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Merck

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

Key Documents

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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

Quality Level

100

Gene Information

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

Related Categories

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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

F3055-VAR: + F3055-5MG: + F3055-1MG: + F3055-BULK: + F3055-25MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000277078
0000277078
0000213400
0000213400
0000173218

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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
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
Anne Pumfery et al.
Current pharmaceutical design, 12(16), 1949-1961 (2006-06-22)
Cyclin-dependent kinases (CDKs) are key regulators of the cell cycle and RNA polymerase II transcription. Several pharmacological CDK inhibitors (PCIs) are currently in clinical trials as potential cancer therapeutics since CDK hyperactivation is detected in the majority of neoplasias. Within
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
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
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