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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 Code

11 - Combustible Solids

WGK

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)
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
Petra Kovarikova et al.
Journal of pharmaceutical and biomedical analysis, 76, 243-251 (2013-01-24)
Dexrazoxane (DEX) is the only clinically used drug effective against anthracycline-induced cardiotoxicity and extravasation injury. However, the mechanism of its cardioprotective action still remains elusive. This paucity of comprehensive data is at least partially caused by the analytical difficulties associated
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®
Rachel O Venable et al.
Journal of the American Veterinary Medical Association, 240(3), 304-307 (2012-01-20)
4 dogs were treated with dexrazoxane for known or suspected doxorubicin extravasation. Records were retrospectively reviewed. Doses and number of doses of dexrazoxane were variable. Dexrazoxane was administered within 2 hours after known extravasation in 3 dogs and 48 hours
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