268203-93-6 Usage
Description
Udenafil, also known by the brand name Zydena, is an oral phosphodiesterase 5 (PDE5) inhibitor. It is the fourth in a class of drugs that target the inhibition of the enzyme PDE5 for the treatment of erectile dysfunction. Udenafil works by increasing endogenous cyclic guanosine monophosphate (cGMP) concentrations in the penile corpus cavernosum, which leads to smooth muscle cell relaxation and increased blood flow, resulting in a sustainable erection. It is a potent antagonist of human PDE5 with an IC50 of 8.25nM and has a comparable selectivity profile as sildenafil for other PDEs. Udenafil is an off-white solid and has demonstrated effectiveness in treating erectile dysfunction, with up to a 91% vaginal penetration success rate and up to a 67% intercourse completion rate compared to a 29% completion rate by placebo. The most frequently recorded adverse events are mild-to-moderate facial flushing and headache.
Uses
Used in Erectile Dysfunction Treatment:
Udenafil is used as a PDE5 inhibitor for the treatment of erectile dysfunction. It increases cGMP levels, leading to smooth muscle cell relaxation and increased blood flow in the penile corpus cavernosum, resulting in a sustainable erection. Udenafil has shown significant improvement in patient satisfaction, with an overall satisfaction rate of 86% compared to only 26% in the placebo group.
Used in Pulmonary Hypertension Treatment:
In a rat model of monocrotaline-induced pulmonary hypertension, Udenafil (1 and 5 mg/kg) is used as an inhibitor to increase lung cGMP levels, attenuate the development of compensatory right ventricular hypertrophy, and reduce pulmonary arterial wall thickening.
Used in Renal Ischemia-Reperfusion Injury Treatment:
Udenafil is used to increase creatinine clearance and decrease blood urea nitrogen (BUN) and serum malondialdehyde (MDA) levels in a rat model of renal ischemia-reperfusion injury.
Used in Penile Erection Induction:
Udenafil (0.3 and 10 mg/kg) is used to induce penile erections in conscious rabbits and in rabbits with acute spinal cord injury.
Originator
Dong-A (South Korea)
Synthesis
Udenafil has a unique pharmacokinetic
profile with a relatively rapid onset and sufficiently long
duration (Tmax 1-1.5 hr, t1/2 11-13 hr) to make it effective
for up to 24 hours. Synthesis of this racemic compound
started with commercially available 2-propoxybenzoic
acid (160). The free acid 160 was converted to
it acyl chloride with thinoy chloride in refluxing dichloromethane,
which was condensed with 4-amino-1-methyl-3-
propyl-1H-pyrazole-5-carboxamide (161) with TEA and
DMAP in dichloromethane to yield carboxamide 162 in 85%
yield from 160. Compound 162 was sulfonated with chlorosulfonic
acid to yield benzenesulfonyl chloride 163 in 67%
yield, which was treated with racemic 2-(1-methylpyrrolidin-
2-yl)ethylamine (164) in dichloromethane to afford sulfonamide
165 in 80% yield. Finally, compound 165 was cyclized
with tBuOK in refluxing tBuOH to give udenafil (XXII) in
81% yield.
Check Digit Verification of cas no
The CAS Registry Mumber 268203-93-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,6,8,2,0 and 3 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 268203-93:
(8*2)+(7*6)+(6*8)+(5*2)+(4*0)+(3*3)+(2*9)+(1*3)=146
146 % 10 = 6
So 268203-93-6 is a valid CAS Registry Number.
InChI:InChI=1/C25H36N6O4S/c1-5-8-20-22-23(31(4)29-20)25(32)28-24(27-22)19-16-18(10-11-21(19)35-15-6-2)36(33,34)26-13-12-17-9-7-14-30(17)3/h10-11,16-17,26H,5-9,12-15H2,1-4H3,(H,27,28,32)
268203-93-6Relevant articles and documents
Preparation method for heterocyclic compounds
-
, (2018/03/24)
The invention specifically relates to a preparation method for heterocyclic compounds with udenafil as a representative, belonging to the field of chemical pharmaceutical technology. The invention aims to overcome the technical problems of high production cost, low yield, great treatment quantities of waste acid and exhaust gas and potential safety hazards in conventional synthetic methods. To overcome the technical problems, the invention provides the preparation method for the heterocyclic compounds. The preparation method comprises the following steps: 1, subjecting a starting raw materialA to a reaction under the action of an organic solvent and alkali to produce an intermediate 1; 2, reacting the intermediate 1 with a sulfonating agent to produce an intermediate 2; and 3, reacting the intermediate 2 with a starting raw material B in an organic solvent to obtain a finished compound as shown in a formula I. The preparation method provided by the invention uses easily available andcheap raw materials, avoids usage of expensive coupling reagents, improves the selectivity of next-step sulfonation, and is high in product yield and purity, mild in reaction conditions and beneficialfor scaled-up production in workshops.
HIGHLY SELECTIVE and LONG-ACTING PDE5 MODULATORS
-
Page/Page column 59, (2008/12/07)
Disclosed herein are substituted phosphodiesterase type 5 enzyme modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.
