3D Mol Similar

Vardenafil hydrochloride

: Iupac Name：2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-3H-imidazo[5,1-f][1,2,4]triazin-4-one;hydrochloride; CAS No.: 224785-91-5; Molecular Weight：525.06; Modify Date.: 2022-10-26 20:06; Introduction: Vardenafil was the second agent to be marketed and had the advantage that its onset time was notreduced by taking the medication on a full stomach . It is 30 times more potentas an inhibitor of PDE5 (mean IC50, 3.9 nM) than sildenafil and 10 times more potent than tadalafil,with a greater selectivity (>1,000 times) for human PDE5 than for human PDE2, PDE3, and PDE4and moderate selectivity (>80 times) for PDE1. The PDE inhibitory selectivityand both the in vitro and in vivo potency of the new PDE5 inhibitor vardenafil. Vardenafil specificallyinhibited the hydrolysis of cGMP by PDE5, with an IC50 of 0.7 nM (sildenafil 6.6 nM). The IC50 ofvardenafil for PDE1 was 180 nM, for PDE6 11 nM, and for PDE2, PDE3 and PDE4 more than 1,000nM. View more+

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1. Names and Identifiers

: 1.1 Name; Vardenafil hydrochloride; 1.2 Synonyms; 1-((3-(1,4-Dihydro-5-methyl-4-oxo-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)-4-ethoxyphenyl)sulfonyl)-4-ethylpiperazine Hydrochloride 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-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-piperazine dihydrochloride 2-[2-Ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1H-imidazo[5,1-f][1,2,4]triazin-4-one hydrochloride 2-{2-éthoxy-5-[(4-éthylpipérazin-1-yl)sulfonyl]phényl}-5-méthyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one chlorhydrate 2-{2-Ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one hydrochloride (1:1) 2-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one hydrochloride 2-{2-Ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-onhydrochlorid 4-{[4-ethoxy-3-(4-hydroxy-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-2-yl)phenyl]sulfonyl}-1-ethylpiperazin-1-ium chloride Imidazo[5,1-f][1,2,4]triazin-4(1H)-one, 2-[2-ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]phenyl]-5-methyl-7-propyl-, hydrochloride (1:1) Levitra Levitra,Valdenafil Levitra,Valdenafil.HCl Nuviva 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-, monohydrochloride VARDENAFIL Vardenafil (hydrochloride) VARDENAFIL HCL Vardenafil Hydrochloride Trihydrate 224785-90-4 / VARDENAFIL,HYDROCHLORIDE SALT VARDENAFILMONOHYDROCHLORIDE(SUBJECTTOPATENTFREE); View all

1.3 CAS No.: 224785-91-5

1.4 CID: 135438569

1.5 EINECS(EC#): 606-590-1

1.6 Molecular Formula: C23H33ClN6O4S (isomer)

1.7 Inchi: InChI=1S/C23H32N6O4S.ClH/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

1.8 InChIkey: XCMULUAPJXCOHI-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCC1=NC(=C2N1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CC)OCC)C.Cl

1.10 Isomers Smiles: CCCC1=NC(=C2N1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)N4CCN(CC4)CC)OCC)C.Cl

2. Properties

2.1 Melting point: 214-216

2.1 Boiling point: 692.2 °C at 760 mmHg

2.1 Flash Point: 372.5 °C

2.1 Precise Quality: 524.19700

2.1 PSA: 121.28000

2.1 logP: 3.82900

2.1 Appearance: White to Off-White Cyrstalline Solid

2.2 Chemical Properties: White to Off-White Cyrstalline Solid

3. Use and Manufacturing

3.1 General Description: Vardenafil, 4-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,6,8-tetrazabicyclo[4.3.0]nona-3,7,9-trien-2-one(Levitra), was the second PDE5 introduced in the U.S. market.The metabolism of vardenafil is primarily by CYP3A4.As such, concomitant use of CYP3A4 inhibitors such as ritonavir,indinavir, ketoconazole, as well as moderate CYP3Ainhibitors such as erythromycin typically results in significantincreases of plasma levels of vardenafil.

3.2 Usage: A selective phsphodiesterase type 5 (PDE5) inhibitor

4. Safety and Handling

4.1 Specification: ?Vardenafil hydrochloride (CAS NO.224785-91-5) is?a white to off-white cyrstalline solid. Vardenafil hydrochloride (CAS NO.224785-91-5) is also named as?2-(2-Ethoxy-5-((4-ethyl-1-piperazinyl)sulfonyl)phenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one Hydrochloride Trihydrate?;?2-{2-Ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one hydrochloride trihydrate?;?2-{2-Ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one hydrochloride trihydrate?; 2-{2-Ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]phenyl}-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-onhydrochloridtrihydrat ;?imidazo[5,1-f][1,2,4]triazin-4(1H)-one, 2-[2-ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]phenyl]-5-methyl-7-propyl-, hydrochloride, hydrate (1:1:3)?.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Other Information

7.0 体外研究: Vardenafil specifically inhibits the hydrolysis of cGMP by PDE5 with an IC ₅₀ of 0.7 nM.

7.1 Description: Vardenafil was the second agent to be marketed and had the advantage that its onset time was not reduced by taking the medication on a full stomach . It is 30 times more potent as an inhibitor of PDE5 (mean IC50, 3.9 nM) than sildenafil and 10 times more potent than tadalafil, with a greater selectivity (>1,000 times) for human PDE5 than for human PDE2, PDE3, and PDE4 and moderate selectivity (>80 times) for PDE1. The PDE inhibitory selectivity and both the in vitro and in vivo potency of the new PDE5 inhibitor vardenafil. Vardenafil specifically inhibited the hydrolysis of cGMP by PDE5, with an IC50 of 0.7 nM (sildenafil 6.6 nM). The IC50 of vardenafil for PDE1 was 180 nM, for PDE6 11 nM, and for PDE2, PDE3 and PDE4 more than 1,000 nM.

7.2 Chemical Properties: White to Off-White Cyrstalline Solid

7.3 Uses: A selective phsphodiesterase type 5 (PDE5) inhibitor

7.4 Uses: A phsphodiesterase 5 inhibitor.

7.5 Uses: A phosphodiesterase 5 inhibitor.

7.6 General Description: Vardenafil, 4-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonyl-phenyl]-9-methyl-7-propyl-3,5,6,8-tetrazabicyclo[4.3.0]nona-3,7,9-trien-2-one(Levitra), was the second PDE5 introduced in the U.S. market.The metabolism of vardenafil is primarily by CYP3A4.As such, concomitant use of CYP3A4 inhibitors such as ritonavir,indinavir, ketoconazole, as well as moderate CYP3Ainhibitors such as erythromycin typically results in significantincreases of plasma levels of vardenafil.

7.7 Chemical Synthesis: The synthesis started with 2- hydroxybenzonitrile. 2-Hydroxybenzonitrile (181) was alkylated with ethyl bromide to give 2-ethoxybenzonitrile in 97% yield as a liquid which was subsequently treated with AlMeClNH2, prepared from AlMe3 and NH4Cl, to give corresponding 2-ethoxybenzamidine (182) in 76% yield as a solid. Compound 182 was treated with hydrazine hydrate in ethanol to give hydrazide 183, which was used in the next step without isolation. Dakin-West reaction of 2- butyrylaminopropionic acid (184) with ethyl oxalyl chloride (185) in the presence of DMAP in refluxing pyridine/THF to give corresponding α-oxoamino-acid ester 186 which was also used for next step without isolation. Hydrazide 183 was condensed with ester 186 in refluxing ethanol to give triazinone 187 intermediate which was then cyclized to the final core structure, imidazo[5,1-f]triazin-4-one, using POCl3 to give 188 in 28% yield from 183. Compound 188 was sulfonylated with chlorosulfonic acid to give sulfonyl chloride 189 in 91% yield. Finally, 189 was condensed with N-ethylpiperazine (190) in dichloromethane to give vardenafil (XXIII) in 66% yield.; View all

7.8 Enzyme inhibitor: Vardenafil also is rapidly absorbed and peaks in concentration (9.05 μg/mL after a 10-mg dose) after 0.9 hours, displaying a half-life of 4 to 5 hours. The absorption rate of both sildenafil and vardenafil are reduced when taken with a high-fat diet. The drug also is metabolized by hepatic CYP3A4, and a potential for drug–drug interaction with inhibitors or enhancers of CYP3A4 exists. Biochemical studies demonstrate a significant increase in selectivity of vardenafil over sildenafil for PDE5 versus PDE6. Whether this translates into a significant improvement in side effects must await studies in a greater population of patients.

8. Computational chemical data

Molecular Weight: 525.06g/mol
Molecular Formula: C₂₃H₃₃ClN₆O₄S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 524.1972524
Monoisotopic Mass: 524.1972524
Complexity: 854
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 118
Heavy Atom Count: 35
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcfB7uABEAAAAAAAAAAAAAAAAAWAAAAA8QIAAAAAAAEABwAAAHgQYQAAADAzh3wYzl5fIFAKoAydydHDSjD0nMKAdmBm+XNiMbrrE+TuWOajuzBPIqWeQwCAOAIAAgAAIAAABAAEAABAAAAAAAAAAAA==

9. Question & Answer

Is Vardenafil hydrochloride the Solution for Male Erectile Dysfunction? Feb 14 2023
Vardenafil hydrochloride, also known as Levitra, is an FDA-approved medication for the treatment of male erectile dysfunction. How Does It Work? Vardenafil hydrochloride is an effective and highly sel..
What is Vardenafil hydrochloride and how is it prepared? Feb 05 2022
Vardenafil hydrochloride, also known as Vardenafilhydrochloride, is a chemical compound used for the treatment of erectile dysfunction (ED) in men. It is marketed under the brand name Levitra and was ..
Can Vardenafil hydrochloride solve male erectile dysfunction? Oct 21 2021
Currently, many men experience various issues that lead to incomplete sexual function, including erectile dysfunction. As a result, they explore different medications to improve their sexual life. So..
Medical use and Precautions of Vardenafil hydrochloride Apr 13 2021
Vardenafil (Levitra) hydrochloride is an oral therapy for the treatment of erectile dysfunction. It is a selective inhibitor of cyclic guanosine。 It is used to treat male sexual function problems (im..

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