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Sildenafil citrate

Sildenafil citrate
Sildenafil citrate structure
CAS No.
171599-83-0
Chemical Name:
Sildenafil citrate
Synonyms
VIAGRA;denafiL;Sildenafi;Xidinafei;uk92480-10;sildinafil;citrate saL;Viagra citrate;Revatio citrate;UK-92480 citrate
CBNumber:
CB9407725
Molecular Formula:
C28H38N6O11S
Formula Weight:
666.7
MOL File:
171599-83-0.mol

Sildenafil citrate Properties

Melting point:
187-189°C
storage temp. 
Desiccate at RT
solubility 
DMSO: >20mg/mL
form 
white powder
Water Solubility 
3.488g/L(temperature not stated)
Merck 
14,8489
Stability:
Store in Freezer
InChIKey
DEIYFTQMQPDXOT-UHFFFAOYSA-N
CAS DataBase Reference
171599-83-0(CAS DataBase Reference)
FDA UNII
BW9B0ZE037
NCI Dictionary of Cancer Terms
Viagra
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P305+P351+P338-P261
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  36
WGK Germany  3
RTECS  TL4284390
HS Code  2933595960

Sildenafil citrate price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1807 Sildenafil citrate Pharmaceutical Secondary Standard; Certified Reference Material 171599-83-0 500mg $129 2020-08-18 Buy
Sigma-Aldrich 1612561 Sildenafil citrate United States Pharmacopeia (USP) Reference Standard 171599-83-0 100mg $769 2020-08-18 Buy
TCI Chemical S0986 Sildenafil Citrate >98.0%(HPLC) 171599-83-0 25mg $12 2020-06-24 Buy
TCI Chemical S0986 Sildenafil Citrate >98.0%(HPLC) 171599-83-0 100mg $34 2020-06-24 Buy
Cayman Chemical 14008 Sildenafil Citrate ≥98% 171599-83-0 10mg $37 2020-06-24 Buy

Sildenafil citrate Chemical Properties,Uses,Production

Chemical Properties

White Solid

Originator

Alsigra,Alembic Ltd.,India

Uses

An orally active selective type 5 cGMP phosphodiesterase inhibitor

Uses

agent

Uses

Enzyme inhibitor

Definition

ChEBI: The citrate salt of sildenafil.

Manufacturing Process

A mixture of 3-n-propylpyrazole-5-carboxylic acid ethyl ester (24.1 g, 0.132 mol) (prepared by the method of Chem. Pharm. Bull., 1984, 32, 1568) and dimethyl sulfate (16.8 g, 0.133 mol) were heated to 90°C for 2.5 h. The mixture was dissolved in dichloromethane and the solution washed with sodium carbonate solution. The organic phase was separated, dried (MgSO4) and evaporated under vacuum to give a solid. Chromatography on silica gel (300 g), eluting with dichloromethane gave the 1-methyl-3-n-propylpyrazole- 5-carboxylic acid ethyl ester as a colourless oil (20.4 g, 79%).
1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester (20.2 g, 0.10 mol) was suspended in 6 N aqueous sodium hydroxide solution (50 ml, 0.30 mol). The mixture was heated to 80°C for 2 h then diluted with water (50 ml) and acidified with concentrated hydrochloric acid (25 ml). Filtration gave the 1- methyl-3-n-propylpyrazole-5-carboxylic acid as pale brown crystals (12.3 g, 71%), melting point 150°-154°C.
1-Methyl-3-n-propylpyrazole-5-carboxylic acid (12.1 g, 0.072 mol) was added portionwise to a mixture of oleum (13 ml) and fuming nitric acid (11 ml), keeping the temperature below 60°C. After the addition, the mixture was heated at 60°C overnight and then cooled to room temperature before being poured onto ice. Filtration of the precipitate gave the 1-methyl-4-nitro-3-npropylpyrazole- 5-carboxylic acid as a white solid (11.5 g, 75%), melting point 124°-127°C.
1-Methyl-4-nitro-3-n-propylpyrazole-5-carboxylic acid (11.3 g, 0.053 mol) was added to thionyl chloride (50 ml) and the resulting mixture heated under reflux for 3 h. The reaction mixture was then cooled and excess thionyl chloride removed by evaporation under vacuum. The oily residue was dissolved in acetone (50 ml) and the solution cautiously added to a mixture of ice (50 g) and concentrated aqueous ammonium hydroxide solution (50 ml). The precipitate was collected by filtration to provide the 1-methyl-4-nitro-3-npropylpyrazole- 5-carboxamide as a pale yellow solid (8.77 g, 78%), melting point 141°-143°C.
1-Methyl-4-nito-3-n-propylpyrazole-5-carboxamide (3.45 g, 16.2 mmol) and stannous chloride dihydrate (18.4 g, 81 mmol) were suspended in ethanol and the mixture heated under reflux for 2 h. The resulting solution was cooled to room temperature, basified to pH 9 by the addition of 2 N aqueous sodium hydroxide solution and extracted with dichloromethane (3 x 150 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum. Trituration of the residue with ether gave the 4-amino-1-methyl-3-npropylpyrazole- 5-carboxamide as an off-white solid (2.77 g, 94%), melting point 98°-101°C.
A solution of 2-ethoxybenzoyl chloride (6.1 g, 33.0 mmol) in dichloromethane (50 ml) was added to a stirred solution of 4-amino-1-methyl-3-npropylpyrazole- 5-carboxamide (3.0 g, 16.4 mmol), 4-dimethylaminopyridine (0.02 g, 0.1 64 mmol) and triethylamine (3.34 g, 33.0 mmol) in dichloromethane (50 ml) at 0°C. The resulting mixture was allowed to warm to room temperature and stirred for a further 2 h. The solvent was evaporated under vacuum, the residue dissolved in a 19:1 mixture of dichloromethane and methanol (250 ml), and then the solution washed with 1 N hydrochloric acid (100 ml), dried (MgSO4) and evaporated under vacuum. The crude material was chromatographed on silica gel (200 g), eluting with a 97:3 mixture of dichloromethane and methanol, to give a pink solid; crystallisation from ethyl acetate-hexane gave the 4-(2-ethoxybenzamido)-1-methyl-3-npropylpyrazole- 5-carboxamide as a pale pink solid (2.2 g, 40%), melting point 153°-155°C.
4-(2-Ethoxybenzamido)-1-methyl-3-n-propylpyrazole-5-carboxamide (223 g, 0.676 mol) was added portionwise to a solution of sodium hydroxide (54 g, 1.35 mol) and 30% hydrogen peroxide solution (224 ml) in water (2000 ml). Ethanol (700 ml) was added and the resulting mixture heated under reflux for 2.5 h, cooled, then evaporated under vacuum. The resulting solid was treated with 2 N hydrochloric acid (380 ml), with external cooling, and the mixture was extracted with dichloromethane (1 x 700 ml, 3 x 200 ml). The combined organic extracts were washed successively with saturated aqueous sodium carbonate solution (3 x 400 ml) and brine (300 ml), then dried (Na2SO4) and evaporated under vacuum. Chromatography of the residue on silica gel (1000 g), using a methanol in dichloromethane elution gradient (0-1%), followed by trituration of the crude product with ether (300 ml), gave the 5-(2- ethoxyphenyl)-1-methyl-3-n-propyl-l,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin- 7-one as a colourless solid (152.2 g, 72%), melting point 143°-146°C.
5-(2-Ethoxyphenyl)-1-methyl-3-n-propyl-l,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-one (10.0 g, 32.1 mmol) was added portionwise to chlorosulfonic acid (20 ml) at 0°C under a nitrogen atmosphere. After being stirred overnight, the reaction solution was cautiously added to ice-water (150ml) and the aqueous mixture extracted with a 9:1 mixture of dichloromethane and methanol (4 x 100 ml). The combined extracts were dried (Na2SO4) and evaporated under vacuum to give the required 5-(5-chlorosulphonyl-2- ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin- 7-one as a white solid (12.8 g, 97%), melting point 179°-181°C.
4-Methylpiperidine was added to a stirred suspension of 5-(5-chlorosulphonyl- 2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3- d]pyrimidin-7-one in ethanol at room temperature. The resulting mixture was stirred for 4 days before removing the solvent by evaporation under vacuum. The residue was dissolved in a 9:1 mixture of dichloromethane and methanol and the solution washed with saturated aqueous sodium carbonate solution. The aqueous phase was further extracted with dichloromethane-methanol mixtures (3 x 100 ml) and all the organic fractions were combined, dried (MgSO4) and evaporated under vacuum to give a solid. Crystallisation from a mixture of methanol-dimethylformamide gave the 5-[2-ethoxy-5-(4- methylpiperidinylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7Hpyrazolo[ 4,3-d]-pyrimidin-7-one as an off-white solid, melting point 187°- 189°C.
After addition of citric acid to the 5-[2-ethoxy-5-(4- methylpiperidinylsulphonyl)phenyl]-1-methyl-3-n-propyl-1,6-dihydro-7Hpyrazolo[ 4,3-d]-pyrimidin-7-one (sildenafil) the it's salt is obtained, namely sildenafil citrate.

brand name

Viagra (Pfizer).

Therapeutic Function

Vasodilator

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 .

Safety Profile

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

Veterinary Drugs and Treatments

Sildenafil may be of benefit in the adjunctive treatment of pulmonary hypertension in small animals.
In humans, sildenafil is indicated for erectile dysfunction or pulmonary hypertension.

structure and hydrogen bonding

Sildenafil citrate (SC) has been widely used for the treatment of erectile disorder. A detailed study concerning solid-state structure of this compound is very important for understanding enzyme (PDE5)-inhibitor (sildenafil) interaction. It is also of interest to determine sildenafil’s protonation sites, as they may be responsible for its binding to the phosphodiesterase acidic amino acids.
Sildenafil citrate (Viagra)  and sildenafil base in pure form were characterized by 1H, 13C, 15N NMR spectroscopy in solution, solid-state, and pharmaceutical dosage forms.42 The analysis of chemical shifts showed that: (i) N6-H forms intramolecular hydrogen bonds, (ii) N25 is protonated in the salt, and (iii) intermolecular OH. . .N hydrogen bonds involving N2 and N4 are present in the solid sildenafil citrate. The 13C CPMAS spectra of the tablets containing different amounts of sildenafil citrate were recorded and showed that chemical shifts of sildenafil citrate in pure form and in pharmaceutical dosage forms are the same. SC is easily detected in the pharmaceutical dosage forms since only two of its carbon resonances (OCH2 and quaternary carbon of the citrate anion) fall into carbohydrate-type region of the excipient.
Solid-state 13C and 15N MAS NMR have recently been used to investigate how water interacts with SC.43 When the humidity is altered, the water concentration in the solid compound changes but does not reach a stoichiometric (e.g., 1:1) ratio to form a true hydrate. Only one set of 15N and 13C signals was observed for each humidity level indicating that water incorporated into the crystal lattice of SC is very mobile and exchanges rapidly between various sites. The 13C data showed the formation of a hydrogen bond between water molecule and one carbonyl of the citrate anion. The spectra also show that the water content affects the conformation of the propyl group. Additionally, 15N dipolar dephasing (DD) experiments confirmed that the sildenafil molecule is only protonated in the piperazine ring.

Sildenafil citrate Preparation Products And Raw materials

Raw materials

Preparation Products


Sildenafil citrate Suppliers

Global( 330)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Beijing Yibai Biotechnology Co., Ltd
0086-182-6772-3597
sales04@yibaibiotech.com CHINA 420 58
Cangzhou Wanyou New Material Technology Co.,Ltd
18631714998
sales@czwytech.com CHINA 914 58
Shanghai Longyu Biotechnology Co., Ltd.
+8615821988213
info@longyupharma.com CHINA 894 58
Shenzhen Excellent Biotech Co., Ltd.
13480692018
ramyan@ex-biotech.com;sale@ex-biotech.com CHINA 960 58
Hebei Bonster Technology Co.,Limited
+86-13315996897
0086-13315996897 Wendy@bsterltd.com CHINA 986 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22625 55
Nanjing Finetech Chemical Co., Ltd.
025-85710122 17714198479
025-85710122 sales@fine-chemtech.com CHINA 890 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 24886 60
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 2754 55

View Lastest Price from Sildenafil citrate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2020-09-09 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
171599-83-0
US $10.00 / g 1g 99% 50tons Xingtai pinmai biology science and technology co., ltd
2020-08-24 Sildenafil citrate
171599-83-0
US $115.00 / KG 1KG 99%min 1500 Kilogram/Kilograms per Day Hebei Runbin Biotechnology Co. LTD
2019-08-16 Sildenafil citrate
171599-83-0
US $0.00-0.00 / KG 1g 99%+ 500kg/month Beijing Yibai Biotechnology Co., Ltd

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