structure of Theophylline-8-butyric acid

Theophylline-8-butyric acid

CAS No.: 5438-71-1
M. Wt: 266.25300
M. Fa: C11H14N4O4
InChI Key: NGBYKZGOXFIONW-UHFFFAOYSA-N

Names and Identifiers of Theophylline-8-butyric acid

CAS Number

5438-71-1

IUPAC Name

4-(1,3-dimethyl-2,6-dioxo-7H-purin-8-yl)butanoic acid

InChI

InChI=1S/C11H14N4O4/c1-14-9-8(10(18)15(2)11(14)19)12-6(13-9)4-3-5-7(16)17/h3-5H2,1-2H3,(H,12,13)(H,16,17)

InChIKey

NGBYKZGOXFIONW-UHFFFAOYSA-N

Canonical SMILES

CN1C2=C(C(=O)N(C1=O)C)NC(=N2)CCCC(=O)O

UNII

1UR2VV86WO

Physical and chemical properties of Theophylline-8-butyric acid

Boiling Point

613.3ºC at 760mmHg

Density

1.451g/cm3

Exact Mass

266.10200

Flash Point

324.7ºC

Index of Refraction

1.609

Molecular Formula

C11H14N4O4

Molecular Weight

266.25300

PSA

109.98000

Applications of Theophylline-8-butyric acid

Theophylline-8-butyric acid has potential applications in various fields:

  • Pharmaceuticals: It is primarily investigated for use as a bronchodilator in respiratory diseases.
  • Research: Its unique properties make it a candidate for studying the mechanisms of action of xanthines and their derivatives in cellular signaling pathways.
  • Biotechnology: The compound can be utilized in developing therapeutic agents targeting specific inflammatory pathways .

Interaction Studies of Theophylline-8-butyric acid

Research on the interactions of theophylline-8-butyric acid focuses on its pharmacokinetics and pharmacodynamics:

  • Drug Interactions: Studies indicate that this compound may interact with other medications metabolized by cytochrome P450 enzymes, particularly affecting the metabolism of other xanthines and anti-inflammatory drugs .
  • Receptor Binding Studies: Investigations into its binding affinity for adenosine receptors reveal insights into its potential therapeutic effects and side effects associated with xanthine derivatives .

Biological Activity of Theophylline-8-butyric acid

Theophylline-8-butyric acid exhibits several biological activities primarily related to its interaction with adenosine receptors and phosphodiesterase enzymes.

  • Bronchodilation: Similar to theophylline, it may relax bronchial smooth muscle and improve airflow in conditions like asthma and chronic obstructive pulmonary disease.
  • Anti-inflammatory Effects: The compound has been shown to inhibit inflammatory responses by modulating histone deacetylase activity, thus preventing the transcription of pro-inflammatory genes .
  • Cyclic Adenosine Monophosphate Modulation: It acts as a phosphodiesterase inhibitor, leading to increased levels of cyclic adenosine monophosphate, which contributes to its bronchodilatory effects .