7UH
Doxofylline
Created: | 2021-10-27 |
Last modified: | 2023-09-20 |
Find Related PDB Entry |
---|
Find related ligands: |
---|
Chemical Details | |
---|---|
Formal Charge | 0 |
Atom Count | 33 |
Chiral Atom Count | 0 |
Bond Count | 35 |
Aromatic Bond Count | 5 |
Chemical Component Summary | |
---|---|
Name | Doxofylline |
Synonyms | 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-purine-2,6-dione |
Systematic Name (OpenEye OEToolkits) | 7-(1,3-dioxolan-2-ylmethyl)-1,3-dimethyl-purine-2,6-dione |
Formula | C11 H14 N4 O4 |
Molecular Weight | 266.253 |
Type | NON-POLYMER |
Chemical Descriptors | |||
---|---|---|---|
Type | Program | Version | Descriptor |
SMILES | CACTVS | 3.385 | CN1C(=O)N(C)c2ncn(CC3OCCO3)c2C1=O |
SMILES | OpenEye OEToolkits | 2.0.7 | CN1c2c(n(cn2)CC3OCCO3)C(=O)N(C1=O)C |
Canonical SMILES | CACTVS | 3.385 | CN1C(=O)N(C)c2ncn(CC3OCCO3)c2C1=O |
Canonical SMILES | OpenEye OEToolkits | 2.0.7 | CN1c2c(n(cn2)CC3OCCO3)C(=O)N(C1=O)C |
InChI | InChI | 1.03 | InChI=1S/C11H14N4O4/c1-13-9-8(10(16)14(2)11(13)17)15(6-12-9)5-7-18-3-4-19-7/h6-7H,3-5H2,1-2H3 |
InChIKey | InChI | 1.03 | HWXIGFIVGWUZAO-UHFFFAOYSA-N |
Drug Info: DrugBank
DrugBank ID | DB09273 |
---|---|
Name | Doxofylline |
Groups | experimental |
Description | Doxofylline is a methylxanthine derivative with the presence of a dioxolane group in position 7. As a drug used in the treatment of asthma, doxofylline has shown similar efficacy to theophylline but with significantly fewer side effects in animal and human studies. In contrast with other xanthine derivatives, doxofylline does not significantly bind to adenosine alpha-1 or alpha-2 receptors and lacks stimulating effects. Decreased affinity for adenosine receptors may account for the better safety profile of doxofylline compared to theophylline [L1169]. Unlike theophylline, doxofylline does not affect calcium influx and does not antagonize the actions of calcium channel blockers which could explain reduced cardiac adverse reactions associated with the drug [A7885]. The anti-asthmatic effects of doxophylline are mediated by other mechanisms, primarily through inhibiting the activities of the phosphodiesterase (PDE) enzyme. |
Synonyms |
|
Indication | Indicated for the treatment of chronic obstructive pulmonary disease (COPD), bronchial asthma and pulmonary disease with spastic bronchial component. |
Categories |
|
ATC-Code | R03DA11 |
CAS number | 69975-86-6 |
Drug Targets
Name | Target Sequence | Pharmacological Action | Actions |
---|---|---|---|
Beta-2 adrenergic receptor | MGQPGNGSAFLLAPNGSHAPDHDVTQERDEVWVVGMGIVMSLIVLAIVFG... | unknown | agonist |
Adenosine receptor A2a | MPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA... | unknown | antagonist |
cGMP-dependent 3',5'-cyclic phosphodiesterase | MGQACGHSILCRSQQYPAARPAEPRGQQVFLKPDEPPPPPQPCADSLQDA... | unknown | inhibitor |
Cytochrome P450 1A2 | MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL... | unknown | substrate |
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison
T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS.
Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682
Related Resource References
Resource Name | Reference |
---|---|
PubChem | 50942 |
ChEMBL | CHEMBL1527608 |
ChEBI | CHEBI:94714 |
CCDC/CSD | PEYGOQ, YICCOD, MISDIC |
COD | 2212333, 2213530, 2214660, 2216996 |