7-(2-hydroxyethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase ID: 103907
• Molecular Formular: C9H12N4O3
• Molecular Mass: 224.21658
• Monoisotopic Mass: 224.09094026
• SMILES: Cn1c(=O)n(C)c2c(n(CCO)cn2)c1=O
• Canonical SMILES: OCCn1cnc2c1c(=O)n(C)c(=O)n2C
• InChI: InChI=1S/C9H12N4O3/c1-11-7-6(8(15)12(2)9(11)16)13(3-4-14)5-10-7/h5,14H,3-4H2,1-2H3
• InChIKey: NWPRCRWQMGIBOT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-(2-hydroxyethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC Traditional name: etofylline; 7-(2-hydroxyethyl)-1,3-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• Synonyms: 7-(2-Hydroxyethyl)theophylline; 3,7-Dihydro-7-(2-hydroxyethyl)-1,3-dimethyl-1H-purine-2,6-dione; 7-(2-Hydroxyethyl)-1,3-dimethylxanthine; 7-Theophyllineethanol; Aethophyllinum; Ascorphylline; Bio-phylline; Cordalin; Corophyllin-N; Dilaphyllin; Etophyllin; Etophylline; Frekaphyllin; Hydroxyethyltheophylline; KT 200G; NSC 113373; Oxphylline; Oxyethophylline; Oxyethyltheophylline; Oxyphyllin; Oxyphylline; Oxytheonyl; Phyllocormin N; Soluphylline; Etofylline; 1,3-Dimethyl-7-(2-hydroxyethyl)xanthine; 7-(β-Hydroxyethyl)theophylline; 1,3-Dimethyl-7-( β-hydroxyethyl-xanthine; 7-(β-HYDROXYETHYL)-THEOPHYLLINE; Theostat; Etofylline

Database IDs

• CAS Number: 519-37-9
• EC Number: 208-269-8
• MDL Number: MFCD00055055
• PubChem SID: 24895836; 162091056
• PubChem CID: 1892

CALCULATED PROPERTIES

• Acid pKa: 15.447594
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.2357477
• LogD (pH = 7.4): -1.2357476
• Log P: -1.2357476
• Molar Refractivity: 56.1235 cm^3
• Polarizability: 20.37684 Å^3
• Polar Surface Area: 78.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; ethanol: moderately soluble (Solutions may be stored for several days at 4°C.); H2O: soluble (Solutions may be stored for several days at 4°C.); Methanol
• Apperance: white solid; White Solid
• Melting Point: 153-155°C; 161-163°C

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: XH5850000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ADORA2B(136)
• Mechanism of Action: CNS-stimulant; Phosphodiesterase inhibitor; Prostaglandin antagonist; Purine antagonist

Product Information

• Application(s): Cardiant; Diuretic; Vasodilator

DETAILS

Sigma Aldrich - H9006

Application
Useful synthetic intermediate in the preparation of 7-substituted xanthines.
Biochem/physiol Actions
Pharmacological profile similar to theophylline.

Toronto Research Chemicals - E933200

An inhibitor of 3’,5’-Cyclic Nucleotide Phosphodiesterase. Therapeutically, this compound has diuretic, muscle relaxant, bronchial dilation and CNS stimulant activities.

REFERENCES

• Geraets, L., et al.: Biochem. Pharmacol., 72, 902 (2006)
• Kumar, A., et al.: J. Clin. Diagnostic Res., 2, 938 (2006)
• Tanno, F., et al.: J. Pharm. Sci., 97, 2665 (2006)
• Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2006)
• Taugner, R. et al., Arzneim.-Forsch., 1956, 6, 601, (pharmacol)
• Roth, H.J., Arch. Pharm. (Weinheim, Ger.), 1959, 292, 234, (synth)
• Schlemmer, W., J. Chromatogr., 1971, 63, 121, (tlc)
• Kamei, K. et al., Chem. Pharm. Bull., 1973, 21, 1228, (glc, ms)
• Ostrovska, V. et al., J. Liq. Chromatogr., 1989, 12, 2793, (metab, hplc)
• Biagi, G.L. et al., J. Chromatogr., 1990, 498, 179, (tlc)
• Franzone, J.S. et al., Methods Find. Exp. Clin. Pharmacol., 1991, 13, 289, (pharmacol, tox)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1318
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 1511, (synonyms)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HLC000