U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C10H14N4O4
Molecular Weight 254.2426
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DYPHYLLINE

SMILES

CN1C2=C(N(CC(O)CO)C=N2)C(=O)N(C)C1=O

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

Molecular Formula C10H14N4O4
Molecular Weight 254.2426
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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

-5.9400002E11
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

-5.9400002E11
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

-5.9400002E11
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
n = 20
Health Status: healthy
Age Group: 20 - 35 years
Sex: F
Population Size: 20
Sources:
250 mg single, respiratory
Dose: 250 mg
Route: respiratory
Route: single
Dose: 250 mg
Sources:
unhealthy, adult
n = 2
Health Status: unhealthy
Condition: asthmatics
Age Group: adult
Sex: unknown
Population Size: 2
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
n = 2
Health Status: unhealthy
Condition: asthmatics
Age Group: adult
Sex: unknown
Population Size: 2
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
n = 2
Health Status: unhealthy
Condition: asthmatics
Age Group: adult
Sex: unknown
Population Size: 2
Sources:
Bronchospasm 2 patients
375 mg single, respiratory
Dose: 375 mg
Route: respiratory
Route: single
Dose: 375 mg
Sources:
unhealthy, adult
n = 2
Health Status: unhealthy
Condition: asthmatics
Age Group: adult
Sex: unknown
Population Size: 2
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
Electrophoretic behaviour of pharmacologically active alkylxanthines.
2002 Mar 15
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
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
New validated liquid chromatographic and chemometrics-assisted UV spectroscopic methods for the determination of two multicomponent cough mixtures in syrup.
2008 Jan-Feb
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
Screening-based discovery of drug-like O-GlcNAcase inhibitor scaffolds.
2010 Feb 19
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:15:55 UTC 2023
Edited
by admin
on Fri Dec 15 16:15:55 UTC 2023
Record UNII
263T0E9RR9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DYPHYLLINE
HSDB   INCI   MI   ORANGE BOOK   USP   USP-RS   VANDF  
INCI  
Official Name English
diprophylline [INN]
Common Name English
Diprophylline [WHO-DD]
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 Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
WHO-VATC QR03DA51
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
WHO-ATC R03DB01
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
WHO-ATC R03DA51
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
WHO-VATC QR03DB01
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
WHO-VATC QR03DA01
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
WHO-ATC R03DA01
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
NCI_THESAURUS C319
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
LIVERTOX 338
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
Code System Code Type Description
MESH
D004400
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
WIKIPEDIA
DYPHYLLINE
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-526-1
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
EVMPD
SUB07225MIG
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
NSC
14305
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
CHEBI
4728
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
RXCUI
3714
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY RxNorm
DRUG CENTRAL
976
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID6022975
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
PUBCHEM
3182
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
SMS_ID
100000092608
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
CAS
479-18-5
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
DRUG BANK
DB00651
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
IUPHAR
7070
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
HSDB
3322
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
INN
1365
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
FDA UNII
263T0E9RR9
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
LACTMED
Dyphylline
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
MERCK INDEX
m4796
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY Merck Index
ChEMBL
CHEMBL1752
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
ALANWOOD
dilor
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
NCI_THESAURUS
C47504
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
RS_ITEM_NUM
1231502
Created by admin on Fri Dec 15 16:15:55 UTC 2023 , Edited by admin on Fri Dec 15 16:15:55 UTC 2023
PRIMARY
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC