DEXRAZOXANE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H16N4O4
Molecular Weight	268.2691
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

C[C@@H](CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2

InChI

InChIKey=BMKDZUISNHGIBY-ZETCQYMHSA-N

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)/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C11H16N4O4
Molecular Weight	268.2691
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Dexrazoxane is a cardioprotective drug used in patients with breast cancer to reduce cardiomyopathy associated with doxorubicin administration. Dexrazoxane is believed to act by two mechanisms: it inhibits DNA topoisomerase II and acts as a chelator for iron ions.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase II 66	Inhibitor 8,297		13.0 µM [IC50]
Iron 18	Chelating Agent 142		17.4 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Breast cancer 434	Secondary		Approved 8,429	ZINECARD

C_max

Value	Dose	Co-administered	Analyte	Population
337 μM	60 mg/kg single, intraperitoneal		DEXRAZOXANE plasma	Oryctolagus cuniculus

AUC

Value	Dose	Co-administered	Analyte	Population
838 μM × h	60 mg/kg single, intraperitoneal		DEXRAZOXANE plasma	Oryctolagus cuniculus

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.5 h	500 mg/m² single, intravenous	DOXORUBICIN	DEXRAZOXANE plasma	Homo sapiens
2 h	60 mg/kg single, intraperitoneal		DEXRAZOXANE plasma	Oryctolagus cuniculus

F_unbound

Value	Dose	Co-administered	Analyte	Population
100%	500 mg/m² single, intravenous	DOXORUBICIN	DEXRAZOXANE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
250 mg/m2 1 times / 4 weeks multiple, intravenous (total) MTD	unhealthy, 57 years (range: 46-76 years) n = 22	Disc. AE: Thrombocytopenia...
900 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose	unhealthy, adult n = 6	DLT: Neutropenia...
600 mg/m2 1 times / 3 weeks multiple, intravenous RP2D	unhealthy, adult n = 9	DLT: Neutropenia...
500 mg/m2 1 times / day multiple, intravenous Recommended	unhealthy, adult n = 102	Other AEs: Alopecia, Nausea...
500 mg/m2 1 times / day multiple, intravenous Recommended	unhealthy, adult n = 413	Other AEs: Alopecia, Nausea...

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AEs

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AE	Significance	Dose	Population
Thrombocytopenia	grade 4, 2 patients Disc. AE	250 mg/m2 1 times / 4 weeks multiple, intravenous (total) MTD	unhealthy, 57 years (range: 46-76 years) n = 22
Neutropenia	4 patients DLT	900 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose	unhealthy, adult n = 6
Neutropenia	4 patients DLT	600 mg/m2 1 times / 3 weeks multiple, intravenous RP2D	unhealthy, adult n = 9
Administration site recall reaction	1%	500 mg/m2 1 times / day multiple, intravenous Recommended	unhealthy, adult n = 102
Neurotoxicity	10%	500 mg/m2 1 times / day multiple, intravenous Recommended	unhealthy, adult n = 102

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-1307	http://www.3bsc.com/index/pro_info.php?id=55023
AA Blocks	AA002OL7	https://www.aablocks.com/goods/Goods/detail?id=AA002OL7
AEchem Scientific Corp., USA	AE1-014835	http://www.aechemsc.com/info_products/AE1-014835.php
AHH Chemical co.,ltd	MT-49873	http://www.ahhchemical.com/product/MT-49873.html
AK Scientific, Inc. (AKSCI)	69488	http://www.aksci.com/item_detail.php?cat=69488

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PubMed

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Title	Date	PubMed
Effect of sodium 2,3-dimercaptopropane-1-sulphonate (DMPS) on chronic daunorubicin toxicity in rabbits: comparison with dexrazoxane.	2002	12515046
Minimising the long-term adverse effects of childhood leukaemia therapy.	2002	12452732
Troponins in experimental studies.	2002	12143108
Dexrazoxane (ICRF-187) protects cardiac myocytes against doxorubicin by preventing damage to mitochondria.	2003	14501028
Dexrazoxane-a promising antidote in the treatment of accidental extravasation of anthracyclines.	2003	12841619

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage ratio of dexrazoxane to doxorubicin is 10:1 (e.g., 500 mg/m2 dexrazoxane to 50 mg/m2 doxorubicin). Do not administer doxorubicin before dexrazoxane.

Route of Administration: Intravenous

In Vitro Use Guide

Human osteoblasts P2 cells and Human ginigiva fibroblasts P2 cells were treated with zoledronic acid (50 umol/L) and the cytoprotectant dexrazoxane (600 umol/L). At that concentration dexrazoxane showed significant cytoprotective effect.

Substance Class	Chemical
Record UNII	048L81261F
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

DEXRAZOXANE

Official Name

English

(+)-1,2-BIS(3,5-DIOXOPIPERAZIN-1-YL)PROPANE

Systematic Name

English

Dexrazoxane [WHO-DD]

Common Name

English

dexrazoxane [INN]

Common Name

English

DEXRAZOXANE [USAN]

Common Name

English

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Classification Tree

Code System

Code

Detoxifying agents for antineoplastic treatment

WHO-ATC

V03AF02

Established Pharmacologic Class

NDF-RT

N0000180854

Designated/Approved

FDA ORPHAN DRUG

181103

Designated/Approved

FDA ORPHAN DRUG

63291

Detoxifying agents for antineoplastic treatment

WHO-VATC

QV03AF02

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Code System

Code

Type

Description

USAN

Z-72

PRIMARY

CAS

24584-09-6

PRIMARY

ChEMBL

CHEMBL1738

PRIMARY

DAILYMED

048L81261F

PRIMARY

PUBCHEM

71384

PRIMARY

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Related Record

Type

Details


					5AR83PR647

RAZOXANE

RACEMATE -> ENANTIOMER


					5346058Q7S

DEXRAZOXANE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

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Related Record

Type

Details


					048L81261F

DEXRAZOXANE

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound