Doxorubicin
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1974
- First approval year
- 1974
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Doxorubicin
- Molecular weight
- 543.53
- Structure (SMILES)
- COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
- adriblastina
- Adriblastina
- (8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE
- 5 12 naphthacenedione 10 3 amino 2 3 6 trideoxy alpha l lyxo hexopyranosyl oxy 7 8 9 10 tetrahydro 6 8 11 trihydroxy 8 hydroxyacetyl 1 methoxy 8s cis
- 5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-
- 8s 10s 10 3 amino 2 3 6 trideoxy alpha l lyxo hexopyranosyl oxy 8 glycoloyl 7 8 9 10 tetrahydro 6 8 11 trihydroxy 1 methoxy 5 12 naphthacenedione
- adriablastin
- Adriablastin
- DAUNORUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]
- daunorubicin hydrochloride impurity d ep impurity
- doxorubicin
- Doxorubicin
- DOXORUBICIN [HSDB]
- doxorubicin [INN]
- DOXORUBICIN [MART.]
- DOXORUBICIN [MI]
- DOXORUBICIN [USAN]
- DOXORUBICIN [VANDF]
- Doxorubicin [WHO-DD]
- doxorubicin hsdb
- doxorubicin inn
- doxorubicin mart
- doxorubicin mi
- doxorubicin usan
- doxorubicin vandf
- doxorubicin who dd
- doxorubicina
And 19 more, listed on the interactive page.
- CAS registry numbers
- 23214-92-8
- ChEMBL ID
- CHEMBL53463
- InChIKey
- AOJJSUZBOXZQNB-TZSSRYMLSA-N
- PubChem compound IDs
- 31703
- FDA ingredient codes (UNII)
- 80168379AG
- L01DB
- L01DB01
Sources for recorded values
- 3639
- 142433
- Applicant
- PFIZER
- Approval date
- 7 Aug 1974
- Application number
- NDA050467
- Status
- Authorised
- Status date
- 20 Jun 1996
- Authorisation date
- 20 Jun 1996
- Approved indications
- Caelyx pegylated liposomal is indicated: as monotherapy for patients with metastatic breast cancer, where there is an increased cardiac risk; for treatment of advanced ovarian cancer in women who have failed a first-line platinum-based chemotherapy regimen; in combination with bortezomib for the treatment of progressive multiple myeloma in patients who have received at least one prior therapy and who have already undergone or are unsuitable for bone marrow transplant; for treatment of AIDS-related Kaposi’s sarcoma (KS) in patients with low CD4 counts (<200 CD4 lymphocytes/mm3) and extensive mucocutaneous or visceral disease. Caelyx pegylated liposomal may be used as first-line systemic chemotherapy, or as second line chemotherapy in AIDS-KS patients with disease that has progressed with, or in patients intolerant to, prior combination systemic chemotherapy comprising at least two of the following agents: a vinca alkaloid, bleomycin and standarddoxorubicin (or other anthracycline).
- Product number
- EMEA/H/C/000089
- Authorisation holder
- Baxter Holding B.V.
- Priority medicines scheme
- No
- Generic
- No
- Biosimilar
- No
- Generic medicines
- 0
- Biosimilar medicines
- 0
- Advanced therapy
- No
- Conditional approval
- No
- Additional monitoring
- No
- Accelerated assessment
- No
- Exceptional circumstances
- No
Therapeutic areas
- Breast Neoplasms
- Multiple Myeloma
- Ovarian Neoplasms
- Sarcoma, Kaposi
European medicines record
- Patents
- 0
- Designations
- 2
- First in class
- No
- Fast track
- No
- Breakthrough designation
- No
- Orphan designation
- No
- Priority review
- No
- Orphan exclusivity
- No
- Accelerated approval
- No
- Availability
- Prescription only
- Boxed warning
- Yes
- United States (FDA)
- Approved
- European Union (EMA)
- Authorised
- Pharmacology name
- doxorubicin
- Type
- Natural product
- Drug name stem
- -rubicin
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Parenteral
Mechanisms of action
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- DNA topoisomerase II alpha
- Gene symbol
- TOP2A
- Protein identifier
- P11388
- Median affinity
- 6
- Affinity units
- pIC50
Open Targets mechanisms
- Mechanism
- DNA topoisomerase II alpha inhibitor
- Action type
- Inhibitor
- Target
- DNA topoisomerase 2-alpha
DrugCentral mechanisms
- Action type
- Inhibitor
- Gene symbol
- TOP2A
- Protein identifier
- P11388
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000094
- Subject identifier
- D015456
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- Lymphoma, Follicular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000096
- Subject identifier
- D008224
- Condition
- Sarcoma, Ewing
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000174
- Subject identifier
- D012512
- Condition
- Carcinoma, Hepatocellular
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000182
- Subject identifier
- D006528
- Condition
- Hodgkin Disease
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000183
- Subject identifier
- D006689
- Condition
- Myelodysplastic Syndromes
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000198
- Subject identifier
- D009190
- Condition
- Neoplasms, Plasma Cell
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000200
- Subject identifier
- D054219
- Condition
- Leukemia, Biphenotypic, Acute
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000209
- Subject identifier
- D015456
- Condition
- Lymphoma, T-Cell, Peripheral
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000211
- Subject identifier
- D016411
- Condition
- Precursor Cell Lymphoblastic Leukemia-Lymphoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000220
- Subject identifier
- D054198
- Condition
- Leukemia, Myeloid, Acute
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000222
- Subject identifier
- D015470
- Condition
- Carcinoma, Adenoid Cystic
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000231
- Subject identifier
- D003528
- Condition
- Immunoblastic Lymphadenopathy
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000255
- Subject identifier
- D007119
- Condition
- Astrocytoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000272
- Subject identifier
- D001254
- Condition
- Breast Neoplasms
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000305
- Subject identifier
- D001943
- Condition
- Burkitt Lymphoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000309
- Subject identifier
- D002051
- Condition
- Carcinoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000313
- Subject identifier
- D002277
- Condition
- Lymphoma, Large B-Cell, Diffuse
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000403
- Subject identifier
- D016403
- Condition
- Carcinoma, Intraductal, Noninfiltrating
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000432
- Subject identifier
- D002285
- Condition
- Ganglioneuroblastoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000502
- Subject identifier
- D018305
- Condition
- Stomach Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000503
- Subject identifier
- D013274
- Condition
- Glioblastoma
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000519
- Subject identifier
- D005909
- Condition
- Sarcoma, Kaposi
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000558
- Subject identifier
- D012514
- Condition
- Leiomyosarcoma
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000564
- Subject identifier
- D007890
And 112 more, listed on the interactive page.
- Condition identifier
- EFO_0000096
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000174
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000182
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000183
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000200
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000211
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000220
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000231
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000305
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000313
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000403
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000409
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000432
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000519
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000558
- Condition identifier
- EFO_0000564
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000565
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000574
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000588
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000621
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000637
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000638
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000681
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000691
- Highest recorded phase
- 3
And 254 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- carcinogenicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- cardiotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hematological toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- hepatotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- musculoskeletal toxicity
- Country
- United States
- Event
- acute myeloid leukaemia
- Reports
- 430
- Reporting signal score
- 776.985
- Event
- anaemia
- Reports
- 1,733
- Reporting signal score
- 801.902
- Event
- bone marrow failure
- Reports
- 547
- Reporting signal score
- 605.928
- Event
- cardiomyopathy
- Reports
- 454
- Reporting signal score
- 630.174
- Event
- cardiotoxicity
- Reports
- 618
- Reporting signal score
- 1,400.85
- Event
- diffuse large b-cell lymphoma
- Reports
- 293
- Reporting signal score
- 578.151
- Event
- diffuse large b-cell lymphoma recurrent
- Reports
- 345
- Reporting signal score
- 1,105.16
- Event
- disease progression
- Reports
- 1,323
- Reporting signal score
- 1,169.55
- Event
- disease recurrence
- Reports
- 580
- Reporting signal score
- 745.871
- Event
- ejection fraction decreased
- Reports
- 484
- Reporting signal score
- 675.828
- Event
- febrile bone marrow aplasia
- Reports
- 204
- Reporting signal score
- 374.929
- Event
- febrile neutropenia
- Reports
- 4,246
- Reporting signal score
- 9,262.78
- Event
- haematotoxicity
- Reports
- 561
- Reporting signal score
- 1,122.58
- Event
- hepatitis b reactivation
- Reports
- 179
- Reporting signal score
- 385.564
- Event
- leukopenia
- Reports
- 902
- Reporting signal score
- 786.5
- Event
- malignant neoplasm progression
- Reports
- 792
- Reporting signal score
- 611.552
- Event
- mucosal inflammation
- Reports
- 990
- Reporting signal score
- 1,497.72
- Event
- myelodysplastic syndrome
- Reports
- 466
- Reporting signal score
- 743.6
- Event
- myelosuppression
- Reports
- 282
- Reporting signal score
- 400.993
- Event
- neutropenia
- Reports
- 2,928
- Reporting signal score
- 3,269.59
- Event
- neutropenic sepsis
- Reports
- 363
- Reporting signal score
- 712.061
- Event
- pancytopenia
- Reports
- 902
- Reporting signal score
- 813.541
- Event
- pneumocystis jirovecii pneumonia
- Reports
- 324
- Reporting signal score
- 516.08
- Event
- pyrexia
- Reports
- 1,539
- Reporting signal score
- 429.853
- Event
- thrombocytopenia
- Reports
- 1,630
- Reporting signal score
- 1,158.44
And 1 more, listed on the interactive page.
- NCT00001300
- NCT00189137
- NCT00204568
- NCT00204646
- NCT00288431
- NCT00626704
- NCT00755261
- NCT00796120
- NCT00949325
- NCT01027910
- NCT01104298
- NCT01185964
- NCT01605526
- NCT01746238
- NCT02326025
- NCT02448537
- NCT02732015
- NCT02812654
- NCT03678883
- NCT03802071
- NCT03880695
- NCT04199026
- NCT04535713
- NCT04968106
- NCT05210374
And 941 more, listed on the interactive page.
- Dose
- 50 mg/m2
- Route
- Intravenous
- How often
- Every 4 weeks
- Hydrogen bond acceptors
- 12
- Hydrogen bond donors
- 6
- Polar surface area
- 206.07
- Calculated partition coefficient (ALogP)
- 0
- Calculated partition coefficient (XLogP)
- 1.3
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 39
- Molecular formula
- C27H29NO11
- Monoisotopic mass
- 543.17406074
- Natural product
- Yes
- Recorded assays
- 15,810
- Active assays
- 7,084
- Confirmatory
- Other
- Screening
- Antibiotics, Antineoplastic
- Topoisomerase II Inhibitors
These details could not be displayed.
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- A Comparison of DOX-SL Versus Adriamycin Plus Bleomycin Plus Vincristine in the Treatment of Severe AIDS-Related Kaposi's Sarcoma
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Approved for (2)
In development for (235)
- Acquired polycythemia vera Phase 2
- Acral lentiginous melanoma Phase 1
- Acute kidney injury Phase 2
- Acute leukemia of ambiguous lineage Phase 3
- Acute lymphoblastic leukemia Phase 3
- Acute myeloid leukemia Phase 2
- Acute promyelocytic leukemia Phase 3
- Adenocarcinoma Phase 2
- Adenoid cystic carcinoma Phase 2
- Adrenal cortex carcinoma Phase 2
- Adult hepatocellular carcinoma Phase 3
- Adult T-cell leukemia/lymphoma Phase 3
- Alveolar rhabdomyosarcoma Phase 2
- Alveolar soft part sarcoma Phase 1
- Amyloidosis Phase 2
- Anaplastic astrocytoma Phase 2
- Anaplastic large cell lymphoma Phase 2
- Angioimmunoblastic T-cell lymphoma Phase 3
- Angiosarcoma Phase 2
- Astrocytoma (excluding glioblastoma) Phase 2
Other linked conditions (2)
- Female reproductive organ cancer
- Intrahepatic cholangiocarcinoma
Targets (1)
- TOP2A DNA topoisomerase II alpha inhibitor