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R8657

Sigma-Aldrich

Razoxane

>98% (HPLC)

Synonym(s):

(±)-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

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About This Item

Empirical Formula (Hill Notation):
C11H16N4O4
CAS Number:
21416-67-1
Molecular Weight:
268.27
EC Number:
244-379-2
MDL number:
MFCD00430424
UNSPSC Code:
12352200
PubChem Substance ID:
329824039
NACRES:
NA.77

assay

>98% (HPLC)

form

solid

solubility

DMSO: 40 mg/mL

storage temp.

room temp

SMILES string

CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

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)

InChI key

BMKDZUISNHGIBY-UHFFFAOYSA-N

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dynamics of tumour angiogenesis: effect of razoxane-induced growth rate slowdown.
K Hellmann
Clinical & experimental metastasis, 20(2), 95-102 (2003-04-23)
W Rhomberg et al.
Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al], 175(3), 102-104 (1999-03-27)
Angiosarcomas of the heart are rare neoplasms bearing an unfavorable prognosis. In recent series, the median survival is about 5 months. The response to radiation therapy is uncertain. A 65-year-old copper smith with an angiosarcoma of the right atrium and
Dana M Walker et al.
Pediatric blood & cancer, 60(4), 616-620 (2012-09-06)
Acute lymphoblastic (ALL) and myeloid leukemia (AML) account for approximately 26% of pediatric cancers. Anthracyclines are widely used to treat these leukemias, but dosing is limited by cardiotoxicity. Data support the efficacy of dexrazoxane as a cardioprotectant in children; however
K Hellmann et al.
Cancer treatment reviews, 18(4), 225-240 (1991-12-01)
Razoxane blocks cell division in the G2/M phase of the cell generation cycle and appears to normalize tumour neovasculature development. These were the principal reasons for the examination and probably for the demonstration of the radiosensitizing activity of Rz. Specially
Annie Calvé et al.
Canadian journal of physiology and pharmacology, 90(11), 1527-1534 (2012-11-28)
Childhood cancer survivors can develop significant cardiac dysfunction in adulthood as a consequence of their cancer treatment. Studies have linked heart failure during pregnancy to childhood doxorubicin (DOX) exposure. We hypothesized that DOX injection would reduce cardiac function peripartum and
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