ChemicalBook--->CAS DataBase List--->21416-67-1

21416-67-1

21416-67-1 Structure

21416-67-1 Structure
IdentificationBack Directory
[Name]

4,4'-propylenebis(piperazine-2,6-dione)
[CAS]

21416-67-1
[Synonyms]

RAZOXANUM
Troxozone
Propyliminum
rac-Dexrazoxane
4,4'-(Propane-1,2-diyl)
bis(piperazine-2,6-dione)
-propylenebis(piperazine-2,6-dione)
4,4'-propylenebis(piperazine-2,6-dione)
4,4'-Propane-1,2-diyldipiperazine-2,6-dione
4,4'-(1-Methylethylene)bis(2,6-piperazinedione)
4,4'-(Propane-1,2-diyl)bis(piperazine-2,6-dione)
4,4'-propylenebis(piperazine-2,6-dione) USP/EP/BP
4,5,9,10-Pyrenetetrone,2,7-bis(1,6-dimethylethyl)-
4-[3-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
ICRF 159,ICRF159,ICRF-159,Topoisomerase II Inhibitor,Razoxane,RCC,Inhibitor,Topoisomerase,renal cell carcinoma,inhibit
[EINECS(EC#)]

244-379-2
[Molecular Formula]

C11H16N4O4
[MDL Number]

MFCD00430424
[MOL File]

21416-67-1.mol
[Molecular Weight]

268.269
Chemical PropertiesBack Directory
[Melting point ]

237-239°
[Boiling point ]

411.43°C (rough estimate)
[density ]

1.2576 (rough estimate)
[refractive index ]

1.6081 (estimate)
[storage temp. ]

room temp
[solubility ]

DMSO: soluble40mg/mL
[form ]

solid
[pka]

11.00±0.20(Predicted)
[color ]

White to off-white
[Water Solubility ]

3g/L(25 ºC)
[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
[SMILES]

CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
Safety DataBack Directory
[WGK Germany ]

3
[RTECS ]

TL6389900
[Storage Class]

11 - Combustible Solids
[Safety Profile]

Suspected human carcinogen producing leukemia and skin tumors. Moderately toxic by intraperitoneal route. Human effects: normocytic anemia and thrombocytopenia. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard InformationBack Directory
[Uses]

Razoxane is an inhibitor of Topo II.
[Definition]

ChEBI: Razoxane is a N-alkylpiperazine.
[Biological Activity]

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 th at razoxane inhibits specifically the vasculogenic mimicry of B16F10 melanoma cells.
[in vivo]

Early treatment with Razoxane (30 mg/kg i.p. from day -2 to +14) shows a greater inhibition of pulmonary metastases than later treatment (30 mg/kg i.p. from day +14 to +28 after transplantation)[2].

Animal Model:Sprague-Dawley rats[2]
Dosage:30 mg/kg or 10 mg/kg per day
Administration:Intraperitoneally (i.p.) from 2 days before to 14 days after tumor transplantation
Result:Resulted in a dose-dependent prolongation of median survival time (83 or 48 days respectively, versus 38 days for the control group), but showed no influence on the growth of the primary tumor.
[IC 50]

Topoisomerase II
Spectrum DetailBack Directory
[Spectrum Detail]

4,4'-propylenebis(piperazine-2,6-dione)(21416-67-1)1HNMR
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