ChemicalBook CAS DataBase List 202646-80-8

202646-80-8

Name	FR-194921
CAS	202646-80-8
Molecular Formula	C23H23N5O
MDL Number	MFCD27965870
Molecular Weight	385.46
MOL File	202646-80-8.mol

Chemical Properties

density	1.29±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: 2mg/mL, clear (warmed)
form	Solid
pka	8.51±0.10(Predicted)
color	Off-white to light yellow
InChI	1S/C23H23N5O/c1-26-15-12-18(13-16-26)28-21(29)11-10-19(24-28)22-20-9-5-6-14-27(20)25-23(22)17-7-3-2-4-8-17/h2-11,14,18H,12-13,15-16H2,1H3
InChIKey	YHDRUTMZCJZJAL-UHFFFAOYSA-N
SMILES	CN(CC1)CCC1N2N=C(C=CC2=O)C3=C4N(N=C3C5=CC=CC=C5)C=CC=C4

Safety Data

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Hazard Information

Uses

FR194921 is a potent, selective and orally active and cross the blood-brain barrier Adenosine A1 antagonist with Ki value of 6.6, 5400 nM for A1, A2A, respectively. FR194921 shows cognitive-enhancing and anxiolytic activity[1][2].

Biological Activity

FR194921 is a blood-brain barrier-permeable A1R adenosine receptor antagonist. The measured Ki values of FR194921 for the human adenosine A1 receptors have been in the low nM range with no binding affinity for A2A and A3 receptors up to 1μM. It is orally active and has good bioavailability. FR194921 was used in a recent study to restore auditory cortex plasticity. Paired with sound exposureFR194921 resulted in cortical map plasticity and improved auditory perception in adult mice.

in vivo

FR194921 (32 mg/kg; p.o.) shows good oral bioavailability with AUC of 6.91 μg·h/mL, C_max of 2.13 μg/mL and T_max OF 0.63 h, BA of 60.6% in rats^[1].
FR194921 (0.032, 0.1, 0.32 mg/kg; p.o.) dose-dependently attenuates the hypolocomotion induced by CPA (HY-103181)^[2].
FR194921 (0.1-10 mg/kg; i.p.) significantly ameliorates scopolamine (HY-N0296)-induced memory deficits^[2].

Animal Model:	SD rats^[2]
Dosage:	0.032, 0.1, 0.32 mg/kg
Administration:	P.o.; administered orally 25 min prior to intraperitoneal administration of CPA (0.056 mg/kg; i.p.)
Result:	Dose-dependently attenuated the hypolocomotion induced by CPA with an ED50 value of 0.08 mg/kg and statistical significance at 0.32 mg/kg.

Animal Model:	SD rats^[2]
Dosage:	0.1, 0.32, 1, 3.2, 10 mg/kg
Administration:	I.p.; Scopolamine (HY-N0296)(1 mg/kg, i.p.)
Result:	Significant cognitive enhanced following scopolamine-induced memory deficits in rats.

IC 50

A1R: 6.6 nM (Ki); A_2AR: 5400 nM (Ki)

References

[1] Kuroda S, et al. Design, synthesis and biological evaluation of a novel series of potent, orally active adenosine A1 receptor antagonists with high blood-brain barrier permeability. Chem Pharm Bull (Tokyo). 2001 Aug;49(8):988-98. DOI:10.1248/cpb.49.988
[2] Maemoto T, et al. Pharmacological characterization of FR194921, a new potent, selective, and orally active antagonist for central adenosine A1 receptors. J Pharmacol Sci. 2004 Sep;96(1):42-52. DOI:10.1254/jphs.fp0040359

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