nitrogen mustard
McGraw-Hill Science & Technology Dictionary:
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nitrogen mustard
(′nī·trə·jən ′məs·tərd)
(organic chemistry) Any of the substituted mustard gases in which the sulfur is replaced by an amino nitrogen, such as for methyl bis(2-chlorethyl)amine, (CH2ClCH2)2NCH3; useful in cancer research.
Drug Info:
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Mechlorethamine, Nitrogen Mustard
Brand names: Mustargen®
Chemical formula:
Mechlorethamine Hydrochloride Solution for injection
What is this medicine?
MECHLORETHAMINE (me klor ETH a meen) is a chemotherapy drug. This medicine is used to treat many types of cancer like Hodgkin's disease, non-Hodgkin's lymphoma, mycosis fungoides, and some blood and lung cancers.
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
•blood disorders
•gout
•infection (especially a virus infection such as chickenpox, cold sores, or herpes)
•recent or ongoing radiation therapy
•an unusual or allergic reaction to mechlorethamine, other chemotherapy, other medicines, foods, dyes, or preservatives
•pregnant or trying to get pregnant
•breast-feeding
How should I use this medicine?
This drug is usually given as an injection into a vein or infused into a body cavity. It is administered in a hospital or clinic by a specially trained health care professional.
Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.
Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.
What if I miss a dose?
Missing a dose is probably not harmful. If you miss a dose, simply resume taking it on your previous schedule. Do not take double doses to catch up, however.What may interact with this medicine?
Do not take this medicine with any of the following medications:
•nalidixic acid
This medicine may also interact with the following medications:
•medicines to increase blood counts like filgrastim, pegfilgrastim, sargramostim
•vaccines
Talk to your doctor or health care professional before taking any of these medicines:
•acetaminophen
•aspirin
•ibuprofen
•ketoprofen
•naproxen
This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.
What should I watch for while using this medicine?
Visit your doctor for checks on your progress. This drug may make you feel generally unwell. This is not uncommon, as chemotherapy can affect healthy cells as well as cancer cells. Report any side effects. Continue your course of treatment even though you feel ill unless your doctor tells you to stop.
In some cases, you may be given additional medicines to help with side effects. Follow all directions for their use.
Call your doctor or health care professional for advice if you get a fever, chills or sore throat, or other symptoms of a cold or flu. Do not treat yourself. This drug decreases your body's ability to fight infections. Try to avoid being around people who are sick.
This medicine may increase your risk to bruise or bleed. Call your doctor or health care professional if you notice any unusual bleeding.
Be careful brushing and flossing your teeth or using a toothpick because you may get an infection or bleed more easily. If you have any dental work done, tell your dentist you are receiving this medicine.
Avoid taking products that contain aspirin, acetaminophen, ibuprofen, naproxen, or ketoprofen unless instructed by your doctor. These medicines may hide a fever.
Do not become pregnant while taking this medicine. Women should inform their doctor if they wish to become pregnant or think they might be pregnant. There is a potential for serious side effects to an unborn child. Talk to your health care professional or pharmacist for more information. Do not breast-feed an infant while taking this medicine.
Men should inform their doctor if they wish to father a child. This medicine may lower sperm counts.
What side effects may I notice from receiving this medicine?
Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
•low blood counts - this medicine may decrease the number of white blood cells, red blood cells and platelets. You may be at increased risk for infections and bleeding.
•signs of infection - fever or chills, cough, sore throat, pain or difficulty passing urine
•signs of decreased platelets or bleeding - bruising, pinpoint red spots on the skin, black, tarry stools, blood in the urine
•signs of decreased red blood cells - unusually weak or tired, fainting spells, lightheadedness
•breathing problems
•changes in hearing
•feeling faint or lightheaded, falls
•pain, swelling, redness at site where injected
•unusual bleeding or bruising
•unusually weak or tired
•vomiting
•yellowing of the eyes or skin
Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•diarrhea
•hair loss
•loss of appetite
•metallic taste or changes in taste
•missed menstrual periods
•nausea
This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.
Where should I keep my medicine?
This drug is given in a hospital or clinic and will not be stored at home.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
Columbia Encyclopedia:
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Mechlorethamine, Nitrogen Mustard
nitrogen mustard, any of various poisonous compounds originally developed for military use (see poison gas). Like mustard gas and lewisite, it is a vesicant (blistering agent). In the form of its crystalline hydrochloride it is used as a drug in the treatment of Hodgkin's disease, non-Hodgkin's lymphomas, and brain tumors. Nitrogen mustards cause mutations in the genetic material of cells, thereby disrupting mitosis, or cell division. Cells vary in their susceptibility to nitrogen mustards, with rapidly proliferating tumor and cancer cells most sensitive; bone marrow, which produces red blood cells, is also sensitive, and depression of red blood cell production is a frequent side effect of nitrogen mustard therapy. The nitrogen mustards also suppress the immune response (see immunity).
Oxford Dictionary of Biochemistry:
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nitrogen mustard
any of a group of bis(2-chloroalkyl)amines, as typified by the volatile base bis(2-chloroethyl)ethylamine, CH3−CH2−N(CH2−CH2Cl)2, a nitrogen-containing analogue of mustard gas. They are potent alkylating agents, vesicants, and mutagens. They cross-link DNA chains and have been used as immunosuppressive and antineoplastic agents.
| nitrogen fixation, nitrogen equilibrium, nitrogen cycle | |
| nitrogen regulatory protein, nitrogen-13, nitrogen-15 |
Wikipedia on Answers.com:
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Nitrogen mustard
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The nitrogen mustards are cytotoxic chemotherapy agents similar to mustard gas. Although their common use is medicinal, in principle these compounds can also be deployed as chemical warfare agents. Nitrogen mustards are nonspecific DNA alkylating agents. Nitrogen mustard gas was stockpiled by several nations during the Second World War, but it was never used in combat. As with all types of mustard gas, nitrogen mustards are powerful and persistent blister agents and the main examples (HN1, HN2, HN3, see below) are therefore classified as Schedule 1 substances within the Chemical Weapons Convention. Production and use is therefore strongly restricted.
During WWII nitrogen mustards were studied at Yale University and classified human clinical trials of nitrogen mustards for the treatment of lymphoma started in December 1942.[1] Also during WWII, an incident during the air raid on Bari, Italy led to the release of mustard gas that affected several hundred soldiers and civilians. Medical examination of the survivors showed a decreased number of lymphocytes.[2] After WWII was over, the Bari incident and the Yale group's studies eventually converged prompting a search for other similar compounds. Due to its use in previous studies, the nitrogen mustard known as "HN2" became the first chemotherapy drug mustine.
Examples
The original nitrogen mustard drug, mustine (HN2), is no longer commonly in use. Other nitrogen mustards developed as treatments include cyclophosphamide, chlorambucil, uramustine, ifosfamide, melphalan and bendamustine.[3] Bendamustine has recently reemerged as a viable chemotheraputic treatment.[4]
Nitrogen mustards that can be used for chemical warfare purposes are tightly regulated. Their weapon designations are:
Mechanism of action
Nitrogen mustards (NMs) form cyclic aminium ions (aziridinium rings) by intramolecular displacement of the chloride by the amine nitrogen. This azidirium group then alkylates DNA by attacking the N-7 nucleophilic center on the guanine base. A second attack after the displacement of the second chlorine forms the second alkylation step that results in the formation of interstrand cross-links (ICLs) as it was shown in the early 1960s. At that time it was proposed that the ICLs were formed between N-7 atom of guanine residue in a 5’-d(GC) sequence.[5][6] These kind of lesion are highly cytotoxic, since they block fundamental metabolic processes such as replication and transcription.
Later was it clearly demonstrated that NMs form a 1,3 ICL in the 5’-d(GNC) sequence.[7][8][9]
The strong cytotoxic effect caused by the formation of ICLs is what makes NMs an effective chemotherapeutic agent. Other compounds used in cancer chemotherapy that have the ability to form ICLs are cisplatin, mitomycin C, carmustine, and psoralen.[10]
References
- ^ Gilman A (May 1963). "The initial clinical trial of nitrogen mustard". Am. J. Surg. 105 (5): 574–8. doi:10.1016/0002-9610(63)90232-0. PMID 13947966.
- ^ Hirsch J (September 2006). "An anniversary for cancer chemotherapy". JAMA 296 (12): 1518–20. doi:10.1001/jama.296.12.1518. PMID 17003400.
- ^ Mattes, W. B.; Hartley, J. A.; Kohn, K. W. (1986). "DNA sequence selectivity of guanine–N7 alkylation by nitrogen mustards". Nucleic Acids Research 14 (7): 2971–2987. doi:10.1093/nar/14.7.2971. PMC 339715. PMID 3960738. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=339715.
- ^ Cheson BD, Rummel MJ (March 2009). "Bendamustine: rebirth of an old drug". J. Clin. Oncol. 27 (9): 1492–501. doi:10.1200/JCO.2008.18.7252. PMID 19224851. http://www.jco.org/cgi/pmidlookup?view=long&pmid=19224851.
- ^ Geiduschek EP (July 1961). ""Reversible" DNA". Proc. Natl. Acad. Sci. U.S.A. 47 (7): 950–5. doi:10.1073/pnas.47.7.950. PMC 221307. PMID 13704192. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=221307.
- ^ Brookes P, Lawley PD (September 1961). "The reaction of mono- and di-functional alkylating agents with nucleic acids". Biochem. J. 80 (3): 496–503. PMC 1243259. PMID 16748923. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1243259.
- ^ Rink SM, Solomon MS, Taylor MJ, Rajur SB, McLaughlin LW, Hopkins PB (1993). "Covalent structure of a nitrogen mustard-induced DNA interstrand cross-link: An N7-to-N7 linkage of deoxyguanosine residues at the duplex sequence 5'-d(GNC)". Journal of the American Chemical Society 115 (7): 2551–7. doi:10.1021/ja00060a001.
- ^ Dong Q, Barsky D, Colvin ME, et al. (December 1995). "A structural basis for a phosphoramide mustard-induced DNA interstrand cross-link at 5'-d(GAC)". Proc. Natl. Acad. Sci. U.S.A. 92 (26): 12170–4. doi:10.1073/pnas.92.26.12170. PMC 40318. PMID 8618865. http://www.pnas.org/cgi/pmidlookup?view=long&pmid=8618865.
- ^ Bauer GB, Povirk LF (March 1997). "Specificity and kinetics of interstrand and intrastrand bifunctional alkylation by nitrogen mustards at a G-G-C sequence". Nucleic Acids Res. 25 (6): 1211–8. doi:10.1093/nar/25.6.1211. PMC 146567. PMID 9092631. http://nar.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=9092631.
- ^ Guainazzi, A.; Schärer, O. D. (2010). "Using synthetic DNA interstrand crosslinks to elucidate repair pathways and identify new therapeutic targets for cancer chemotherapy". Cellular and Molecular Life Sciences 67 (21): 3683–3697. doi:10.1007/s00018-010-0492-6. PMID 20730555.
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McGraw-Hill Dictionary of Scientific and Technical Terms. Copyright © 2003, 1994, 1989, 1984, 1978, 1976, 1974 by McGraw-Hill Companies, Inc. All rights reserved.
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Columbia Encyclopedia
The Columbia Electronic Encyclopedia, Sixth Edition Copyright © 2012, Columbia University Press. Licensed from Columbia University Press. All rights reserved. www.cc.columbia.edu/cu/cup/.
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Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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