Udenafil

Base Information

• Chemical Name: Udenafil
• CAS No.: 268203-93-6
• Molecular Formula: C25H36N6O4S
• Molecular Weight: 516.665
• Mol file: 268203-93-6.mol

Synonyms:Benzenesulfonamide,3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-4-propoxy-(9CI);DA 8159;Udenafil;Zydena;

Chemical Property of Udenafil

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 2.83E-19mmHg at 25°C
• Melting Point: 157-159°C
• Refractive Index: 1.648
• Boiling Point: 697 °C at 760 mmHg
• PKA: 11.07±0.50(Predicted)
• Flash Point: 375.3 °C
• PSA: 130.59000
• Density: 1.35 g/cm³
• LogP: 4.23710
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Sparingly)

Purity/Quality:

99%, ^*data from raw suppliers

Udenafil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 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. 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.
• Uses: Udenafil is an oral phosphodiesterase 5 inhibitor used for the treatment of erectile dysfunction. An oral phosphodiesterase 5 inhibitor used for the treatment of erectile dysfunction.

Technology Process of Udenafil

There total 5 articles about Udenafil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

2-(2-AMINOETHYL)-1-METHYLPYRROLIDINE (51387-90-7,422545-96-8) + 5-(5-chlorosulphonyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (139756-24-4) → 5-[2-propyloxy-5-[2-(1-methyl-2-pyrrolidinyl)ethylaminosulfonyl]phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one (268203-93-6)

Guidance literature:

at 10 - 20 ℃; for 1h; Temperature;

Reference yield: 53.0%

2-methyl-4-{5-[2-(1-methyl-pyrrolidin-2-yl)-ethylsulfamoyl]-2-propoxy-benzoylamino}-5-propyl-2H-pyrazole-3-carboxamide (382592-28-1) → 5-[2-propyloxy-5-[2-(1-methyl-2-pyrrolidinyl)ethylaminosulfonyl]phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one (268203-93-6)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; for 8h; Heating / reflux;

Reference yield:

1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide (139756-04-0) → 5-[2-propyloxy-5-[2-(1-methyl-2-pyrrolidinyl)ethylaminosulfonyl]phenyl]-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one (268203-93-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / ethanol / Reflux

2: thionyl chloride; chlorosulfonic acid / 20 - 25 °C

3: 1 h / 10 - 20 °C

With chlorosulfonic acid; thionyl chloride; sodium hydroxide; In ethanol;

upstream raw materials:

2-methyl-4-{5-[2-(1-methyl-pyrrolidin-2-yl)-ethylsulfamoyl]-2-propoxy-benzoylamino}-5-propyl-2H-pyrazole-3-carboxamide

2-(2-AMINOETHYL)-1-METHYLPYRROLIDINE

5-(5-chlorosulphonyl-2-n-propoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

1-Methyl-4-(2-n-propoxybenzamido)-3-n-propylpyrazole-5-carboxamide

Downstream raw materials:

udenafil benzenesulfonate

udenafil cyclamate

Refernces

• 1、 -. "PHARMACOLOGICAL COMPOSITION FOR PREVENTION AND TREATMENT OF RESPIRATORY DISEASE CONTAINING PYRAZOLOPYRIMIDINONE COMPOUND OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF". Page/Page column 6. . Retrieved 2010/04/03.
• 2、 -. "AGENT FOR THE PREVENTION AND TREATMENT OF LIVER DISEASES CONTAINING PYRAZOLOPYRIMIDINE DERIVATIVE". Page/Page column 7. . Retrieved 2008/06/13.