Drug Information

Drug (ID: DG00023) and It's Reported Resistant Information
Name
Daunorubicin
Synonyms
Daunorubicin; Daunomycin; 20830-81-3; Rubidomycin; Cerubidine; Daunorubicine; Acetyladriamycin; Leukaemomycin C; Daunorubicinum; Daunarubicinum; Daunorrubicina; Daunamycin; Cerubidin; DaunoXome; Rubomycin C; (+)-Daunomycin; Daunoblastin; Anthracyline; Rubomycin; Daunorubicinum [INN-Latin]; RP 13057; Daunorubicin [INN:BAN]; RCRA waste no U059; FI6339; NSC-82151; DAUNORUBICIN HCL; DaunoXome (TN); UNII-ZS7284E0ZP; CCRIS 914; ZS7284E0ZP; CHEBI:41977; HSDB 5095; C27H29NO10; NCI-C04693; EINECS 244-069-7; Ondena; NSC 83142; Acetyladriamycin; Daunoblastine; Antibiotics from Streptomyces coeruleorubidus; DM1; FI 6339; Dauno-Rubidomycine; Daunorubicin (INN); Daunorubicin (liposomal); Daunorubicin, Hydrochloride; VS-103; (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; (1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside; (7S,9R)-9-Acetyl-7-[(2S,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (8S-cis)-8-Acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyrannosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-napthacenedione; (8S-cis)-8-Acetyl-10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-5,12-naphthacenedione; Anthracycline
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Indication
In total 3 Indication(s)
Acute myeloid leukaemia [ICD-11: 2A60]
Approved
[1]
Kaposi sarcoma [ICD-11: 2B57]
Approved
[1]
Solid tumour/cancer [ICD-11: 2A00-2F9Z]
Phase 2
[1]
Structure
Drug Resistance Disease(s)
Disease(s) with Clinically Reported Resistance for This Drug (3 diseases)
Acute lymphocytic leukemia [ICD-11: 2B33]
[2]
Acute myeloid leukemia [ICD-11: 2A60]
[3]
Pneumonia [ICD-11: CA40]
[6]
Disease(s) with Resistance Information Discovered by Cell Line Test for This Drug (5 diseases)
Acute myeloid leukemia [ICD-11: 2A60]
[5]
Acute lymphocytic leukemia [ICD-11: 2B33]
[7]
Breast cancer [ICD-11: 2C60]
[8]
Chronic myeloid leukemia [ICD-11: 2A20]
[9]
Gastric cancer [ICD-11: 2B72]
[10]
Target DNA replication (DNA repli) NOUNIPROTAC [1]
Human Deoxyribonucleic acid (hDNA) NOUNIPROTAC [1]
Click to Show/Hide the Molecular Information and External Link(s) of This Drug
Formula
C27H29NO10
IsoSMILES
C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](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
PubChem CID
30323
ChEBI ID
CHEBI:41977
TTD Drug ID
D01XWG
VARIDT ID
DR00284
INTEDE ID
DR0424
DrugBank ID
DB00694
Type(s) of Resistant Mechanism of This Drug due to Structure Alteration
  EADR: Epigenetic Alteration of DNA, RNA or Protein
Drug Resistance Data Categorized by Their Corresponding Diseases
ICD-02: Benign/in-situ/malignant neoplasm
Click to Show/Hide the Resistance Disease of This Class
Acute myeloid leukemia [ICD-11: 2A60]
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Drug Resistance Data Categorized by Their Corresponding Mechanisms
  Epigenetic Alteration of DNA, RNA or Protein (EADR) Click to Show/Hide
Key Molecule: DNA (cytosine-5)-methyltransferase 3A (DNMT3A) [3]
Resistant Disease Acute myeloid leukemia [ICD-11: 2A60.0]
 Disease Info 
Molecule Alteration Missense mutation
p.R882H
 Molecule Info 
Wild Type Structure Method: X-ray diffraction Resolution: 2.40  Å
PDB: 6W8B
Mutant Type Structure Method: X-ray diffraction Resolution: 2.44  Å
PDB: 6W8J
   Download The Information of Sequence       Download The Structure File   
RMSD: 0.46
TM score: 0.99493
Amino acid change:
R882H
 : Wild Type Structure
 : Mutant Type Structure
  Mutation site(s) have been marked in red
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A
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E
E
630
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640
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I
I
A
A
T
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650
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D
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R
660
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Y
Y
I
I
A
A
S
S
E
E
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C
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E
D
D
S
S
670
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I
I
T
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V
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G
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G
680
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M
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S
690
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E
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W
W
G
G
700
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F
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I
G
G
G
G
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710
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C
N
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I
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A
720
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G
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730
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740
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750
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F
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F
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760
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A
A
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M
G
G
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770
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N
N
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M
M
780
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H
790
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A
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Y
F
F
W
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G
G
N
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800
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G
G
M
M
N
N
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L
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810
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E
L
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E
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C
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820
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E
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830
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V
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840
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850
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V
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F
M
M
N
N
E
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K
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E
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860
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W
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C
C
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870
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F
F
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880
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890
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900
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E
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910
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A
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C
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V
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Click to Show/Hide the Structure
Experimental Note Identified from the Human Clinical Data
Cell Pathway Regulation ADAM9/EGFR signaling pathway Inhibition hsa01521
AKT signaling pathway Inhibition hsa04151
Experiment for
Molecule Alteration		 Next-generation sequencing assay
Mechanism Description DNMT3A mutations are most common in AML. DNMT3A mutant AML has been linked to anthracycline resistance and poor prognosis in some studies. Many of these mutations occur in genes with established roles in the regulation and maintenance of DNA methylation and/or chromatin modifications in hematopoietic stem/progenitor cells.
References
Ref 1 MicroRNA-33b regulates sensitivity to daunorubicin in acute myelocytic leukemia by regulating eukaryotic translation initiation factor 5A-2. J Cell Biochem. 2020 Jan;121(1):385-393. doi: 10.1002/jcb.29192. Epub 2019 Jun 21.
Ref 2 BCR-ABL1 mutations in patients with imatinib-resistant Philadelphia chromosome-positive leukemia by use of the PCR-Invader assay. Leuk Res. 2011 May;35(5):598-603. doi: 10.1016/j.leukres.2010.12.006. Epub 2011 Jan 15.
Ref 3 The role of mutations in epigenetic regulators in myeloid malignancies. Immunol Rev. 2015 Jan;263(1):22-35. doi: 10.1111/imr.12246.
Ref 4 M2 macrophages secrete CCL20 to regulate iron metabolism and promote daunorubicin resistance in AML cells. Life Sci. 2025 Jan 15;361:123297.
Ref 5 Combination of RSK inhibitor LJH-685 and FLT3 inhibitor FF-10101 promoted apoptosis and proliferation inhibition of AML cell lines. Cell Oncol (Dordr). 2022 Oct;45(5):1005-1018.
Ref 6 AbeM, an H+-coupled Acinetobacter baumannii multidrug efflux pump belonging to the MATE family of transporters. Antimicrob Agents Chemother. 2005 Oct;49(10):4362-4. doi: 10.1128/AAC.49.10.4362-4364.2005.
Ref 7 Involvement of miR-21 in resistance to daunorubicin by regulating PTEN expression in the leukaemia K562 cell line. FEBS Lett. 2011 Jan 21;585(2):402-8. doi: 10.1016/j.febslet.2010.12.027. Epub 2010 Dec 25.
Ref 8 A multidrug resistance transporter from human MCF-7 breast cancer cells. Proc Natl Acad Sci U S A. 1998 Dec 22;95(26):15665-70. doi: 10.1073/pnas.95.26.15665.
Ref 9 MicroRNA-18a-5p regulates the Warburg effect by targeting hypoxia-inducible factor 1alpha in the K562/ADM cell line. Exp Ther Med. 2021 Oct;22(4):1069.
Ref 10 NBS1 lactylation is required for efficient DNA repair and chemotherapy resistance. Nature. 2024 Jul;631(8021):663-669.

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