4,6-dioxo-N-phenyl-2-sulfanylidene-1,3-diazinane-5-carboxamide

• ChemBase ID: 153849
• Molecular Formular: C11H9N3O3S
• Molecular Mass: 263.27246
• Monoisotopic Mass: 263.03646216
• SMILES: c1ccc(cc1)NC(=O)C1C(=O)NC(=S)NC1=O
• Canonical SMILES: O=C(C1C(=O)NC(=S)NC1=O)Nc1ccccc1
• InChI: 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)
• InChIKey: JARCFMKMOFFIGZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,6-dioxo-N-phenyl-2-sulfanylidene-1,3-diazinane-5-carboxamide
• IUPAC Traditional name: merbarone
• Synonyms: 5-(N-Phenylcarbamoyl)-2-thiobarbituric acid; NSC-336628; Merbarone

Database IDs

• CAS Number: 97534-21-9
• MDL Number: MFCD00866337
• PubChem SID: 162247988; 24724534
• PubChem CID: 4990817

CALCULATED PROPERTIES

• Acid pKa: -3.2966475
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.3114381
• LogD (pH = 7.4): -1.3158467
• Log P: -1.288991
• Molar Refractivity: 68.5347 cm^3
• Polarizability: 25.906008 Å^3
• Polar Surface Area: 87.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: solid

Safety Information

• Storage Condition: under inert gas
• RTECS: UV7714625
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H9N3O3S

DETAILS

Sigma Aldrich - M2070

Biochem/physiol Actions
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.