PROXYPHYLLINE Chemical Properties

Melting point:

134-136°C

Boiling point:

487.2±51.0 °C(Predicted)

Density 

1.46±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMF: 10 mg/ml
DMSO: 10 mg/ml
Ethanol: 1 mg/mlPBS (pH 7.2): 1 mg/ml

form 

Solid

pka

14.55±0.20(Predicted)

color 

White to Off-White

Water Solubility 

285.7g/L(temperature not stated)

Merck 

14,7905

InChI

InChI=1S/C10H14N4O3/c1-6(15)4-14-5-11-8-7(14)9(16)13(3)10(17)12(8)2/h5-6,15H,4H2,1-3H3

InChIKey

KYHQZNGJUGFTGR-UHFFFAOYSA-N

SMILES

N1(CC(O)C)C2=C(N(C)C(=O)N(C)C2=O)N=C1

CAS DataBase Reference

603-00-9(CAS DataBase Reference)

NIST Chemistry Reference

Proxyphylline(603-00-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

RTECS 

XH5907500

HS Code 

2939.59.0000

MSDS

• Language:English Provider:SigmaAldrich

PROXYPHYLLINE Usage And Synthesis

Chemical Properties

White Solid

Uses

A metabolite of Theophylline in human plasma.

Definition

ChEBI: Proxyphylline is an oxopurine.

Biological Activity

ki: 82 nm for bovine brain a1 adenosine receptorproxyphylline is an a1 adenosine receptor antagonist.the a1 adenosine receptor, the best characterized purinergic receptor family, can mediate responses via multiple pertussis toxin-sensitive gtp binding proteins to various different effectors.

in vitro

previous study showed that proxyphylline could selectively antagonize a1 adenosine receptors versus a2 adenosine receptors (ki = 850 μm for platelets) [1].

in vivo

in a previous study, rats that were allodynic following the vincristine injections were randomly allocated into four groups. theoesberiven f (a combination of proxyphylline and melilotus extract) was administered to rats. results showed that the decreased paw withdrawal threshold induced by vincristine injection was increased by theoesberiven f treatment and the increased withdrawal frequency to cold stimuli was also reduced by theoesberiven f treatment [2].

Purification Methods

Crystallise it from EtOH, aqueous MeOH or EtOAc. Roth Archiv Pharmazie 292 234 1959, Zelnik et al. Bull Soc Chim Fr 1733 1956, Beilstein 26 III/IV 2366.]

References

[1] BRUNS R F. Adenosine antagonism by purines, pteridines and benzopteridines in human fibroblasts[J]. Biochemical pharmacology, 1981, 30 4: Pages 325-333. DOI: 10.1016/0006-2952(81)90062-9
[2] KEISUKE TAKEDA . EFFECTS OF AMINOPHYLLINE, PROXYPHYLLINE AND A PROXYPHYLINE-MELILOTUS EXTRACT-RUTIN MIXTURE (THEOESBERIVEN) ON THE HEART AND THE CORONARY CIRCULATION[J]. Japanese journal of pharmacology, 1977, 27 5: Pages 709-720. DOI: 10.1254/jjp.27.709
[3] LUCYNA KORZYCKA  Dorota G. Synthesis, pharmacological activity and nitric oxide generation by nitrate derivatives of theophylline.[J]. Journal of Pharmacy and Pharmacology, 2008, 60 5: 637-645. DOI: 10.1211/jpp.60.5.0010
[4] KNUT DALAKER  Hans P. Effect of some drugs on thromboplastin activity in mouse trophoblast cells in vitro and in vivo[J]. Biochemical pharmacology, 1986, 35 20: Pages 3433-3439. DOI: 10.1016/0006-2952(86)90609-x

PROXYPHYLLINE(603-00-9)Related Product Information

• Diprophylline
• diniprofylline
• Tazifylline
• Xanthinol nicotinate
• PROXYPHYLLINE
• Theophylline
• Xanthinol
• 1,3-DIMETHYL-7-(OXIRAN-2-YLMETHYL)-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE
• (S)-Proxyphylline
• (R)-Proxyphylline
• Xantifibrate
• 8-CHLORO-7-(3-CHLORO-2-HYDROXYPROPYL)-1,3-DIMETHYL-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE
• 7-(3-CHLORO-2-HYDROXYPROPYL)-1,3-DIMETHYL-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE
• 8-BROMO-7-(2-HYDROXYPROPYL)-1,3-DIMETHYL-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE
• 8-BROMO-7-(3-CHLORO-2-HYDROXYPROPYL)-1,3-DIMETHYL-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE
• 1,3-DIMETHYL-8-MORPHOLINO-7-(2-OXIRANYLMETHYL)-2,3,6,7-TETRAHYDRO-1H-2,6-PURINEDIONE
• 8-BROMO-7-(2-HYDROXYBUTYL)-1,3-DIMETHYL-2,3,6,7-TETRAHYDRO-1H-PURINE-2,6-DIONE
• 8-(BENZYLAMINO)-7-(3-CHLORO-2-HYDROXYPROPYL)-1,3-DIMETHYL-2,3,6,7-TETRAHYDRO-1H-2,6-PURINEDIONE