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Sildenafil citrate

Sildenafil citrate Structure
CAS No.
171599-83-0
Chemical Name:
Sildenafil citrate
Synonyms
sildinafil;Xidinafei;5-[2-Ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4H-pyrazolo[5,4-e]pyrimidin-7-one citrate salt;Viagra;denafiL;Sildenafi;uk92480-10;silaenafil;citrate saL;Revatio citrate
CBNumber:
CB9407725
Molecular Formula:
C28H38N6O11S
Molecular Weight:
666.7
MOL File:
171599-83-0.mol
MSDS File:
SDS
Modify Date:
2024/9/25 14:54:50
Request For Quotation

Sildenafil citrate Properties

Melting point 187-189°C
storage temp. 2-8°C
solubility DMSO: >20mg/mL
form white powder
color White
Water Solubility 3.488g/L(temperature not stated)
Merck 14,8489
BCS Class 1
Stability Store in Freezer
InChIKey DEIYFTQMQPDXOT-UHFFFAOYSA-N
SMILES C1(=CC(=CC=C1OCC)S(=O)(=O)N1CCN(C)CC1)C1=NC(C2N(N=C(CCC)C=2N1)C)=O.C(O)(C(=O)O)(CC(=O)O)CC(=O)O
CAS DataBase Reference 171599-83-0(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  36
WGK Germany  3
RTECS  TL4284390
HS Code  2933595960
NFPA 704
0
2 0

Sildenafil citrate price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) SML3033 Sildenafil citrate ≥98% (HPLC) 171599-83-0 10MG ₹9093 2022-06-14 Buy
Sigma-Aldrich(India) SML3033 Sildenafil citrate ≥98% (HPLC) 171599-83-0 50MG ₹36707.58 2022-06-14 Buy
Sigma-Aldrich(India) PHR1807 Sildenafil Citrate Pharmaceutical Secondary Standard; Certified Reference Material 171599-83-0 500MG ₹16053.48 2022-06-14 Buy
TCI Chemicals (India) S0986 Sildenafil Citrate 171599-83-0 25MG ₹3000 2022-05-26 Buy
TCI Chemicals (India) S0986 Sildenafil Citrate 171599-83-0 100MG ₹5700 2022-05-26 Buy
Product number Packaging Price Buy
SML3033 10MG ₹9093 Buy
SML3033 50MG ₹36707.58 Buy
PHR1807 500MG ₹16053.48 Buy
S0986 25MG ₹3000 Buy
S0986 100MG ₹5700 Buy

Sildenafil citrate Chemical Properties,Uses,Production

Description

Sildenafil is a potent inhibitor of phosphodiesterase 5 (PDE5) with IC50 values of 3.6 and 3 nM for PDE5 activity in isolated rabbit platelets and human corpus cavernosum, respectively. It is selective for PDE5 over PDE1 and PDE3 (IC50s = 0.26 and 65 μM, respectively). Sildenafil reverses glucose-induced decreases in angiopoietin 1 (ANG1) expression and reduction of capillary-like tube formation by mouse dermal endothelial cells in vitro and increases the number of functional blood vessels and regional blood flow in the sciatic nerve in a db/db mouse model of diabetic peripheral neuropathy. It increases the ratio of maximum intracavernosal pressure to mean arterial blood pressure (ICP/MAP), a measure of erectile function, in castrated rats when administered at a dose of 20 mg/kg per day. Sildenafil (0.5 mg/kg) also reduces cardiac arrest and resuscitation-induced increases in angiotensin II , angiotensin converting enzyme (ACE), ACE2, and various angiotensin receptors and increases survival in a porcine model of ischemia/reperfusion injury. Formulations containing sildenafil have been used in the treatment of erectile dysfunction, pulmonary arterial hypertension, and high-altitude pulmonary edema associated with altitude sickness.

Chemical Properties

Sildenafil citrate is a white to off-white crystalline powder soluble in DMF, acetic acid and slightly soluble in methanol. Solubility of sildenafil citrate is pH dependent and it decreases with increase of pH. pH ranges between 3.7 and 3.8 and the pKa from 8.2 to 9.6.

Uses

Sildenafil citrate is an orally active selective type 5 cgmp phosphodiesterase inhibitor that is used in the treatment of erectile dysfunction and primary pulmonary hypertension.

Definition

ChEBI: Sildenafil citrate is the citrate salt of sildenafil. It has a role as a vasodilator agent and an EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor. It contains a sildenafil.

General Description

Sildenafil Citrate is the citrate salt form of sildenafil, an orally bioavailable pyrazolopyrimidinone derivative structurally related to zaprinast, with vasodilating and potential anti-inflammatory activities. Upon oral administration, sildenafil selectively targets and inhibits cyclic guanosine monophosphate (cGMP)-specific phosphodiesterase type 5 (PDE5), thereby inhibiting the PDE5-mediated degradation of cGMP found in smooth muscle and increasing cGMP availability. This results in prolonged smooth muscle relaxation in the corpus cavernosum of the penis, thereby causing vasodilation, blood engorgement and a prolonged penile erection.  In the smooth muscle of the pulmonary vasculature, the increase in cGMP results in smooth muscle relaxation, vasodilation of the pulmonary vascular bed, relieving pulmonary hypertension and increasing blood flow in the lungs. In addition, sildenafil may reduce airway inflammation and mucus production.

Biological Activity

Orally active, potent inhibitor of phosphodiesterase 5 (PDE5) (IC 50 = 4 nM). Enhances nitric oxide-dependent relaxation of human corpus cavernosum in vitro .

Pharmacokinetics

Analysis of Middle Eastern data (mean ± SD) revealed Cmax = 398.9 ± 107.7 ng/ml; Tmax = 1.84 ± 0.22 h; t1/2 = 2.66 ± 0.97 h; AUC0–24 = 1475 ± 515.3 ng.h/ml; AUC0-∞ = 1556 ± 567.58 ng.h/ml.

Side effects

The more common side effects of sildenafil citrate include: headache, skin flushing, indigestion, abnormal vision, nasal congestion, back pain, nausea, dizziness, rash, etc.

Safety Profile

A poison by ingestion. Human systemic effects. When heated to decomposition it emits toxic vapors of NOx and SOx.

Synthesis

The synthesis of sildenafil citrate was first reported in the Bioorganic & Medicinal Chemistry Letters, Vol 6, pp. 1819, 1824, 1996. The reaction scheme is reproduced below. Sildenafil was reported in this journal as "a potent and selective inhibitor of type 5 PDE with utility for the treatment of male erectile dysfunction".
synthesis of sildenafil citrate
The first step of the synthesis is the reaction of a diketoester (1) and hydrazine to give the pyrazole ring. The regioselective N-methylation of the pyrazole and hydrolysis gives a carboxylic acid (3). Compound (3) is then reacted with HNO3 and H2SO4 to give a nitrated product.
This is then followed by a carboxamide formation and the reduction of the nitro group. The compound (4) is then acylated under basic conditions and this produces the pyrazolopyrimidinone (6). (6) is then chlorosulphonylated selectively on the 5'-position of the phenyl ring. This can then couple with an amine to give sildenafil (7).
www.ch.ic.ac.uk/local/projects/p_hazel/synthesis2.html

Sildenafil citrate Preparation Products And Raw materials

Raw materials

Dimethyl sulfate 4-Dimethylaminopyridine Ethyl 3-n-propylpyrazole-5-carboxylate Thionyl chloride Sodium hydroxide
Nitric acid Hydrochloric acid Triethylamine 2-Ethoxybenzoyl chloride 4-Methylpiperidine
Hydrogen peroxide Stannous chloride dihydrate
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Preparation Products

Sildenafil citrate Suppliers

Global( 734)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
Cadila Pharmaceuticals Ltd +91-7069076657 +91-7069076657 Ahmedabad, India 54 58 Inquiry
ANWITA APIS +919000311012 Hyderabad, India 198 58 Inquiry
THE MOLECULEZ +91-7506703683 +91-7506703683 Maharashtra, India 79 58 Inquiry
AARTIA KEM SCIENCE +91-8291072530 +91-8291072530 Maharashtra, India 70 58 Inquiry
Apotex Pharmachem India Pvt Ltd +91-8022891034 +91-8022891000 Karnataka, India 109 58 Inquiry
Macleods Pharmaceuticals Limited +91-2266762800 +91-2266762800 Maharashtra, India 116 58 Inquiry
Hetero Drugs Limited +91-4023704923 +91-4023704923 Telangana, India 296 58 Inquiry
Virchow Groups +919394860022 Telangana, India 24 58 Inquiry
Smilax Laboratories Limited +91-8919514965 +91-8008333438 Telangana, India 28 58 Inquiry
HRV Global Life Sciences +91-9820219686 +91-9820219686 Telangana, India 379 58 Inquiry
Supplier Advantage
Cadila Pharmaceuticals Ltd 58
ANWITA APIS 58
THE MOLECULEZ 58
AARTIA KEM SCIENCE 58
Apotex Pharmachem India Pvt Ltd 58
Macleods Pharmaceuticals Limited 58
Hetero Drugs Limited 58
Virchow Groups 58
Smilax Laboratories Limited 58
HRV Global Life Sciences 58

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Sildenafil citrate Spectrum

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1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine citrate salt 1-[[3-(6,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine, 2-hydroxy-1,2,3-propanetricarboxylate Sildenafil Citrate (100 mg) Sildenafil citrate, >=99% Sildenafil citrate, Professional supply 5-[2-Ethoxy-5-[(4-methyl-piperazin-1-yl)sulfonyl]phenyl]-1,6-dihydro-1-methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one citrate 5-(2-Ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]py SILDENAFIL CITRATE PH.EUR 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4H-pyrazolo[5,4-e]pyrimidin-7 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl)sulfonyl-phenyl]-1-methyl-3-propyl-6H-pyrazolo[4,3-d]pyrimidin-7-one citrate salt din-5-yl)-4-ethoxyphenyl)sulfonyl)-4-methyl-,2-hydroxy-1,2,3-propanetricarbo piperazine,1-((3-(4,7-dihydro-1-methyl-7-oxo-3-propyl-1h-pyrazolo(4,3-d)pyrimi 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-,2-hydroxy-1,2,3-propanetricarboxylate(1:1) uk92480-10 SILDENAFIL CITRATE 1-[[3-(4,7-DIHYDRO-1-METHYL-7-OXO-3-PROPYL-1H-PYRAZOLO[4,3-D]PYRIMIDIN-5-YL)-4-ETHOXYPHENYL]SULFONYL]-4-METHYLPIPERAZINE, CITRATE 1-[[3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1h-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine citrate SILDANAFIL CITRATE (BULK) SildenafilBaseC28H38N6O11S SildenafilCitrate/SildenafilBaseC28H38N6O11S 5(2-ETHOXY-5(4-METHYLPIPERAZINE)SULPHONYLPHENYL)-1 SILDENAFIL CITRATE(RG) Methylpiperazine citrate Revatio citrate UK-92480 citrate 1-[[3-(6,7-dihydro-1-Methyl-7-oxo-3-propyl-1h-pyrazolo[4,3-d]pyriMidin-5-yl)-4-ethoxyphenyl] 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxyphenyl]sulfonyl]-4-methylpiperazine citrate SildenafilCitrate, aimee(at)speedgainpharma.com 99% high purity sex powder sildenafil and sildenafile citrate 5-(2-ETHOXY PHENYL)-1-METHYL-3-N-PROPYL- 1, 6-DIHYDRO-7H-PYRAZOLO-4,3-D-PYRIMIDIN E-ONE Sildenal Citrate ldenafil Citrate IN STOCK SILDENAFIL CITRATE CAS NO.171599-83-0 Sildenafili citras Sildenafil citrate sex powder enhancement kf-wang(at)kf-chem.com SILDENAFIL CITRATE USP (5-[2-ETHOXY-5-[ 4-METHYLPIPERAZIN-1-YL SULFONYL) PHENYL] 1-METHYL-3-PROPYL-1 6-DIHYDRO-7H-PYRAZO citrate saL denafiL Sildenafi Sildenafil Citrate Standard Sildenafil citrate CRS 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl-sulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazol[4,3d]pyrimidin-7-one citrate Sex Powder Sildenafil 5-(2-Ethoxy-5-((4-methylpiperazin-1-yl)sulfonyl)phenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(4H)-one 2-hydroxypropane-1,2,3-tricarboxylate sildnafil sildnafile Sildena Citrate Viag Raw Powder Sildenafil citrate USP/EP/BP silaenafil Sildenafil Citrate (UK-92480 citrate 1-[[3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d Sildenaf citrate Sildenafil and Sildenafil Citrate Sildenafil for peak identification (Y0001891) Sildenafil citrateQ: What is Sildenafil citrate Q: What is the CAS Number of Sildenafil citrate Q: What is the storage condition of Sildenafil citrate Sildenafil citrate (Y0001578) Sildenafil Citrate (1612561) 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4H-pyrazolo[5,4-e]pyrimidin-7-one citrate salt Xidinafei