DYPHYLLINE

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 Search

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=136395

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
cAMP signaling pathway 8 Target ID: map04024 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1545351	Inhibitor 7728

Conditions

Condition	Modality	Highest Phase	Product
Acute bronchial asthma 1 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=136395	Primary	Approved 8043	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
Chronic bronchitis 48 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=136395	Primary	Approved 8043	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
Emphysema 13 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=136395	Primary	Approved 8043	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/7309903/	healthy, 20 - 35 years n = 20 Health Status: healthy Age Group: 20 - 35 years Sex: F Population Size: 20 Sources: https://pubmed.ncbi.nlm.nih.gov/7309903/	Sources: https://pubmed.ncbi.nlm.nih.gov/7309903/
250 mg single, respiratory Dose: 250 mg Route: respiratory Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/	unhealthy, adult n = 2 Health Status: unhealthy Condition: asthmatics Age Group: adult Sex: unknown Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/	Other AEs: Bronchospasm... Other AEs: Bronchospasm (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/
375 mg single, respiratory Dose: 375 mg Route: respiratory Route: single Dose: 375 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/	unhealthy, adult n = 2 Health Status: unhealthy Condition: asthmatics Age Group: adult Sex: unknown Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/	Other AEs: Bronchospasm... Other AEs: Bronchospasm (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/

AEs

AE	Significance	Dose	Population
Bronchospasm	2 patients	250 mg single, respiratory Dose: 250 mg Route: respiratory Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/	unhealthy, adult n = 2 Health Status: unhealthy Condition: asthmatics Age Group: adult Sex: unknown Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/
Bronchospasm	2 patients	375 mg single, respiratory Dose: 375 mg Route: respiratory Route: single Dose: 375 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/	unhealthy, adult n = 2 Health Status: unhealthy Condition: asthmatics Age Group: adult Sex: unknown Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/6957527/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 643

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 713	inhibitor 3045 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3286305/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:4728	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4728
ChemicalBook	CB7177891	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7177891
MolPort	MolPort-001-783-701	https://www.molport.com/shop/molecule-link/MolPort-001-783-701
Selleck Chemicals	Dyphylline(Dilor)	http://www.selleckchem.com/products/Dyphylline(Dilor).html
eMolecules	502884	https://www.emolecules.com/cgi-bin/more?vid=502884

PubMed

Title	Date	PubMed
Application of micellar electrokinetic chromatography to the quality control of a pharmaceutical preparation containing three bronchodilators.	2002 Feb	11870768
Electrophoretic behaviour of pharmacologically active alkylxanthines.	2002 Mar 15	11991004
Kinetic-spectrophotometric determination of theophylline, dyphylline, and proxyphylline by use of partial least-squares regression.	2002 Sep	12207237
Accuracy of Veterans Affairs databases for diagnoses of chronic diseases.	2009 Oct	19755002
Feasibility of Raman spectroscopy as PAT tool in active coating.	2010 Feb	19778159

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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

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