268203-93-6 Usage
Description
Different sources of media describe the Description of 268203-93-6 differently. You can refer to the following data:
1. Udenafil is the fourth in a class of drugs targeting the inhibition of the enzyme
phosphodiesterase 5 (PDE5) for the treatment of erectile dysfunction. Inhibition of
PDE5 results in the increase in endogenous cyclic guanosine monophosphate
(cGMP) concentrations in the penile corpus cavernosum. cGMP induces smooth
muscle cell relaxation and subsequent increased blood flow leading to a sustainable
erection. Udenafil is a potent antagonist of human PDE5 with an IC50 of 8.25nM
and a comparable selectivity profile as sildenafil for the other PDEs. Unlike tadalafil,
it does not inhibit PDE11, which has been implicated in myalgia and
testicular toxicity. Furthermore, udenafil produced up to a 91% vaginal
penetration success rate and up to a 67% intercourse completion rate compared to a
29% completion rate by placebo. Overall patient satisfaction, measured by a
standard global assessment question, was 86% compared to only 26% in the placebo
group. The most frequently recorded adverse events were mild-to-moderate
facial flushing and headache.
2. Udenafil is an inhibitor of phosphodiesterase 5 (PDE5). In vivo, udenafil (1 and 5 mg/kg) increases lung cGMP levels, attenuates the development of compensatory right ventricular hypertrophy, and reduces pulmonary arterial wall thickening in a rat model of monocrotaline-induced pulmonary hypertension. It increases creatine clearance and decreases blood urea nitrogen (BUN) and serum malondialdehyde (MDA) levels in a rat model of renal ischemia-reperfusion injury. Udenafil (0.3 and 10 mg/kg) induces penile erections in conscious rabbits and in rabbits with acute spinal cord injury.
Chemical Properties
Off-White Solid
Originator
Dong-A (South Korea)
Uses
Different sources of media describe the Uses of 268203-93-6 differently. You can refer to the following data:
1. Udenafil is an oral phosphodiesterase 5 inhibitor used for the treatment of erectile dysfunction.
2. An oral phosphodiesterase 5 inhibitor used for the treatment of erectile dysfunction.
Brand name
Zydena
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
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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.
