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224785-90-4 molecular structure
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2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one

ChemBase ID: 740
Molecular Formular: C23H32N6O4S
Molecular Mass: 488.60298
Monoisotopic Mass: 488.22057453
SMILES and InChIs

SMILES:
S(=O)(=O)(N1CCN(CC1)CC)c1cc(c(OCC)cc1)c1[nH]n2c(nc(c2c(=O)n1)C)CCC
Canonical SMILES:
CCOc1ccc(cc1c1nc(=O)c2n([nH]1)c(CCC)nc2C)S(=O)(=O)N1CCN(CC1)CC
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

Cite this record

CBID:740 http://www.chembase.cn/molecule-740.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propyl-1H,4H-imidazo[4,3-f][1,2,4]triazin-4-one
IUPAC Traditional name
vardenafil
Brand Name
Levitra
Synonyms
VDN
Vardenafil
CAS Number
224785-90-4
PubChem SID
46506777
160964203
PubChem CID
110634

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.007337  H Acceptors
H Donor LogD (pH = 5.5) 0.6368539 
LogD (pH = 7.4) 1.3132267  Log P 1.3251204 
Molar Refractivity 142.7097 cm3 Polarizability 50.337387 Å3
Polar Surface Area 109.13 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.18  LOG S -3.18 
Solubility (Water) 3.25e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
0.11 mg/mL (HCl salt) expand Show data source
Hydrophobicity(logP)
1.4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00862 external link
Item Information
Drug Groups approved
Description Vardenafil (Levitra) is an oral therapy for the treatment of erectile dysfunction. It is a selective inhibitor of cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5). Penile erection is a hemodynamic process initiated by the relaxation of smooth muscle in the corpus cavernosum and its associated arterioles. During sexual stimulation, nitric oxide is released from nerve endings and endothelial cells in the corpus cavernosum. Nitric oxide activates the enzyme guanylate cyclase resulting in increased synthesis of cyclic guanosine monophosphate (cGMP) in the smooth muscle cells of the corpus cavernosum. The cGMP in turn triggers smooth muscle relaxation, allowing increased blood flow into the penis, resulting in erection. The tissue concentration of cGMP is regulated by both the rates of synthesis and degradation via phosphodiesterases (PDEs). The most abundant PDE in the human corpus cavernosum is the cGMPspecific phosphodiesterase type 5 (PDE5); therefore, the inhibition of PDE5 enhances erectile function by increasing the amount of cGMP.
Indication Used for the treatment of erectile dysfunction
Pharmacology Vardenafil is used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH). Part of the physiological process of erection involves the release of nitric oxide (NO) in the corpus cavernosum. This then activates the enzyme guanylate cyclase which results in increased levels of cyclic guanosine monophosphate (cGMP), leading to smooth muscle relaxation in the corpus cavernosum, resulting in increased inflow of blood and an erection. Vardenafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. This means that, with vardenafil on board, normal sexual stimulation leads to increased levels of cGMP in the corpus cavernosum which leads to better erections. Without sexual stimulation and no activation of the NO/cGMP system, vardenafil should not cause an erection.
Toxicity Symptoms of overdose include vision changes and back and muscle pain.
Affected Organisms
Humans and other mammals
Biotransformation Vardenafil is metabolized predominantly by the hepatic enzyme CYP3A4, with contribution from the CYP3A5 and CYP2C isoforms. The major circulating metabolite, M1, results from desethylation at the piperazine moiety of vardenafil. M1 shows a phosphodiesterase selectivity profile similar to that of vardenafil and an in vitro inhibitory potency for PDE5 28% of that of vardenafil.
Absorption Vardenafil is rapidly absorbed with absolute bioavailability of approximately 15%.
Half Life 4-5 hours
Protein Binding 95%
Elimination After oral administration, vardenafil is excreted as metabolites predominantly in the feces (approximately 91-95% of administered oral dose) and to a lesser extent in the urine (approximately 2-6% of administered oral dose).
Distribution * 208 L
Clearance * 56 L/h
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

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