Drug Details

General Information of the Drug (ID: DR7295)
Name
Dexrazoxane
Synonyms
Dexrazoxane; 24584-09-6; Zinecard; (S)-4,4'-(Propane-1,2-diyl)bis(piperazine-2,6-dione); Cardioxane; ICRF-187; Dextrorazoxane; Dexrazoxanum; Dexrazoxano; Dexrazoxanum [INN-Latin]; Dexrazoxano [INN-Spanish]; ADR 529; ICRF 187; ADR-529; (+)-(S)-4,4'-Propylenedi-2,6-piperazinedione; Dexrazone; (+)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane; Desrazoxane; 2,6-Piperazinedione, 4,4'-[(1S)-1-methyl-1,2-ethanediyl]bis-; UNII-048L81261F; NSC169780; CHEBI:50223; NSC-169780; NSC 169780; MFCD00866449; Razoxanum [INN-Latin]; Razoxana [INN-Spanish]; 048L81261F; 4-[(2S)-1-(3,5-dioxopiperazin-1-yl)propan-2-yl]piperazine-2,6-dione; (S)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane; DSSTox_CID_20647; DSSTox_RID_79520; DSSTox_GSID_40647; (S)-4,4'-(Propane-1,2-diyl)-bis(piperazine-2,6-dione); (+)-dexrazoxane; 4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione; CAS-24584-09-6; 2,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-, (+)-; 2,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-, (S)-; HSDB 7319; 2,6-Piperazinedione, 4,4'-propylenedi-, (+)-; SR-01000883995; Dexrazoxane HCl (ICRF-187, ADR-529); BRN 5759131; Soluble ICRF (L-isosomer); Dexrazoxane [USAN:INN:BAN]; CCRIS 9394; NCGC00164737-01; CHEMBL1738; SCHEMBL18400; MLS006010158; BIDD:GT0068; Dexrazoxane (JAN/USAN/INN); (S)-(+)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane; 4,4'-(2S)-propane-1,2-diyldipiperazine-2,6-dione; GTPL7330; DTXSID3040647; Dexrazoxane, >=95% (HPLC); AMY39004; EBD45155; HY-B0581; Tox21_112256; 2, 4,4'-propylenedi-, (+)-; ANW-44923; s5651; ZINC87515509; AKOS015896392; Tox21_112256_1; (+)-1,5-dioxopiperazin-1-yl)propane; CCG-267131; DB00380; DS-1394; MP-0159; NCGC00263544-01; NCGC00263544-02; Dexrazoxane, analytical reference material; NCI60_001367; SMR002529680; AB0011515; (S)-(+)-1,5-dioxopiperazin-1-yl)propane; D4227; D03730; J90038; AB01273932-01; AB01273932-02; AB01273932_03; 2,4,4'-[(1S)-1-methyl-1,2-ethanediyl]bis-; 584D096; A817380; Q524995; 2,4,4'-(1-methyl-1,2-ethanediyl)bis-, (S)-; J-015579; J-520219; SR-01000883995-1; SR-01000883995-2; SR-01000883995-5; (S)-4,4'-(propane-1,2-diyl)dipiperazine-2,6-dione; BRD-K07265709-003-01-5; (S)-4,4-(Propane-1,2-diyl)bis(piperazine-2,6-dione); 4,4'-[(2S)-1,2-Propanediyl]di(2,6-piperazinedione); UNII-5AR83PR647 component BMKDZUISNHGIBY-ZETCQYMHSA-N; 4-[(2S)-2-(3,5-dioxo-1-piperazinyl)propyl]piperazine-2,6-dione; 2,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-, (+)- (9CI); 4-[(2S)-2-[3,5-bis(oxidanylidene)piperazin-1-yl]propyl]piperazine-2,6-dione; 6-hydroxy-4-[(2S)-2-(5-hydroxy-3-oxo-1,2,3,6-tetrahydropyrazin-1-yl)propyl]-2,3,4,5-tetrahydropyrazin-2-one
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Molecular Type
Small molecule
Disease Breast cancer [ICD-11: 2C60] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.1 mL/min/kg
Elimination
42% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 2.5 hours
Metabolism
The drug is metabolized via the enzyme dihydropyrimidine amidohydrolase in the liver and kidney
Unbound Fraction
The unbound fraction of drug in plasma is 1%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.55 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 11 mg/mL
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Formula
C11H16N4O4
PubChem CID
71384
Canonical SMILES
CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
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
InChIKey
BMKDZUISNHGIBY-ZETCQYMHSA-N
CAS Number
CAS 24584-09-6
ChEBI ID
CHEBI:50223
TTD Drug ID
D07XVN
DrugBank ID
DB00380
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Schisandrol B      Schisandra chinensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model A total of 150 healthy New Zealand white rabbits, weight 1.98 + 0.15 kg, male and female in equal numbers were used in this study.
                    Experimental
                    Result(s)		 Schisandrin B had dose-dependent effects in decreasing the magnitude of doxorubicin-induced indicators of cardiomyopathy to a degree that approximated the decrease produced by dexrazoxane treatment.
Target and Pathway
Target(s) DNA topoisomerase II (TOP2)  Molecule Info  [3]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7330).
Reference 2 Prevention and treatment of doxorubicin-induced cardiotoxicity by dexrazoxane and schisandrin B in rabbits. Int J Toxicol. 2011 Dec;30(6):681-9.
Reference 3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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