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Details

Stereochemistry RACEMIC
Molecular Formula C10H14N4O4
Molecular Weight 254.243
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DYPHYLLINE

SMILES

Cn1c2c(c(=O)n(C)c1=O)n(CC(CO)O)cn2

InChI

InChIKey=KSCFJBIXMNOVSH-UHFFFAOYSA-N
InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3

HIDE SMILES / InChI
Dyphylline is 7-(2,3-dihydroxypropyl)-theophylline, a white, extremely bitter, amorphous powder that is freely soluble in water and soluble in alcohol. Dyphylline is stable in gastrointestinal fluids over a wide range of pH. Dyphylline is a xanthine derivative with pharmacologic actions similar to theophylline and other members of this class of drugs. Its primary action is that of bronchodilation, but it also exhibits peripheral vasodilatory and other smooth muscle relaxant activity to a lesser degree. The bronchodilatory action of dyphylline, as with other xanthines, is thought to be mediated through competitive inhibition of phosphodiesterase with a resulting increase in cyclic AMP producing relaxation of the bronchial smooth muscle. Dyphylline exerts its bronchodilatory effects directly and, unlike theophylline, is excreted unchanged by the kidneys without being metabolized by the liver. Because of this, dyphylline pharmacokinetics and plasma levels are not influenced by various factors that affect liver function and hepatic enzyme activity, such as smoking, age, congestive heart failure, or concomitant use of drugs which affect liver function.

CNS Activity

Curator's Comment:: https://core.ac.uk/download/pdf/10195919.pdf

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NEOTHYLLINE

Approved Use

Indications and Usage For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.

Launch Date

-594000000000
Primary
NEOTHYLLINE

Approved Use

Indications and Usage For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.

Launch Date

-594000000000
Primary
NEOTHYLLINE

Approved Use

Indications and Usage For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema.

Launch Date

-594000000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.21 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DYPHYLLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
20.16 μg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DYPHYLLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.13 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DYPHYLLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
5 mg/kg single, intragluteal
Dose: 5 mg/kg
Route: intragluteal
Route: single
Dose: 5 mg/kg
Sources:
healthy, 20 - 35 years
Health Status: healthy
Age Group: 20 - 35 years
Sex: F
Sources:
250 mg single, respiratory
Dose: 250 mg
Route: respiratory
Route: single
Dose: 250 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Bronchospasm...
Other AEs:
Bronchospasm (2 patients)
Sources:
375 mg single, respiratory
Dose: 375 mg
Route: respiratory
Route: single
Dose: 375 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Other AEs: Bronchospasm...
Other AEs:
Bronchospasm (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Bronchospasm 2 patients
250 mg single, respiratory
Dose: 250 mg
Route: respiratory
Route: single
Dose: 250 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Bronchospasm 2 patients
375 mg single, respiratory
Dose: 375 mg
Route: respiratory
Route: single
Dose: 375 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Multi-component kinetic-spectrophotometric analysis. Selection of wavelength and time ranges.
2001 Jul
Application of micellar electrokinetic chromatography to the quality control of a pharmaceutical preparation containing three bronchodilators.
2002 Feb
Electrophoretic behaviour of pharmacologically active alkylxanthines.
2002 Mar 15
Kinetic-spectrophotometric determination of theophylline, dyphylline, and proxyphylline by use of partial least-squares regression.
2002 Sep
Wet granulation fine particle ethylcellulose tablets: effect of production variables and mathematical modeling of drug release.
2003
Simultaneous determination of theophylline and dyphylline by micellar electrokinetic chromatography and application in drug formulations.
2003 Oct 5
Modeling of drug release from partially coated matrices made of a high viscosity HPMC.
2004 May 19
Optimization and characterization of controlled release multi-particulate beads coated with starch acetate.
2005 Apr 27
HPLC and chemometric assisted spectrophotometric methods for simultaneous determination of diprophylline, phenobarbitone and papaverine hydrochloride.
2005 Sep
[Clinical observation on shufei granule in improving right ventricular function of patients with chronic pulmonary heart disease].
2006 Aug
Rapid determination of acyclovir in plasma and cerebrospinal fluid by micellar electrokinetic chromatography with direct sample injection and its clinical application.
2006 Feb
Extruded and spheronized beads containing Carbopol 974P to deliver nonelectrolytes and salts of weakly basic drugs.
2006 Sep 14
[Combining LABA and ICS in patients with severe COPD].
2007 Jan-Feb
Hydroxypropyl methylcellulose acetate succinate: potential drug-excipient incompatibility.
2008
A comparison of the stability of ertapenem and meropenem in pharmaceutical preparations in solid state.
2008 Jan 7
New validated liquid chromatographic and chemometrics-assisted UV spectroscopic methods for the determination of two multicomponent cough mixtures in syrup.
2008 Jan-Feb
Synthesis and activity against HBV of novel Tetra-seconucleoside analogues of dyphlline having the acyclic chains of ACV and HBG.
2008 Mar
Synthesis, pharmacological activity and nitric oxide generation by nitrate derivatives of theophylline.
2008 May
Expression and purification of human mPGES-1 in E. coli and identification of inhibitory compounds from a drug-library.
2008 Nov 30
Accuracy of Veterans Affairs databases for diagnoses of chronic diseases.
2009 Oct
Validation of Raman spectroscopic procedures in agreement with ICH guideline Q2 with considering the transfer to real time monitoring of an active coating process.
2010 Dec 1
Feasibility of Raman spectroscopy as PAT tool in active coating.
2010 Feb
Screening-based discovery of drug-like O-GlcNAcase inhibitor scaffolds.
2010 Feb 19
Modeling drug release from PVAc/PVP matrix tablets.
2010 Jan 25
Spectrophotometric and reversed-phase high-performance liquid chromatographic method for the determination of doxophylline in pharmaceutical formulations.
2010 Jul
Patents

Patents

Sample Use Guides

Usual adult dosage: Up to 15 mg/kg every six hours. Dosage should be individually titrated according to the severity of the condition and the response of the patient. Appropriate dosage adjustments should be made in patients with impaired renal function
Route of Administration: Oral
Human acute T-lymphocytic leukemia cells CEM-GH (CEM) were cultured with Dyphylline (10 -1000 mkg/mL) for 4 days, and MTT assay measurements are expressed as a viability ratio of drug-treated cells to untreated control cells in each experiment. Dyphylline suppress the growth of human CEM ALL cells in culture with EC50~100 mkg/mL.
Name Type Language
DYPHYLLINE
HSDB   INCI   MI   ORANGE BOOK   USP   USP-RS   VANDF  
INCI  
Official Name English
DIPROPHYLLINE [WHO-DD]
Common Name English
DIPROPHYLLINE [INN]
Common Name English
DYPHYLLINE [ORANGE BOOK]
Common Name English
DYPHYLLINE [HSDB]
Common Name English
1H-PURINE-2,6-DIONE, 7-(2,3-DIHYDROXYPROPYL)-3,7-DIHYDRO-1,3-DIMETHYL-, (+/-)-
Systematic Name English
DIPROPHYLLINE [EP MONOGRAPH]
Common Name English
NSC-14305
Code English
DYPHILLINE
Common Name English
DILOR
Brand Name English
DYPHYLLINE [USP-RS]
Common Name English
DIPROPHYLLINE
EP   INN   JAN   MART.   WHO-DD  
INN  
Official Name English
NEOTHYLLINE
Brand Name English
DIPROPHYLLINE [JAN]
Common Name English
DYPHYLLINE [USP MONOGRAPH]
Common Name English
DYPHYLLINE [INCI]
Common Name English
(+/-)-7-(2,3-DIHYDROXYPROPYL)THEOPHYLLINE
Systematic Name English
DYPHYLLINE [VANDF]
Common Name English
LUFYLLIN
Brand Name English
DYPHYLLINE [MI]
Common Name English
DIPROPHYLLINE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C744
Created by admin on Fri Jun 25 20:55:16 UTC 2021 , Edited by admin on Fri Jun 25 20:55:16 UTC 2021
WHO-VATC QR03DA51
Created by admin on Fri Jun 25 20:55:16 UTC 2021 , Edited by admin on Fri Jun 25 20:55:16 UTC 2021
WHO-ATC R03DB01
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WHO-ATC R03DA51
Created by admin on Fri Jun 25 20:55:16 UTC 2021 , Edited by admin on Fri Jun 25 20:55:16 UTC 2021
WHO-VATC QR03DB01
Created by admin on Fri Jun 25 20:55:16 UTC 2021 , Edited by admin on Fri Jun 25 20:55:16 UTC 2021
WHO-VATC QR03DA01
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WHO-ATC R03DA01
Created by admin on Fri Jun 25 20:55:16 UTC 2021 , Edited by admin on Fri Jun 25 20:55:16 UTC 2021
NCI_THESAURUS C319
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LIVERTOX 338
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Code System Code Type Description
MESH
D004400
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PRIMARY
WIKIPEDIA
DYPHYLLINE
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PRIMARY
ECHA (EC/EINECS)
207-526-1
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PRIMARY
EVMPD
SUB07225MIG
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PRIMARY
RXCUI
3714
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PRIMARY RxNorm
DRUG CENTRAL
976
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PRIMARY
EPA CompTox
479-18-5
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PRIMARY
PUBCHEM
3182
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PRIMARY
USP_CATALOG
1231502
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PRIMARY USP-RS
CAS
479-18-5
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PRIMARY
DRUG BANK
DB00651
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PRIMARY
IUPHAR
7070
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PRIMARY
HSDB
3322
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PRIMARY
INN
1365
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PRIMARY
FDA UNII
263T0E9RR9
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PRIMARY
LACTMED
Dyphylline
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PRIMARY
MERCK INDEX
M4796
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PRIMARY Merck Index
ChEMBL
CHEMBL1752
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PRIMARY
NCI_THESAURUS
C47504
Created by admin on Fri Jun 25 20:55:16 UTC 2021 , Edited by admin on Fri Jun 25 20:55:16 UTC 2021
PRIMARY