4-[2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

• ChemBase ID: 70615
• Molecular Formular: C11H16N4O4
• Molecular Mass: 268.26914
• Monoisotopic Mass: 268.11715501
• SMILES: C(C(C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1
• Canonical SMILES: O=C1NC(=O)CN(C1)CC(N1CC(=O)NC(=O)C1)C
• InChI: InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)
• InChIKey: BMKDZUISNHGIBY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
• IUPAC Traditional name: razoxane
• Synonyms: 4,4'-(Propane-1,2-diyl)bis(piperazine-2,6-dione); (±)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane; (±)-1,2-Bis(3,5-dioxopiperazinyl)propane; 1,2-Bis(3,5-dioxo-1-piperazinyl)propane; 4,4′-Propylenebis(2,6-piperazinedione); ICI 59118; ICRF 159; NSC 129943; Razoxin; Tepirone; Troxozone; Razoxane

Database IDs

• CAS Number: 21416-67-1
• EC Number: 244-379-2
• MDL Number: MFCD00430424
• PubChem SID: 162036330
• PubChem CID: 30623

CALCULATED PROPERTIES

• Polar Surface Area: 98.82 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 11.198792
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.6580358
• LogD (pH = 7.4): -2.6527913
• Log P: -2.652655
• Molar Refractivity: 64.2532 cm^3
• Polarizability: 25.298058 Å^3

PROPERTIES

Physical Property

• Solubility: DMSO: soluble40 mg/mL
• Apperance: solid

Safety Information

• Storage Warning: IRRITANT
• RTECS: TL6389900
• German water hazard class: 3
• TSCA Listed: false
• Storage Temperature: room temp

Product Information

• Purity: >98% (HPLC); 95+%
• Empirical Formula (Hill Notation): C11H16N4O4

DETAILS

Sigma Aldrich - R8657

Biochem/physiol Actions
Razoxane is clinically active against angiogenesis and metastasis. Razoxane specifically inhibits topoisomerase II without inducing DNA strand breaks (topo II catalytic inhibitor). It is an antimitotic agent with immunosuppressive properties. Razoxane inhibits blood-borne and lymphatic metastases in different experimental models. Studies have shown that razoxane inhibits specifically the vasculogenic mimicry of B16F10 melanoma cells.