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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

Quality Level

100

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.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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
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
Dexrazoxane does not affect treatment outcome in non-Hodgkin's lymphoma patients.
Anat Rabinovich et al.
American journal of hematology, 87(8), 830-832 (2012-06-01)
Martin Stěrba et al.
Antioxidants & redox signaling, 18(8), 899-929 (2012-07-17)
Anthracyclines (doxorubicin, daunorubicin, or epirubicin) rank among the most effective anticancer drugs, but their clinical usefulness is hampered by the risk of cardiotoxicity. The most feared are the chronic forms of cardiotoxicity, characterized by irreversible cardiac damage and congestive heart
Christel Fontaine et al.
Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer, 20(5), 1109-1112 (2012-01-27)
Anthracycline extravasation (ACEV) is a rare but potentially devastating event which can result in severe injuries including ulceration and necrosis, slow-healing lesions, serious joint damage and permanent disfigurement. It can delay further scheduled chemotherapy and affect cancer treatment outcome. Savene®
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