Details of the Drug

General Information of Drug (ID: DMD7X1O)

Drug Name
Dexrazoxane
Synonyms
24584-09-6; Zinecard; (S)-4,4'-(Propane-1,2-diyl)bis(piperazine-2,6-dione); Cardioxane; ICRF-187; Dexrazoxano; Dexrazoxanum; Dextrorazoxane; Dexrazoxanum [INN-Latin]; Dexrazoxano [INN-Spanish]; Desrazoxane; Eucardion; ADR 529; ICRF 187; (+)-(S)-4,4'-Propylenedi-2,6-piperazinedione; Dexrazone; ADR-529; (+)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane; HSDB 7319; UNII-048L81261F; NSC169780; dyzoxane; BRN 5759131; CHEBI:50223; 4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione; NSC 169780; AK-72797; Razoxanum; Cardioxane; Dyzoxane; Savene; TopoTect; Totect; Dexrazoxane HCl; Dexrazoxane hydrochloride; ICRF 187 hydrochloride; Cardioxane (TN); Dexrazoxane (TN); Totect (TN); Zinecard (TN); Dexrazoxane (USAN/INN); Dexrazoxane [USAN:BAN:INN]; Soluble ICRF (L-isosomer); Razoxane, (S)-Isomer; Totect, ICRF-187, Zinecard, Cardioxane, Dexrazoxane Hydrochloride;(+)-(S)-4,4'-Propylenedi-2,6-piperazinedione; (+)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane; (S)-(+)-1,2-Bis(3,5-dioxopiperazin-1-yl)propane; 2,6-Piperazinedione, 4,4'-(1-methyl-1,2-ethanediyl)bis-, (+)-(9CI); 4,4'-(2S)-propane-1,2-diyldipiperazine-2,6-dione; 4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione hydrochloride; Icrf-187
Indication
Disease Entry ICD 11 Status REF
Breast cancer 2C60-2C65 Approved [1]
Chemoprotection N.A. Approved [2]
Inflammatory breast cancer 2C62 Approved [3]
Respiratory tract disease CB7Z Investigative [4]
Therapeutic Class
Anticancer Agents
Affected Organisms
Humans and other mammals
ATC Code
V03AF02: Dexrazoxane
V03AF: Detoxifying agents for antineoplastic treatment
V03A: ALL OTHER THERAPEUTIC PRODUCTS
V03: ALL OTHER THERAPEUTIC PRODUCTS
V: VARIOUS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 268.27
Logarithm of the Partition Coefficient (xlogp) -1.4
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [5]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3.1 mL/min/kg [6]
Elimination
42% of drug is excreted from urine in the unchanged form [5]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.5 hours [6]
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% [6]
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 [6]
Water Solubility
The ability of drug to dissolve in water is measured as 11 mg/mL [5]
Chemical Identifiers
Formula
C11H16N4O4
IUPAC Name
4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione
Canonical SMILES
C[C@@H](CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2
InChI
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
Cross-matching ID
PubChem CID
71384
ChEBI ID
CHEBI:50223
CAS Number
24584-09-6
UNII
048L81261F
DrugBank ID
DB00380
TTD ID
D07XVN
VARIDT ID
DR00417
INTEDE ID
DR1772
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
DNA topoisomerase II (TOP2) TT0IHXV TOP2A_HUMAN ; TOP2B_HUMAN Modulator [7]
DNA topoisomerase II beta (TOP2B) TT4NVEM TOP2B_HUMAN Inhibitor [8]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Dihydropyrimidinase-related protein 1 (DRP1)
Main DME 		DE0EUXB DPYL1_HUMAN Substrate [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
DNA topoisomerase 2-alpha (TOP2A) OT6LPS08 TOP2A_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Dexrazoxane (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Tecfidera DM2OVDT Moderate Additive immunosuppressive effects by the combination of Dexrazoxane and Tecfidera. Multiple sclerosis [8A40] [11]

References

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).
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Dexrazoxane FDA Label
4 Design and development of antisense drugs. Expert Opin. Drug Discov. 2008 3(10):1189-1207.
5 BDDCS applied to over 900 drugs
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
8 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
9 Metabolism of the cardioprotective drug dexrazoxane and one of its metabolites by isolated rat myocytes, hepatocytes, and blood. Drug Metab Dispos. 2005 Jun;33(6):719-25.
10 Investigation of novel dexrazoxane analogue JR-311 shows significant cardioprotective effects through topoisomerase IIbeta but not its iron chelating metabolite. Toxicology. 2017 Dec 1;392:1-10. doi: 10.1016/j.tox.2017.09.012. Epub 2017 Sep 21.
11 Product Information. Vumerity (diroximel fumarate). Alkermes, Inc, Cambridge, MA.