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F3055

Flavopiridol hydrochloride hydrate

≥98% (HPLC), CDK and CDC25 phosphatase family inhibitor, powder

Synonym(s):

(−)-2-(2-Chlorophenyl)-5,7-dihydroxy-8-[(3S,4R)-3-hydroxy-1-methyl-4-piperidinyl]-4H-1-benzopyran-4-one hydrochloride, L-86-8276, NSC-649890

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About This Item

Empirical Formula (Hill Notation):
C21H20ClNO5 ·HCl · xH2O
CAS Number:
131740-09-5
Molecular Weight:
438.30 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
24724481
NACRES:
NA.77
MDL number:
MFCD26792554
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated
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Product Name

Flavopiridol hydrochloride hydrate, ≥98% (HPLC), powder

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to light brown

solubility

H2O: ~2 mg/mL, DMSO: >5 mg/mL

storage temp.

2-8°C

SMILES string

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

InChI

1S/C21H20ClNO5.ClH/c1-23-7-6-12(17(27)10-23)19-14(24)8-15(25)20-16(26)9-18(28-21(19)20)11-4-2-3-5-13(11)22;/h2-5,8-9,12,17,24-25,27H,6-7,10H2,1H3;1H/t12-,17+;/m0./s1

InChI key

LGMSNQNWOCSPIK-LWHGMNCYSA-N

Gene Information

human ... CDK1(983), CDK2(1017), CDK4(1019), CDK6(1021), CDK7(1022), CDK9(1025)

Application

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

Biochem/physiol Actions

Flavopiridol hydrochloride is a potent CDK (cyclin-dependent kinase), and a CDC25 phosphatase family inhibitor.
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).

Features and Benefits

This compound is featured on the CDKs page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000277078
0000277078
0000213400
0000213400
0000173217

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Articles

Using Human iPS Cell-derived Colon Organoids for Cytotoxicity Screening of Drug Compounds

Human epithelial intestinal colonic organoids can be used as an alternative to Caco-2 drug permeability assays for drug screening and compound toxicity testing.

Saowaluk Saisomboon et al.
Heliyon, 5(5), e01675-e01675 (2019-06-14)
Flavopiridol, a pan-cyclin-dependent kinase (CDK) inhibitor, was recently identified as an effective antitumor agent for several cancers. We investigated the antitumor effect of flavopiridol on cholangiocarcinoma (CCA), in vitro and in vivo. A methylthiotetrazole assay revealed that the proliferation of
Stefano de Pretis et al.
Genome research, 27(10), 1658-1664 (2017-09-15)
Overexpression of the MYC transcription factor causes its widespread interaction with regulatory elements in the genome but leads to the up- and down-regulation of discrete sets of genes. The molecular determinants of these selective transcriptional responses remain elusive. Here, we
Uma Raju et al.
Cancer research, 63(12), 3263-3267 (2003-06-18)
Flavopiridol, a cyclin-dependent kinase (cdk) inhibitor, can cause cell cycle arrest, induce apoptosis in cancer cells, and inhibit tumor cell growth in vivo. The present study investigated the in vitro radiosensitizing effect of flavopiridol and the underlying molecular mechanisms in
View All Related Papers

Global Trade Item Number

SKUGTIN
F3055-25MG04061832434025
F3055-5MG04061832434032