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Nitrosourea
Nitrosourea is both the name of a molecule, and a class of compounds that include a nitroso (R-NO) group and a urea. Examples Examples include: * Arabinopyranosyl-''N''-methyl-''N''-nitrosourea (Aranose) * Carmustine (BCNU, BiCNU) * Chlorozotocin * Ethylnitrosourea (ENU) * Fotemustine * Lomustine (CCNU) * Nimustine * ''N''-Nitroso-''N''-methylurea (NMU) * Ranimustine (MCNU) * Semustine * Streptozocin (Streptozotocin) Nitrosourea compounds are DNA alkylating agents and are often used in chemotherapy. They are lipophilic and thus can cross the blood–brain barrier, making them useful in the treatment of brain tumors such as glioblastoma multiforme. File:Aranose (Haworth).svg, Arabinopyranosyl-''N''-methyl-''N''-nitrosourea File:Carmustine.svg, Carmustine File:Chlorozotocin (Haworth).svg, Chlorozotocin File:ENU.svg, Ethylnitrosourea File:Fotemustine.svg, Fotemustine File:Lomustine.svg, Lomustine File:N-Nitroso-N-methylurea.svg, ''N''-Nitroso-''N''-methylurea Fil ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Semustine
Semustine (1-(2-chloroethyl)-3-(''trans''-4-methylcyclohexyl)-1-nitrosourea, MeCCNU) is an alkylating nitrosourea compound used in chemotherapy treatment of various types of tumours. Due to its lipophilic property, semustine can cross the blood-brain barrier for the chemotherapy of brain tumours, where it interferes with DNA replication in the rapidly-dividing tumour cells. Semustine, just as lomustine, is administered orally. Evidence has been found that treatment with semustine can cause acute leukaemia as a delayed effect in very rare cases. Structure and reactivity Semustine (Me-CCNU) is an organochlorine compound that is urea in which the two hydrogens on one of the amino groups are replaced by nitroso and 2-chloroetyl groups and one hydrogen from the other amino group is replaced by a 4-methylcyclohexcyl group. Semustine is also known as a 4-methyl derivative of lomustine. Synthesis The synthesis of semustine originates from a systematic synthesis scheme revolving a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ranimustine
Ranimustine ( INN, marketed under the tradename Cymerin; also known as MCNU) is a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera. It has never been filed for FDA evaluation in the United States, where it is not marketed. Synthesis : Ranimustine is made by reacting the primary amine of a pyranose In organic chemistry, pyranose is a collective term for saccharides that have a chemical structure that includes a six-membered ring consisting of five carbon atoms and one oxygen atom (a heterocycle). There may be other carbons external to the ... sugar (2) with ''o''-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (1) to form the nitrosourea group. References External links *Cymerin サイメリン(PDF) Mitsubishi Tanabe Pharma. October 2007. Alkylating antineoplastic agents Nitrosamines Nitrosoureas Ureas Chloroethyl compounds {{antineoplastic-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Arabinopyranosyl-N-methyl-N-nitrosourea
Arabinopyranosyl-''N''-methyl-''N''-nitrosourea, also known as Aranose (Араноза) is a cytostatic cancer, anticancer chemotherapy (oncology), chemotherapeutic drug of an alkylating antineoplastic agent, alkylating type. Chemically it is a nitrosourea derivative. It was developed in the Soviet Union in the 1970s. It was claimed by its developers that its advantages over other nitrosoureas are a relatively low hematological toxicity (compared to other nitrosoureas available at that time) and a wider therapeutic index, which allows for its outpatient administration. History It was first synthesized in late 1970s in the Laboratory of Organic Synthesis of Soviet Cancer Research Institute (which belonged to Academy of Medical Sciences of the USSR). Its first clinical trials in USSR were conducted in the late 1980s. Those trials confirmed its potential clinical efficacy in melanoma and better relative safety & improved tolerability over other nitrosourea antineoplastic compounds ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carmustine
Carmustine, sold under the brand name BiCNU among others, is a medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro- nitrosourea compound used as an alkylating agent. Description Carmustine is an orange-yellow solid medication used mainly for chemotherapy. It is a nitrogen mustard β-chloro- nitrosourea compound. Mechanism of action As an alkylating agent, carmustine can form interstrand crosslinks in DNA, which prevents DNA replication and DNA transcription. Uses Carmustine is used as an alkylating agent to treat several types of brain cancer including glioma, glioblastoma multiforme, medulloblastoma and astrocytoma, multiple myeloma, and lymphoma ( Hodgkin's and non-Hodgkin). Carmustine is sometimes used in conjunction with alkyl guanine transferase (AGT) inhibitors, such as ''O''6-benzylguanine. The AGT-inhibitors increase the efficacy of carmustine by inhibiting the direct reversal pathway of DNA repair, which will prevent formation of the inters ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chlorozotocin
Chlorozotocin is a nitrosourea. It is used for cancer therapy. The International Agency for Research on Cancer concluded it was "probably carcinogenic" in 1990 It is an analogue of streptozotocin Streptozotocin or streptozocin ( INN, USP) (STZ) is a naturally occurring alkylating antineoplastic agent that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals. It is used in medicine for treating certain can .... References Alkylating antineoplastic agents IARC Group 2A carcinogens Monosaccharide derivatives Nitrosoureas Chloroethyl compounds {{antineoplastic-drug-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fotemustine
Fotemustine is a nitrosourea alkylating agent used in the treatment of metastatic melanoma Melanoma is the most dangerous type of skin cancer; it develops from the melanin-producing cells known as melanocytes. It typically occurs in the skin, but may rarely occur in the mouth, intestines, or eye (uveal melanoma). In very rare case .... It is available in Europe but has not been approved by the United States FDA. A study has shown that fotemustine produces improved response rates and but does not increase survival (over dacarbazine in the treatment of disseminated cutaneous melanoma. Median survival was 7.3 months with fotemustine versus 5.6 months with DTIC (P=.067). There was also toxicity prevalence in fotemustine arm. The main toxicity was grade 3 to 4 neutropenia (51% with fotemustine v 5% with DTIC) and thrombocytopenia (43% v 6%, respectively). External links Nitrosamines Nitrosoureas Phosphonate esters Ureas Chloroethyl compounds {{antineoplastic-dr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lomustine
Lomustine ( INN; abbreviated as CCNU; original brand name CeeNU, now marketed as Gleostine) is an alkylating nitrosourea compound used in chemotherapy. It is closely related to semustine and is in the same family as streptozotocin. It is a highly lipid-soluble drug, thus it crosses the blood–brain barrier. This property makes it ideal for treating brain tumors, which is its primary use, although it is also used to treat Hodgkin lymphoma as a second-line option. It has also been used in veterinary practice as a treatment for cancers in cats and dogs. Lomustine is a bifunctional alkylating agent, alkylates both DNA and RNA, has the ability to created interstrand cross-links (ICLs) in DNA. As with other nitrosoureas, it may also inhibit several key enzymatic processes by carbamoylation of amino acids in proteins. Lomustine is cell-cycle nonspecific. Medical uses Chemotherapy in human medicine Lomustine is an alkylating chemotherapy drug that is indicated by the FDA for ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nimustine
Nimustine () is a nitrosourea alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting .... It is used to treat malignant brain tumors and has proven to be rather effective. References Alkylating antineoplastic agents Nitrosamines Nitrosoureas[...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
N-Nitroso-N-methylurea
''N''-Nitroso-''N''-methylurea (NMU) is a highly reliable carcinogen, mutagen, and teratogen. NMU is an alkylating agent, and exhibits its toxicity by transferring its methyl group to nucleobases in nucleic acids, which can lead to AT:GC transition mutations. NMU is the traditional precursor in the synthesis of diazomethane. It has the potentially advantageous property that the stoichiometric byproducts formed are water, carbon dioxide, and ammonia, which are innocuous or easily removed. However, because it is unstable at temperatures beyond 20 °C and somewhat shock-sensitive, it has become obsolete for this purpose and replaced by other N-nitroso compounds: (''N''-methyl)nitrosamides and nitrosamines. Most chemical supply houses have stopped carrying it. Acute exposure to NMU in humans can result in skin and eye irritation, headache, nausea, and vomiting. [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Streptozocin
Streptozotocin or streptozocin (INN, USP) (STZ) is a naturally occurring alkylating antineoplastic agent that is particularly toxic to the insulin-producing beta cells of the pancreas in mammals. It is used in medicine for treating certain cancers of the islets of Langerhans and used in medical research to produce an animal model for hyperglycemia and Alzheimer's in a large dose, as well as type 2 diabetes or type 1 diabetes with multiple low doses. Usage Streptozotocin is approved by the U.S. Food and Drug Administration (FDA) for treating metastatic cancer of the pancreatic islet cells. Since it carries a substantial risk of toxicity and rarely cures the cancer, its use is generally limited to patients whose cancer cannot be removed by surgery. In these patients, streptozotocin can reduce the tumor size and reduce symptoms (especially hypoglycemia due to excessive insulin secretion by insulinomas). A typical dose is 500 mg/m2/day by intravenous injection, for 5 days, rep ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkylating Antineoplastic Agent
An alkylating antineoplastic agent is an alkylating agent used in cancer treatment that attaches an alkyl group (CnH2n+1) to DNA. Since cancer cells, in general, proliferate faster and with less error-correcting than healthy cells, cancer cells are more sensitive to DNA damage—such as being alkylated. Alkylating agents are used to treat several cancers. However, they are also toxic to normal cells (cytotoxic), particularly cells that divide frequently, such as those in the gastrointestinal tract, bone marrow, testicles and ovaries, which can cause loss of fertility. Most of the alkylating agents are also carcinogenic. History Before their use in chemotherapy, alkylating agents were better known for their use as sulfur mustard, ("mustard gas") and related chemical weapons in World War I. The nitrogen mustards were the first alkylating agents used medically, as well as the first modern cancer chemotherapies. Goodman, Gilman, and others began studying nitrogen mustards at Yale ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemotherapy
Chemotherapy (often abbreviated chemo, sometimes CTX and CTx) is the type of cancer treatment that uses one or more anti-cancer drugs (list of chemotherapeutic agents, chemotherapeutic agents or alkylating agents) in a standard chemotherapy regimen, regimen. Chemotherapy may be given with a cure, curative intent (which almost always involves combinations of drugs), or it may aim only to prolong life or to Palliative care, reduce symptoms (Palliative care, palliative chemotherapy). Chemotherapy is one of the major categories of the medical discipline specifically devoted to pharmacotherapy for cancer, which is called ''oncology#Specialties, medical oncology''. The term ''chemotherapy'' now means the non-specific use of intracellular poisons to inhibit mitosis (cell division) or to induce DNA damage (naturally occurring), DNA damage (so that DNA repair can augment chemotherapy). This meaning excludes the more-selective agents that block extracellular signals (signal transduction) ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
