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バイアグラ

バイアグラ 化学構造式
171599-83-0
CAS番号.
171599-83-0
化学名:
バイアグラ
别名:
バイアグラ;クエン酸シルデナフィル;シルデナフィルくえん酸塩;1-[[3-(4,7-ジヒドロ-1-メチル-7-オキソ-3-プロピル-1H-ピラゾロ[4,3-d]ピリミジン-5-イル)-4-エトキシフェニル]スルホニル]-4-メチルピペラジンくえん酸塩;5-[2-エトキシ-5-[(4-メチルピペラジン-1-イル)スルホニル]フェニル]-1-メチル-3-プロピル-1H-ピラゾロ[4,3-d]ピリミジン-7(6H)-オンくえん酸塩;シルデナフィルくえん酸塩標準品;シルデナフィル クエン酸塩;シルデナフィルクエン酸塩 (JAN)
英語化学名:
Sildenafil citrate
英語别名:
VIAGRA;denafiL;Xidinafei;Sildenafi;uk92480-10;sildinafil;silaenafil;citrate saL;Viagra citrate;Revatio citrate
CBNumber:
CB9407725
化学式:
C28H38N6O11S
分子量:
666.7
MOL File:
171599-83-0.mol

バイアグラ 物理性質

融点 :
187-189°C
貯蔵温度 :
2-8°C
溶解性:
DMSO: >20mg/mL
外見 :
white powder
水溶解度 :
3.488g/L(temperature not stated)
Merck :
14,8489
安定性::
Store in Freezer
InChIKey:
DEIYFTQMQPDXOT-UHFFFAOYSA-N
CAS データベース:
171599-83-0(CAS DataBase Reference)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xi
Rフレーズ  36/37/38
Sフレーズ  36
WGK Germany  3
RTECS 番号 TL4284390
HSコード  2933595960
絵表示(GHS)
注意喚起語 Warning
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H319 強い眼刺激 眼に対する重篤な損傷性/眼刺激 性 2A 警告 P264, P280, P305+P351+P338,P337+P313P
H335 呼吸器への刺激のおそれ 特定標的臓器毒性、単回暴露; 気道刺激性 3 警告
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P305+P351+P338 眼に入った場合:水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

バイアグラ 価格 もっと(19)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01TOC3784 くえん酸シルデナフィル
Sildenafil citrate
171599-83-0 5mg ¥24000 2020-09-21 購入
富士フイルム和光純薬株式会社(wako) W01TOC3784 くえん酸シルデナフィル
Sildenafil citrate
171599-83-0 10mg ¥41000 2018-12-26 購入
東京化成工業 S0986 シルデナフィルくえん酸塩 >98.0%(HPLC)
Sildenafil Citrate >98.0%(HPLC)
171599-83-0 25mg ¥3000 2021-03-23 購入
東京化成工業 S0986 シルデナフィルくえん酸塩 >98.0%(HPLC)
Sildenafil Citrate >98.0%(HPLC)
171599-83-0 100mg ¥6500 2021-03-23 購入
Sigma-Aldrich Japan PHR1807 Pharmaceutical Secondary Standard; Certified Reference Material
Sildenafil Citrate Pharmaceutical Secondary Standard; Certified Reference Material
171599-83-0 500mg ¥24400 2021-03-23 購入

バイアグラ 化学特性,用途語,生産方法

外観

白色~わずかにうすい褐色、結晶~粉末

溶解性

水及びメタノールに溶けにくく、エタノール(95)にほとんど溶けない。

解説

C22H30N6O4S(474.6).ホスホジエステラーゼの阻害剤で,インポテンツの改善薬として使われている.[CAS 171599-83-0]"
森北出版「化学辞典(第2版)

用途

強力なホスホジエステラーゼ 5(PDE5)阻害剤です(IC50=4 nM)。経口活性があります。

用途

強力なホスホジエステラーゼ 5(PDE5)阻害剤です(IC50=4 nmol/l)。経口活性があります。

用途

ホスホジエステラーゼ5 (PDE-5)酵素活性阻害作用を示します。

用途

ホスホジエステラーゼ5 (PDE-5)酵素活性阻害作用を示します。

効能

血管拡張薬, 勃起不全治療薬, ホスホジエステラーゼV阻害薬

商品名

シルデナフィル (あすか製薬); シルデナフィル (キッセイ薬品工業); シルデナフィル (シオノケミカル); シルデナフィル (大興製薬); シルデナフィル (大興製薬); シルデナフィル (大興製薬); シルデナフィル (富士化学工業); シルデナフィル (東和薬品); シルデナフィル (武田テバファーマ); シルデナフィル (辰巳化学); シルデナフィル (陽進堂); バイアグラ (ファイザー); レバチオ (ファイザー)

使用上の注意

アルゴン封入

化学的特性

White Solid

Originator

Alsigra,Alembic Ltd.,India

使用

An orally active selective type 5 cGMP phosphodiesterase inhibitor

使用

agent

使用

Enzyme inhibitor

定義

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

生物活性

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

安全性プロファイル

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.

バイアグラ 上流と下流の製品情報

原材料

準備製品


バイアグラ 生産企業

Global( 419)Suppliers
名前 電話番号 ファックス番号 電子メール 国籍 製品カタログ 優位度
Beijing Yibai Biotechnology Co., Ltd
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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
+86 15821988213 info@longyupharma.com China 2471 58
Shenzhen Excellent Biotech Co., Ltd.
13480692018
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Hebei Bonster Technology Co.,Limited
+86-13315996897
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Qingdao kaimoshi biochemical technology co., ltd.
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Shanghai UCHEM Inc.
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Beijing Cooperate Pharmaceutical Co.,Ltd
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171599-83-0(バイアグラ)キーワード:


  • 171599-83-0
  • Viagra, 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 salt
  • 5-[2-Ethoxy-5-(4-methylpiperazin-1-yl)sulfonylphenyl]-1-methyl-3-propyl-4H-pyrazolo[5,4-e]pyrimidin-7-one 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
  • VIAGRA
  • 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
  • Sildenafil citrate - Viagra | UK 92480
  • 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
  • Xidinafei
  • SILDANAFIL CITRATE (BULK)
  • SildenafilBaseC28H38N6O11S
  • SildenafilCitrate/SildenafilBaseC28H38N6O11S
  • バイアグラ
  • クエン酸シルデナフィル
  • シルデナフィルくえん酸塩
  • 1-[[3-(4,7-ジヒドロ-1-メチル-7-オキソ-3-プロピル-1H-ピラゾロ[4,3-d]ピリミジン-5-イル)-4-エトキシフェニル]スルホニル]-4-メチルピペラジンくえん酸塩
  • 5-[2-エトキシ-5-[(4-メチルピペラジン-1-イル)スルホニル]フェニル]-1-メチル-3-プロピル-1H-ピラゾロ[4,3-d]ピリミジン-7(6H)-オンくえん酸塩
  • シルデナフィルくえん酸塩標準品
  • シルデナフィル クエン酸塩
  • シルデナフィルクエン酸塩 (JAN)
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