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

General Information of Drug (ID: DR0424)
Drug Name
Daunorubicin
Synonyms
Daunamycin; Daunarubicinum; DaunoXome; DaunoXome (TN); Daunoblastin; Daunomycin; Daunorrubicina; Daunorubicin [INN:BAN]; Daunorubicine; Daunorubicinum; Daunorubicinum [INN-Latin]; FI6339; Leukaemomycin C; Ondena; RCRA waste no. U059; Acetyladriamycin; Anthracyline; Cerubidin; Cerubidine; RP 13057; Rubidomycin; Rubomycin; Rubomycin C; ZS7284E0ZP; daunorubicin; (+)-Daunomycin; 20830-81-3; C27H29NO10; CCRIS 914; CHEBI:41977; EINECS 244-069-7; HSDB 5095; NCI-C04693; NSC 83142; NSC-82151; UNII-ZS7284E0ZP
Indication Acute myeloid leukaemia [ICD11: 2A60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 527.5 Topological Polar Surface Area 186
Heavy Atom Count 38 Rotatable Bond Count 4
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 11
Cross-matching ID
PubChem CID
30323
PubChem SID
5016 ; 596008 ; 866161 ; 7887073 ; 7979028 ; 8171488 ; 11114094 ; 14763056 ; 15481415 ; 24769892 ; 26697306 ; 26701813 ; 26704223 ; 26715132 ; 26718351 ; 26718779 ; 29215022 ; 34672588 ; 46508433 ; 47440436 ; 47736668 ; 48110630 ; 48415843 ; 49699346 ; 49855159 ; 50070917 ; 50104250 ; 53788227 ; 56465013 ; 57288764 ; 57310919 ; 74382025 ; 74462219 ; 85788867 ; 92307396 ; 92308820 ; 96024474 ; 103477782 ; 104066339 ; 104307942 ; 117393873 ; 124766118 ; 124886869 ; 124886870 ; 124886871 ; 125299287 ; 126663226 ; 127301039 ; 127301040 ; 127301041
ChEBI ID
ChEBI:41977
CAS Number
20830-81-3
TTD Drug ID
D01XWG
Formula
C27H29NO10
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)C)O)N)O
InChI
1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
InChIKey
STQGQHZAVUOBTE-VGBVRHCVSA-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
Daunorubicinol DM001932
443832
Reduction - Reduction 1 [6] , [7] , [8] , [9]
Deoxydaunorubicin aglycone DM001938
161893
Hydrolysis - Hydrolysis 1 [10]
Daunorubicinol aglycone DM001939
147191
Hydrolysis - Hydrolysis 2 [6]
Deoxydaunorubicinol aglycone DM001933
99903
Reduction - Reduction 2 [6]
Deoxydaunorubicinol aglycone DM001933
99903
Hydrolysis - Hydrolysis 2 [6]
Deoxydaunorubicinol aglycone-13-O-beta-glucuronide DM001937 N. A. Conjugation - Glucuronidation 2 [6]
Demethyl deoxydaunorubicinol aglycone DM001934 N. A. Oxidation - Demethylation 3 [6]
Demethyl deoxydaunorubicinol aglycone-4-O-beta-glucuronide metabolite DM001935 N. A. Conjugation - Glucuronidation 3 [6]
Demethyl deoxydaunorubicinol aglycone-4-O-sulfate metabolite DM001936 N. A. Conjugation - Sulfation 3 [6]
Deoxydaunorubicinol aglycone DM001933
99903
Reduction - Reduction 3 [6]
Demethyl deoxydaunorubicinol aglycone-4-O-beta-glucuronide metabolite DM001935 N. A. Conjugation - Glucuronidation 4 [6]
Demethyl deoxydaunorubicinol aglycone-4-O-sulfate metabolite DM001936 N. A. Conjugation - Sulfation 4 [6]
Deoxydaunorubicinol aglycone-13-O-beta-glucuronide DM001937 N. A. Conjugation - Glucuronidation 4 [6]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003242 Daunorubicin Daunorubicinol Reduction - Reduction CBR3 ... [6], [7], [8], [9]
MR003243 Daunorubicin Deoxydaunorubicin aglycone Hydrolysis - Hydrolysis Unclear [10]
MR003231 Daunorubicinol Deoxydaunorubicinol aglycone Hydrolysis - Hydrolysis Unclear [6]
MR003232 Daunorubicinol Daunorubicinol aglycone Hydrolysis - Hydrolysis Unclear [6]
MR003240 Deoxydaunorubicin aglycone Deoxydaunorubicinol aglycone Reduction - Reduction Unclear [6]
MR003241 Deoxydaunorubicin aglycone Deoxydaunorubicinol aglycone-13-O-beta-glucuronide Conjugation - Glucuronidation Unclear [6]
MR003233 Deoxydaunorubicinol aglycone Deoxydaunorubicinol aglycone Reduction - Reduction Unclear [6]
MR003234 Deoxydaunorubicinol aglycone Demethyl deoxydaunorubicinol aglycone Oxidation - Demethylation Unclear [6]
MR003235 Deoxydaunorubicinol aglycone Demethyl deoxydaunorubicinol aglycone-4-O-beta-glucuronide metabolite Conjugation - Glucuronidation Unclear [6]
MR003236 Deoxydaunorubicinol aglycone Demethyl deoxydaunorubicinol aglycone-4-O-sulfate metabolite Conjugation - Sulfation Unclear [6]
MR003237 Deoxydaunorubicinol aglycone Deoxydaunorubicinol aglycone-13-O-beta-glucuronide Conjugation - Glucuronidation Unclear [6]
MR003238 Demethyl deoxydaunorubicinol aglycone Demethyl deoxydaunorubicinol aglycone-4-O-beta-glucuronide metabolite Conjugation - Glucuronidation Unclear [6]
MR003239 Demethyl deoxydaunorubicinol aglycone Demethyl deoxydaunorubicinol aglycone-4-O-sulfate metabolite Conjugation - Sulfation Unclear [6]
⏷ Show the Full List of 13 MR(s)
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]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
NADPH-cytochrome P450 reductase (CPR) DME0076 Homo sapiens
NCPR_HUMAN
1.6.2.4
[3]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[4]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[5]
⏷ Show the Full List of 6  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Km = 0.0852 microM
CBR1_HUMAN
[4]
References
1 Daunorubicin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The effect of new lipophilic chelators on the activities of cytosolic reductases and P450 cytochromes involved in the metabolism of anthracycline antibiotics: studies in vitro. Physiol Res. 2004;53(6):683-91.
3 Lack of mechanism-based inactivation of rat hepatic microsomal cytochromes P450 by doxorubicin. Can J Physiol Pharmacol. 1999 Aug;77(8):589-97.
4 Flavonoids as inhibitors of human carbonyl reductase 1. Chem Biol Interact. 2008 Jul 30;174(2):98-108.
5 Naturally occurring variants of human CBR3 alter anthracycline in vitro metabolism. J Pharmacol Exp Ther. 2010 Mar;332(3):755-63.
6 Daunorubicin metabolites in human urine J Pharmacol Exp Ther. 1975 Oct;195(1):41-9.
7 Daunorubicin and Its Active Metabolite Pharmacokinetic Profiles in Acute Myeloid Leukaemia Patients: A Pharmacokinetic Ancillary Study of the BIG-1 Trial. Pharmaceutics. 2022 Apr 5;14(4):792. doi: 10.3390/pharmaceutics14040792.
8 The electromembrane extraction of pharmaceutical compounds from animal tissues. Anal Chim Acta. 2021 Sep 8;1177:338742. doi: 10.1016/j.aca.2021.338742.
9 Electromembrane extraction of anthracyclines from plasma: Comparison with conventional extraction techniques. Talanta. 2021 Feb 1;223(Pt 2):121748. doi: 10.1016/j.talanta.2020.121748.
10 U. S. FDA Label -Daunorubicin

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