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
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
Molecular Formula | C10H14N4O4 |
Molecular Weight | 254.2426 |
Charge | 0 |
Count |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4083583
Curator's Comment: https://core.ac.uk/download/pdf/10195919.pdf
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: map04024 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1545351 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NEOTHYLLINE Approved UseIndications and Usage For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Launch Date1951 |
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Primary | NEOTHYLLINE Approved UseIndications and Usage For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Launch Date1951 |
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Primary | NEOTHYLLINE Approved UseIndications and Usage For relief of acute bronchial asthma and for reversible bronchospasm associated with chronic bronchitis and emphysema. Launch Date1951 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
17.1 μg/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
21.8 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/495617/ |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
23.99 μg/mL |
1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
16.6 μg/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
8.21 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/4009445 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2944 μg × min/mL |
1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2829.7 μg × min/mL |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
20.16 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/4009445 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.1 h |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
11.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7229976/ |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE blood | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/495617/ |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.99 h |
1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1.87 h |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
DYPHYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/4009445 |
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
Dose | Population | Adverse 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... |
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... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
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Multi-component kinetic-spectrophotometric analysis. Selection of wavelength and time ranges. | 2001 Jul |
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Application of micellar electrokinetic chromatography to the quality control of a pharmaceutical preparation containing three bronchodilators. | 2002 Feb |
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Electrophoretic behaviour of pharmacologically active alkylxanthines. | 2002 Mar 15 |
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Kinetic-spectrophotometric determination of theophylline, dyphylline, and proxyphylline by use of partial least-squares regression. | 2002 Sep |
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Wet granulation fine particle ethylcellulose tablets: effect of production variables and mathematical modeling of drug release. | 2003 |
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Simultaneous determination of theophylline and dyphylline by micellar electrokinetic chromatography and application in drug formulations. | 2003 Oct 5 |
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Modeling of drug release from partially coated matrices made of a high viscosity HPMC. | 2004 May 19 |
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Optimization and characterization of controlled release multi-particulate beads coated with starch acetate. | 2005 Apr 27 |
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HPLC and chemometric assisted spectrophotometric methods for simultaneous determination of diprophylline, phenobarbitone and papaverine hydrochloride. | 2005 Sep |
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[Clinical observation on shufei granule in improving right ventricular function of patients with chronic pulmonary heart disease]. | 2006 Aug |
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Rapid determination of acyclovir in plasma and cerebrospinal fluid by micellar electrokinetic chromatography with direct sample injection and its clinical application. | 2006 Feb |
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Extruded and spheronized beads containing Carbopol 974P to deliver nonelectrolytes and salts of weakly basic drugs. | 2006 Sep 14 |
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[Combining LABA and ICS in patients with severe COPD]. | 2007 Jan-Feb |
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Hydroxypropyl methylcellulose acetate succinate: potential drug-excipient incompatibility. | 2008 |
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A comparison of the stability of ertapenem and meropenem in pharmaceutical preparations in solid state. | 2008 Jan 7 |
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New validated liquid chromatographic and chemometrics-assisted UV spectroscopic methods for the determination of two multicomponent cough mixtures in syrup. | 2008 Jan-Feb |
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Synthesis and activity against HBV of novel Tetra-seconucleoside analogues of dyphlline having the acyclic chains of ACV and HBG. | 2008 Mar |
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Synthesis, pharmacological activity and nitric oxide generation by nitrate derivatives of theophylline. | 2008 May |
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Expression and purification of human mPGES-1 in E. coli and identification of inhibitory compounds from a drug-library. | 2008 Nov 30 |
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Accuracy of Veterans Affairs databases for diagnoses of chronic diseases. | 2009 Oct |
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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 |
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Feasibility of Raman spectroscopy as PAT tool in active coating. | 2010 Feb |
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Screening-based discovery of drug-like O-GlcNAcase inhibitor scaffolds. | 2010 Feb 19 |
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Modeling drug release from PVAc/PVP matrix tablets. | 2010 Jan 25 |
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Spectrophotometric and reversed-phase high-performance liquid chromatographic method for the determination of doxophylline in pharmaceutical formulations. | 2010 Jul |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11964308
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
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admin
on
Edited
Mon Mar 31 18:23:27 GMT 2025
by
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on
Mon Mar 31 18:23:27 GMT 2025
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Record UNII |
263T0E9RR9
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C744
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WHO-VATC |
QR03DA51
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WHO-ATC |
R03DB01
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WHO-ATC |
R03DA51
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WHO-VATC |
QR03DB01
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WHO-VATC |
QR03DA01
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WHO-ATC |
R03DA01
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NCI_THESAURUS |
C319
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LIVERTOX |
338
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D004400
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DYPHYLLINE
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207-526-1
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SUB07225MIG
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14305
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3714
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976
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100000092608
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479-18-5
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DB00651
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1365
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263T0E9RR9
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Dyphylline
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m4796
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CHEMBL1752
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dilor
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C47504
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1231502
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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