Structure via PubChem · Public domain (PubChem)
doxorubicin
Sign in to saveAlso known as 14-hydroxydaunorubicine, 14-hydroxydaunomycin, (1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside, (8S-cis)-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-5,12-naphthacenedione, hydroxydaunorubicin, adriamycin
Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used together with other chemotherapy agents. Doxorubicin is given by injection into a vein.
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 458446335
- Drug.image
- Doxorubicin.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Doxorubicin ball-and-stick model from xtal 2018.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Adriamycin, Caelyx, Myocet, others
- Drug.MedlinePlus
- a682221
- Drug.licence_EU
- yes
- Drug.DailyMedID
- Doxorubicin
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- intravenous, intravesical
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- DB01
- Drug.biosimilars
- Zolsketil pegylated liposomal, Celdoxome pegylated liposomal
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C27H29NO11
- Molecular weight
- 543.5 g/mol
- 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
- 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
- InChIKey
- AOJJSUZBOXZQNB-TZSSRYMLSA-N
- XLogP
- 1.3
- Polar surface area
- 206 Ų
- H-bond donors
- 6
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
94,892 papers- Doxorubicin alone versus doxorubicin with trabectedin followed by trabectedin alone as first-line therapy for metastatic or unresectable leiomyosarcoma (LMS-04): a randomised, multicentre, open-label phase 3 trial.The Lancet. Oncology · 2022
- An overview of doxorubicin formulations in cancer therapy.Journal of cancer research and therapeutics · 2014
- A comprehensive review on doxorubicin: mechanisms, toxicity, clinical trials, combination therapies and nanoformulations in breast cancer.Drug delivery and translational research · 2025
- Liposomal doxorubicin.Journal of drug targeting · 1996
- Doxorubicin Action on Mitochondria: Relevance to Osteosarcoma Therapy?Current drug targets · 2018
via PubMed
Wikidata facts
- Subclass of
- anthracycline antibiotic
- Mass
- 543.174
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₇H₂₉NO₁₁
- isomeric SMILES
- C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
- canonical SMILES
- CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
- World Health Organisation international non-proprietary name
- doxorubicin
- Commons category
- Doxorubicin
- subject has role
- anthracycline antibiotic
- stylized name
- DOXOrubicin
via Wikidata · CC0
~17 min read
Encyclopedic overview
18 sectionsContents
- Medical uses
- Side effects
- Cardiotoxicity
- Other
- Liposomal formulations
- Biosynthesis
- Mechanism of action
- History
- Society and culture
- Legal status
- Names
- Formulations
- Popular culture
- Research
- Antimalarial activity
- Fluorescence
- References
- External links
Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used together with other chemotherapy agents. Doxorubicin is given by injection into a vein.
Common side effects include hair loss, bone marrow suppression, vomiting, rash, and inflammation of the mouth. Other serious side effects may include allergic reactions such as anaphylaxis, heart damage, tissue damage at the site of injection, radiation recall, and treatment-related leukemia. People often experience red discoloration of the urine for a few days. Doxorubicin is in the anthracycline and antitumor antibiotic family of medications. It works in part by interfering with the function of DNA.
Excerpted from Wikipedia’s “doxorubicin” article, available under the CC BY-SA 4.0 licence.