2-hydroxypropane-1,2,3-tricarboxylic acid; 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one

• ChemBase编号: 72676
• 分子式: C28H38N6O11S
• 平均质量: 666.69992
• 单一同位素质量: 666.23192707
• SMILES: c1(ccc(c(c1)c1nc2c(c(=O)[nH]1)n(nc2CCC)C)OCC)S(=O)(=O)N1CCN(CC1)C.C(C(=O)O)C(CC(=O)O)(O)C(=O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)(CC(=O)O)O.CCCc1nn(c2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C)C
• InChI: InChI=1S/C22H30N6O4S.C6H8O7/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28;7-3(8)1-6(13,5(11)12)2-4(9)10/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
• InChIKey: DEIYFTQMQPDXOT-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-hydroxypropane-1,2,3-tricarboxylic acid; 5-{2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]phenyl}-1-methyl-3-propyl-1H,6H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC传统名: citro; sildenafil; citric acid; sildenafil
• 别名: Viagra; Revatio; 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; UK-92,480; Sildenafil citrate salt; 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

登记号

• CAS号: 171599-83-0
• MDL号: MFCD09026931
• PubChem SID: 162037597
• PubChem CID: 62853

理论计算性质

• Acid pKa: 7.6270576
• 质子受体: 7
• 质子供体: 1
• LogD (pH = 5.5): 0.7387564
• LogD (pH = 7.4): 1.158596
• Log P: 1.229504
• 摩尔折射率: 139.8739 cm^3
• 极化性: 48.292347 Å^3
• 极化表面积: 109.13 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; DMSO: >20 mg/mL
• 外观: white powder; White Solid
• 熔点: 187-189°C

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: Store in Freezer
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 保存温度: room temp

药理学性质

• 作用靶点: PDE

产品相关信息

• 纯度: ≥98% (HPLC); 97%
• 成盐信息: Citrate
• Empirical Formula (Hill Notation): C22H30N6O4S ·C6H8O7

详细说明

Selleck Chemicals - S1431

Research Area: Cardiovascular Disease
Biological Activity:
Sildenafil citrate is an agent used to treat erectile dysfunction and pulmonary arterial hypertension (PAH). It acts by inhibiting cGMP specific phosphodiesterase type 5, an enzyme that regulates blood flow in the penis. Sildenafil has been the prime treatment for erectile dysfunction. [1]

Sigma Aldrich - PZ0003

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Sildenafil is a potent, selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5). Sildenafil is used to treat erectile dysfunction and pulmonary arterial hypertension. NO activates guanylate cyclase, which results in increased levels of cGMP, producing smooth muscle relaxation. Sildenafil enhances the effect of NO by inhibiting PDE5, which is responsible for degradation of cGMP.

Toronto Research Chemicals - S435000

An orally active selective type 5 cGMP phosphodiesterase inhibitor.

参考文献

• http://en.wikipedia.org/wiki/Sildenafil_citrate
• Terrett, N.K., et al.: Bioorg. Med. Chem. Lett., 6, 1819 (1996)
• Goldstein, I., et al.: N. Engl. J. Med., 338, 1397 (1996)