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Theophylline monohydrate

Names

[ CAS No. ]:
5967-84-0

[ Name ]:
Theophylline monohydrate

[Synonym ]:
EINECS 200-385-7
MFCD00151659
Theophylline monohydrate

Biological Activity

[Description]:

Theophylline (1,3-Dimethylxanthine) monohydrate is a potent phosphodiesterase (PDE) inhibitor, adenosine receptor antagonist, and histone deacetylase (HDAC) activator. Theophylline (1,3-Dimethylxanthine) monohydrate inhibits PDE3 activity to relax airway smooth muscle. Theophylline (1,3-Dimethylxanthine) monohydrate has anti-inflammatory activity by increase IL-10 and inhibit NF-κB into the nucleus. Theophylline (1,3-Dimethylxanthine) monohydrate induces apoptosis. Theophylline (1,3-Dimethylxanthine) monohydrate can be used for asthma and chronic obstructive pulmonary disease (COPD) research[1][2][3][4][5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer
Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)
Signaling Pathways >> Immunology/Inflammation >> Interleukin Related
Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC
Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor
Signaling Pathways >> Epigenetics >> HDAC

[Target]

Human Endogenous Metabolite


[In Vitro]

Theophylline (1,3-Dimethylxanthine) monohydrate (1-1000 µM) inhibits cAMP hydrolysis by PDE in homogenates of bronchial tissue to relax human bronchus and pulmonary arteries[1]. Theophylline (1,3-Dimethylxanthine) monohydrate (10 µg/mL; 24 h; eosinophils) induces apoptosis through a reduction in the antiapoptotic protein Bcl-2[2]. Theophylline (1,3-Dimethylxanthine) monohydrate (0-500 µM; 2 h; A549 cells) inhibits NF-κB activation, I kappa B alpha (I-κBα) degradation and decreases the level of IL-6 in a concentration-dependent manner[3]. Theophylline (1,3-Dimethylxanthine) monohydrate (0-1000 µM; 30 min; A549 cells) induces histone deacetylase activity to decrease inflammatory gene expression[4]. Western Blot Analysis[3] Cell Line: A549 cells Concentration: 0, 20, 100 and 500 µM Incubation Time: 2 hours Result: Decreased the expression of NF-κB p65 and I-κBα degradation in a concentration-dependent manner. Western Blot Analysis[2] Cell Line: Eosinophils Concentration: 10 µg/mL Incubation Time: 24 hours Result: Decreased the expression of Bcl-2.

[In Vivo]

Theophylline (1,3-Dimethylxanthine) (100 mg/kg; i.p.; daily, for 9 d; male Swiss mice) has anti-inflammatory activity in mice and increases IL-6 and IL-10 levels and inhibits TNF-α and NO[1]. Animal Model: Male Swiss mice[1] Dosage: 100 mg/kg Administration: Intraperitoneal injection; daily, for 9 days Result: Increased IL-6 and IL-10 levels and inhibited TNF-α and NO.

[References]

[1]. Rabe KF, et, al. Theophylline and selective PDE inhibitors as bronchodilators and smooth muscle relaxants. Eur Respir J. 1995 Apr;8(4):637-42.

[2]. Chung IY, et, al. The downregulation of Bcl-2 expression is necessary for theophylline-induced apoptosis of eosinophil. Cell Immunol. 2000 Aug 1;203(2):95-102.

[3]. Ichiyama T, et, al. Theophylline inhibits NF-kappa B activation and I kappa B alpha degradation in human pulmonary epithelial cells. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):558-61.

[4]. Ito K, et, al, Adcock IM, Barnes PJ. A molecular mechanism of action of theophylline: Induction of histone deacetylase activity to decrease inflammatory gene expression. Proc Natl Acad Sci U S A. 2002 Jun 25;99(13):8921-6.

[5]. Barnes PJ. Theophylline. Am J Respir Crit Care Med. 2013 Oct 15;188(8):901-6.

Chemical & Physical Properties

[ Boiling Point ]:
454.1ºC at 760 mmHg

[ Melting Point ]:
270-274°C

[ Molecular Formula ]:
C7H10N4O3

[ Molecular Weight ]:
198.17900

[ Exact Mass ]:
198.07500

[ PSA ]:
81.91000

Safety Information

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S22-S36/37/39

[ RIDADR ]:
2811

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%


Related Compounds