Sildenafil citrate

Base Information

• Chemical Name: Sildenafil citrate
• CAS No.: 171599-83-0
• Molecular Formula: C₆H₈O₇*C₂₂H₃₀N₆O₄S
• Molecular Weight: 666.709
• Hs Code.: 2933595960
• Mol file: 171599-83-0.mol

Synonyms:Piperazine,1-[[3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methyl-(9CI);5-[2-Ethoxy-5-(4-methyl-1-piperazinylsulfonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one;Revatio;

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Chemical Property of Sildenafil citrate

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 187-189 °C
• Refractive Index: 1.683
• Boiling Point: 672.4 °C at 760 mmHg
• Flash Point: 360.5 °C
• PSA: 253.93000
• Density: 1.447g/cm3
• LogP: 1.31900
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: >20mg/mL
• Water Solubility.: 3.488g/L(temperature not stated)

Purity/Quality:

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Composition and Structure: Sildenafil citrate, marketed under the brand name Viagra?, is a salt of a pyrazolopyrimidine derivative. Its chemical structure resembles cyclic guanosine monophosphate (cGMP), responsible for vasodilation effects.
• Uses: Sildenafil citrate was developed by Pfizer-Pharmaceutical Company and has been marketed since 1998.; Sildenafil citrate is primarily used for the treatment of erectile dysfunction (ED) and pulmonary hypertension. It has demonstrated efficacy in improving erectile function and increasing exercise capacity in patients with pulmonary arterial hypertension.
• Mechanism of Action: Sildenafil citrate is a potent and selective inhibitor of cGMP-specific phosphodiesterase type 5 (PDE5). By blocking PDE5, it increases levels of cGMP, leading to smooth muscle relaxation and vasodilation, particularly in the corpus cavernosum of the penis.
• Regulatory Status: Sildenafil citrate was approved by the FDA in March 1998 for the on-demand treatment of erectile dysfunction. It was the first phosphodiesterase type 5 (PDE5) inhibitor licensed for this indication. Since then, it has become one of the most widely prescribed medications worldwide.
• Pharmacokinetics: Sildenafil citrate is orally administered and absorbed quickly, with onset of action within 1 hour. However, its relative bioavailability is limited (~41%) due to hepatic first-pass metabolism. Various formulation strategies have been developed to improve its solubility and bioavailability.
• Other Uses: Sildenafil citrate has been investigated for various indications beyond erectile dysfunction and pulmonary hypertension, including flap survival, wound healing, and management of pressure ulcers.

Technology Process of Sildenafil citrate

There total 5 articles about Sildenafil citrate 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:

citric acid (77-92-9,906507-37-7) + sildenafil (139755-83-2) → sildenafil citrate (171599-83-0)

Guidance literature:

at 80 - 90 ℃; for 0.166667h; pH=3 - 4; pH-value;

Reference yield:

1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxamide (139756-01-7) → sildenafil citrate (171599-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sulfuric acid / ethyl acetate / 0.5 h / 40 - 45 °C / pH 2 - 3

1.2: 3.83 h / 60 - 65 °C

2.1: thionyl chloride / 25 - 35 °C

3.1: 1 h / 70 - 80 °C

4.1: chlorosulfonic acid / 2 h / 25 - 30 °C

4.2: 3 h / Reflux

5.1: 2 h / 20 - 30 °C

6.1: 0.17 h / 80 - 90 °C / pH 3 - 4

With chlorosulfonic acid; thionyl chloride; sulfuric acid; In ethyl acetate;

Reference yield:

C17H20N4O2 → sildenafil citrate (171599-83-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chlorosulfonic acid / 2 h / 25 - 30 °C

1.2: 3 h / Reflux

2.1: 2 h / 20 - 30 °C

3.1: 0.17 h / 80 - 90 °C / pH 3 - 4

With chlorosulfonic acid;

upstream raw materials:

citric acid

sildenafil

4-[(2-ethoxybenzoyl)amino]-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carboxamide

Refernces