RCSB PDB - 7UH Ligand Summary Page

7UH

Doxofylline

Created: 2021-10-27
Last modified:  2023-09-20

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Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count0
Bond Count35
Aromatic Bond Count5
2D diagram of 7UH

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Chemical Component Summary

NameDoxofylline
Synonyms7-(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
FormulaC11 H14 N4 O4
Molecular Weight266.253
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385CN1C(=O)N(C)c2ncn(CC3OCCO3)c2C1=O
SMILESOpenEye OEToolkits2.0.7CN1c2c(n(cn2)CC3OCCO3)C(=O)N(C1=O)C
Canonical SMILESCACTVS3.385 CN1C(=O)N(C)c2ncn(CC3OCCO3)c2C1=O
Canonical SMILESOpenEye OEToolkits2.0.7 CN1c2c(n(cn2)CC3OCCO3)C(=O)N(C1=O)C
InChIInChI1.03 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
InChIKeyInChI1.03 HWXIGFIVGWUZAO-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB09273 
NameDoxofylline
Groups experimental
DescriptionDoxofylline 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
  • Doxophylline
  • Doxofylline
  • doxofilina
IndicationIndicated for the treatment of chronic obstructive pulmonary disease (COPD), bronchial asthma and pulmonary disease with spastic bronchial component.
Categories
  • Adrenergic Agonists
  • Adrenergic beta-2 Receptor Agonists
  • Adrenergic beta-Agonists
  • Agents producing tachycardia
  • Agents that produce hypertension
ATC-CodeR03DA11
CAS number69975-86-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Beta-2 adrenergic receptorMGQPGNGSAFLLAPNGSHAPDHDVTQERDEVWVVGMGIVMSLIVLAIVFG...unknownagonist
Adenosine receptor A2aMPIMGSSVYITVELAIAVLAILGNVLVCWAVWLNSNLQNVTNYFVVSLAA...unknownantagonist
cGMP-dependent 3',5'-cyclic phosphodiesteraseMGQACGHSILCRSQQYPAARPAEPRGQQVFLKPDEPPPPPQPCADSLQDA...unknowninhibitor
Cytochrome P450 1A2MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...unknownsubstrate
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 NameReference
PubChem 50942
ChEMBL CHEMBL1527608
ChEBI CHEBI:94714
CCDC/CSD PEYGOQ, YICCOD, MISDIC
COD 2212333, 2213530, 2214660, 2216996