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

General Information of Drug (ID: DR0173)
Drug Name
AN-16649
Synonyms
Banoxantrone; Banoxantrone [INN:BAN]; Banoxantrone dihydrochloride; SCHEMBL3676563; W5H7E45YT3; YZBAXVICWUUHGG-UHFFFAOYSA-N; ZINC3776950; 1,4-Bis((2-(dimethylamino)ethyl)amino)-5,8-dihydroxy-9,10-anthracenedione N,N'-dioxide; 1,4-Bis(2-(dimethylazinoyl)ethylamino)-5,8-dihydroxy-9,10-anthraquinone; 136470-65-0; 9,10-Anthracenedione, 1,4-bis((2-(dimethyloxidoamino)ethyl)amino)-5,8-dihydroxy-; AN-16649; AQ 4N; AQ-4N; AQ4N; CHEMBL117391; DB04975; NCGC00346890-01; UNII-W5H7E45YT3
Indication Acute lymphoblastic leukemia [ICD11: 2B33] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 444.5 Topological Polar Surface Area 135
Heavy Atom Count 32 Rotatable Bond Count 8
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
9955116
CAS Number
136470-65-0
TTD Drug ID
D00PIE
Formula
C22H28N4O6
Canonical SMILES
C[N+](C)(CCNC1=C2C(=C(C=C1)NCC[N+](C)(C)[O-])C(=O)C3=C(C=CC(=C3C2=O)O)O)[O-]
InChI
1S/C22H28N4O6/c1-25(2,31)11-9-23-13-5-6-14(24-10-12-26(3,4)32)18-17(13)21(29)19-15(27)7-8-16(28)20(19)22(18)30/h5-8,23-24,27-28H,9-12H2,1-4H3
InChIKey
YZBAXVICWUUHGG-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
AQ4 DM004145
135468
Unclear 1 [2] , [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004542 AN-16649 AQ4 Unclear CYP2S1 ... [2], [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2] , [3] , [4]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2] , [3] , [4]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2S1 (CYP2S1) DME0033 Homo sapiens
CP2S1_HUMAN
1.14.14.1
[2] , [3] , [4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [7]
⏷ Show the Full List of 6  DME(s)
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004590)
2 Effects of cytokine-induced macrophages on the response of tumor cells to banoxantrone (AQ4N)
3 Bioreductively activated antitumor N-oxides: the case of AQ4N, a unique approach to hypoxia-activated cancer chemotherapy
4 CYP2S1 is negatively regulated by corticosteroids in human cell lines. Toxicol Lett. 2012 Feb 25;209(1):30-4.
5 Tumor-selective drug activation: a GDEPT approach utilizing cytochrome P450 1A1 and AQ4N. Cancer Gene Ther. 2006 Jun;13(6):598-605.
6 Bioreductive GDEPT using cytochrome P450 3A4 in combination with AQ4N. Cancer Gene Ther. 2003 Jan;10(1):40-8.
7 Activation of multiple chemotherapeutic prodrugs by the natural enzymolome of tumour-localised probiotic bacteria. J Control Release. 2016 Jan 28;222:9-17.

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