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Vardenafil(CAS No. 224785-90-4)

Vardenafil C23H32N6O4S (cas 224785-90-4) Molecular Structure

224785-90-4 Structure

Identification and Related Records

【Name】
Vardenafil
【Iupac name】
2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-
1H-imidazo[5,1-f][1,2,4]triazin-4-one
【CAS Registry number】
224785-90-4
【Synonyms】
Piperazine,1-[[3-(1,4-dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl]sulfonyl]-4-ethyl-(9CI)
2-[2-Ethoxy-5-(4-ethylpiperazin-1-yl-1-sulfonyl)phenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one
Nuviva
BAY 38-9456
1-((3-(3,4-Dihydro-5-methyl-4-oxo-7-propylimidazo(5,1-f)-as-triazin-2-yl)-4-ethoxyphenyl)sulfonyl)-4-ethylpiperazine
Vivanza
【Molecular Formula】
C23H32N6O4S (Products with the same molecular formula)
【Molecular Weight】
579.11
【Inchi】
InChI=1/C23H32N6O4S.ClH.3H2O/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);1H;3*1H2
【Canonical SMILES】
CCCC1=NC(=C2N1NC(=NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CC)OCC)C
【MOL File】
224785-90-4.mol

Chemical and Physical Properties

【Appearance】
White crystalline powder
【Density】
1.37g/cm3
【Melting Point】
214-216 oC
【Boiling Point】
692.2°Cat760mmHg
【Vapour】
5.17E-19mmHg at 25°C
【Flash Point】
372.5°C
【Water】
Soluble in water
【Solubilities】
Soluble in water and alcohol
【Color/Form】
White
【Computed Properties】
Molecular Weight:488.60298 [g/mol]
Molecular Formula:C23H32N6O4S
XLogP3-AA:2.5
H-Bond Donor:1
H-Bond Acceptor:6
Rotatable Bond Count:8
Tautomer Count:21
Exact Mass:488.220574
MonoIsotopic Mass:488.220574
Topological Polar Surface Area:118
Heavy Atom Count:34
Formal Charge:0
Complexity:854
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:2
Feature 3D Cation Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:4
Effective Rotor Count:9.2
Conformer Sampling RMSD:1
CID Conformer Count:63

Safety and Handling

【Formulations/Preparations】
Oral: Tablets, film-coated: 2.5 mg (of vardenafil) Levitra (Bayer), 5 mg (of vardenafil) Levitra (Bayer), 10 mg (of vardenafil) Levitra (Bayer), 20 mg (of vardenafil) Levitra (Bayer).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl vardenafil hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Vardenafil Hydrochloride/
【Octanol/Water Partition Coefficient】
log Kow = 2.79 /Estimated/
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds that specifically inhibit PHOSPHODIESTERASE 5.
- Drugs used to cause dilation of the blood vessels.
【Therapeutic Uses】
Vardenafil is indicated for the treatment of erectile dysfunction. /Included in US product labeling/
【Biomedical Effects and Toxicity】
Protein binding: Very high: 95% bound to plasma proteins; reversible and independent of total drug concentrations
Rapidly absorbed; absolute bioavailability is approximately 15%. Maximum observed plasma concentrations after a single 20 mg dose in healthy volunteers are usually reached between 30 minutes and 2 hours (median 60 minutes) after oral dosing in the fasted state. A high-fat meal causes a reduction in Cmax by 18% to 50%.
Enhancement of nitric oxide (NO)-induced erections in rabbits by 0.1 mg/kg vardenafil is limited by its pharmacokinetic properties (Tmax=1 h; T1/2=1.2 h), although erectile effects have been observed after 7 h. In humans, vardenafil is rapidly absorbed (Tmax approximately 40 min) and more slowly metabolized (T1/2 approximately 4 h), with an absolute bioavailability of 14.5% (vs 40% for sildenafil). Although the consumption of high-fat meals does not affect the drug's relative bioavailability, it retards intestinal absorption. Coadministration of CYP3A4 inhibitors such as ritonavir can affect hepatic metabolism. M1, an active metabolite of vardenafil, is a four-fold-less potent inhibitor of PDE5 than its parent compound, contributing approximately 7% to vardenafil's overall efficacy. [Bischoff E; Int J Impot Res 16(Suppl 1): S34-7 (2004)] PubMed Abstract
Time to peak concentration: 30 minutes to 2 hours (oral dosing, fasted state)
Elimination: Feces: 91% - 95% of administered dose. Urine: 2% - 6% of administered dose. Total body clearance: 56 L /hr
Geriatrics: Elderly males age 65 years and older have higher vardenafil plasma concentrations than younger males (18 - 45 years), mean Cmax and AUC were 34% and 52% higher, respectively. Renal Insufficiency: CrCl 50-80 mL/min: pharmacokinetics similar to normal renal function; CrCl
It is not known whether vardenafil is distributed into human breast milk. However, vardenafil is distributed into the milk of rats at concentrations approximately 10-fold greater than found in plasma. Following a single oral dose of 3 mg per kg, 3.3% of the administered dose was excreted into the milk within 24 hours.
The effects of food on the pharmacokinetics of vardenafil were examined in 25 healthy adult males. Single-dose vardenafil 20 mg was administered in a randomized four-way crossover design after an overnight fast (at 8 a.m.), after consumption of a high-fat breakfast (at 8 a.m.), on an empty stomach (at 6 p.m.), and after a typical moderate-fat evening meal (at 6 p.m.). Serial blood samples were analyzed for vardenafil and metabolite (M1) levels. When administered after an overnight fast and after a high-fat breakfast, vardenafil geometric mean Cmax was 17.14 and 14.0 micrograms/L, respectively, and AUC was 66.78 and 67.09 micrograms/hr/L, respectively; the median tmax was 1 hour under fasting conditions and 2 hours with consumption of high-fat breakfast. When administered in the evening on an empty stomach and after a moderate-fat meal, vardenafil geometric mean Cmax was 14.22 and 13.04 micrograms/L, respectively, and AUC was 51.97 and 59.12 micrograms/hr/L, respectively. The median tmax was 1 hour after fasting or a moderate-fat meal in the evening. All treatments were well tolerated. Thus, while a high-fat meal may alter Cmax slightly and delay the absorption up to 1 hour, a moderate-fat meal has no clinically relevant effect on vardenafil pharmacokinetics. [Rajagopalan P et al; J Clin Pharmacol 43 (3): 260-7 (2003)] PubMed Abstract
In volunteers with mild hepatic impairment (Child-Pugh A), the C max and AUC following a 10 mg vardenafil dose were increased by 22% and 17%, respectively, compared to healthy control subjects. In volunteers with moderate hepatic impairment (Child-Pugh B), the C max and AUC following a 10 mg vardenafil dose were increased by 130% and 160%, respectively, compared to healthy control subjects. Consequently, a starting dose of 5 mg is recommended for patients with moderate hepatic impairment, and the maximum dose should not exceed 10 mg. Vardenafil has not been evaluated in patients with severe (Child-Pugh C) hepatic impairment.
Vss: 208 L; indicates extensive tissue distribution. A mean of 0.00018% of the dose was obtained in semen 1.5 hours after dosing.
... Differences in pharmacokinetic properties among the PDE5 inhibitors include the fact that sildenafil and vardenafil have a shorter duration of action (approximately 4 hr) compared with the longer period of responsiveness observed with tadalafil (up to 36 hr). In addition, in the presence of high-fat food, absorption of sildenafil and vardenafil may be delayed; however, the rate and extent of tadalafil absorption are unaffected by high-fat food. [Seftel AD; Clin Cardiol 27 (4 Suppl 1): I14-19 (2004)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1X10+6(SRC), determined from a structure estimation method(2), indicates that vardenafil is expected to be immobile in soil(SRC). The estimated pKa's of vardenafil are 4.72 and 6.21(tertiary amine)(3), indicating that this compound will partially exist in cation form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(4). Volatilization of vardenafil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-21 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Vardenafil is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.4X10-19 mm Hg(SRC), determined from a fragment constant method(6). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1X10+6(SRC), determined from a structure estimation method(2), indicates that vardenafil is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.9X10-21 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 28(SRC), from an estimated log Kow of 2.79(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), vardenafil, which has an estimated vapor pressure of 3.4X10-19 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase vardenafil may be removed from the air by wet and dry deposition(SRC).

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