Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

SML2113

Sigma-Aldrich

FR194921

≥98% (HPLC)

Synonym(s):

2-(1-Methyl-4-piperidinyl)-6-[2-phenylpyrazolo-(1,5-a)pyridin-3-yl]-3(2H)-pyridazinone

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C23H23N5O
CAS Number:
202646-80-8
Molecular Weight:
385.46
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

CN(CC1)CCC1N2N=C(C=CC2=O)C3=C4N(N=C3C5=CC=CC=C5)C=CC=C4

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

InChI key

YHDRUTMZCJZJAL-UHFFFAOYSA-N

Biochem/physiol Actions

A1R adenosine receptor antagonist
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 exposure, FR194921 resulted in cortical map plasticity and improved auditory perception in adult mice.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

It looks like we've run into a problem, but you can still download Certificates of Analysis from our Documents section.

If you need assistance, please contact Customer Support

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Takuya Maemoto et al.
Journal of pharmacological sciences, 96(1), 42-52 (2004-09-08)
Adenosine A1 receptors in the brain are believed to play an important role in brain functioning. We have discovered a novel adenosine A1 receptor antagonist, FR194921 (2-(1-methyl-4-piperidinyl)-6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-3(2H)-pyridazinone), and characterized the pharmacological activity in the present study. FR194921 showed potent and
S Kuroda et al.
Chemical & pharmaceutical bulletin, 49(8), 988-998 (2001-08-23)
A novel series of 3-(2-substituted-3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridines (5-38) were synthesized and evaluated for their in vitro adenosine A1 and A(2A) receptor binding activities, and in vitro metabolism by rat liver in order to search for orally active compounds. Most of the test
Jay A Blundon et al.
Science (New York, N.Y.), 356(6345), 1352-1356 (2017-07-01)
Circuits in the auditory cortex are highly susceptible to acoustic influences during an early postnatal critical period. The auditory cortex selectively expands neural representations of enriched acoustic stimuli, a process important for human language acquisition. Adults lack this plasticity. Here

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service