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Encyclopedia > Cytarabine
Cytarabine
Systematic (IUPAC) name
4-amino-1-[(2R,3S,4R,5R)-3,4-dihydroxy-5- (hydroxymethyl)oxolan-2-yl] pyrimidin-2-one
Identifiers
CAS number 147-94-4
ATC code L01BC01
PubChem 6253
DrugBank APRD00499
Chemical data
Formula C9H13N3O5 
Mol. mass 243.217 g/mol
Pharmacokinetic data
Bioavailability Orally, less than 20% of a dose of cytarabine is absorbed from the gastrointestinal tract and is ineffective by this route. Subcutaneously or intramuscularly, tritium labelled cytarabine produces peak plasma concentrations of radioactivity within 20 to 60 minutes which are considerably lower than those attained after intravenous administration. Continuous intravenous infusions produce relatively constant plasma levels in 8 to 24 hours.
Protein binding 13%
Metabolism Liver
Half life Intravenous doses of cytarabine exhibit a biphasic elimination, with an initial distribution half-life of about ten minutes during which time a major portion of the drug is metabolised in the liver to the inactive metabolite uracil arabinoside. The secondary elimination half-life is longer, approximately one to three hours. Metabolism also occurs in the kidneys, gastrointestinal mucosa, granulocytes and other tissues.
Excretion Cytarabine is mainly excreted via the kidney with 70 to 80% of a dose administered by any route appearing in the urine within 24 hours; approximately 90% as the metabolite and 10% as unchanged drug
Therapeutic considerations
Pregnancy cat.

D (USA); D (Aus) Image File history File links Cytarabine. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series Nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Atomic mass 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Many drugs are bound to Blood plasma proteins. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status
Routes Injectable (intravenous injection or infusion, or subcutaneously)

Cytarabine is a shortened form of cytosine arabinoside, a commonly used chemotherapy agent used mainly in the treatment of leukemia and non-Hodgkin lymphoma. It is also known as Ara-C. The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Chemotherapy is the use of chemical substances to treat disease. ... Leukemia or leukaemia (see spelling differences) is a cancer of the blood or bone marrow and is characterized by an abnormal proliferation (production by multiplication) of blood cells, usually white blood cells (leukocytes). ... Non-Hodgkin lymphoma is a cancer arising from lymphocytes, a type of white blood cells. ...

Contents

History

Cytarabine was discovered in Europe in the 1960s. It gained FDA approval in June 1969 and was initially marketed in the US by Upjohn as Cytosar-U. The Upjohn Company was a pharmaceutical manufacturing firm founded in 1886 by Dr. William E. Upjohn in Kalamazoo, Michigan. ...


Mechanism

Cytosine arabinoside is an antimetabolic agent with the chemical name of 1β-arabinofuranosylcytosine. Its mode of action is due to its rapid conversion into cytosine arabinoside triphosphosphate, which damages DNA when the cell cycle holds in the S phase (synthesis of DNA). Rapidly dividing cells, which require DNA replication for mitosis, are therefore most affected. Cytosine arabinoside also inhibits both DNA and RNA polymerases and nucleotide reductase enzyme needed for the DNA synthesis. Cytarabine is rapidly deaminated in the body into the inactive uracil derivative form and therefore, it is often given by continuous intravenous infusion. An antimetabolite is a chemical with a similar structural to a substance (a metabolite) required for normal biochemical reactions, yet different enough to interfere with the normal functions of cells, including cell division. ... The cell cycle, or cell-division cycle (CDC), is the series of events in a eukaryotic cell between one cell division and the next. ... DNA replication. ... Mitosis divides genetic information during cell division. ... The structure of part of a DNA double helix Deoxyribonucleic acid (DNA) is a nucleic acid that contains the genetic instructions for the development and function of living organisms. ... This article or section does not adequately cite its references or sources. ... ITaq DNA polymerase A polymerase (EC 2. ... A nucleotide is a chemical compound that consists of a heterocyclic base, a sugar, and one or more phosphate groups. ... Uracil is a pyrimidine which is common and naturally occurring. ...


Clinical uses

Cytarabine is mainly used in the treatment of lymphomas and also for acute myelogenous leukemia where it is the backbone of induction chemotherapy. Cytarabine possessess also an antiviral activity, and it has been used for the treatment of generalised herpes infection. However, cytarabine is not very selective and causes bone marrow suppression and other severe side effects, so it is used mainly for the chemotherapy of hematologic cancers. Acute myelogenous leukemia (AML), also known as acute myeloid leukemia, is a cancer of the myeloid line of blood cells. ... Antiviral drugs are a class of medication used specifically for treating viral infections. ... Genera Subfamily Alphaherpesvirinae    Simplexvirus    Varicellovirus    Mardivirus    Iltovirus Subfamily Betaherpesvirinae    Cytomegalovirus    Muromegalovirus    Roseolovirus Subfamily Gammaherpesvirinae    Lymphocryptovirus    Rhadinovirus Unassigned    Ictalurivirus The Herpesviridae are a family of DNA viruses that cause diseases in humans and animals. ... Bone marrow suppression is a serious side effect of chemotherapy and certain drugs affecting the immune system such as azathioprine. ...


One of the unique toxicities of cytarabine is cerebellar toxicity when given in high doses. Figure 1a: A human brain, with the cerebellum in purple. ...


Cytarabine is also used in the study of the nervous system to control the proliferation of glial cells in cultures, the amount of glial cells having an important impact on neurons. The Human Nervous System The nervous system of an animal coordinates the activity of the muscles, monitors the organs, constructs and also stops input from the senses, and initiates actions. ... Neuroglia cells of the brain shown by Golgis method. ... Drawing by Santiago Ramón y Cajal of neurons in the pigeon cerebellum. ...


Brand names

  • Cytosar-U®
  • Tarabine® PFS
  • Depocyt® (longer-lasting liposomal formulation)

A liposome is a spherical vesicle with a membrane composed of a phospholipid and cholesterol bilayer. ...

External links

  • MedlinePlus page on cytarabine
  • ADAP drugs page on cytarabine
  • BC Cancer network page on cytarabine
  • Chembank entry
  • Sea to Ara C An essay on the history of cytarabine.

References

  • Hobbs J.B. in Comprehensive Medicinal Chemistry Vol. 2: (ed. Sammes, Peter G.) Pergamon Press, 1990
  • Männistö P.T., Tuominen R.K. in Farmakologia ja Toksikologia, 5th edition: (ed. Koulu, Tuomisto, Paasonen) Medicina, 1996
  • Rang H.P., Dale M.M., Ritter J.M.: Pharmacology, 3rd edition. Pearson Professional Ltd, 1995.

  Results from FactBites:
 
MedlinePlus Drug Information: Cytarabine (476 words)
Cytarabine can cause a decrease in the number of blood cells in your bone marrow.
Cytarabine belongs to a group of drugs known as antimetabolites.
Cytarabine is also used to treat non-Hodgkin's lymphoma.
Cytarabine - definition of Cytarabine in Encyclopedia (252 words)
Cytarabine is a shortened form of cytosine arabinoside, a commonly used chemotherapy agent used mainly in the treatment of leukemia and non-Hodgkin lymphoma.
Cytarabine is rapidly deaminated in the body into the inactive uracil derivative form and therefore, it is often given by continuous intravenous infusion.
Cytarabine is also used in the study of the nervous system to control the proliferation of glial cells in cultures, the amount of glial cells having an important impact on neurons.
  More results at FactBites »

 
 

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