Drug Information

Drug (ID: DG01471) and It's Reported Resistant Information
Name
Idarubicin
Synonyms
IDARUBICIN; 58957-92-9; 4-Demethoxydaunorubicin; 4-Demethoxydaunomycin; Idarubicine [INN-French]; Idarubicinum [INN-Latin]; Idarubicina [INN-Spanish]; UNII-ZRP63D75JW; NSC 256439; NSC-256439; ZRP63D75JW; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; Idarubicina; CHEBI:42068; (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; 5,12-Naphthacenedione, 9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, (7S-cis)-; Idarubicine; Idarubicinum; Idarubicin [INN:BAN]; Idarubicinhydrochloride; DM5; MLS001401448; Daunomycin, 4-demethoxy-; NSC256439; (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; (7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione; Idarubicin (INN); Zavedos (TN); CCRIS 5083; NCGC00093976-03; SMR000466355; 4-DMD; SR-01000075934; I 1656; SCHEMBL3750; CHEMBL1117; Lopac0_000600; KBioSS_002388; Idarubicin hydrochloride, solid; cid_636362; GTPL7083; 4-DEMETHOXY-DAUNORUBICIN; DTXSID7023142; IDARUBICIN(Hydrochloride form); BDBM58490; BCPP000207; HMS2089D05; HMS3261H22; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride; ZINC3920266; Tox21_500600; AKOS015895563; AC-9384; BCP9000773; CCG-204689; DB01177; LP00600; SDCCGSBI-0050582.P002; NCGC00093976-01; NCGC00093976-02; NCGC00093976-04; NCGC00093976-05; NCGC00093976-18; NCGC00261285-01; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-; EU-0100600; D08062; AB00698511-06; AB00698511-08; AB00698511-09; AB00698511-10; AB00698511_11; 957I929; A832088; A935911; Q1063862; SR-01000075934-1; BRD-K69650333-001-01-1; BRD-K69650333-001-02-9; BRD-K69650333-003-14-0; Idarubicin, United States Pharmacopeia (USP) Reference Standard; (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-7-[(2R,4S,5S,6S)-4-azanyl-6-methyl-5-oxidanyl-oxan-2-yl]oxy-9-ethanoyl-6,9,11-tris(oxidanyl)-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride; (7S,9S)-9-Acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione; (7S,9S)-9-acetyl-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione; (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-quinone;hydrochloride; (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-9-acetyl-7-[[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-2-oxanyl]oxy]-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride; 4-Demethoxydaunorubicin; ; ; IMI-30; ; ; NSC-256439; ; ; (7S,9S)-9-Acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione; 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-.alpha.-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-
    Click to Show/Hide
Indication
In total 1 Indication(s)
Heart arrhythmia [ICD-11: BC65]
Approved
[1]
Structure
Drug Resistance Disease(s)
Disease(s) with Resistance Information Discovered by Cell Line Test for This Drug (1 diseases)
Acute myeloid leukemia [ICD-11: 2A60]
[2]
Disease(s) with Clinically Reported Resistance for This Drug (1 diseases)
Acute myeloid leukemia [ICD-11: 2A60]
[3]
Click to Show/Hide the Molecular Information and External Link(s) of This Drug
Formula
3
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=CC=CC=C5C4=O)O)(C(=O)C)O)N)O
InChI
InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
InChIKey
XDXDZDZNSLXDNA-TZNDIEGXSA-N
PubChem CID
42890
ChEBI ID
CHEBI:42068
TTD Drug ID
D0Y9LL
VARIDT ID
DR0852
INTEDE ID
DR00386
DrugBank ID
DB01177
Type(s) of Resistant Mechanism of This Drug due to Structure Alteration
  UAPP: Unusual Activation of Pro-survival Pathway
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 Sensitivity Data Categorized by Their Corresponding Mechanisms
  Unusual Activation of Pro-survival Pathway (UAPP) Click to Show/Hide
Key Molecule: DNA (cytosine-5)-methyltransferase 3A (DNMT3A) [1]
Sensitive Disease Acute myeloid leukemia [ICD-11: 2A60.0]
 Disease Info 
Molecule Alteration Missense mutation
p.R882H (c.2645G>A)
 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
A
E
E
630
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K
K
R
R
K
K
P
P
I
I
R
R
V
V
L
L
S
S
L
L
640
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F
F
D
D
G
G
I
I
A
A
T
T
G
G
L
L
L
L
V
V
650
|
L
L
K
K
D
D
L
L
G
G
I
I
Q
Q
V
V
D
D
R
R
660
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Y
Y
I
I
A
A
S
S
E
E
V
V
C
C
E
E
D
D
S
S
670
|
I
I
T
T
V
V
G
G
M
M
V
V
R
R
H
H
Q
Q
G
G
680
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K
K
I
I
M
M
Y
Y
V
V
G
G
D
D
V
V
R
R
S
S
690
|
V
V
T
T
Q
Q
K
K
H
H
I
I
Q
Q
E
E
W
W
G
G
700
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P
P
F
F
D
D
L
L
V
V
I
I
G
G
G
G
S
S
P
P
710
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C
C
N
N
D
D
L
L
S
S
I
I
V
V
N
N
P
P
A
A
720
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R
R
K
K
G
G
L
L
Y
Y
E
E
G
G
T
T
G
G
R
R
730
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L
L
F
F
F
F
E
E
F
F
Y
Y
R
R
L
L
L
L
H
H
740
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D
D
A
A
R
R
P
P
K
K
E
E
G
G
D
D
D
D
R
R
750
|
P
P
F
F
F
F
W
W
L
L
F
F
E
E
N
N
V
V
V
V
760
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A
A
M
M
G
G
V
V
S
S
D
D
K
K
R
R
D
D
I
I
770
|
S
S
R
R
F
F
L
L
E
E
S
S
N
N
P
P
V
V
M
M
780
|
I
I
D
D
A
A
K
K
E
E
V
V
S
S
A
A
A
A
H
H
790
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R
R
A
A
R
R
Y
Y
F
F
W
W
G
G
N
N
L
L
P
P
800
|
G
G
M
M
N
N
R
R
P
P
L
L
A
A
S
S
T
T
V
V
810
|
N
N
D
D
K
K
L
L
E
E
L
L
Q
Q
E
E
C
C
L
L
820
|
E
E
H
H
G
G
R
R
I
I
A
A
K
K
F
F
S
S
K
K
830
|
V
V
R
R
T
T
I
I
T
T
T
T
R
R
S
S
N
N
S
S
840
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I
I
K
K
Q
Q
G
G
K
K
D
D
Q
Q
H
H
F
F
P
P
850
|
V
V
F
F
M
M
N
N
E
E
K
K
E
E
D
D
I
I
L
L
860
|
W
W
C
C
T
T
E
E
M
M
E
E
R
R
V
V
F
F
G
G
870
|
F
F
P
P
V
V
H
H
Y
Y
T
T
D
D
V
V
S
S
N
N
880
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M
M
S
S
R
H
L
L
A
A
R
R
Q
Q
R
R
L
L
L
L
890
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G
G
R
R
S
S
W
W
S
S
V
V
P
P
V
V
I
I
R
R
900
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H
H
L
L
F
F
A
A
P
P
L
L
K
K
E
E
Y
Y
F
F
910
|
A
A
C
C
V
V
Click to Show/Hide the Structure
Experimental Note Identified from the Human Clinical Data
In Vitro Model Bone marrow N.A.
In Vivo Model NOD/SCID mouse xenograft model Mus musculus
Mechanism Description The missense mutation p.R882H (c.2645G>A) in gene DNMT3A cause the sensitivity of Idarubicin by unusual activation of pro-survival pathway
References
Ref 1 Do AML patients with DNMT3A exon 23 mutations benefit from idarubicin as compared to daunorubicin A single center experienceOncotarget. 2011 Nov;2(11):850-61. doi: 10.18632/oncotarget.347.
Ref 2 Silencing of the DNA damage repair regulator PPP1R15A sensitizes acute myeloid leukemia cells to chemotherapy. Ann Hematol. 2024 Aug;103(8):2853-2863.
Ref 3 VS-5584, a novel and highly selective PI3K/mTOR kinase inhibitor for the treatment of cancerMol Cancer Ther. 2013 Feb;12(2):151-61. doi: 10.1158/1535-7163.MCT-12-0466. Epub 2012 Dec 27.

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