| Identification | More | [Name]
Dexrazoxane | [CAS]
24584-09-6 | [Synonyms]
DEXRAZOXANE
(s)-4,4'-(1-methyl-1,2-ethanediyl)bis-2,6-piperazinedione
4’-(1-methyl-1,2-ethanediyl)bis-6-piperazinedion(+)-4
4’-propylenedi-6-piperazinedion(+)-4
adr529
cardioxane
DEXTRAZOXANE
DEXTRORAZOXANE
(S)-ICRF-187
[S,(+)]-4,4'-Propylenebis(2,6-piperazinedione)
4,4'-[(S)-1-Methyl-1,2-ethanediyl]bis(2,6-piperazinedione) | [Molecular Formula]
C11H16N4O4 | [MDL Number]
MFCD00866449 | [Molecular Weight]
268.27 | [MOL File]
24584-09-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
194-196°C | [alpha ]
D +11.35° (c = 5 in DMF) | [Boiling point ]
531.5±50.0 °C(Predicted) | [density ]
1.333±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >20mg/mL | [form ]
powder | [pka]
2.1(at 25℃) | [color ]
white to off-white | [Merck ]
14,8123 | [InChIKey]
BMKDZUISNHGIBY-ZETCQYMHSA-N | [CAS DataBase Reference]
24584-09-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Dexrazoxane is the dextro-isomer of razoxane approved as a protectant against the
cardiotoxicity of doxorubicin in breast cancer patients. This agent does not alter the
anticancer effect of doxorubicin. Its mode of action suggests a chelation of free
radicals. In mice, dexrazoxane also offers protection against cardiac side effects of
epirubicin, but not mitoxantrone. | [Originator]
Imperial Cancer Research Fund (United Kingdom) | [Uses]
Cardioprotectant. | [Definition]
ChEBI: (+)-dexrazoxane is a razoxane. It has a role as a chelator, an antineoplastic agent, a cardiovascular drug and an immunosuppressive agent. | [Brand name]
Zinecard (Pharmacia & Upjohn);Cardioxane. | [General Description]
Dexrazoxane is a member of bis(2,6-dioxopiperazines), that functions as a topoisomerase 2 catalytic inhibitor. Dexrazoxane is a free radical scavenger. It might protect the heart from doxorubicin-associated damage. Dexrazoxane acts as a cardiopulmonary protectant, while treating Hodgkin′s disease (HD). It functions as a chelating agent, which limits the formation of anthracycline-iron complexes. It is used to synthesize antimalarial drugs. | [Biological Activity]
Topoisomerase II inhibitor and intracellular ion chelator. Bridges and stabilizes an interface between two ATPase promoters to inhibit topoisomerase II activity. Cardioprotective when co-administered with doxorubicin; decreases formation of reactive oxygen species (ROS) and activates the PI3K/Akt survival pathway. | [Biochem/physiol Actions]
Dexrazoxane is a cardioprotective compound against anthracyclines. It functions by inhibiting topoisomerase II without inducing DNA strand breaks. Dexrazoxane is a + enantiomer of razoxane. | [Clinical Use]
Cardioxane?
Prevention of cardiotoxicity in patients
receiving doxorubicin or epirubicin for breast cancer
Savene?
: Treatment of extravasation caused by
anthracyclines | [Veterinary Drugs and Treatments]
Dexrazoxane may be useful to attenuate the cardiotoxic effects of
doxorubicin in patients who are showing signs of anthracycline
cardiotoxicity, have cardiac disease, or are at maximum cumulative
dosages of doxorubicin. It is also used to treat extravasation injuries
associated with doxorubicin.
While dexrazoxane has been shown to be cardioprotective when
given at dosages of 10 times the doxorubicin dose, there is evidence
that it may also partially protect the cancer cells being treated. | [Drug interactions]
Potentially hazardous interactions with other drugs
Antiepileptics: may reduce absorption of
fosphenytoin and phenytoin.
Ciclosporin: increased risk of immunosuppression
with risk of lymphoproliferative disease.
Tacrolimus: increased risk of immunosuppression
with risk of lymphoproliferative disease.
Vaccines: risk of generalised infections with live
vaccines - avoid. | [Metabolism]
Dexrazoxane is hydrolysed by the enzyme
dihydropyrimidine amidohydrolase in the liver and
kidney to active metabolites that are capable of binding to
metal ions.
It is excreted unchanged via the kidney | [storage]
Store at -20°C |
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