SML2113
FR194921
≥98% (HPLC)
Synonym(s):
2-(1-Methyl-4-piperidinyl)-6-[2-phenylpyrazolo-(1,5-a)pyridin-3-yl]-3(2H)-pyridazinone
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About This Item
Empirical Formula (Hill Notation):
C23H23N5O
CAS Number:
Molecular Weight:
385.46
NACRES:
NA.77
UNSPSC Code:
12352200
Product Name
FR194921, ≥98% (HPLC)
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
SMILES string
CN(CC1)CCC1N2N=C(C=CC2=O)C3=C4N(N=C3C5=CC=CC=C5)C=CC=C4
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear (warmed)
storage temp.
2-8°C
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
11 - Combustible Solids
wgk
WGK 3
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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
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
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