Daunorubicin

Summary

Daunorubicin (CHEMBL178) is an approved small-molecule antineoplastic agent (ATC L01DB02); indicated across 20 conditions including neoplasm and acute myeloid leukemia.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L01DB02
• Indications: 20 conditions
• Clinical trials: 155
• Chemistry: 527.5 Da · C27H29NO10

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL178
Name	Daunorubicin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	30323
ChEBI	CHEBI:41977
ATC	L01DB02
Molecular formula	C27H29NO10
Molecular weight	527.5
InChIKey	STQGQHZAVUOBTE-VGBVRHCVSA-N

SMILES: 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

IUPAC name: (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

ChEBI definition: A natural product found in Actinomadura roseola.

Pharmacological roles (ChEBI): antineoplastic agent.

Other ChEBI roles (chemical / environmental): bacterial metabolite.

Also known as: Daunomycin, Daunorubicin, Daunorubicin component of vyxeos, Daunorubicina, Daunorubicine, Daunoxome, Epirubicin hydrochloride impurity, daunorubicin-, FI 6339, FI-6339, NSC-83142, RP 13057

Parent form; salt/anhydrous children: CHEMBL1563, CHEMBL1200475

Patent coverage: 51,143 distinct patent families (203,756 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 202,932 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 64 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Microtubule-associated protein tau, Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Fructose-bisphosphate aldolase, ATP-dependent DNA helicase Q1, RecQ-like DNA helicase BLM, Inositol monophosphatase 1, 4’-phosphopantetheinyl transferase ffp, Ferritin light chain.

Bioactivity

ChEMBL activities: 27 potent at pChembl ≥ 5 of 86 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
TOP2A	8	IC50	10	nM	CHEMBL_ACT_25724244
HDAC6	7.7	IC50	20	nM	CHEMBL_ACT_24723625
HDAC1	7.33	IC50	47	nM	CHEMBL_ACT_24723611
P51450	7.2	Potency	63.1	nM	CHEMBL_ACT_4094552
ABCC1	7.16	Ki	70	nM	CHEMBL_ACT_11002253
NR3C1	6.96	AC50	110	nM	CHEMBL_ACT_25175693
HDAC8	6.66	IC50	220	nM	CHEMBL_ACT_24723646
PEPD	6.52	IC50	300	nM	CHEMBL_ACT_26011178
ABCC1	6.02	Ki	950	nM	CHEMBL_ACT_11002311
MMP2	5.72	IC50	1900	nM	CHEMBL_ACT_353542
HTT	5.65	Potency	2239	nM	CHEMBL_ACT_3758371
ABCB1	5.6	Ki	2500	nM	CHEMBL_ACT_11002756
PTGS2	5.55	AC50	2800	nM	CHEMBL_ACT_25166022
MEN1	5.55	Potency	2818	nM	CHEMBL_ACT_3620692
P51450	5.55	Potency	2818	nM	CHEMBL_ACT_4807151
Q9F4F7	5.5	Potency	3162	nM	CHEMBL_ACT_4386240
AVPR1A	5.44	AC50	3600	nM	CHEMBL_ACT_25161950
ESR1	5.41	AC50	3900	nM	CHEMBL_ACT_25116446
MAPT	5.35	Potency	4467	nM	CHEMBL_ACT_4027233
MAPT	5.3	Potency	5012	nM	CHEMBL_ACT_4051683
GHSR	5.29	AC50	5165	nM	CHEMBL_ACT_25172585
P51450	5.2	Potency	6310	nM	CHEMBL_ACT_4087766
PGR	5.13	AC50	7423	nM	CHEMBL_ACT_25222907
ABCC1	5.1	IC50	8000	nM	CHEMBL_ACT_11001896
P51450	5.1	Potency	7943	nM	CHEMBL_ACT_4818803
NR1I2	5.03	AC50	9400	nM	CHEMBL_ACT_25224254
APEX1	5	Potency	10000	nM	CHEMBL_ACT_3798959

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

20 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
neoplasm	4	MONDO:0005070	EFO:0000616
acute myeloid leukemia	4	MONDO:0018874	EFO:0000222
leukemia	3	MONDO:0005059	EFO:0000565
acute lymphoblastic leukemia	3	MONDO:0004967	EFO:0000220
non-Hodgkin lymphoma	3	MONDO:0018908	EFO:0005952
Kaposi’s sarcoma	3	MONDO:0005055	EFO:0000558
myeloid leukemia	3	MONDO:0004643	MONDO:0004643
chronic hepatitis B virus infection	3	MONDO:0005366	EFO:0004239
myelodysplastic syndrome	2	MONDO:0018881	EFO:0000198
myelodysplastic syndrome with single lineage dysplasia	2	MONDO:0005272	EFO:0003802
lymphoid leukemia	2	MONDO:0005402	EFO:0004289
chronic myeloid leukemia	1	MONDO:0011996	EFO:0000339
B-cell acute lymphoblastic leukemia	1	MONDO:0004947	EFO:0000094
essential thrombocythemia	1	MONDO:0005029	EFO:0000479
acquired polycythemia vera	1	MONDO:0009891	EFO:0002429
hematopoietic and lymphoid system neoplasm	1	MONDO:0002334	MONDO:0044881
primary myelofibrosis	1	MONDO:0009692	MONDO:0044903

3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 155.

Phase distribution

Phase	Trials
PHASE2	46
PHASE3	38
PHASE1	25
PHASE4	16
PHASE1/PHASE2	11
Not specified	11
PHASE2/PHASE3	7
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06289673	PHASE4	RECRUITING	Identification of Necessary Information for Treatment Induction in Newly Diagnosed Acute Lymphoblastic Leukemia/Lymphoma
NCT07561892	PHASE4	RECRUITING	Study of the Effectiveness and Safety of Daunorubicin /Idarubicin ± Silibinin in Treating Newly Diagnosed AML (Non-M3).
NCT00180128	PHASE4	UNKNOWN	AIDA2000 - Risk-Adapted Therapy for Patients With Acute Promyelocytic Leukemia
NCT00198991	PHASE4	COMPLETED	German Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (07/2003)
NCT00199004	PHASE4	COMPLETED	Trial for Treatment of Adult Patients With Standard Risk Acute Lymphoblastic Leukemia With Chemotherapy and Rituximab
NCT00199017	PHASE4	COMPLETED	German Multicenter Trial for the Treatment of Newly Diagnosed T-lymphoblastic Lymphoma in Adults
NCT00199056	PHASE4	COMPLETED	German Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (06/99)
NCT00199069	PHASE4	COMPLETED	German Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (05/93)
NCT00494897	PHASE4	COMPLETED	PETHEMA LAL-RI/96: Treatment for Patients With Standard Risk Acute Lymphoblastic Leukemia
NCT00526175	PHASE4	COMPLETED	LAL-BR/2001: Study Treatment to Low Risk ALL
NCT00526305	PHASE4	COMPLETED	LAL-Ph-2000: Treatment of Acute Lymphoblastic Leukemia Chromosome Philadelphia Positive
NCT00526409	PHASE4	COMPLETED	LAL-AR-N-2005:Study Treatment for Children High Risk Acute Lymphoblastic Leukemia
NCT00853008	PHASE4	COMPLETED	Treatment of High Risk Adult Acute Lymphoblastic Leukemia
NCT02036489	PHASE4	COMPLETED	Pethema LAL-RI/2008: Treatment for Patients With Standard Risk Acute Lymphoblastic Leukemia
NCT02894645	PHASE4	UNKNOWN	Malaysia-Singapore Acute Lymphoblastic Leukemia 2010 Study
NCT03026842	PHASE4	UNKNOWN	Decitabine Versus Conventional Chemotherapy for Maintenance Therapy of Acute Myeloid Leukemia With t(8;21)
NCT02003222	PHASE3	ACTIVE_NOT_RECRUITING	Combination Chemotherapy With or Without Blinatumomab in Treating Patients With Newly Diagnosed BCR-ABL-Negative B Lineage Acute Lymphoblastic Leukemia
NCT02112916	PHASE3	ACTIVE_NOT_RECRUITING	Combination Chemotherapy With or Without Bortezomib in Treating Younger Patients With Newly Diagnosed T-Cell Acute Lymphoblastic Leukemia or Stage II-IV T-Cell Lymphoblastic Lymphoma
NCT02416388	PHASE2/PHASE3	RECRUITING	Study to Improve OS in 18 to 60 Year-old Patients, Comparing Daunorubicin Versus High Dose Idarubicin Induction Regimens, High Dose Versus Intermediate Dose Cytarabine Consolidation Regimens, and Standard Versus MMF Prophylaxis of GvHD in Allografted Patients in First CR
NCT02724163	PHASE3	RECRUITING	International Randomised Phase III Clinical Trial in Children With Acute Myeloid Leukaemia
NCT02845882	PHASE3	ACTIVE_NOT_RECRUITING	LBL-2016 for Children or Adolescents in China
NCT03021330	PHASE3	ACTIVE_NOT_RECRUITING	Efficacy of Intermediate-Dose Cytarabine Induction Regimen in Adult AML
NCT03117751	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Total Therapy XVII for Newly Diagnosed Patients With Acute Lymphoblastic Leukemia and Lymphoma
NCT03643276	PHASE3	RECRUITING	Treatment Protocol for Children and Adolescents With Acute Lymphoblastic Leukemia - AIEOP-BFM ALL 2017
NCT03701308	PHASE2/PHASE3	ACTIVE_NOT_RECRUITING	Daunorubicin and Cytarabine With or Without Uproleselan in Treating Older Adult Patients With Acute Myeloid Leukemia Receiving Intensive Induction Chemotherapy
NCT03897127	PHASE3	ACTIVE_NOT_RECRUITING	Study of Standard Intensive Chemotherapy Versus Intensive Chemotherapy With CPX-351 in Adult Patients With Newly Diagnosed AML and Intermediate- or Adverse Genetics
NCT04043494	PHASE3	RECRUITING	International Cooperative Treatment Protocol for Children and Adolescents With Lymphoblastic Lymphoma
NCT05681260	PHASE3	RECRUITING	Capizzi Escalating Methotrexate Versus High Dose Methotrexate in Children With Newly Diagnosed T-cell Lymphoblastic Lymphoma (T-LBL)
NCT05726110	PHASE3	RECRUITING	Selinexor in Combination With HAD or CAG Rregimens in Relapsed or Refractory Acute Myeloid Leukemia
NCT05939180	PHASE2/PHASE3	RECRUITING	VA vs DA for Newly Diagnosed Hig-risk AML
NCT06345365	PHASE3	RECRUITING	MA+AZA Regimen for the Treatment of Newly Diagnosed Acute Myeloid Leukemia (AML)
NCT06361329	PHASE3	RECRUITING	Comparing the Efficacy of VHAG and Traditional Chemotherapy Regimens in Newly Diagnosed ETP-ALL
NCT06744504	PHASE3	RECRUITING	Standard-dose vs Intermediate-dose Cytarabine Induction in the Treatment of Acute Myeloid Leukemia With RUNX1-RUNX1T1
NCT07007312	PHASE3	RECRUITING	Studies to Assess Ziftomenib in Combination With Ven+Aza or 7+3 in Patients With Untreated NPM1-m or KMT2A-r AML
NCT07132684	PHASE3	RECRUITING	Comparison of VA and D/IA Induction Regimens in Elderly Fit Acute Myeloid Leukemia Patients
NCT07255872	PHASE2/PHASE3	NOT_YET_RECRUITING	A Study of BL-M11D1 in Combination With Cytarabine + Daunorubicin or Venetoclax + Azacitidine in Patients With Acute Myeloid Leukemia
NCT00002093	PHASE3	COMPLETED	A Randomized Phase III Clinical Trial of Daunoxome Versus Combination Chemotherapy With Adriamycin/Bleomycin/Vincristine (ABV) in the Treatment of HIV-Associated Kaposi’s Sarcoma.
NCT00049517	PHASE3	COMPLETED	Combination Chemotherapy With or Without Monoclonal Antibody Therapy in Treating Patients With AML Leukemia
NCT00085709	PHASE3	COMPLETED	S0106 Cytarabine and Daunorubicin w/ or w/o Gemtuzumab Followed By HD Cytarabine and Either Gemtuzumab or Nothing in de Novo AML
NCT00111345	PHASE2/PHASE3	UNKNOWN	Therapy-Optimization Trial for the Treatment of Acute Myeloid Leukemias (AML) in Children and Adolescents

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPNDS Guideline for daunorubicin, doxorubicin and RARG,	CPNDS	RARG;SLC28A3;UGT1A6		yes

PharmGKB also curates 16 clinical and 131 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).