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 |
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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 |
---|---|---|---|---|
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 |
---|---|---|---|---|
2.13 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 n = 20 Health Status: healthy Age Group: 20 - 35 years Sex: F Population Size: 20 Sources: |
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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... |
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... |
AEs
AE | Significance | Dose | Population |
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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: |
PubMed
Title | Date | PubMed |
---|---|---|
Kinetic-spectrophotometric determination of theophylline, dyphylline, and proxyphylline by use of partial least-squares regression. | 2002 Sep |
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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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Hydroxypropyl methylcellulose acetate succinate: potential drug-excipient incompatibility. | 2008 |
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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, pharmacological activity and nitric oxide generation by nitrate derivatives of theophylline. | 2008 May |
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Screening-based discovery of drug-like O-GlcNAcase inhibitor scaffolds. | 2010 Feb 19 |
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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Edited
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Record UNII |
263T0E9RR9
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Record Status |
Validated (UNII)
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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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R03DA51
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QR03DB01
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QR03DA01
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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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3714
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976
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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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LIGAND->BINDER | |||
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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)
EP
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Related Record | Type | Details | ||
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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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