Acefylline (also known as Theophylline-7-acetic acid and Theophyllineacetic acid), is an antagonist of the adenosine receptor and an activator of the peptidylarginine deiminase (PAD). It is a stimulant medication that is an analog of xanthine. In the pharmaceutical preparation etanautine, acefylline and diphenhydramine work together to counteract the drowsiness that diphenhydramine induces.
Physicochemical Properties
| Molecular Formula | C9H10N4O4 | |
| Molecular Weight | 238.2 | |
| Exact Mass | 238.07 | |
| Elemental Analysis | C, 45.38; H, 4.23; N, 23.52; O, 26.87 | |
| CAS # | 652-37-9 | |
| Related CAS # | 18833-13-1 (piperazine); 652-37-9 | |
| PubChem CID | 69550 | |
| Appearance | White to off-white solid powder | |
| Density | 1.6±0.1 g/cm3 | |
| Boiling Point | 555.7±56.0 °C at 760 mmHg | |
| Melting Point | 270-272 °C | |
| Flash Point | 289.9±31.8 °C | |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C | |
| Index of Refraction | 1.714 | |
| LogP | -0.49 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 5 | |
| Rotatable Bond Count | 2 | |
| Heavy Atom Count | 17 | |
| Complexity | 385 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | O=C1C2=C(N=C([H])N2C([H])([H])C(=O)O[H])N(C([H])([H])[H])C(N1C([H])([H])[H])=O |
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| InChi Key | HCYFGRCYSCXKNQ-UHFFFAOYSA-N | |
| InChi Code | 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) | |
| Chemical Name | 2-(1,3-dimethyl-2,6-dioxopurin-7-yl)acetic acid | |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | adenosine receptor | ||
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| Animal Protocol |
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| References |
[1]. Inhibitory effect of theophylline, theophylline-7-acetic acid, ambroxol and ambroxol-theophylline-7-acetate on rat lung cAMP phosphodiesterase isoenzymes. Int J Tissue React. 1992;14(1):31-6. [2]. Acefylline activates filaggrin deimination by peptidylarginine deiminases in the upper epidermis. J Dermatol Sci. 2016 Feb;81(2):101-6. [3]. Esterification of 7-theophyllineacetic acid with diethylene glycol monomethyl ether. Acta Pharm. 2006 Jun;56(2):251-7. PMID: 16613730. |
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| Additional Infomation |
2-(1,3-dimethyl-2,6-dioxo-7-purinyl)acetic acid is an oxopurine. Acefylline has been reported in Pogostemon cablin with data available. |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.50 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.1982 mL | 20.9908 mL | 41.9815 mL | |
| 5 mM | 0.8396 mL | 4.1982 mL | 8.3963 mL | |
| 10 mM | 0.4198 mL | 2.0991 mL | 4.1982 mL |