Dexrazoxane

Names

[ Name ]:
Dexrazoxane

[Synonym ]:
4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
(+)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione
2,6-Piperazinedione, 4,4'-[(1S)-1-methyl-1,2-ethanediyl]bis-
4,4'-(2S)-Propan-1,2-diyldipiperazin-2,6-dion
4,4'-[(2S)-1,2-Propanediyl]di(2,6-piperazinedione)
(+)-4,4'-Propylenedi-2,6-piperazinedione
Dexrazoxane
Desrazoxane
Razoxane (+)-form
(S)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane
4,4'-(2S)-Propane-1,2-diyldipiperazine-2,6-dione
Eucardion
MFCD00866449
(+)-dexrazoxane
4,4'-(2S)-propane-1,2-diyldipipérazine-2,6-dione
(s)-4,4'-(1-methyl-1,2-ethanediyl)bis-2,6-piperazinedione

Biological Activity

[Description]:

Dexrazoxane(ICRF187) is a cardioprotective agent.Target: OthersDexrazoxane is a cardioprotective agent. Dexrazoxane is a derivative of EDTA, dexrazoxane chelates iron and thus reduces the number of metal ions complexed with anthracycline and, consequently, decrease the formation of superoxide radicals. The exact chelation mechanism is unknown, but it has be postulated that dexrazoxane can be converted into ring-opened form intracellularly and interfere with iron-mediated free radical generation that is in part thought to be responsible for anthryacycline induced cadiomyopathy. It was speculated that dexrazoxane could be used for further investigation to synthesize new antimalarial drugs [1, 2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Cardiovascular Disease

[References]

[1]. Jones, R.L., Utility of dexrazoxane for the reduction of anthracycline-induced cardiotoxicity. Expert Rev Cardiovasc Ther, 2008. 6(10): p. 1311-7.

[2]. Loyevsky, M., et al., Plasmodium falciparum and Plasmodium yoelii: effect of the iron chelation prodrug dexrazoxane on in vitro cultures. Exp Parasitol, 1999. 91(2): p. 105-14.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
531.5±50.0 °C at 760 mmHg

[ Melting Point ]:
194-196ºC

[ Molecular Formula ]:
C₁₁H₁₆N₄O₄

[ Molecular Weight ]:
268.269

[ Flash Point ]:
275.3±30.1 °C

[ Exact Mass ]:
268.117157

[ PSA ]:
98.82000

[ LogP ]:
-0.37

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.540

[ Storage condition ]:
Desiccate at RT

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TL6390000

CHEMICAL NAME :: 2,6-Piperazinedione, 4,4'-propylenedi-, (+)-

CAS REGISTRY NUMBER :: 24584-09-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C11-H16-N4-O4

MOLECULAR WEIGHT :: 268.31

WISWESSER LINE NOTATION :: T6VMV ENTJ EY1&U1- ET6VMV ENTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 383 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Liver - liver function tests impaired Blood - leukopenia

TYPE OF TEST :: LD10 - Lethal Dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1250 mg/kg/5D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - hemorrhage Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1875 mg/kg/33D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Blood - changes in erythrocyte (RBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 20 mg/L

REFERENCE :: INNDDK Investigational New Drugs. The Journal of New Anticancer Agents. Kluwer Academic Pub., POB 358, Accord Stn., Hingham, MA 02018) V.1- 1983- Volume(issue)/page/year: 1,283,1983

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ HS Code ]:
2933599090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Multiple studies suggest creatine mediates anti-oxidant activity in addition to its established role in cellular energy metabolism. The functional significance for the heart has yet to be established,...

Related Compounds

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