5-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]pyridin-3-yl}-3-ethyl-2-(2-methoxyethyl)-2H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one; benzenesulfonic acid

• ChemBase ID: 154937
• Molecular Formular: C29H39N7O8S2
• Molecular Mass: 677.79206
• Monoisotopic Mass: 677.23015324
• SMILES: CCc1c2c(c(=O)nc([nH]2)c2cc(cnc2OCC)S(=O)(=O)N2CCN(CC2)CC)nn1CCOC.c1ccc(cc1)S(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)c1ccccc1.COCCn1nc2c(c1CC)[nH]c(nc2=O)c1cc(cnc1OCC)S(=O)(=O)N1CCN(CC1)CC
• InChI: InChI=1S/C23H33N7O5S.C6H6O3S/c1-5-18-19-20(27-30(18)12-13-34-4)22(31)26-21(25-19)17-14-16(15-24-23(17)35-7-3)36(32,33)29-10-8-28(6-2)9-11-29;7-10(8,9)6-4-2-1-3-5-6/h14-15H,5-13H2,1-4H3,(H,25,26,31);1-5H,(H,7,8,9)
• InChIKey: STFRDYSZKVPPQF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{2-ethoxy-5-[(4-ethylpiperazin-1-yl)sulfonyl]pyridin-3-yl}-3-ethyl-2-(2-methoxyethyl)-2H,4H,7H-pyrazolo[4,3-d]pyrimidin-7-one; benzenesulfonic acid
• IUPAC Traditional name: 5-[2-ethoxy-5-(4-ethylpiperazin-1-ylsulfonyl)pyridin-3-yl]-3-ethyl-2-(2-methoxyethyl)-4H-pyrazolo[4,3-d]pyrimidin-7-one; benzenesulfonic acid
• Synonyms: 5-[2-Ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]-3-pyridinyl]-3-ethyl-2,6-dihydro-2-(2-methoxyethyl)-7H-pyrazolo[4,3-d]pyrimidin-7-one benzenesulfonate besylate salt; UK 369003-26; UK 369003; Gisadenafil besylate salt; 5-[2-Ethoxy-5-[(4-ethyl-1-piperazinyl)sulfonyl]-3-pyridinyl]-3-ethyl-2,6-dihydro-2-(2-methoxyethyl)-7H-pyrazolo[4,3-d]pyrimidin-7-one Benzenesulfonate; 1-[[6-Ethoxy-5-[3-ethyl-4,7-dihydro-2-(2-methoxyethyl)-7-oxo-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-pyridinyl]sulfonyl]-4-ethylpiperazine Monobenzenesulfonate; Gisadenafil Besylate

Database IDs

• CAS Number: 334827-98-4
• MDL Number: MFCD18384964
• PubChem SID: 162249075
• PubChem CID: 23449797

CALCULATED PROPERTIES

• Acid pKa: 6.6059513
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 0.70507246
• LogD (pH = 7.4): 0.58143
• Log P: 0.96082014
• Molar Refractivity: 148.994 cm^3
• Polarizability: 52.0381 Å^3
• Polar Surface Area: 131.25 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >35 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C23H33N7O5S · C6H6O3S

DETAILS

Sigma Aldrich - PZ0172

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
Gisadenafil (UK 369003) is a PDE5 inhibitor. It is 80 fold selective over PDE6, and greater than 3000 fold selective over PDEs 1-4 and 7.

Toronto Research Chemicals - G388700

Gisadenafil (UK 369003) is a PDE5 inhibitor. It is 80 fold selective over PDE6, and greater than 3000 fold selective over PDEs 1-4 and 7. Gisadenafil is used for the treatment of LUTS.

REFERENCES

• Bloch, W., et al.: Prostate, 33, 1 (1997)
• Glowienke, S., et al.: Mutat. Res., 581, 23 (1997)
• Chapple, C., et al.: Eur. Urol., 54, 563 (1997)
• Elder, D., et al.: J. Pharm. Pharmacol., 61, 269 (1997)