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 ID: 72676
• Molecular Formular: C28H38N6O11S
• Molecular Mass: 666.69992
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: citro; sildenafil; citric acid; sildenafil
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 7.6270576
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.7387564
• LogD (pH = 7.4): 1.158596
• Log P: 1.229504
• Molar Refractivity: 139.8739 cm^3
• Polarizability: 48.292347 Å^3
• Polar Surface Area: 109.13 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >20 mg/mL
• Apperance: white powder; White Solid
• Melting Point: 187-189°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: Store in Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: room temp

Pharmacology Properties

• Target: PDE

Product Information

• Purity: ≥98% (HPLC); 97%
• Salt Data: Citrate
• Empirical Formula (Hill Notation): C22H30N6O4S ·C6H8O7

DETAILS

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.

REFERENCES

• 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)