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FLAVOPIRIDOL HYDROCHLORIDE

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FLAVOPIRIDOL HYDROCHLORIDE Basic information

Product Name:
FLAVOPIRIDOL HYDROCHLORIDE
Synonyms:
  • Flavopiridol hydrochloride, >=98%
  • Alvocidib HCL
  • Flavopiridol (Alvocidib) hydrochloride
  • Flavopiridol hydrochloride hydrate
  • NSC-649890 hydrochloride
  • HL 275; NSC 649890; MDL 107826A; FLAVOPIRIDOL HCL; ALVOCIDIB HYDROCHLORIDE
  • FLAVOPIRIDOL HYDROCHLORIDE
  • FLAVOPIRIDOL HCL
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
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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
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
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Safety Information

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
DJ2978830
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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

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 HYDROCHLORIDESupplier

Shanghai Boyle Chemical Co., Ltd.
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J & K SCIENTIFIC LTD.
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Chembest Research Laboratories Limited
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Chemsky(shanghai)International Co.,Ltd.
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Jinan Trio PharmaTech Co., Ltd.
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