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

• ChemBase ID: 130421
• Molecular Formular: C28H38N6O11S
• Molecular Mass: 666.69992
• Monoisotopic Mass: 666.23192707
• SMILES: O=S(=O)(N1CCN(C)CC1)c1cc(c2nc(=O)c3c([nH]2)c(nn3C)CCC)c(OCC)cc1.O=C(O)C(O)(CC(=O)O)CC(=O)O
• Canonical SMILES: OC(=O)CC(C(=O)O)(CC(=O)O)O.CCCc1nn(c2c1[nH]c(nc2=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,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one
• IUPAC Traditional name: citro; revatio
• Brand Name: Viagra
• Synonyms: Sildenafil

Database IDs

• CAS Number: 139755-83-2
• PubChem SID: 162224700
• PubChem CID: 5281023; 62853
• CHEBI ID: 58987
• ATC CODE: G04BE03
• CHEMBL: 1737
• Chemspider ID: 56586
• DrugBank ID: DB00203
• KEGG ID: D08514
• Unique Ingredient Identifier: 3M7OB98Y7H
• Wikipedia Title: Sildenafil
• Medline Plus: a699015

CALCULATED PROPERTIES

• Acid pKa: 7.2715216
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.248865
• LogD (pH = 7.4): 1.4989928
• Log P: 1.6464821
• Molar Refractivity: 139.4405 cm^3
• Polarizability: 48.495518 Å^3
• Polar Surface Area: 109.13 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 40%
• Excretion: Fecal (80%) and renal (around 13%)
• Half Life: 3 to 4 hours
• Metabolism: Hepatic (mostly CYP3A4, also CYP2C9)
• Legal Status: Rx-only
• Pregnancy Category: B (US)
• US Licence: Sildenafil
• EU Licence: Viagra