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An antimetabolite is a chemical with a similar structure to a substance (a metabolite) required for normal biochemical reactions, yet different enough to interfere with the normal functions of cells, including cell division. A metabolite is the product of metabolism. ...
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Function
Cancer treatment Antimetabolites can be used in cancer 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. Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...
Anti-metabolites masquerade as purine (azathioprine, mercaptopurine) or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the S phase (of the cell cycle), stopping normal development and division. Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ...
Azathioprine is a chemotherapy drug, now rarely used for chemotherapy but more for immunosuppression in organ transplantation, autoimmune disease such as rheumatoid arthritis or inflammatory bowel disease such as Crohns disease. ...
Mercaptopurine: chemical structure Mercaptopurine (also called 6-MP or by its brand name Purinethol®) is an immunosuppressive drug used to treat leukemia. ...
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 [1]. It is isomeric with two other forms of diazine. ...
DNA replication. ...
The cell cycle, or cell-division cycle, is the series of events that take place in an eukaryotic cell between its formation and the moment it replicates itself. ...
They also affect RNA synthesis. However, because thymidine is used in DNA but not in RNA (where uracil is used instead), inhibition of thymidine sythesis via thymidylate synthase selectively inhibits DNA synthesis over RNA synthesis. The chemical structure of deoxythymidine Thymidine (more precisely called deoxythymidine can also be labelled deoxyribosylthymine, and thymine deoxyriboside) is a chemical compound, more precisely a pyrimidine deoxynucleoside. ...
Uracil is a pyrimidine which is common and naturally occurring. ...
Thymidylate synthase is the enzyme used to generate thymidine monophosphate (dTMP), which is subsequently phosphorylated to thymidine triphosphate for use in DNA synthesis. ...
Due to their efficiency, these drugs are the most widely used cytostatics. Chemotherapy is the use of chemical substances to treat disease. ...
In the ATC system, they are classified under L01B. The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ...
A section of the Anatomical Therapeutic Chemical Classification System. ...
Antibiotics Antimetabolites may also be antibiotics, such as sulfanilamide drugs, which inhibit dihydrofolate synthesis in bacteria by competing with para-aminobenzoic acid.[1] An antibiotic is a drug that kills or slows the growth of bacteria. ...
Sulfonamides, also known as sulfa drugs, are synthetic antimicrobial agents derived from sulfonic acid. ...
Dihydrofolic acid is a folic acid derivative acted upon by dihydrofolate reductase. ...
Para-Aminobenzoic acid (PABA) is a chemical used in sunscreen that is an essential nutrient for some bacteria. ...
Types Main representatives of these drugs are:
Folic acid Folic acid and folate (the anion form) are forms of the water-soluble Vitamin B9. ...
Methotrexate (rINN) (IPA: ), abbreviated MTX and formerly known as amethopterin, is an antimetabolite drug used in treatment of cancer and autoimmune diseases. ...
Folic acid and folate (the anion form) are forms of the water-soluble Vitamin B9. ...
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Categories: Biochemistry stubs | EC 1. ...
Serine (IPA ), organic compound, one of the 20 amino acids commonly found in animal proteins. ...
Methionine (Met, M. C5H11NO2S) is an essential nonpolar amino acid, and a lipotropic. ...
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Folic acid and folate (the anion form) are forms of the water-soluble Vitamin B9. ...
| Methotrexate Methotrexate, drawn on OpenOffice. ...
Methotrexate (rINN) (IPA: ), abbreviated MTX and formerly known as amethopterin, is an antimetabolite drug used in treatment of cancer and autoimmune diseases. ...
| Pemetrexed Image File history File links This is a lossless scalable vector image. ...
Pemetrexed chemical structure Pemetrexed (brand name Alimta) is a chemotherapy drug. ...
| Raltitrexed Image File history File links Raltitrexed. ...
Raltitrexed (brand name Tomudex®) is a chemotherapy drug manufactured AstraZeneca Company, is an antimetabolite used in chemotherapy. ...
| - Azathioprine is the main immunosuppressive cytotoxic substance. It is widely used in transplantations to control rejection reactions. It is nonenzymatically cleaved to 6-mercaptopurine that acts as a purine analogue and an inhibitor of DNA synthesis. By preventing the clonal expansion of lymphocytes in the induction phase of the immune response, it affects both the cell and the humoral immunity. It also successfully suppresses autoimmunity.
- Mercaptopurine
- Thioguanine is used to treat acute leukemias and induction of remissions in acute granulocytic leukemias
- Fludarabine inhibits function of multiple DNA polymerases, DNA primase, DNA ligase I and is S phase-specific (since these enzymes are highly active during DNA replication).
- Pentostatin and cladribine are adenosine analogs which are primarily used to treat Hairy cell leukemia.
 Purine Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ...
Azathioprine is a chemotherapy drug, now rarely used for chemotherapy but more for immunosuppression in organ transplantation, autoimmune disease such as rheumatoid arthritis or inflammatory bowel disease such as Crohns disease. ...
Mercaptopurine (also called 6-MP or by its brand name Purinethol®) is an immunosuppressive drug used to treat leukemia. ...
Cell-mediated immunity is an immune response that does not involve antibodies but rather involves the activation of macrophages and NK-cells, the production of antigen-specific cytotoxic T-lymphocytes, and the release of various cytokines in response to an antigen. ...
Humoral immunity is the aspect of immunity that is mediated by secreted antibodies, produced in the cells of the B lymphocyte lineage (B cell). ...
Autoimmunity is the failure of an organism to recognize its own constituent parts (down to the sub-molecular levels) as self, which results in an immune response against its own cells and tissues. ...
Mercaptopurine: chemical structure Mercaptopurine (also called 6-MP or by its brand name Purinethol®) is an immunosuppressive drug used to treat leukemia. ...
Tioguanine (INN), formerly Thioguanine (BAN), is a drug that is used in the treatment of cancer. ...
Fludarabine is a chemotherapy drug used in the firstline treatment of chronic lymphocytic leukemia. ...
3D structure of the DNA-binding helix-hairpin-helix motifs in human DNA polymerase beta A DNA polymerase is an enzyme that assists in DNA replication. ...
DNA primase is form of RNA polymerase and a product of the dnaG gene. ...
This article or section does not cite any references or sources. ...
DNA replication. ...
Pentostatin (Deoxycoformycin) is an anticancer chemotherapeutic drug. ...
Cladribine is a drug used to treat hairy cell leukemia (leukemic reticuloendotheliosis). ...
Hairy cell leukemia is a B cell neoplasm. ...
Image File history File links Size of this preview: 657 Ã 599 pixelsFull resolution (1095 Ã 999 pixel, file size: 6 KB, MIME type: image/png) Afterwards please add the following code to : (Please review the discussion here. ...
Purine is a heterocyclic aromatic organic compound, consisting of a pyrimidine ring fused to an imidazole ring. ...
| Mercaptopurine Image File history File links This is a lossless scalable vector image. ...
Mercaptopurine: chemical structure Mercaptopurine (also called 6-MP or by its brand name Purinethol®) is an immunosuppressive drug used to treat leukemia. ...
| Tioguanine Image File history File links No higher resolution available. ...
Tioguanine (INN), formerly Thioguanine (BAN), is a drug that is used in the treatment of cancer. ...
| Fludarabine Image File history File links This is a lossless scalable vector image. ...
Fludarabine is a chemotherapy drug used in the firstline treatment of chronic lymphocytic leukemia. ...
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 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 [1]. It is isomeric with two other forms of diazine. ...
Fluorouracil (5-FU) is a drug that is used in the treatment of cancer. ...
Thymidylate synthase is the enzyme used to generate thymidine monophosphate (dTMP), which is subsequently phosphorylated to thymidine triphosphate for use in DNA synthesis. ...
Floxuridine is an oncology drug that belongs to the class known as antimetabolites. ...
Cytarabine is a shortened form of cytosine arabinoside, a commonly used chemotherapy agent used mainly in the treatment of leukemia and non-Hodgkin lymphoma. ...
Image File history File links No higher resolution available. ...
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 [1]. It is isomeric with two other forms of diazine. ...
| Fluorouracil Image File history File links This is a lossless scalable vector image. ...
Fluorouracil (5-FU) is a drug that is used in the treatment of cancer. ...
| Floxuridine Image File history File links No higher resolution available. ...
Floxuridine is an oncology drug that belongs to the class known as antimetabolites. ...
| Gemcitabine Image File history File links Gemcitabine. ...
Gemcitabine is a nucleoside used as chemotherapy. ...
| See also A base analog is a chemical that can substitute a normal nucleobase in nucleic acids. ...
External links Seal of the University of Nebraska The University of Nebraska is one of two public university systems in the state of Nebraska, USA. The system has four universities and a technical college: University of Nebraska-Lincoln University of Nebraska at Omaha University of Nebraska at Kearney University of Nebraska Medical...
References - ^ "The Organic Chemistry of Drug Design and Drug Action" (2nd edition), R. B. Silverman, 2004.
| Chemotherapeutic agents/Antineoplastic agents (L01) | | Alkylating agents | Nitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan). Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin). Platinum: (Carboplatin, Cisplatin, Oxaliplatin, BBR3464). Busulfan, Dacarbazine, Mechlorethamine, Procarbazine, Temozolomide, ThioTEPA, Uramustine | | Antimetabolites | Folic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine). Pyrimidine:(Capecitabine, Cytarabine, Fluorouracil, Floxuridine, Gemcitabine) | | Spindle poison plant alkaloids | Taxane: (Docetaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine). | | Cytotoxic/antitumor antibiotics | Anthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Valrubicin). Bleomycin, Hydroxyurea, Mitomycin, Actinomycin | | Topoisomerase inhibitors | Camptotheca: (Camptothecin, Topotecan, Irinotecan), Podophyllum:(Etoposide, Teniposide). | | CI monoclonal antibodies | Alemtuzumab, Bevacizumab, Cetuximab, Gemtuzumab, Panitumumab, Rituximab, Tositumomab, Trastuzumab | | Photosensitizers | Aminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin | | Kinase inhibitors | Dasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Nilotinib, Sorafenib, Sunitinib, Vandetanib (ZD6474) | | Other | Alitretinoin, Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase, Bexarotene, Bortezomib, Denileukin diftitox, Estramustine, Hydroxycarbamide, Masoprocol, Mitotane, Pegaspargase, Tretinoin | |