All Topics  
Anthracycline

 

 
   Email Print
   Bookmark   Link
 

 

Anthracycline
 
 
  Topics Anthracycline Topic Home

Anthracyclines (or anthracycline antibiotics) are a class of drugs used in cancer chemotherapy
Chemotherapy

Chemotherapy, in its most general sense, refers to treatment of disease by chemicals that kill cells, specifically those of micro-organisms or cancer....
 derived from Streptomyces
Streptomyces

Streptomyces is the largest genus of Actinobacteria and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described....
 bacteria (more specifically, Streptomyces peucetius var. caesius).

These compounds are used to treat a wide range of cancers, including leukemia
Leukemia

Leukemia is a cancer of the blood or bone marrow and is characterized by an abnormal proliferation of blood Cell , usually white blood cells ....
s, lymphoma
Lymphoma

Lymphoma is a type of cancer that originates in lymphocytes of the immune system. They often originate in lymph nodes, presenting as an enlargement of the node ....
s, and breast
Breast cancer

Breast cancer is a cancer that starts in the Cell of the breast in women and men. Worldwide, breast cancer is the second most common type of cancer after lung cancer and the fifth most common cause of cancer death....
, uterine
Uterine cancer

The term uterine cancer may refer to any of several different types of cancer which occur in the uterus, namely:*Uterine sarcomas: sarcomas of the myometrium, or muscular layer of the uterus, are most commonly leiomyosarcomas....
, ovarian
Ovarian cancer

Ovarian cancer is a malignant tumor arising from an ovary. Although ovarian cancer is known to occur in many species, the majority of the medical literature and the focus of this article is on ovarian cancer in humans....
, and lung cancer
Lung cancer

Lung cancer is a disease of uncontrolled cell growth in tissue of the lung. This growth may lead to metastasis, which is the invasion of adjacent tissue and infiltration beyond the lungs....
s.

The anthracyclines are some of the most effective anticancer treatments ever developed, and are effective against more types of cancer than any other class of chemotherapy agents.






Discussion
Ask a question about 'Anthracycline'
Start a new discussion about 'Anthracycline'
Answer questions from other users
Full Discussion Forum



Encyclopedia


Anthracyclines (or anthracycline antibiotics) are a class of drugs used in cancer chemotherapy
Chemotherapy

Chemotherapy, in its most general sense, refers to treatment of disease by chemicals that kill cells, specifically those of micro-organisms or cancer....
 derived from Streptomyces
Streptomyces

Streptomyces is the largest genus of Actinobacteria and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described....
 bacteria (more specifically, Streptomyces peucetius var. caesius).

These compounds are used to treat a wide range of cancers, including leukemia
Leukemia

Leukemia is a cancer of the blood or bone marrow and is characterized by an abnormal proliferation of blood Cell , usually white blood cells ....
s, lymphoma
Lymphoma

Lymphoma is a type of cancer that originates in lymphocytes of the immune system. They often originate in lymph nodes, presenting as an enlargement of the node ....
s, and breast
Breast cancer

Breast cancer is a cancer that starts in the Cell of the breast in women and men. Worldwide, breast cancer is the second most common type of cancer after lung cancer and the fifth most common cause of cancer death....
, uterine
Uterine cancer

The term uterine cancer may refer to any of several different types of cancer which occur in the uterus, namely:*Uterine sarcomas: sarcomas of the myometrium, or muscular layer of the uterus, are most commonly leiomyosarcomas....
, ovarian
Ovarian cancer

Ovarian cancer is a malignant tumor arising from an ovary. Although ovarian cancer is known to occur in many species, the majority of the medical literature and the focus of this article is on ovarian cancer in humans....
, and lung cancer
Lung cancer

Lung cancer is a disease of uncontrolled cell growth in tissue of the lung. This growth may lead to metastasis, which is the invasion of adjacent tissue and infiltration beyond the lungs....
s.

The anthracyclines are some of the most effective anticancer treatments ever developed, and are effective against more types of cancer than any other class of chemotherapy agents. Their main adverse effects
Adverse drug reaction

An adverse drug reaction or adverse drug event is an expression that describes the unwanted, negative consequences associated with the use of given medications....
 are heart damage (cardiotoxicity
Cardiotoxicity

Cardiotoxicity is the occurrence of heart muscle damage. The heart becomes weaker and is not as efficient in pumping and therefore circulating blood....
), which considerably limits their usefulness, and vomiting.

The first anthracycline discovered was daunorubicin
Daunorubicin

Daunorubicin or daunomycin is chemotherapy of the anthracycline family that is given as a treatment for some types of cancer. It is most commonly used to treat specific types of leukaemia ....
 (trade name Daunomycin), which is produced naturally by Streptomyces peucetius
Streptomyces

Streptomyces is the largest genus of Actinobacteria and the type genus of the family Streptomycetaceae. Over 500 species of Streptomyces bacteria have been described....
, a species of actinobacteria
Actinobacteria

Actinobacteria or actinomycetes are a group of Gram-positive bacterium with high G+C ratio. ...
. Doxorubicin
Doxorubicin

Doxorubicin is a pharmaceutical used in cancer chemotherapy. It is an anthracycline antibiotic, closely related to the natural product daunorubicin, and like all anthracyclines it intercalation DNA....
 (Adriamycin) was developed shortly after, and many other related compounds
Analog (chemistry)

In chemistry, analogs or analogues are chemical compound in which one or more individual atoms have been replaced, either with a different atom, or with a different functional group....
  have followed, although few are in clinical use.

Examples

Available agents include:

  • Daunorubicin
    Daunorubicin

    Daunorubicin or daunomycin is chemotherapy of the anthracycline family that is given as a treatment for some types of cancer. It is most commonly used to treat specific types of leukaemia ....
     (Daunomycin)
  • Daunorubicin
    Daunorubicin

    Daunorubicin or daunomycin is chemotherapy of the anthracycline family that is given as a treatment for some types of cancer. It is most commonly used to treat specific types of leukaemia ....
     (liposomal
    Liposome

    A liposome is a tiny bubble , made out of the same material as a biological membrane. Liposomes can be filled with drugs, and used to deliver drugs for cancer and other diseases....
    )
  • Doxorubicin
    Doxorubicin

    Doxorubicin is a pharmaceutical used in cancer chemotherapy. It is an anthracycline antibiotic, closely related to the natural product daunorubicin, and like all anthracyclines it intercalation DNA....
     (Adriamycin)
  • Doxorubicin
    Doxorubicin

    Doxorubicin is a pharmaceutical used in cancer chemotherapy. It is an anthracycline antibiotic, closely related to the natural product daunorubicin, and like all anthracyclines it intercalation DNA....
     (liposomal)
  • Epirubicin
    Epirubicin

    Epirubicin is an anthracycline medication used for chemotherapy. It is marketed by Pfizer under the trade name Ellence in the US and Pharmorubicin or Epirubicin "Ebewe" elsewhere....
  • Idarubicin
    Idarubicin

    Idarubicin or 4-demethoxydaunorubicin is an anthracycline antileukemic drug that is currently combined with cytosine arabinoside as a first line treatment of acute myeloid leukemia....
  • Valrubicin
    Valrubicin

    Valrubicin is a chemotherapy medication used to treat bladder cancer. Valrubicin is a semisynthetic analog of the anthracycline doxorubicin, and is administered by infusion directly into the Urinary bladder....
    , used only to treat bladder cancer
    Bladder cancer

    Bladder cancer refers to any of several types of malignant growths of the urinary bladder. It is a disease in which abnormal cells multiply without control in the bladder....


Since they are antibiotics, anthracyclines can kill or inhibit the growth of bacteria, but because they are so toxic to humans, they are never used to treat infections.

Mechanism of action


Anthracycline has three mechanisms of action:

  1. Inhibits DNA
    DNA replication

    DNA replication, the basis for heredity, is a fundamental process occurring in all living organisms to copy their DNA. This process is "semiconservative replication" in that each strand of the original double-stranded DNA molecule serves as template for the reproduction of the complementary strand....
     and RNA synthesis by intercalating
    Intercalation (chemistry)

    In chemistry, intercalation is the reversible inclusion of a molecule between two other molecules . Examples include DNA intercalation and in graphite intercalation compounds....
     between base pairs of the DNA/RNA strand, thus preventing the replication of rapidly-growing cancer cells.
  2. Inhibits topoiosomerase II
    Type II topoisomerase

    Type II topoisomerases cut both strands of the DNA helix simultaneously in order to change the linking number of the molecule....
     enzyme, preventing the relaxing of supercoiled DNA
    DNA supercoil

    In a "relaxed" double-helical segment of DNA, the two strands twist around the helical axis once every 10.4-10.5 base pairs of DNA sequence. Adding or subtracting twists, as some enzymes can do, imposes strain....
     and thus blocking DNA transcription
    Transcription

    Transcription may refer to:*Transcription , the conversion of spoken words into written language. Also the conversion of handwriting, or a photograph of text into pure text...
     and replication
    DNA replication

    DNA replication, the basis for heredity, is a fundamental process occurring in all living organisms to copy their DNA. This process is "semiconservative replication" in that each strand of the original double-stranded DNA molecule serves as template for the reproduction of the complementary strand....
    .
  3. Creates iron-mediated free oxygen radicals that damage the DNA and cell membranes.


Cardiotoxicity

As well as many of the expected adverse reactions of chemotherapeutic agents, anthracyclines are notorious for causing cardiotoxicity. This cardiotoxicity may be caused by many factors, which may include interference with the ryanodine receptor
Ryanodine receptor

Ryanodine receptors form a class of intracellular calcium channels in various forms of excitable animal tissue like muscles and neurons. It is the major cellular mediator of calcium-induced calcium release in animal cell s....
s of the sarcoplasmic reticulum in the heart muscle cells, free radical formation in the heart or from buildup of metabolic products of the anthracycline in the heart. The cardiotoxicity often presents as EKG
Electrocardiogram

An electrocardiogram is a recording of the electricity activity of the heart over time produced by an electrocardiograph, usually in a Non-invasive recording via skin electrodes....
 changes and arrhythmias, or as a cardiomyopathy
Cardiomyopathy

Cardiomyopathy, which literally means "heart muscle disease," is the deterioration of the function of the myocardium for any reason. People with cardiomyopathy are often at risk of arrhythmia or sudden cardiac death or both....
 leading to congestive heart failure
Congestive heart failure

Heart failure is a condition in which a problem with the structure or function of the heart impairs its ability to supply sufficient blood flow to meet the body's needs....
 (sometimes presenting many years after treatment). This cardiotoxicity is related to a patient's cumulative lifetime dose. A patient's lifetime dose is calculated during treatment, and anthracycline treatment is usually stopped (or at least re-evaluated by the oncologist) upon reaching the maximum cumulative dose of the particular anthracycline.

There exists evidence that the affect of cardiotoxicity increases in long term survivors, from 2% after 2 years to 5% after 15 years.

Dexrazoxane
Dexrazoxane

Dexrazoxane hydrochloride is a medication....
 is a cardioprotectant that is sometimes used to reduce the risk of cardiotoxicity; it has been found to reduce the risk of anthracycline cardiotoxicity by about two thirds, without affecting response to chemotherapy or overall survival. The liposomal formulations of daunorubicin and doxorubicin appear to be somewhat less toxic to cardiac tissue than the non-liposomal form.

See also

  • Anthracenedione
    Anthracenedione

    File:Mitoxantrone skeletal.svgFile:Pixantrone.svgThe anthracenediones are antineoplastics used in the treatment of cancer. They are sometimes grouped with the anthracyclines....