EMAIL THIS PAGE TO A FRIEND
M2070 Sigma-Aldrich

Merbarone

≥98% (HPLC), solid

Synonym: 5-(N-Phenylcarbamoyl)-2-thiobarbituric acid, NSC-336628

  • CAS Number 97534-21-9

  • Empirical Formula (Hill Notation) C11H9N3O3S

  • Molecular Weight 263.27

  •  MDL number MFCD00866337

  •  PubChem Substance ID 24724534

Purchase

Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Gene Regulation and Expression,
assay   ≥98% (HPLC)
form   solid
drug control   regulated under CDSA - not available from Sigma-Aldrich Canada
solubility   DMSO: >5 mg/mL
storage temp.   2-8°C
SMILES string   O=C1NC(=S)NC(=O)C1C(=O)Nc2ccccc2
InChI   1S/C11H9N3O3S/c15-8(12-6-4-2-1-3-5-6)7-9(16)13-11(18)14-10(7)17/h1-5,7H,(H,12,15)(H2,13,14,16,17,18)
InChI key   JARCFMKMOFFIGZ-UHFFFAOYSA-N

Description

Application

Merbarone has been used to study its effect on the occurrence of DNA lesions.

Packaging

25 mg in glass bottle

Biochem/physiol Actions

Thiobarbituric acid with aniline joined by an amide linkage forms merbarone. It is known to prolong cell cycle progression by inducing DNA double strand breaks, retarding S phase and arresting G2 phase. This delays cell entry into mitosis. Merbarone possesses cytotoxic and genotoxic action and promotes endoreduplication. Merbarone has mild antitumor action and is also found to nephrotoxic.

Selective topoisomerase II inhibitor. Blocks topo II-mediated DNA cleavage without stabilizing DNA-topo II-cleavable complexes. Induces apoptosis in CEM cells via caspase 3 dependent mechanism.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
UV7714625
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

Please Enter a Lot Number
Protocols & Articles

Articles

Caspases

Caspases (Cysteine dependant Aspartate Specific Proteases) form a family of closely related enzymes (family C14; clan CD) involved in regulating a type of cell death known as apoptosis, inflammatory ...
Keywords: Alkylations, Alzheimer Disease, Apoptosis, Cancer, Catalysis, Clinical, Diseases, Gene expression, Huntington Disease, Inflammation, Ligands, Oncology, Parkinson Disease, Polymorphisms

Peer-Reviewed Papers
15

References

Related Products

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?