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Antimetabolite

 

 
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Antimetabolite
 
 
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An antimetabolite is a chemical that inhibits the use of a metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
, which is another chemical that is part of normal metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolate
Antifolate

Antifolates are drugs which impair the function of folic acids. Many are used in cancer chemotherapy, some are used as antibiotics or antiprotozoal agents....
s that interfere with the use of folic acid
Folic acid

Folic acid and Folate are forms of the water-soluble B vitamins. Vitamin B9 is essential to numerous bodily functions ranging from nucleotide synthesis to the remethylation of homocysteine....
.






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Methotrexate and Folic Acid Compared
An antimetabolite is a chemical that inhibits the use of a metabolite
Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
, which is another chemical that is part of normal metabolism
Metabolism

Metabolism is the set of chemical reactions that occur in living organisms in order to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments....
. Such substances are often similar in structure to the metabolite that they interfere with, such as the antifolate
Antifolate

Antifolates are drugs which impair the function of folic acids. Many are used in cancer chemotherapy, some are used as antibiotics or antiprotozoal agents....
s that interfere with the use of folic acid
Folic acid

Folic acid and Folate are forms of the water-soluble B vitamins. Vitamin B9 is essential to numerous bodily functions ranging from nucleotide synthesis to the remethylation of homocysteine....
. The presence of antimetabolites can have toxic effects on cells, such as halting cell growth
Cell growth

The term cell growth is used in the contexts of Cell development and cell division . When used in the context of cell division, it refers to growth of cell populations, where one cell grows and divides to produce two "daughter cells"....
 and cell division
Cell division

Cell division is a process by which a cell , called the parent cell, divides into two or more cells, called daughter cells. Cell division is usually a small segment of a larger cell cycle....
, so these compounds are used as 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....
 for cancer.

Function


Cancer treatment

Antimetabolites can be used in cancer
Cancer

Cancer is a class of diseases in which a group of cell display uncontrolled growth , invasion , and sometimes metastasis . These three malignant properties of cancers differentiate them from benign tumors, which are self-limited, do not invade or metastasize....
 treatment, as they interfere with DNA production and therefore cell division and the growth of tumors. Because cancer cells spend more time dividing than other cells, inhibiting cell division harms tumor cells more than other cells.

Anti-metabolites masquerade as a purine
Purine

Purine is a heterocyclic compound aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. Purines, including substituted purines and their tautomers, are the most widely distributed kind of nitrogen-containing heterocycle in nature....
 (azathioprine
Azathioprine

Azathioprine is an immunosuppressant used in organ transplantation, autoimmune disease such as rheumatoid arthritis and pemphigus or inflammatory bowel disease such as Crohn's disease and ulcerative colitis as well as multiple sclerosis....
, mercaptopurine
Mercaptopurine

Mercaptopurine is an immunosuppressive drug.It is a thiopurine....
) or a pyrimidine
Pyrimidine

Pyrimidine is a heterocyclic aromatic organic compound similar to benzene and pyridine, containing two nitrogen atoms at positions 1 and 3 of the six-member ring....
 - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the S phase
S phase

The S phase, short for synthesis phase, is a period in the cell cycle during interphase, between G1 phase and the G2 phase. Following G1, the cell enters the S stage, when DNA DNA synthesis or DNA replication occurs....
 (of the cell cycle
Cell cycle

The cell cycle, or cell-division cycle, is the series of events that take place in a cell leading to its division and duplication . In cells without a nucleus , the cell cycle occurs via a process termed binary fission....
), stopping normal development and division.

They also affect RNA synthesis. However, because thymidine
Thymidine

Thymidine is a chemical Chemical compound, more precisely a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine in double-stranded DNA....
 is used in DNA but not in RNA (where uracil
Uracil

Uracil is a common and naturally occurring pyrimidine derivative. Originally discovered in 1900, it was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring, sperm, and wheat germ....
 is used instead), inhibition of thymidine synthesis via thymidylate synthase
Thymidylate synthase

Thymidylate synthetase is the enzyme used to generate thymidine monophosphate , which is subsequently phosphorylated to thymidine triphosphate for use in DNA synthesis and repair....
 selectively inhibits DNA synthesis over RNA synthesis.

Due to their efficiency, these drugs are the most widely used cytostatics.

In the ATC system
Anatomical Therapeutic Chemical Classification System

The Anatomical Therapeutic Chemical Classification System is used for the taxonomic classification of Medications. It is controlled by the World Health Organization Collaborating Centre for Drug Statistics Methodology, and was first published in 1976....
, they are classified under L01B
ATC code L01

L01 Antineoplastic agents is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System.It is part of the anatomical group ATC code L....
.

Antibiotics

Antimetabolites may also be antibiotics, such as sulfanilamide drugs, which inhibit dihydrofolate synthesis in bacteria by competing with para-aminobenzoic acid.

Types

Main representatives of these drugs are:

  • purine analogue
    Purine analogue

    Purine analogues are antimetabolites which mimic the structure of metabolic purines....
    s


  • pyrimidine analogue
    Pyrimidine analogue

    Pyrimidine analogues are antimetabolites which mimic the structure of metabolic pyrimidines....
    s


  • antifolate
    Antifolate

    Antifolates are drugs which impair the function of folic acids. Many are used in cancer chemotherapy, some are used as antibiotics or antiprotozoal agents....
    s


See also

  • Base analog
    Base analog

    A base analog is a chemical that can substitute for a normal nucleobase in nucleic acids.A common example would be 5-bromouracil , the abnormal base found in the mutagenic nucleotide analog BrdU....
  • Nucleoside analogues
    Nucleoside analogues

    Nucleoside analogues are a range of antiviral products used to prevent viral replication in infected cells. The most commonly used is Aciclovir....


External links

  • at University of Nebraska