CAS 24584-09-6|Dexrazoxane

Introduction：Basic information about CAS 24584-09-6|Dexrazoxane, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Dexrazoxane BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles35
8. Synonyms

Common Name	Dexrazoxane
CAS Number	24584-09-6	Molecular Weight	268.269
Density	1.3±0.1 g/cm3	Boiling Point	531.5±50.0 °C at 760 mmHg
Molecular Formula	C₁₁H₁₆N₄O₄	Melting Point	194-196ºC
MSDS	ChineseUSA	Flash Point	275.3±30.1 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	(+)-dexrazoxane
Synonym	More Synonyms

Dexrazoxane BiologicalActivity

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 >>OthersResearch 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.

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 >>OthersResearch 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.

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
InChIKey	BMKDZUISNHGIBY-ZETCQYMHSA-N
SMILES	CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1
Storage condition	Desiccate at RT

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

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%

Articles35

Translational downregulation of HSP90 expression by iron chelators in neuroblastoma cells.

Mol. Pharmacol. 87(3) , 513-24, (2015)

Iron is an essential cellular nutrient, being a critical cofactor of several proteins involved in cell growth and replication. Compared with normal cells, neoplastic cells have been shown to require a...

Doxorubicin impairs the insulin-like growth factor-1 system and causes insulin-like growth factor-1 resistance in cardiomyocytes.

PLoS ONE 10 , e0124643, (2015)

Insulin-like growth factor-1 (IGF-1) promotes the survival of cardiomyocytes by activating type 1 IGF receptor (IGF-1R). Within the myocardium, IGF-1 action is modulated by IGF binding protein-3 (IGFB...

Myocardial creatine levels do not influence response to acute oxidative stress in isolated perfused heart.

PLoS ONE 9(10) , e109021, (2014)

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,...

Synonyms

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

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