| Identification | Back Directory | [Name]
FLAVOPIRIDOL HYDROCHLORIDE | [CAS]
131740-09-5 | [Synonyms]
HL 275
L-86-8276
NSC 649890
MDL 107826A
NSC 649890 HCl
Flavopiridol HCI
FLAVOPIRIDOL HCL
Alvocidib Hydrochloride
FLAVOPIRIDOL HYDROCHLORIDE
Flavopiridol (Alvocidib)hcl
2-(2-chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one hydrochloride
(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride
(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride
4H-1-Benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-(3-hydroxy-1-methyl-4-piperidinyl)-, hydrochloride, (-)-cis-
rel-(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one Hydrochloride
4H-1-Benzopyran-4-one, 2-(2-chlorophenyl)-5,7-dihydroxy-8-[(3R,4S)-3-hydroxy-1-methyl-4-piperidinyl]-, hydrochloride, rel-
L-86-8276, NSC-649890, (-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3s,4r)-3-hydroxy-1-methyl-4-piperidinyl]-4h-1-benzopyran-4-one hydrochloride
Flavopiridol hydrochloride
(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride
(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride Flavopiridol hydrochloride | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C21H21Cl2NO5 | [MDL Number]
MFCD26792554 | [MOL File]
131740-09-5.mol | [Molecular Weight]
438.3 |
| Chemical Properties | Back Directory | [Appearance]
Yellow Powder | [Melting point ]
169.5-170°C | [alpha ]
24D -1.73 to -3.9° | [storage temp. ]
2-8°C | [solubility ]
H2O: ~2mg/mL | [form ]
powder | [pka]
5.68 ± 0.06(at 25℃) | [color ]
white to light brown | [Water Solubility ]
H2O: ~2mg/mL
DMSO: >5mg/mL | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month | [CAS DataBase Reference]
131740-09-5 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Powder | [Usage]
An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells | [Uses]
An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells | [Definition]
ChEBI: A hydrochloride salt resulting from the formal reaction of equimolar amounts of alvocidib and hydrogen chloride. A cyclin-dependent kinase 9 (CDK9) inhibitor, it has been studied for the treatment of acute myeloid leukaemia, arthritis and atherosclerotic p
aque formation. | [Description]
Flavopiridol is an orally bioavailable inhibitor of cyclin dependent kinases (IC50s = ~100, ~100, ~100, and 300 nM for Cdk1, Cdk2, Cdk4, and Cdk7, respectively).1 It also inhibits TEFb, a complex composed of Cdk9 and cyclin T1, with a Ki value of 3 nM.2 Flavopiridol inhibits transcription of a CMV promoter in HeLa nuclear extract (IC50 = 34 nM), Tat-stimulated transcription of an HIV-1 promotor (IC50 = 7 nM), and HIV-1 replication in HEK239T cells (IC50 = <10 nM). In vivo, flavopiridol (5 mg/kg, i.p.) induces apoptosis and cyclin D1 depletion and delays tumor growth in an HN-12 head and neck carcinoma mouse xenograft model.1 It also suppresses synovial hyperplasia and joint destruction in a mouse model of collagen-induced arthritis.3 | [Biochem/physiol Actions]
Flavopiridol?is a semi-synthetic flavone obtained from Dysoxylum binectariferum that acts as an anti-tumor agent against several cancers. It also shows anti-cancer properties due to which it has been studied in the treatment of acute myeloid leukemia (AML). | [storage]
Store at -20°C | [References]
1) Kaur?et al. (1992),?Growth inhibition with reversible cell cycle arrest of carcinoma cells by flavone L86-8275;? J. Natl. Cancer Inst.,?84?1736
2) Cartee?et al. (2002),?Synergistic induction of apoptosis in human myeloid leukemia cells by phorbol 12-myristate 13-acetate and flavopiridol proceeds via activation of both the intrinsic and tumor necrosis factor-mediated extrinsic cell death pathways;? Mol. Pharmacol.,?61?1313
3) Ambrosini?et al. (2008),?The cyclin-dependent kinase inhibitor flavopiridol potentiates the effects of topoisomerase I poisons by suppressing Rad51 expression in a p53-dependent manner;? Cancer Res.?68?2312
4) Schang?et al. (2004),?Effects of pharmacological cyclin-dependent kinase inhibitors on viral transcription and replication;? Biochim. Biophys. Acta,?1697?197 |
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