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Anthracycline

Doxorubicin

An anthracycline for breast cancer, leukemias, lymphomas and sarcomas whose heart damage rises with the cumulative dose.

Drug card

How it works
Intercalating into DNA and trapping topoisomerase II so DNA breaks stay open
Used for
  • Breast cancer, including after surgery
  • Acute lymphoblastic and myeloblastic leukemia
  • Hodgkin and non-Hodgkin lymphoma
  • Soft tissue and bone sarcomas
Known for
  • Cardiomyopathy and heart failure, dose-related
  • Red urine for a day or two after a dose
  • Severe tissue necrosis if it leaks from the vein
Its name
-rubicin means an anthracycline anticancer antibiotic

Study it as a flashcard, and it comes back before you forget it.

Mechanism of action

How does doxorubicin work?

Made by Streptomyces peucetius, it intercalates between DNA base pairs and forms cleavable complexes with topoisomerase II, so DNA can be neither copied nor repaired, and it also produces oxygen free radicals. CYP3A4, CYP2D6 and P-glycoprotein govern its levels, and paclitaxel given first raises them.

Uses

What is doxorubicin used for?

  • Breast cancer, including after surgery
  • Acute lymphoblastic and myeloblastic leukemia
  • Hodgkin and non-Hodgkin lymphoma
  • Soft tissue and bone sarcomas
  • Ovarian cancer
  • Lung cancer

Side effects

Side effects of doxorubicin

  • Cardiomyopathy and heart failure, dose-relatedKnown forSerious
  • Red urine for a day or two after a doseKnown for
  • Severe tissue necrosis if it leaks from the veinKnown forSerious
  • ArrhythmiasSerious
  • Bone marrow suppression, mainly neutropeniaSerious
  • Hair loss, often total
  • Nausea and vomiting
  • Mucositis and mouth sores
  • Secondary AML and myelodysplasiaSerious
  • Infertility and early menopauseSerious
  • Hand-foot syndrome and darkened skin and nails
  • Tumor lysis syndrome with high uric acidSerious

Known for marks what an exam expects you to know it for.

Watch for

Cautions and what sets it apart

  • Contraindicated with severe myocardial insufficiency, a heart attack in the past 4 to 6 weeks, severe liver impairment or severe myelosuppression.
  • Check LVEF before, regularly during and after treatment; the heart risk grows with the total lifetime dose.
  • Avoid with trastuzumab, and for up to 7 months after it, because together they raise the risk of cardiac dysfunction.
  • Avoid strong CYP3A4, CYP2D6 or P-gp inhibitors and inducers; give doxorubicin before paclitaxel, not after.

Good to know: A liposomal form, which spreads differently in the body and causes more hand-foot syndrome, is used for ovarian cancer, Kaposi sarcoma and myeloma.

Remember it

A way to remember it

Red urine, red alert for the heart.

Doxorubicin colors the urine red for a day or two, which is harmless, while its main dose-limiting danger is cardiomyopathy that grows with the total lifetime dose.

Written for biofideX

Its name

  • -rubicin means anthracycline anticancer antibiotic

    Doxorubicin, daunorubicin, epirubicin and idarubicin are anthracyclines. Doxorubicin comes from Streptomyces bacteria; its key toxicity is heart damage that rises with the total dose.

  • Every drug name stem

Its class

Anthracyclines

Anthracyclines are antitumor antibiotics made by Streptomyces bacteria. They slip between DNA base pairs (intercalation), blocking DNA and RNA polymerases, and they trap topoisomerase II on DNA after it has cut both strands, so the breaks are never resealed. They also generate oxygen free radicals that damage cell membranes.

Easily mixed up with topoisomerase II inhibitors and alkylating agents.

Sources

Checked against

Written for biofideX in plain words, after checking these references:

For learning pharmacology, not for treatment decisions: no doses are given, and a prescriber, pharmacist or the product's own label is the word on any one patient. Spotted a mistake? Tell us and we'll correct it.

Practice it

Cancer chemotherapy

Doxorubicin is one of 9 drugs practiced together here: their classes, how they work, what they treat and what they're known for.

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