2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetic acid

• ChemBase ID: 119139
• Molecular Formular: C9H10N4O4
• Molecular Mass: 238.2001
• Monoisotopic Mass: 238.07020482
• SMILES: c12c(c(=O)n(c(=O)n1C)C)n(cn2)CC(=O)O
• Canonical SMILES: OC(=O)Cn1cnc2c1c(=O)n(C)c(=O)n2C
• InChI: InChI=1S/C9H10N4O4/c1-11-7-6(8(16)12(2)9(11)17)13(4-10-7)3-5(14)15/h4H,3H2,1-2H3,(H,14,15)
• InChIKey: HCYFGRCYSCXKNQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetic acid
• IUPAC Traditional name: acefylline; 2-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-7-yl)acetic acid
• Synonyms: 2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetic acid; Acefylline; 1,3-Dimethylxanthin-7-ylacetic acid; Theophylline-7-acetic acid; Aminodal; Stenofillina; Acefylline; 1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-acetic Acid; 7-(Carboxymethyl)theophylline; 7-Theophyllineacetic Acid; 7-Theophyllinylacetic Acid; Acefylline; Acephylline; Carboxymethyltheophylline; N-7-Theophyllineacetic Acid; NSC 52996; Theophyllineacetic Acid; Theophylline-7-acetic Acid; 1,3-Dimethylxanthine-7-acetic acid; Theophylline-7-acetic acid; 茶碱-7-乙酸; 1,3-二甲基黄嘌呤-7-乙酸; 茶碱乙酸

Database IDs

• CAS Number: 652-37-9
• EC Number: 211-490-2
• MDL Number: MFCD00022832
• Beilstein Number: 279221
• Merck Index: 1424
• PubChem SID: 24889080; 162102610
• PubChem CID: 69550
• CHEMBL: 70246
• Chemspider ID: 62754
• Unique Ingredient Identifier: M494UE2YEP
• Wikipedia Title: Acefylline

CALCULATED PROPERTIES

• Acid pKa: 3.2622647
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -3.2863145
• LogD (pH = 7.4): -4.501496
• Log P: -1.0676622
• Molar Refractivity: 55.9158 cm^3
• Polarizability: 20.458141 Å^3
• Polar Surface Area: 95.74 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 268-270°C; 268-272°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: UO7451300
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ADORA2B(136)
• Mechanism of Action: Fatty acid metabolism inhibitor; Glucose transport blocker; Lipoprotein lipase inhibitor; Triglyceride lipase activator

Product Information

• Purity: ≥99.0% (T); 98%
• Application(s): Bronchodilator; Spasmolytic, cardiotonic, diuretic and smooth muscle relaxant
• Empirical Formula (Hill Notation): C9H10N4O4

DETAILS

Sigma Aldrich - 88310

Packaging
100 g in poly bottle

Toronto Research Chemicals - T343860

A xanthine derivative with bronchodilator activity. Typically combined as salt component with other medications such as Ambroxol to treat bronchial and pulmonary diseases.

REFERENCES

• Kim, S., et al.: J. Med. Chem., 45, 2131 (2002)
• Bruno-Blanch, L., et al.: Bioorg. Med. Chem. Lett., 13, 2749 (2002)
• Foppoli, A., et al.: J. Pharm. Sci., 96, 1139(2002)
• U.K. Pat., 1965, 998 971; CA, 63, 9756g, (pharmacol)
• Maslankiewicz, A. et al., Pol. J. Chem. (Rocz. Chem.), 1975, 49, 1935, (synth)
• Zuidema, J. et al., Pharm. Weekbl., 1978, 113, 605, (pharmacol)
• IARC Monog., 1980, 24, 39; Suppl. 7, 171, (rev, tox)
• Szatmari, I. et al., Eur. J. Drug Metab. Pharmacokinet., 1984, 9, 11; 17, (metab, depogen)
• Priimenko, B.A. et al., Farm. Zh. (Kiev), 1985, 40, (synth)
• Ger. Pat., 1987, 3 633 492; CA, 107, 7013t, (synth, depogen)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1178
• Kapui, Z. et al., Thromb. Res., 1992, 66, 693, (pharmacol, depogen)
• Bcskei, Z. et al., Acta Cryst. C, 1995, 51, 1587, (cryst struct, depogen)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1651