DENBUFYLLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H24N4O3
Molecular Weight	320.3868
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCN1C2=C(N(CC(C)=O)C=N2)C(=O)N(CCCC)C1=O

InChI

InChIKey=HJPRDDKCXVCFOH-UHFFFAOYSA-N

InChI=1S/C16H24N4O3/c1-4-6-8-19-14-13(18(11-17-14)10-12(3)21)15(22)20(16(19)23)9-7-5-2/h11H,4-10H2,1-3H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9179387 | https://www.ncbi.nlm.nih.gov/pubmed/8613965 | https://www.ncbi.nlm.nih.gov/pubmed/2474352 | https://www.ncbi.nlm.nih.gov/pubmed/2190256

Denbufylline is a selective xanthine derivative that inhibits PDE IV and has bronchodilatory properties. Shown to exhibit negative inotropic effects by acting on verapamil-sensitive sites of Ca2+ channels in guinea pig ventricle papillary muscle independently of its PDE inhibitory activity. Denbufylline, a selective type 4 phosphodiesterase (PDE-4) inhibitor, is a potent activator of the hypothalamo-pituitary-adrenal (HPA) axis when given orally or intraperitoneally (i.p.) to adult male rats. Denbufylline was being developed as an agent for the therapy of dementia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 4A 13 Target ID: CHEMBL254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15738310	Inhibitor 8504		0.3 µM [IC50]
Phosphodiesterase 4 54 Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12237530 \| https://www.ncbi.nlm.nih.gov/pubmed/7996422 \| http://www.google.com.pg/patents/US20030187056	Inhibitor 8504		1.5 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer's dementia 6 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10559567 https://www.ncbi.nlm.nih.gov/pubmed/1457622 https://www.ncbi.nlm.nih.gov/pubmed/2190256	Primary		Phase I 438	Unknown Approved Use Unknown
Osteopenia 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10361888	Primary		Preclinical	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10559567	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10559567	Sources: https://pubmed.ncbi.nlm.nih.gov/10559567

Sourcing

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM57076718	http://www.alfa-chemistry.com/search.aspx?q=ACM57076718
Angene	AGN-PC-0JK6EO	http://www.angenechemical.com/productshow/AGN-PC-0JK6EO.html
eMolecules	1986455	https://orderbb.emolecules.com/search/#?query=1986455
MuseChem	R006056	https://www.musechem.com/product/R006056.html
Tetrahedron	TS61585	http://www.thsci.com/search.do?q=TS61585
Toronto Research Chemicals	B687252	https://www.trc-canada.com/product-detail/?CatNum=B687252
Toronto Research Chemicals	D231400	https://www.trc-canada.com/product-detail/?CatNum=D231400

PubMed

Title	Date	PubMed
The effect of selective phosphodiesterase 3 and 4 isoenzyme inhibitors and established anti-asthma drugs on inflammatory cell activation.	1996-11	8937731

Patents

Sample Use Guides

In Vivo Use Guide

The patients with dementia of the Alzheimer type (DAT) were randomly allocated to denbufylline 25, 50 or 100 mg or to placebo given twice daily for 16 weeks.

Route of Administration: Oral

In Vitro Use Guide

Cyclic AMP PDE activity of human eosinophil homogenates was inhibited by denbufylline (IC50 = 360 nM).

Name

Type

Language

DENBUFYLLINE

Official Name

English

BRL 30892

Preferred Name

English

denbufylline [INN]

Common Name

English

BRL-30892

Code

English

DENBUFYLLINE [MART.]

Common Name

English

7-ACETONYL-1,3-DIBUTYLXANTHINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C744