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Details

Stereochemistry ACHIRAL
Molecular Formula C11H14N4O4
Molecular Weight 266.2533
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXOFYLLINE

SMILES

CN1C2=C(N(CC3OCCO3)C=N2)C(=O)N(C)C1=O

InChI

InChIKey=HWXIGFIVGWUZAO-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H14N4O4
Molecular Weight 266.2533
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://cathaydrug.ph/product/dilatair/ https://www.ncbi.nlm.nih.gov/pubmed/18376093

Doxofylline (7-(1, 3-dioxalan-2-ylmethyl) theophylline) is a novel xanthine bronchodilator which differs from theophylline in that it contains a dioxalane group in position 7. Doxofylline is indicated for the treatment of bronchial asthma, pulmonary disease with spastic bronchial component and Chronic Obstructive Pulmonary Disease (COPD). Doxofylline does not directly inhibit any of the known HDAC enzymes, and did not inhibit any phosphodiesterase (PDE) enzyme sub types or act as an antagonist at any of the known adenosine receptors, except for PDE2A(1), and adenosine A(2A) and only at the highest tested concentration (10(-4) M). Doxofylline has greatly decreased affinity towards adenosine A1 and A2 receptors, which explain its better safety profile. Moreover, it does not interfere with calcium influx into the cells nor antagonize calcium channel blockers. Doxofylline has been shown to be a more potent bronchodilator with fewer side effects than theophylline. This drug should not be administered together with other xanthine derivatives, including beverages and foods containing caffeine.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Dilatair

Approved Use

Unknown
Palliative
Ddilatair

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Doxofylline: a new generation xanthine bronchodilator devoid of major cardiovascular adverse effects.
2001
Conclusion without support - remarks on 'Efficacy and safely of doxyphyllin compared to Theophylline in chronic reversible asthma- a double-blind randomized placebo-controlled multicentre trial' by Goldstein MF, Chervinsky P (published in MedSciMonit, 2002; 8(4):CR297-304.
2002 Aug
Methylxanthines for exacerbations of chronic obstructive pulmonary disease: meta-analysis of randomised trials.
2003 Sep 20
[Clinical study on doxofylline injection in treatment of children with acute asthma attacks].
2004 Feb
Treatment of moderate chronic obstructive pulmonary disease (stable) with doxofylline compared with slow release theophylline--a multicentre trial.
2008 Dec
Preparation and bioavailability of sustained-release doxofylline pellets in beagle dogs.
2008 Jul
Spectrophotometric and reversed-phase high-performance liquid chromatographic method for the determination of doxophylline in pharmaceutical formulations.
2010 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Elderly Patients: 200 mg tablet two or three times daily. Adults: 400 mg tablet two or three times daily.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Doxofylline inhibited PAF-induced bronchoconstriction in vitro, and the concomitant generation of TXA2-like activity in perfused guinea-pig lungs.
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:54:49 GMT 2023
Edited
by admin
on Fri Dec 15 18:54:49 GMT 2023
Record UNII
MPM23GMO7Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXOFYLLINE
INN   MART.   MI   USAN   USP-RS   WHO-DD  
USAN   INN  
Official Name English
NSC-759645
Code English
1H-PURINE-2,6-DIONE, 7-(1,3-DIOXOLAN-2-YLMETHYL)-3,7-DIHYDRO-1,3-DIMETHYL-
Systematic Name English
DOXOFYLLINE [MART.]
Common Name English
ANSIMAR
Common Name English
DOXOFYLLINE [MI]
Common Name English
DIOXYFILLINE
Common Name English
DOXOFYLLINE [USAN]
Common Name English
DOXOPHYLLINE
Common Name English
doxofylline [INN]
Common Name English
VENTAX
Common Name English
ABC-12/3
Code English
Doxofylline [WHO-DD]
Common Name English
ABC 12/3
Code English
7-(1,3-Dioxolan-2-ylmethyl)theophylline
Systematic Name English
SYNASMA
Common Name English
Classification Tree Code System Code
WHO-VATC QR03DA11
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
FDA ORPHAN DRUG 399413
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
NCI_THESAURUS C744
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
WHO-ATC R03DA11
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID7022968
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
CAS
69975-86-6
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
SMS_ID
100000080795
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
PUBCHEM
50942
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
MERCK INDEX
m4756
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PRIMARY Merck Index
DRUG CENTRAL
959
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
FDA UNII
MPM23GMO7Z
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
DRUG BANK
DB09273
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
USAN
CC-71
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
INN
5156
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
NSC
759645
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
MESH
C029797
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
CHEBI
94714
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
WIKIPEDIA
DOXOFYLLINE
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
NCI_THESAURUS
C76317
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL1527608
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
274-239-6
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
EVMPD
SUB06390MIG
Created by admin on Fri Dec 15 18:54:49 GMT 2023 , Edited by admin on Fri Dec 15 18:54:49 GMT 2023
PRIMARY
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