Udenafil

Iupac Name：3-(1-methyl-7-oxo-3-propyl-4H-pyrazolo[4,
3-d]pyrimidin-5-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-
propoxybenzenesulfonamide

CAS No.: 268203-93-6

Molecular Weight：516.65614

Modify Date.: 2022-11-25 06:25

Introduction: Udenafil is the fourth in a class of drugs targeting the inhibition of the enzymephosphodiesterase 5 (PDE5) for the treatment of erectile dysfunction. Inhibition ofPDE5 results in the increase in endogenous cyclic guanosine monophosphate(cGMP) concentrations in the penile corpus cavernosum. cGMP induces smoothmuscle cell relaxation and subsequent increased blood flow leading to a sustainableerection. Udenafil is a potent antagonist of human PDE5 with an IC50 of 8.25nMand a comparable selectivity profile as sildenafil for the other PDEs. Unlike tadalafil,it does not inhibit PDE11, which has been implicated in myalgia andtesticular toxicity. Furthermore, udenafil produced up to a 91% vaginalpenetration success rate and up to a 67% intercourse completion rate compared to a29% completion rate by placebo. Overall patient satisfaction, measured by astandard global assessment question, was 86% compared to only 26% in the placebogroup. The most frequently recorded adverse events were mild-to-moderatefacial flushing and headache. View more+

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1. Names and Identifiers

1.1 Name: Udenafil
1.2 Synonyms: 3-(1-Methyl-7-oxo-3-propyl-4,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-4-propoxybenzenesulfonamide 3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methyl-2-pyrrolidinyl)ethyl]-4-propoxybenzenesulfonamide 5-(2-Propyloxy-5-(1-methyl-2-pyrollidinylethylamidosulfonyl)phenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo(4,3-D)pyrimidine-7-one 5-[2-propyloxy-5-(2-(1-Methylpyrrolidin-2-yl)ethylaMinosulphonyl)phenyl]-1-Methyl-3-propyl-6,7-dihydro-1H-pyrazolo(4,3-d)pyriMidin-7-one 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 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- BenzenesulfonaMide,3-(6,7-dihydro-1-Methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyriMidin-5-yl)-N-[2-(1-Methyl-2-pyrrolidinyl)ethyl]-4-propoxy- CS-1353 Da-8159 Udenafi Udenafil(DA 8159,Zydena) Udenafil, DA 8159 Zydena

1.3 CAS No.: 268203-93-6

1.4 CID: 135413547

1.5 Molecular Formula: C25H36N6O4S (isomer)

1.6 Inchi: InChI=1S/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)

1.7 InChkey: IYFNEFQTYQPVOC-UHFFFAOYSA-N

1.8 Canonical Smiles: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)NCCC4CCCN4C)OCCC)C

1.9 Isomers Smiles: CCCC1=NN(C2=C1N=C(NC2=O)C3=C(C=CC(=C3)S(=O)(=O)NCCC4CCCN4C)OCCC)C

2. Properties

2.1 Density: 1.35

2.1 Melting point: 157-159°C

2.1 Boiling point: 697°C at 760 mmHg

2.1 Refractive index: 1.648

2.1 Flash Point: 375.3°C

2.1 Precise Quality: 532.22900

2.1 PSA: 145.61000

2.1 logP: 5.60640

2.1 Solubility: 7.98e-02 g/L

2.2 Appearance: Off-White Solid

2.3 Chemical Properties: Off-White Solid

2.4 pKa: 11.07±0.50(Predicted)

2.5 Water Solubility: 7.98e-02 g/L

2.6 StorageTemp: Inert atmosphere,2-8°C

3. Use and Manufacturing

3.1 Usage: An oral phosphodiesterase 5 inhibitor used for the treatment of erectile dysfunction.

4. Safety and Handling

4.1 Specification

The Udenafil is an organic compound with the formula C₂₅H₃₆N₆O₄S. The IUPAC name of this chemical is 3-(1-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methylpyrrolidin-2-yl)ethyl]-4-propoxybenzenesulfonamide. With the CAS registry number 268203-93-6, it is also named as Zydena. Besides, udenafil is a drug used in urology to treat erectile dysfunction.

Physical properties about Udenafil are: (1)ACD/LogP: 3.07; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 7.4): 0.43; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 2.57; (8)#H bond acceptors: 10; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 10; (11)Polar Surface Area: 108.72??²; (12)Index of Refraction: 1.648; (13)Molar Refractivity: 138.95 cm³; (14)Molar Volume: 381.4 cm³; (15)Polarizability: 55.08×10^-24cm³; (16)Surface Tension: 51.8 dyne/cm; (17)Density: 1.35 g/cm³; (18)Flash Point: 375.3 °C; (19)Enthalpy of Vaporization: 102.07 kJ/mol; (20)Boiling Point: 697 °C at 760 mmHg; (21)Vapour Pressure: 2.83E-19 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2\N=C(/Nc1c(nn(c12)C)CCC)c3cc(ccc3OCCC)S(=O)(=O)NCCC4N(C)CCC4
(2)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)
(3)InChIKey: IYFNEFQTYQPVOC-UHFFFAOYAZ
(4)Std. InChI: InChI=1S/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)
(5)Std. InChIKey: IYFNEFQTYQPVOC-UHFFFAOYSA-N

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

268203-93-6Total: 1 Synthesis Route

382592-28-1 1 Suppliers

268203-93-6 33 Suppliers

Literatures:
AUSPEX PHARMACEUTICALS, INC. Patent: US2008/194529 A1, 2008 ; Location in patent: Page/Page column 59 ; US 20080194529 A1
Yield: ~51%

8. Precursor and Product

precursor:

382592-28-1

9. Other Information

9.0 Target: Value

9.1 PDE5 (Cell-free assay): 8.25 nM

9.2 PDE3 (Cell-free assay): 52 nM

9.3 PDE6 (Cell-free assay): 53.3 nM

9.4 PDE2 (Cell-free assay): 101 nM

9.5 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.

9.6 Description: 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.

9.7 Chemical Properties: Off-White Solid

9.8 Originator: Dong-A (South Korea)

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

9.10 Uses: An oral phosphodiesterase 5 inhibitor used for the treatment of erectile dysfunction.

9.11 Brand name: Zydena

9.12 Chemical 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.

10. Computational chemical data

Molecular Weight: 516.65614g/mol
Molecular Formula: C₂₅H₃₆N₆O₄S
Compound Is Canonicalized: True
XLogP3-AA: 3
Exact Mass: 516.25187482
Monoisotopic Mass: 516.25187482
Complexity: 894
Rotatable Bond Count: 11
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 8
Topological Polar Surface Area: 126
Heavy Atom Count: 36
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB7uABAAAAAAAAAAAAAAAAAAWLAAAAwQAAAAAAAAEABwAAAHgQYQAAADCzh3gYzx5PIBAKqAydydHDSDBEnsAAZ2Lm+XNgMZrrE/fuWvajm3BHI6UecyCCOAIAAgAAIAAABAAEAABAAAAAAAAAAAA==

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