al. Long-Term PDE-5A Inhibition Improves Myofilament Function in Left and Right Ventricular Cardiomyocytes through Partially Different Mechanisms in Diabetic Rat Hearts. Antioxidants (Basel) . 2021 Nov 6. 10 (11) :1776.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

Vardenafil

Vardenafil is the sulfonamide resulting from formal condensation of the sulfo group of 4-ethoxy-3-(5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one-2-yl)benzenesulfonic acid and the secondary amino group of 4-ethylpiperazine. It has a role as a vasodilator agent and an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor. It is a N-alkylpiperazine, an imidazotriazine and a N-sulfonylpiperazine.

CAS Number224785-90-4
PubChem CID135400189
IUPAC Name2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Molecular FormulaC23H32N6O4S
Molecular Weight488.6
XLogP2.5
Topological Polar Surface Area118
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Heavy Atom Count34
Formal Charge0
Complexity854
SMILES
CCCC1=NC(=C2N1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CC)OCC)C
InChI
InChI=1S/C23H32N6O4S/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30)
InChIKey
SECKRCOLJRRGGV-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Vardenafil
CAS: 224785-90-4
CID: 135400189
Formula: C23H32N6O4S
MW: 488.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight488.6
XLogP32.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass488.22057470
Monoisotopic Mass488.22057470
Topological Polar Surface Area118 Ų
Heavy Atom Count34
Formal Charge0
Complexity854
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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HY-B0442BRVardenafil (hydrochloride trihydrate) (Standard)
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