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| | Flavopiridol hydrochloride Basic information |
| | 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 | | 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 | | InChIKey | LGMSNQNWOCSPIK-LWHGMNCYSA-N | | SMILES | OC1=C(C(C=C(C2=C(Cl)C=CC=C2)O3)=O)C3=C([C@H]4CCN(C)C[C@H]4O)C(O)=C1.Cl | | CAS DataBase Reference | 131740-09-5 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | RTECS | DJ2978830 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral |
| | 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 | An inhibitor of cyclin-dependent kinases; the (-)-cis form induces apoptosis in certain tumor cells. | | 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
| | 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 | Flavopiridolis 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] G KAUR. Growth inhibition with reversible cell cycle arrest of carcinoma cells by flavone L86-8275.[J]. JNCI Journal of the National Cancer Institute, 1992, 84 22: 1736-1740. DOI:10.1093/jnci/84.22.1736
[2] L. CARTEE. 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.[J]. Molecular Pharmacology, 2002, 135 1: 1313-1321. DOI:10.1124/mol.61.6.1313
[3] GRAZIA AMBROSINI. The cyclin-dependent kinase inhibitor flavopiridol potentiates the effects of topoisomerase I poisons by suppressing Rad51 expression in a p53-dependent manner.[J]. Cancer research, 2008: 2312-2320. DOI:10.1158/0008-5472.can-07-2395
[4] SCHANG L M. Effects of pharmacological cyclin-dependent kinase inhibitors on viral transcription and replication[J]. Biochimica et biophysica acta. Proteins and proteomics, 2004, 1697 1: Pages 197-209. DOI:10.1016/j.bbapap.2003.11.024 |
| | Flavopiridol hydrochloride Preparation Products And Raw materials |
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