224785-91-5 Usage
Description
Vardenafil hydrochloride, also known as Levitra, is a selective phosphodiesterase type 5 (PDE5) inhibitor. It is a potent and selective inhibitor of PDE5, with a greater selectivity for human PDE5 than for human PDE2, PDE3, and PDE4. Vardenafil was the second PDE5 inhibitor introduced in the U.S. market and has the advantage of not having its onset time reduced by taking the medication on a full stomach.
Uses
Used in Urological Applications:
Vardenafil hydrochloride is used as a urological agent for the treatment of erectile dysfunction. It works by inhibiting PDE5, which helps to increase blood flow to the penis, allowing for a stronger and more sustained erection.
Used in Pharmaceutical Research:
Vardenafil hydrochloride is also used in pharmaceutical research due to its high potency and selectivity as an inhibitor of PDE5. This makes it a valuable compound for studying the effects of PDE5 inhibition on various physiological processes and for developing new treatments for related conditions.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 224785-91-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,2,4,7,8 and 5 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 224785-91:
(8*2)+(7*2)+(6*4)+(5*7)+(4*8)+(3*5)+(2*9)+(1*1)=155
155 % 10 = 5
So 224785-91-5 is a valid CAS Registry Number.
InChI:InChI=1/C23H32N6O4S.2ClH/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);2*1H
