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Baicalein

Polyphenol compound

Field	Value
drug_name	Baicalein
image	Baicalein.svg
image_class	skin-invert-image
image2	Baicalein-3D-balls.png
image_class2	bg-transparent
CAS_number	491-67-8
PubChem	5281605
IUPHAR_ligand	5144
ChemSpiderID	4444924
UNII	49QAH60606
KEGG	C10023
ChEBI	2979
ChEMBL	8260
synonyms	Biacalein; Noroxylin
IUPAC_name	5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one
C	15	H=10	O=5
SMILES	O=C\1c3c(O)c(O)c(O)cc3O/C(=C/1)c2ccccc2
StdInChI	1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H
StdInChIKey	FXNFHKRTJBSTCS-UHFFFAOYSA-N

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Baicalein (5,6,7-trihydroxyflavone) is a flavone, a type of flavonoid, originally isolated from the roots of Scutellaria baicalensis and Scutellaria lateriflora. It is also a constituent of Oroxylum indicum (Indian trumpetflower) and thyme. It is the aglycone of baicalin.

Pharmacology

Baicalein, along with its glucuronide baicalin, is a positive allosteric modulator of the benzodiazepine site and a non-benzodiazepine site of the GABAA receptor, but with an affinity over 250× lower than diazepam. It displays subtype selectivity for α2 and α3 subunit-containing GABAA receptors.

The flavonoid has been shown to inhibit certain types of lipoxygenases.

Baicalein is an inhibitor of CYP2C9, an enzyme of the cytochrome P450 system that metabolizes drugs in the body.

A derivative of baicalin is a known prolyl endopeptidase inhibitor.

References

(2024). "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University.
(2008). "Phytochemistry Research Progress". Nova Publishers.
(September 2013). "Baicalein reduces β-amyloid and promotes nonamyloidogenic amyloid precursor protein processing in an Alzheimer's disease transgenic mouse model". Journal of Neuroscience Research.
(August 1998). "Benzodiazepine binding site-interactive flavones from Scutellaria baicalensis root". Planta Medica.
(2004). "Complementary and Alternative Approaches to Biomedicine".
(December 2008). "GABA A receptor subtype selectivity underlying selective anxiolytic effect of baicalin". Neuropharmacology.
(June 2006). "Baicalein is a potent in vitro inhibitor against both reticulocyte 15-human and platelet 12-human lipoxygenases". Bioorganic & Medicinal Chemistry.
(March 2009). "Mechanism of CYP2C9 inhibition by flavones and flavonols". Drug Metabolism and Disposition.
(August 2008). "Baicalin, a prodrug able to reach the CNS, is a prolyl oligopeptidase inhibitor". Bioorganic & Medicinal Chemistry.

Info: Wikipedia Source

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aromatase-inhibitors flavones pyrogallols gabaa-receptor-positive-allosteric-modulators antiestrogens anxiolytics triols

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