Razoxane

Names

[ Name ]:
Razoxane

[Synonym ]:
4,4'-propylenebis(piperazine-2,6-dione)
4,4'-Propane-1,2-diyldipiperazine-2,6-dione
4,4'-(1-Methylethylene)bis(2,6-piperazinedione)
dl-1,2-bis(3,5-dioxopiperazin-1-yl)-propane
Propyliminum
RAZOXANUM
1,2-bis(3,5-dioxopiperazin-1-yl)-propane
(+)-1,2-bis(3,5-dioxopiperazinyl)propane
(+)-1,2-bis(3,5-dioxopiperazinyl-1-yl)propane
Razoxane

Biological Activity

[Description]:

Razoxane (ICRF 159) is an antiangiogenic topoisomerase II inhibitor, can be used for the research of renal cell carcinoma (RCC)[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

[Target]

Topoisomerase II

[In Vitro]

Razoxane (30 mg/kg; i.p.) exhibits antimetastatic effects in a rat osteosarcoma model.

[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.

[References]

[1]. J P Braybrooke, et al. A phase II study of Razoxane, an antiangiogenic topoisomerase II inhibitor, in renal cell cancer with assessment of potential surrogate markers of angiogenesis. Clin Cancer Res.2000; 6(12):4697-704.

[2]. F Wingen, et al. Antimetastatic effects of Razoxane in a rat osteosarcoma model. Clin Exp Metastasis.Jan-Mar 1987; 5(1):9-16.

Chemical & Physical Properties

[ Density]:
1.333g/cm3

[ Boiling Point ]:
531.5ºC at 760mmHg

[ Melting Point ]:
193ºC

[ Molecular Formula ]:
C₁₁H₁₆N₄O₄

[ Molecular Weight ]:
268.26900

[ Flash Point ]:
275.3ºC

[ Exact Mass ]:
268.11700

[ PSA ]:
98.82000

[ Vapour Pressure ]:
1.33E-13mmHg at 25°C

[ Index of Refraction ]:
1.534

[ Storage condition ]:
room temp

[ Water Solubility ]:
DMSO: soluble40mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TL6389900

CHEMICAL NAME :: 2,6-Piperazinedione, 4,4'-propylenedi-

CAS REGISTRY NUMBER :: 21416-67-1

BEILSTEIN REFERENCE NO. :: 0821182

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C11-H16-N4-O4

MOLECULAR WEIGHT :: 268.31

WISWESSER LINE NOTATION :: T6VMV ENTJ EY1&1- ET6VMV ENTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 3650 mg/kg/2Y-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - hematuria Blood - aplastic anemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 600 mg/kg/34W-I

TOXIC EFFECTS :: Blood - leukopenia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 6467 mg/kg/6Y-I

TOXIC EFFECTS :: Blood - normocytic anemia Blood - thrombocytopenia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 693 mg/kg/77W-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 4650 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 2693 mg/kg/3Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 3650 mg/kg/2Y-I

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - leukemia

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TEST SYSTEM :: Rodent - hamster

DOSE/DURATION :: 100 mg/kg

REFERENCE :: BJCAAI British Journal of Cancer. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.1- 1947- Volume(issue)/page/year: 52,725,1985

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
TL6389900

Articles

Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

J. Med. Chem. 51 , 6740-51, (2008)

The work provides a new model for the prediction of the MAO-A and -B inhibitor activity by the use of combined complex networks and QSAR methodologies. On the basis of the obtained model, we prepared ...

Development of a phospholipidosis database and predictive quantitative structure-activity relationship (QSAR) models.

Toxicol. Mech. Methods 18 , 217-27, (2008)

ABSTRACT Drug-induced phospholipidosis (PL) is a condition characterized by the accumulation of phospholipids and drug in lysosomes, and is found in a variety of tissue types. PL is frequently manifes...

Changes in cardiac biomarkers during doxorubicin treatment of pediatric patients with high-risk acute lymphoblastic leukemia: associations with long-term echocardiographic outcomes.

J. Clin. Oncol. 30(10) , 1042-9, (2012)

Doxorubicin causes cardiac injury and cardiomyopathy in children with acute lymphoblastic leukemia (ALL). Measuring biomarkers during therapy might help individualize treatment by immediately identify...

Related Compounds

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