F3055

Flavopiridol hydrochloride hydrate

Name: Flavopiridol hydrochloride hydrate
Brand: SIGMA

≥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

Product Name

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

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 key

LGMSNQNWOCSPIK-LWHGMNCYSA-N

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

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

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

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000277078

0000213400

0000173217

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Antitumor effects of flavopiridol, a cyclin-dependent kinase inhibitor, on human cholangiocarcinoma in vitro and in an in vivo xenograft model.

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

Rapid and Scalable Profiling of Nascent RNA with fastGRO.

Elisa Barbieri et al.

Cell reports, 33(6), 108373-108373 (2020-11-12)

Genome-wide profiling of nascent RNA has become a fundamental tool to study transcription regulation. Unlike steady-state RNA-sequencing (RNA-seq), nascent RNA profiling mirrors real-time activity of RNA polymerases and provides an accurate readout of transcriptome-wide variations. Some species of nuclear RNAs

Flavopiridol causes cell cycle inhibition and demonstrates anti-cancer activity in anaplastic thyroid cancer models.

Nicole Pinto et al.

PloS one, 15(9), e0239315-e0239315 (2020-09-25)

Anaplastic thyroid cancer (ATC) is a rare, but nearly uniformly fatal disease that is typically resistant to chemotherapy and radiation. Alternative strategies to target this cancer at a molecular level are necessary in order to improve dismal outcomes for ATC

DDX5 promotes oncogene C3 and FABP1 expressions and drives intestinal inflammation and tumorigenesis.

Nazia Abbasi et al.

Life science alliance, 3(10) (2020-08-21)

Tumorigenesis in different segments of the intestinal tract involves tissue-specific oncogenic drivers. In the colon, complement component 3 (C3) activation is a major contributor to inflammation and malignancies. By contrast, tumorigenesis in the small intestine involves fatty acid-binding protein 1

Flavopiridol, a cyclin-dependent kinase inhibitor, enhances radiosensitivity of ovarian carcinoma cells.

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

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