Doxorubicin hydrochloride

Highest phase reached
Approved
www.ebi.ac.uk
Drug type
Small molecule
www.ebi.ac.uk
First approval year
1974
www.ebi.ac.uk

First approval year
1974
www.ebi.ac.uk
Listing at source
Listed
Highest phase reached
Approved
www.ebi.ac.uk

Drug type
Small molecule
www.ebi.ac.uk
Drug name
Doxorubicin hydrochloride
www.ebi.ac.uk
Molecular weight
579.99
www.ebi.ac.uk
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.Cl
www.ebi.ac.uk

  • adriamycin
  • Adriamycin
  • adriamycin pfs
  • Adriamycin pfs
  • adriamycin rdf
  • Adriamycin rdf
  • caelyx
  • Caelyx
  • caelyx pegylated liposomal
  • Caelyx pegylated liposomal
  • celdoxome pegylated liposomal
  • Celdoxome pegylated liposomal
  • doxil
  • Doxil
  • Doxil (liposomal)
  • doxil liposomal
  • doxorubicin hydrochloride
  • Doxorubicin hydrochloride
  • Doxorubicin hydrochloride (liposomal)
  • doxorubicin hydrochloride component of imx 110
  • Doxorubicin hydrochloride component of imx-110
  • doxorubicin hydrochloride liposomal
  • myocet
  • Myocet
  • Myocet liposomal (previously myocet)

And 5 more, listed on the interactive page.

  • (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 HYDROCHLORIDE
  • 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 hydroxylacetyl 1 methoxy hydrochloride 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-(HYDROXYLACETYL)-1-METHOXY-, HYDROCHLORIDE (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 hydrochloride
  • adriablastina cs
  • Adriablastina cs
  • adriamycin
  • Adriamycin
  • ADRIAMYCIN [IARC]
  • adriamycin hydrochloride
  • adriamycin iarc
  • Adriamycin, hydrochloride
  • Adriamycin®
  • Caelyx
  • CAELYX
  • caelyx (pegylated liposomal doxorubicin)
  • Caelyx (Pegylated Lyposomal Doxorubicin)
  • Caelyx®
  • doxil
  • Doxil
  • DOXIL
  • Doxil (Pegylated Liposomal Doxorubicin)
  • Doxil®
  • doxorubicin citrate
  • Doxorubicin citrate

And 66 more, listed on the interactive page.

ATC classification codes
  • L01DB01
CAS registry numbers
  • 25316-40-9
ChEMBL ID
CHEMBL359744
www.ebi.ac.uk
InChIKey
MWWSFMDVAYGXBV-RUELKSSGSA-N
www.ebi.ac.uk
RxNorm IDs (RxCUI)
  • 142433
FDA ingredient codes (UNII)
  • 82F2G7BL4E

  • 443939
  • 657367
  • 11387649

Applicant
PFIZER
Approval date
23 Dec 1987
Application number
NDA050629

Status
lapsed
Status date
22 Sept 2025
Authorisation date
15 Sept 2022
Approved indications
Celdoxome pegylated liposomal is indicated in adults: as monotherapy for patients with metastatic breast cancer, where there is an increased cardiac risk. or 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. Celdoxome 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 standard doxorubicin (or other anthracycline).
Product number
EMEA/H/C/005330
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
www.ema.europa.eu

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

Pharmacology name
doxorubicin
Type
Natural product
Drug name stem
-rubicin

Administration routes

  • Parenteral

  • Action type
    Inhibitor
    Target
    DNA topoisomerase II alpha
    Gene symbol
    DNA topoisomerase II alpha
  • Mechanism
    DNA inhibitor
    Action type
    Inhibitor
    Target
    DNA
  • Mechanism
    DNA topoisomerase II alpha inhibitor
    Action type
    Inhibitor
    Target
    DNA topoisomerase 2-alpha
    Protein identifier
    P11388

Open Targets mechanisms

  • Mechanism
    DNA topoisomerase II alpha inhibitor
    Action type
    Inhibitor
    Target
    DNA topoisomerase 2-alpha

  • Condition
    Leukemia, Biphenotypic, Acute
    Highest recorded phase
    2
    Condition identifier
    EFO:0000094
    Subject identifier
    D015456
  • Condition
    Leukemia, Lymphocytic, Chronic, B-Cell
    Highest recorded phase
    2
    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
    1
    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
    4
    Condition identifier
    EFO:0000183
    Subject identifier
    D006689
  • Condition
    Myelodysplastic Syndromes
    Highest recorded phase
    1
    Condition identifier
    EFO:0000198
    Subject identifier
    D009190
  • Condition
    Neoplasms, Plasma Cell
    Highest recorded phase
    3
    Condition identifier
    EFO:0000200
    Subject identifier
    D054219
  • Condition
    Leukemia, Biphenotypic, Acute
    Highest recorded phase
    2
    Condition identifier
    EFO:0000209
    Subject identifier
    D015456
  • Condition
    Lymphoma, T-Cell, Peripheral
    Highest recorded phase
    2
    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
    Leukemia, Myelomonocytic, Acute
    Highest recorded phase
    4
    Condition identifier
    EFO:0000223
    Subject identifier
    D015479
  • Condition
    Pheochromocytoma
    Highest recorded phase
    3
    Condition identifier
    EFO:0000239
    Subject identifier
    D010673
  • Condition
    Rhabdomyosarcoma, Alveolar
    Highest recorded phase
    2
    Condition identifier
    EFO:0000248
    Subject identifier
    D018232
  • Condition
    Breast Neoplasms
    Highest recorded phase
    4
    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
    4
    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
    Rhabdomyosarcoma, Embryonal
    Highest recorded phase
    2
    Condition identifier
    EFO:0000437
    Subject identifier
    D018233
  • Condition
    Ganglioneuroblastoma
    Highest recorded phase
    3
    Condition identifier
    EFO:0000502
    Subject identifier
    D018305
  • Condition
    Glioblastoma
    Highest recorded phase
    2
    Condition identifier
    EFO:0000519
    Subject identifier
    D005909
  • Condition
    Sarcoma, Kaposi
    Highest recorded phase
    4
    Condition identifier
    EFO:0000558
    Subject identifier
    D012514
  • Condition
    Leiomyosarcoma
    Highest recorded phase
    3
    Condition identifier
    EFO:0000564
    Subject identifier
    D007890
  • Condition
    Leukemia
    Highest recorded phase
    3
    Condition identifier
    EFO:0000565
    Subject identifier
    D007938

And 85 more, listed on the interactive page.

  • Condition identifier
    EFO_0000182
    Highest recorded phase
    3
  • Condition identifier
    EFO_0000183
  • Condition identifier
    EFO_0000200
    Highest recorded phase
    2
  • Condition identifier
    EFO_0000222
    Highest recorded phase
    2
  • Condition identifier
    EFO_0000223
  • Condition identifier
    EFO_0000305
  • Condition identifier
    EFO_0000403
    Highest recorded phase
    3
  • Condition identifier
    EFO_0000558
  • Condition identifier
    EFO_0000565
    Highest recorded phase
    3
  • Condition identifier
    EFO_0000574
    Highest recorded phase
    3
  • Condition identifier
    EFO_0000616
    Highest recorded phase
    3
  • Condition identifier
    EFO_0000621
    Highest recorded phase
    3
  • Condition identifier
    EFO_0000681
    Highest recorded phase
    2
  • Condition identifier
    EFO_0000691
  • Condition identifier
    EFO_0000702
    Highest recorded phase
    1
  • Condition identifier
    EFO_0000765
  • Condition identifier
    EFO_0001075
  • Condition identifier
    EFO_0001378
  • Condition identifier
    EFO_0003144
  • Condition identifier
    EFO_0003820
  • Condition identifier
    EFO_0003869
  • Condition identifier
    EFO_0003893
  • Condition identifier
    EFO_0004251
    Highest recorded phase
    1
  • Condition identifier
    EFO_0005952
  • Condition identifier
    EFO_0006859
    Highest recorded phase
    2

And 149 more, listed on the interactive page.

  • Warning
    Black Box Warning
    Effect
    carcinogenicity
  • Warning
    Black Box Warning
    Effect
    cardiotoxicity
  • Warning
    Black Box Warning
    Effect
    hematological toxicity
  • Warning
    Black Box Warning
    Effect
    hepatotoxicity
  • Warning
    Black Box Warning
    Effect
    musculoskeletal toxicity

  • 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
    571
    Reporting signal score
    1,084.75
  • Event
    anaemia
    Reports
    2,070
    Reporting signal score
    948.68
  • Event
    bone marrow failure
    Reports
    671
    Reporting signal score
    754.653
  • Event
    cardiomyopathy
    Reports
    535
    Reporting signal score
    732.642
  • Event
    cardiotoxicity
    Reports
    710
    Reporting signal score
    1,578.2
  • Event
    diffuse large b-cell lymphoma
    Reports
    309
    Reporting signal score
    571.256
  • Event
    diffuse large b-cell lymphoma recurrent
    Reports
    357
    Reporting signal score
    1,090.49
  • Event
    disease progression
    Reports
    1,449
    Reporting signal score
    1,167.55
  • Event
    ejection fraction decreased
    Reports
    516
    Reporting signal score
    664.034
  • Event
    febrile bone marrow aplasia
    Reports
    379
    Reporting signal score
    772.834
  • Event
    febrile neutropenia
    Reports
    5,214
    Reporting signal score
    11,490
  • Event
    haematotoxicity
    Reports
    599
    Reporting signal score
    1,130.69
  • Event
    injection site pain
    Reports
    5
    Reporting signal score
    576.512
  • Event
    interstitial lung disease
    Reports
    868
    Reporting signal score
    735.319
  • Event
    leukopenia
    Reports
    990
    Reporting signal score
    786.046
  • Event
    malignant neoplasm progression
    Reports
    896
    Reporting signal score
    648.278
  • Event
    mucosal inflammation
    Reports
    1,171
    Reporting signal score
    1,769.72
  • Event
    myelodysplastic syndrome
    Reports
    586
    Reporting signal score
    958.305
  • Event
    neutropenia
    Reports
    3,506
    Reporting signal score
    3,891.51
  • Event
    neutropenic sepsis
    Reports
    347
    Reporting signal score
    605.367
  • Event
    palmar-plantar erythrodysaesthesia syndrome
    Reports
    599
    Reporting signal score
    646.345
  • Event
    pancytopenia
    Reports
    1,098
    Reporting signal score
    1,002.97
  • Event
    pneumocystis jirovecii pneumonia
    Reports
    394
    Reporting signal score
    631.51
  • Event
    pyrexia
    Reports
    2,410
    Reporting signal score
    695.339
  • Event
    second primary malignancy
    Reports
    430
    Reporting signal score
    781.713

And 2 more, listed on the interactive page.

And 568 more, listed on the interactive page.

Dose
50 mg/m2
Route
Intravenous
How often
Every 4 weeks

  • Administer over 60 minutes
  • Do not administer as bolus

Hydrogen bond acceptors
12
Hydrogen bond donors
6
Polar surface area
206.07
Calculated partition coefficient (ALogP)
0
Prodrug
No
Chirality
Single enantiomer
Inorganic
No
Rule-of-five violations
3
Rotatable bonds
5
Heavy atoms
40
Molecular formula
C27H30ClNO11
Monoisotopic mass
579.1507385
Natural product
Yes

  • 0069-0255
  • 0069-0277
  • 0069-0343
  • 0069-0358
  • 0069-1442
  • 0069-1542
  • 0069-3358
  • 0069-4031
  • 0069-4205
  • 0069-5629
  • 0143-9084
  • 0143-9085
  • 0143-9086
  • 0143-9087
  • 0143-9088
  • 0143-9089
  • 0143-9090
  • 0143-9091
  • 0143-9092
  • 0143-9093
  • 0338-0063
  • 0338-0067
  • 0338-0080
  • 0338-0086
  • 0338-9581

And 39 more, listed on the interactive page.

Recorded assays
3,789
Active assays
1,675

  • Confirmatory
  • Other
  • Screening
  • Summary

Distribution coefficient (LogD)

Median
0.07
Mean
0.07
Minimum
0.07
Maximum
0.07
Unit
unitless
Assays
1
Standard deviation
0
Summary method
median
Censored results excluded
0
Other units excluded
0
Unknown units excluded
0

Measurement types

  • LogD

Related records

Trials (1,936)

Approved for (23)

In development for (83)

Other linked conditions (2)

Targets (1)