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

General Information of Drug (ID: DR5961)
Drug Name
Dhaq diacetate
Synonyms
Mitoxantrone diacetate; Anthraquinone, 5,8-bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxy-, 1,4-diacetate (salt); 1,4-Dihydroxy-5,8-bis(2-((2-hydroxyethyl)amino)ethylamino)-9,10-anthracenedione diacetate; 2-[[5,8-dihydroxy-4-[2-(2-hydroxyethylazaniumyl)ethylamino]-9,10-dioxoanthracen-1-yl]amino]ethyl-(2-hydroxyethyl)azanium diacetate; 5,8-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxy-9,10-anthracenedione diacetate; 5,8-Bis((2-((2-hydroxyethyl)amino)ethyl)amino)-1,4-dihydroxyanthraquinone 1,4-diaceate
Indication Solid tumour/cancer [ICD11: 2A00-2F9Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 564.6 Topological Polar Surface Area 253
Heavy Atom Count 40 Rotatable Bond Count 12
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
51151
CAS Number
70711-41-0
TTD Drug ID
D08FPM
Formula
C26H36N4O10
Canonical SMILES
CC(=O)[O-].CC(=O)[O-].C1=CC(=C2C(=C1NCC[NH2+]CCO)C(=O)C3=C(C=CC(=C3C2=O)O)O)NCC[NH2+]CCO
InChI
InChI=1S/C22H28N4O6.2C2H4O2/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32;2*1-2(3)4/h1-4,23-30H,5-12H2;2*1H3,(H,3,4)
InChIKey
ZWCKUVMZBKQQRG-UHFFFAOYSA-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
Dhaq diacetate Metabolite M1 DM018856 N. A. Unclear - Unclear 1 [2]
Dhaq diacetate Metabolite M2 DM018857 N. A. Unclear - Unclear 1 [2]
Dhaq diacetate Metabolite M3 DM018858 N. A. Unclear - Unclear 1 [2]
Dhaq diacetate Metabolite M4 DM018859 N. A. Unclear - Unclear 1 [2]
NAPHT DM018855 N. A. Unclear - Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR011233 Dhaq diacetate NAPHT Unclear - Unclear HRP [3]
MR011234 Dhaq diacetate Dhaq diacetate Metabolite M1 Unclear - Unclear Unclear [2]
MR011235 Dhaq diacetate Dhaq diacetate Metabolite M2 Unclear - Unclear Unclear [2]
MR011236 Dhaq diacetate Dhaq diacetate Metabolite M3 Unclear - Unclear Unclear [2]
MR011237 Dhaq diacetate Dhaq diacetate Metabolite M4 Unclear - Unclear Unclear [2]
References
1 The hypoxia-activated ProDrug AQ4N penetrates deeply in tumor tissues and complements the limited distribution of mitoxantrone. Cancer Res. 2009 Feb 1;69(3):940-7.
2 The metabolic profile of mitoxantrone and its relation with mitoxantrone-induced cardiotoxicity
3 Naphthoquinoxaline metabolite of mitoxantrone is less cardiotoxic than the parent compound and it can be a more cardiosafe drug in anticancer therapy

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