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| | FLAVOPIRIDOL HYDROCHLORIDE Basic information |
| Product Name: | FLAVOPIRIDOL HYDROCHLORIDE | | Synonyms: | Flavopiridol (Alvocidib)hcl;Flavopiridol HCI;L-86-8276;2-(2-chlorophenyl)-5,7-dihydroxy-8-((3S,4R)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one hydrochloride;NSC 649890 HCl;(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride Flavopiridol hydrochloride;Flavopiridol hydrochloride
(-)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride;Flavopiridol hydrochloride, >=98% | | CAS: | 131740-09-5 | | MF: | C21H21Cl2NO5 | | MW: | 438.3 | | EINECS: | 634-346-4 | | Product Categories: | Inhibitors;Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 131740-09-5.mol |  |
| | FLAVOPIRIDOL HYDROCHLORIDE Chemical Properties |
| Melting point | 169.5-170°C | | alpha | 24D -1.73 to -3.9° | | storage temp. | 2-8°C | | solubility | H2O: ~2mg/mL | | pka | 5.68 ± 0.06(at 25℃) | | form | powder | | color | white to light brown | | 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 Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | RTECS | DJ2978830 |
| | FLAVOPIRIDOL HYDROCHLORIDE Usage And Synthesis |
| 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). It also inhibits TEFb, a complex composed of Cdk9 and cyclin T1, with a Ki value of 3 nM. 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. It also suppresses synovial hyperplasia and joint destruction in a mouse model of collagen-induced arthritis. | | Chemical Properties | Yellow Powder | | Uses | Flavopiridol hydrochloride hydrate has been used:
- as a cyclin-dependent kinase 9 (CDK9) inhibitor to study its effects on histone H3 methylation at lysine 36 (H3K36) and deactivation of transcription in porcine fetal fibroblasts
- as an RNA polymerase inhibitor to study its effects on hepatic cells
- as RNA transcription inhibitor to study its effects on euchromatin coarsening in zebrafish embryo
| | 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. | | 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 +4°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 |
| | FLAVOPIRIDOL HYDROCHLORIDE Preparation Products And Raw materials |
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