Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1772)
Drug Name
Dexrazoxane hydrochloride
Synonyms
Dexrazoxane (Hydrochloride); Dexrazoxane HCl; Dexrazoxane hydrochloride; ICRF 187 hydrochloride; ICRF-187; Savene; TopoTect; ADR-529; ADR-529 hydrochloride; Cardioxane; Totect; Zinecard; (S)-4,4'-(1-Methyl-1,2-ethanediyl)bis-2,6-piperazinedione hydrochloride; (S)-4,4'-(propane-1,2-diyl)bis(piperazine-2,6-dione) hydrochloride; 1263283-43-7; 149003-01-0; 4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione hydrochloride; 5346058Q7S; CHEBI:50224; Dexrazoxane HCl (ICRF-187, ADR-529); UNII-5346058Q7S
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 304.73 Topological Polar Surface Area 98.8
Heavy Atom Count 20 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
6918223
ChEBI ID
CHEBI:50224
CAS Number
149003-01-0
TTD Drug ID
D07XVN
Formula
C11H17ClN4O4
Canonical SMILES
CC(CN1CC(=O)NC(=O)C1)N2CC(=O)NC(=O)C2.Cl
InChI
1S/C11H16N4O4.ClH/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);1H/t7-;/m0./s1
InChIKey
BIFMNMPSIYHKDN-FJXQXJEOSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Dexrazoxane metabolite B DM000819 N. A. Hydrolysis - Hydrolysis 1 [3] , [4]
Dexrazoxane metabolite C DM000821 N. A. Hydrolysis - Hydrolysis 1 [3] , [4]
ADR-925 DM000820
126521
Hydrolysis - Hydrolysis 2 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002598 Dexrazoxane hydrochloride Dexrazoxane metabolite B Hydrolysis - Hydrolysis DPYS [3], [4]
MR002599 Dexrazoxane hydrochloride Dexrazoxane metabolite C Hydrolysis - Hydrolysis DPYS [3], [4]
MR002596 Dexrazoxane metabolite B ADR-925 Hydrolysis - Hydrolysis pyrC [3], [4]
MR002597 Dexrazoxane metabolite C ADR-925 Hydrolysis - Hydrolysis pyrC [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Dihydroorotase (pyrC) DME1829 Faecalicatena orotica
A0A2Y9B958_9FIRM
3.5.2.3
[2]
Dihydropyrimidinase (DPYS) DMEN004 Homo sapiens
DPYS_HUMAN
2.7.1.113
[3]
Dihydropyrimidinase-related protein 1 (DRP1) DME0442 Homo sapiens
DPYL1_HUMAN
3.5.2.2
[3]
References
1 Dexrazoxane Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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. doi: 10.1124/dmd.104.003186.
3 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.
4 Clinically Translatable Prevention of Anthracycline Cardiotoxicity by Dexrazoxane Is Mediated by Topoisomerase II Beta and Not Metal Chelation. Circ Heart Fail. 2021 Nov;14(11):e008209. doi: 10.1161/CIRCHEARTFAILURE.120.008209.

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