M2070

Merbarone

≥98% (HPLC), solid

• Synonym(s): 5-(N-Phenylcarbamoyl)-2-thiobarbituric acid, NSC-336628
• Empirical Formula (Hill Notation): C₁₁H₉N₃O₃S
• CAS Number: 97534-21-9
• Molecular Weight: 263.27
• NACRES: NA.77
• PubChem Substance ID: 24724534
• UNSPSC Code: 12352200
• MDL number: MFCD00866337
• Assay: ≥98% (HPLC)
• Form: solid

Properties

• Quality Segment: 200
• 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.

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.[1] This delays cell entry into mitosis.[1] 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 Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)