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Doxorubicin

drug
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Also known as AdriablastinAdriblastinaDoxorubicinaDoxorubicineEpirubicin hydrochloride impuritydoxorubicin-HydroxydaunorubicinNSC-123127NSC-759155Valrubicin impurityAnthracyclin analogueAdriamycinAdriamicinaDoxourbicineAdriblastineadriyamicinDoxorubucinDoxoruibicinSID124886887

Summary

Doxorubicin (CHEMBL53463) is an approved small molecule (ATC L01DB01) targeting TOP2A; indicated across 137 conditions including neoplasm and ovarian neoplasm.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: L01DB01
  • Targets: 1 (TOP2A)
  • Indications: 137 conditions
  • Clinical trials: 915
  • Chemistry: 543.5 Da · C27H29NO11

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL53463
NameDoxorubicin
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID31703
ChEBICHEBI:28748
ATCL01DB01
Molecular formulaC27H29NO11
Molecular weight543.5
InChIKeyAOJJSUZBOXZQNB-TZSSRYMLSA-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)CO)O)N)O

IUPAC name: (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

Other ChEBI roles (chemical / environmental): Escherichia coli metabolite.

Also known as: Adriablastin, Adriblastina, Doxorubicin, Doxorubicina, Doxorubicine, Epirubicin hydrochloride impurity, doxorubicin-, Hydroxydaunorubicin, NSC-123127, NSC-759155, Valrubicin impurity, doxorubicin

Parent form; salt/anhydrous children: CHEMBL216371, CHEMBL272706, CHEMBL359744

Patent coverage: 88,016 distinct patent families (314,282 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 314,242 (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

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
TOP2ADNA topoisomerase II alphaInhibition699.6% (common-essential)P11388

Broader ChEMBL bioactivity targets: 41 (assay-derived). Sample: Solute carrier organic anion transporter family member 1B3, ATP-binding cassette sub-family C member 4, DNA topoisomerase 1, CDGSH iron-sulfur domain-containing protein 1, DNA topoisomerase 2-alpha, Receptor tyrosine-protein kinase erbB-2, 5-hydroxytryptamine receptor 2B, Tyrosine-protein kinase Fyn, Alpha-2A adrenergic receptor, Glutamate carboxypeptidase 2.

Bioactivity

ChEMBL activities: 44 potent at pChembl ≥ 5 of 73 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
TOP2A8.31IC504.9nMCHEMBL_ACT_25724245
AURKA7.4IC5040nMCHEMBL_ACT_6360782
HIF1A6.92EC50120nMCHEMBL_ACT_2664579
EBP6.82IC50150nMCHEMBL_ACT_1840671
EBP6.7IC50200nMCHEMBL_ACT_1840661
EBP6.52IC50300nMCHEMBL_ACT_1840668
ABCB16.3IC50504nMCHEMBL_ACT_25555290
ESR16.28AC50530nMCHEMBL_ACT_25167168
TOP2A6.22IC50600nMCHEMBL_ACT_18903843
TOP2B6.14IC50727nMCHEMBL_ACT_22415172
TOP2A6.06IC50880nMCHEMBL_ACT_18787127
TOP2A6.03IC50940nMCHEMBL_ACT_25036122
TOP2A6IC501000nMCHEMBL_ACT_2194973
TOP2A6IC501000nMCHEMBL_ACT_2194974
TOP2A6IC50990nMCHEMBL_ACT_23202129
MMP25.96IC501100nMCHEMBL_ACT_383367
TOP2A5.92IC501200nMCHEMBL_ACT_18911892
TOP2A5.82IC501500nMCHEMBL_ACT_18911913
PGR5.77AC501700nMCHEMBL_ACT_25192747
HTR2A5.68AC502087nMCHEMBL_ACT_25173553
O705285.68Ki2078nMCHEMBL_ACT_7668917
TOP2A5.64IC502300nMCHEMBL_ACT_18911871
ERBB25.61IC502485nMCHEMBL_ACT_7666870
NR3C15.59AC502590nMCHEMBL_ACT_25175695
TOP2A5.58IC502600nMCHEMBL_ACT_18911828
TOP2A5.52IC503000nMCHEMBL_ACT_16830847
TOP2A5.52IC503000nMCHEMBL_ACT_18081539
O885085.52IC503000nMCHEMBL_ACT_20689586
TOP15.5IC503200nMCHEMBL_ACT_25031393
TOP2A5.48IC503300nMCHEMBL_ACT_18911866

Target pathways

Aggregated over 1 target gene(s): TOP2A.

Top Reactome pathways

2 total, by targets touching each:

PathwayTargetsGenes
Transcription of E2F targets under negative control by DREAM complex1TOP2A
SUMOylation of DNA replication proteins1TOP2A

Dominant GO biological processes

GO termTargets
resolution of meiotic recombination intermediates1
sister chromatid segregation1
hematopoietic progenitor cell differentiation1
DNA topological change1
chromatin organization1
DNA damage response1
chromosome segregation1
female meiotic nuclear division1
apoptotic chromosome condensation1
embryonic cleavage1
regulation of circadian rhythm1
positive regulation of apoptotic process1
positive regulation of single stranded viral RNA replication via double stranded DNA intermediate1
positive regulation of transcription by RNA polymerase II1
rhythmic process1

Indications & clinical

Indications

137 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).

IndicationTrial phaseMONDOEFO
neoplasm4MONDO:0005070EFO:0000616
ovarian neoplasm3MONDO:0021068EFO:0003893
hepatocellular carcinoma3MONDO:0007256EFO:0000182
breast carcinoma3MONDO:0004989EFO:0000305
osteosarcoma3MONDO:0009807EFO:0000637
sarcoma3MONDO:0005089EFO:0000691
ovarian carcinoma3MONDO:0005140EFO:0001075
non-Hodgkin lymphoma3MONDO:0018908EFO:0005952
carcinoma3MONDO:0004993EFO:0000313
acute lymphoblastic leukemia3MONDO:0004967EFO:0000220
lymphoma3MONDO:0005062EFO:0000574
small cell lung carcinoma3MONDO:0008433EFO:0000702
endometrium neoplasm3MONDO:0021251EFO:0004230
mantle cell lymphoma3MONDO:0018876EFO:1001469
breast neoplasm3MONDO:0021100EFO:0003869
B-cell acute lymphoblastic leukemia3MONDO:0004947EFO:0000094
B-cell chronic lymphocytic leukemia3MONDO:0004948EFO:0000095
neoplasm of mature B-cells3MONDO:0004949EFO:0000096
Ewing sarcoma3MONDO:0012817EFO:0000174
Hodgkins lymphoma3MONDO:0004952EFO:0000183
T-cell acute lymphoblastic leukemia3MONDO:0004963EFO:0000209
peripheral T-cell lymphoma, not otherwise specified3MONDO:0004964EFO:0000211
angioimmunoblastic T-cell lymphoma3MONDO:0004977EFO:0000255
diffuse large B-cell lymphoma3MONDO:0018905EFO:0000403
Kaposi’s sarcoma3MONDO:0005055EFO:0000558
leiomyosarcoma3MONDO:0005058EFO:0000564
leukemia3MONDO:0005059EFO:0000565
neuroblastoma3MONDO:0005072EFO:0000621
plasma cell myeloma3MONDO:0009693EFO:0001378
triple-negative breast carcinoma3MONDO:0005494EFO:0005537
inflammatory breast carcinoma3MONDO:0006804EFO:1000984
soft tissue sarcoma3MONDO:0018078EFO:1001968
fallopian tube carcinoma3MONDO:0006206EFO:1000251
peritoneal neoplasm3MONDO:0006901EFO:1001100
ganglioneuroblastoma3MONDO:0005035EFO:0000502
hepatoblastoma3MONDO:0018666EFO:1000292
neutropenia3MONDO:0001475MONDO:0001475
brain cancer3MONDO:0001657MONDO:0001657
fallopian tube neoplasm3MONDO:0021092MONDO:0002158
ovarian cancer3MONDO:0008170MONDO:0008170
follicular lymphoma3MONDO:0018906MONDO:0018906
acute biphenotypic leukemia3MONDO:0020322MONDO:0019460
nasal cavity and paranasal sinus lethal midline granuloma3MONDO:0006828MONDO:0019472
urothelial carcinoma3MONDO:0040679EFO:0008528
Waldenstrom macroglobulinemia3MONDO:0100280MONDO:0000432
kidney cancer3MONDO:0002367MONDO:0002367
mature T-cell and NK-cell non-Hodgkin lymphoma3MONDO:0000430MONDO:0000430
retinoblastoma3MONDO:0008380MONDO:0008380
brain neoplasm3MONDO:0021211EFO:0003833
desmoid tumor3MONDO:0007608EFO:0009907
marginal zone lymphoma3MONDO:0017604EFO:1000630
lymphoid leukemia2MONDO:0005402EFO:0004289
glioblastoma2MONDO:0018177EFO:0000519
adenoid cystic carcinoma2MONDO:0004971EFO:0000231
Burkitt lymphoma2MONDO:0007243EFO:0000309
mesothelioma2MONDO:0005065EFO:0000588
oligoastrocytoma2MONDO:0016702EFO:0000630
oligodendroglioma2MONDO:0016695EFO:0000632
prostate adenocarcinoma2MONDO:0005082EFO:0000673
renal cell carcinoma2MONDO:0005086EFO:0000681
malignant pleural mesothelioma2MONDO:0005112EFO:0000770
anaplastic astrocytoma2MONDO:0016684EFO:0002499
exocrine pancreatic carcinoma2MONDO:0005192EFO:0002618
rhabdomyosarcoma2MONDO:0005212EFO:0002918
anaplastic large cell lymphoma2MONDO:0020325EFO:0003032
nasopharyngeal neoplasm2MONDO:0005375EFO:0004252
cholangiocarcinoma2MONDO:0019087EFO:0005221
plasma cell leukemia2MONDO:0018689EFO:0006475
hereditary breast ovarian cancer syndrome2MONDO:0003582Orphanet:145
myelodysplastic syndrome2MONDO:0018881EFO:0000198
acute myeloid leukemia2MONDO:0018874EFO:0000222
non-small cell lung carcinoma2MONDO:0005233EFO:0003060
optic nerve glioma2MONDO:0003235EFO:0009254
ductal breast carcinoma in situ2MONDO:0005023EFO:0000432
gastric adenocarcinoma2MONDO:0005036EFO:0000503
blast phase chronic myelogenous leukemia, BCR-ABL1 positive2MONDO:0006115EFO:1000131
neuroendocrine neoplasm2MONDO:0019496EFO:1001901
gastric neoplasm2MONDO:0021085MONDO:0001056
carcinosarcoma2MONDO:0002928MONDO:0002928
salivary gland cancer2MONDO:0004669MONDO:0004669
T-cell non-Hodgkin lymphoma2MONDO:0015760MONDO:0015760
astrocytoma (excluding glioblastoma)2MONDO:0019781MONDO:0016691
Wilms tumor2MONDO:0006058MONDO:0019004
glioma2MONDO:0021042MONDO:0100342
angiosarcoma2MONDO:0016982EFO:0003968
bone cancer2MONDO:0002129EFO:1000350
lung neoplasm2MONDO:0021117MONDO:0021117
dedifferentiated liposarcoma2MONDO:0020563EFO:0003085
oral cavity neoplasm2MONDO:0021245EFO:0003868
hematopoietic and lymphoid system neoplasm2MONDO:0002334MONDO:0044881
adrenal cortex carcinoma2MONDO:0006639EFO:1000796
plasma cell neoplasm2MONDO:0004959EFO:0000200
liposarcoma2MONDO:0005060EFO:0000569
lymphoid neoplasm2MONDO:0005157EFO:0001642
bone neoplasm2MONDO:0019060EFO:0003820
pancreatic neoplasm2MONDO:0021040EFO:0003860
CD4+/CD56+ hematodermic neoplasm2MONDO:0019467EFO:0010580
paraganglioma2MONDO:0000448EFO:1000453
primary cutaneous T-cell non-Hodgkin lymphoma1MONDO:0000607EFO:0002913
male breast carcinoma1MONDO:0005628EFO:0006861
thymic carcinoma1MONDO:0006451EFO:1000576
thymoma1MONDO:0006456EFO:1000581
hematologic disorder1MONDO:0005570HP:0001871
breast carcinoma in situ1MONDO:0004658MONDO:0004658
Castleman disease1MONDO:0015564MONDO:0015564
metastatic melanoma1MONDO:0005191EFO:0002617
primary effusion lymphoma1MONDO:0018842EFO:1000491
B-cell non-Hodgkin lymphoma1MONDO:0015759EFO:1001938
pancreatic ductal adenocarcinoma1MONDO:0005184MONDO:0005184

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

Clinical trials

Total trials: 915.

Phase distribution

PhaseTrials
PHASE2432
PHASE3202
PHASE1108
PHASE1/PHASE280
Not specified45
PHASE425
PHASE2/PHASE314
EARLY_PHASE19

Top trials by phase / activity

NCTPhaseStatusTitle
NCT03892330PHASE4NOT_YET_RECRUITINGCombination Therapy of Anthracyclines for Children With Nephroblastoma
NCT05844813PHASE4ENROLLING_BY_INVITATIONNeoadjuvant Chemotherapy Combined With Targeted Treatment in High-risk Retroperitoneal Sarcoma
NCT06831370PHASE4RECRUITINGA Study of Brentuximab Vedotin With Doxorubicin, Vinblastine and Dacarbazine in Adults With Hodgkin Lymphoma in India
NCT00198991PHASE4COMPLETEDGerman Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (07/2003)
NCT00199004PHASE4COMPLETEDTrial for Treatment of Adult Patients With Standard Risk Acute Lymphoblastic Leukemia With Chemotherapy and Rituximab
NCT00199017PHASE4COMPLETEDGerman Multicenter Trial for the Treatment of Newly Diagnosed T-lymphoblastic Lymphoma in Adults
NCT00199056PHASE4COMPLETEDGerman Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (06/99)
NCT00199069PHASE4COMPLETEDGerman Multicenter Trial for Treatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Adults (05/93)
NCT00199082PHASE4COMPLETEDNewly Diagnosed Mature B-ALL, Burkitt’s Lymphoma and Other High-grade Lymphoma in Adults
NCT00199095PHASE4COMPLETEDTreatment of Elderly Patients (>65 Years) With Acute Lymphoblastic Leukemia
NCT00339118PHASE4UNKNOWNEpSSG (European Soft Tissue Sarcoma Study Group) Protocol for Non-Metastatic Rhabdomyosarcoma in Children
NCT00531973PHASE4UNKNOWNA Study of Liposomal Doxorubicin in Women With Breast Cancer Exploiting Tissue Doppler Imaging
NCT00969462PHASE4COMPLETEDDoxorubicin Pharmacokinetics and Response in Non Hodgkin’s Lymphoma
NCT01088724PHASE4COMPLETEDFludarabine, Cyclophosphamide, Doxorubicin and Rituximab for the Treatment of Post-transplant Lymphoproliferative Disease (PTLD)
NCT01358253PHASE4COMPLETEDRituximab Plus Chemotherapy for CD20+ Adult Acute Lymphoblastic Leukemia
NCT01537029PHASE4COMPLETEDEffect of Weight on the Population Pharmacokinetic Analysis of Doxorubicin and Cyclophosphamide
NCT01746992PHASE4UNKNOWNCTOP/ITE/MTX Compared With CHOP as the First-line Therapy for Newly Diagnosed Young Patients With T Cell Lymphoma
NCT02419742PHASE4COMPLETEDSafety and Efficacy of Trastuzumab as Part of Breast Cancer Treatment Regimen
NCT02559154PHASE4UNKNOWNModified Bortezomib-based Combination Therapy for Multiple Myeloma
NCT02577783PHASE4UNKNOWNPDD vs PAD to Treat Initially Diagnosed MM
NCT02853500PHASE4WITHDRAWNEffect of Surefire Infusion Device on Tumor Response to Regional Intra-arterial Therapy for Primary Liver Malignancies
NCT02858804PHASE4COMPLETEDEDOCH Alternating With DHAP for New Diagnosed Younger MCL
NCT02894645PHASE4UNKNOWNMalaysia-Singapore Acute Lymphoblastic Leukemia 2010 Study
NCT02903524PHASE4UNKNOWNDoxorubicin Hydrochloride Liposome Injection Combination With Cyclophosphamide vs Pirarubicin Combination With Cyclophosphamide in Patients With Locally Advanced Breast Cancer
NCT03817853PHASE4COMPLETEDAn Open-Label, Single Arm Study of Obinutuzumab Short Duration Infusion in Patients With Previously Untreated Advanced Follicular Lymphoma
NCT00572169PHASE3ACTIVE_NOT_RECRUITINGUARK 2006-66, Total Therapy 3B: An Extension of UARK 2003-33 Total Therapy
NCT01057069PHASE2/PHASE3ACTIVE_NOT_RECRUITINGNeo Adjuvant Chemotherapy in Triple Negative Breast Cancer
NCT01646034PHASE3ACTIVE_NOT_RECRUITINGHigh Dose Chemotherapy in Oligo-metastatic Homologous Recombination Deficient Breast Cancer
NCT01704716PHASE3RECRUITINGHigh Risk Neuroblastoma Study 1.8 of SIOP-Europe (SIOPEN)
NCT02112916PHASE3ACTIVE_NOT_RECRUITINGCombination 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
NCT02180867PHASE2/PHASE3ACTIVE_NOT_RECRUITINGRadiation Therapy With or Without Combination Chemotherapy or Pazopanib Before Surgery in Treating Patients With Newly Diagnosed Non-rhabdomyosarcoma Soft Tissue Sarcomas That Can Be Removed by Surgery
NCT02306161PHASE3ACTIVE_NOT_RECRUITINGCombination Chemotherapy With or Without Ganitumab in Treating Patients With Newly Diagnosed Metastatic Ewing Sarcoma
NCT02661503PHASE3ACTIVE_NOT_RECRUITINGHD21 for Advanced Stages
NCT02845882PHASE3ACTIVE_NOT_RECRUITINGLBL-2016 for Children or Adolescents in China
NCT03007147PHASE3ACTIVE_NOT_RECRUITINGImatinib Mesylate and Combination Chemotherapy in Treating Patients With Newly Diagnosed Philadelphia Chromosome Positive Acute Lymphoblastic Leukemia
NCT03017326PHASE3ACTIVE_NOT_RECRUITINGPaediatric Hepatic International Tumour Trial
NCT03020030PHASE3ACTIVE_NOT_RECRUITINGTreatment of Newly Diagnosed Acute Lymphoblastic Leukemia in Children and Adolescents
NCT03117751PHASE2/PHASE3ACTIVE_NOT_RECRUITINGTotal Therapy XVII for Newly Diagnosed Patients With Acute Lymphoblastic Leukemia and Lymphoma
NCT03150693PHASE3RECRUITINGInotuzumab Ozogamicin and Frontline Chemotherapy in Treating Young Adults With Newly Diagnosed B Acute Lymphoblastic Leukemia
NCT03533582PHASE3ACTIVE_NOT_RECRUITINGCisplatin and Combination Chemotherapy in Treating Children and Young Adults With Hepatoblastoma or Liver Cancer After Surgery

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (2) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of CPNDS Guideline for daunorubicin, doxorubicin and RARG,CPNDSRARG;SLC28A3;UGT1A6yes
Annotation of CPIC Guideline for aminosalicylic acid, chloramphenicol,CPICG6PD

PharmGKB also curates 77 clinical and 297 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

27 molecules share ≥1 primary target. Top 27 by shared-target count:

MoleculeSourceStatusShared targets
AMSACRINEChEMBLPhase 4 (approved)TOP2A
CIPROFLOXACINChEMBLPhase 4 (approved)TOP2A
DAUNORUBICINChEMBLPhase 4 (approved)TOP2A
DEXRAZOXANEChEMBLPhase 4 (approved)TOP2A
EPIRUBICINChEMBLPhase 4 (approved)TOP2A
ETOPOSIDEChEMBLPhase 4 (approved)TOP2A
IDARUBICINChEMBLPhase 4 (approved)TOP2A
MITOXANTRONEChEMBLPhase 4 (approved)TOP2A
TENIPOSIDEChEMBLPhase 4 (approved)TOP2A
TOPOTECANChEMBLPhase 4 (approved)TOP2A
CURCUMINChEMBLPhase 3TOP2A
GEPOTIDACINChEMBLPhase 3TOP2A
AXL-1717ChEMBLPhase 2TOP2A
DECERNOTINIBChEMBLPhase 2TOP2A
LOSOXANTRONEChEMBLPhase 2TOP2A
NEMORUBICINChEMBLPhase 2TOP2A
PIROXANTRONEChEMBLPhase 2TOP2A
AfatinibPubChemApprovedTOP2A
BinimetinibPubChemApprovedTOP2A
CrizotinibPubChemApprovedTOP2A
GefitinibPubChemApprovedTOP2A
IdelalisibPubChemApprovedTOP2A
PazopanibPubChemApprovedTOP2A
podofiloxPubChemApprovedTOP2A
regorafenibPubChemApprovedTOP2A
SelumetinibPubChemApprovedTOP2A
TrametinibPubChemApprovedTOP2A

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot