1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one

• ChemBase ID: 70247
• Molecular Formular: C5H4N4O
• Molecular Mass: 136.11146
• Monoisotopic Mass: 136.03851077
• SMILES: O=c1c2c([nH]nc2)nc[nH]1
• Canonical SMILES: O=c1[nH]cnc2c1cn[nH]2
• InChI: InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
• InChIKey: OFCNXPDARWKPPY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC Traditional name: zyloprim; 1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one
• Synonyms: Allopurinol; Allopurinol; 1,5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one; 1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one; Zyloprim; Allohexal; Allosig; Progout; Zyloric; 1H-Pyrazolo(3,4-d)pyrimidin-4-ol; 4-Hydroxypyrazolo(3,4-d)pyrimidine; 4-Hydroxypyrazolo[3,4-d]pyrimidine; HPP; Allopurinol

Database IDs

• CAS Number: 315-30-0
• EC Number: 206-250-9
• MDL Number: MFCD00599413
• PubChem SID: 24278141; 162035970
• PubChem CID: 2094

CALCULATED PROPERTIES

• Acid pKa: 8.871503
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.88196087
• LogD (pH = 7.4): -0.89559996
• Log P: -0.8817832
• Molar Refractivity: 35.8401 cm^3
• Polarizability: 11.920649 Å^3
• Polar Surface Area: 70.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: UR0785000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-43
• Safety Statements: 28-36/37-45
• TSCA Listed: false
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H317
• GHS Precautionary statements: P280-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... XDH(7498)
• Mechanism of Action: Inhibitor of ATP synthesis from guanine and of RNA biosynthesis; Reported free-radical-scavenger; Reported to decrease free-radical production; Reported to protect adenine nucleotide pool.; Reported transition metal chelator; Urate-synthesis-inhibitor; Xanthine oxidase inhibitor

Product Information

• Purity: 95+%
• Application(s): Shows antithrombotic and antiparasitic activities; Used in treatment of chronic gout and related diseases

DETAILS

Sigma Aldrich - A8003

Biochem/physiol Actions
Inhibitor of xanthine oxidase and de novo pyrimidine biosynthesis. A classical agent in treatment of hyperuricemia and gout.1

REFERENCES

• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 581C, (nmr)
• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 708D, (ir)
• Robins, R.K., J.A.C.S., 1956, 78, 784, (synth)
• Thang, K.V. et al., C. R. Hebd. Seances Acad. Sci., 1969, 268, 525, (synth, ir)
• Hildick, B.G. et al., J.C.S.(C), 1971, 1610, (synth)
• Prusiner, P. et al., Acta Cryst. B, 1972, 28, 2148, (cryst struct)
• Benezra, S.A. et al., Anal. Profiles Drug Subst., 1978, 7, 1, (rev)
• Tisler, M. et al., Heterocycles, 1982, 17, 405, (synth)
• Wang, Y. et al., CA, 1983, 99, 105210, (synth)
• Marr, J.J., Adv. Exp. Med. Biol., 1985, 165A, 231, (rev, metab)
• Rundles, R.W., Arch. Intern. Med., 1985, 145, 1492, (rev, pharmacol, use)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 262, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 333
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, ZVJ000