(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.
nitrogen mustard
| Sci-Tech Dictionary: nitrogen mustard |
(′nī·trə·jən ′məs·tərd)
| 5min Related Video: nitrogen mustard |
| Drug Info: Mechlorethamine, Nitrogen Mustard |
Brand names: Mustargen®
Chemical formula:
Mechlorethamine Hydrochloride Solution for injection
What is this medicine?
MECHLORETHAMINE 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: 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).
| Wikipedia: Nitrogen mustard |
|
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. The drug mustin was developed after a war accident in 1943 in Bari, Italy where civilians and soldiers were exposed to mustard gas. It was observed that survivors had a decreased number of lymphocytes suggesting a possible therapy to cure lymphomas.
Examples
The prototype nitrogen mustard drug is mustine, which is no longer commonly in use. It was the first anticancer chemotherapeutic. It is a schedule 1 substance in the Chemical Weapons Convention. Other nitrogen mustards include cyclophosphamide, chlorambucil, uramustine and melphalan.
Examples of nitrogen mustards that can be used for chemical warfare purposes and their weapon designations include:
- HN1: Bis(2-chloroethyl) ethylamine
- HN2: Bis(2-chloroethyl) methylamine
- HN3: Tris(2-chloroethyl) amine
Mechanism of action
Main articles: Sulfur mustard#Chemistry and sulfur mustard chemistry
Nitrogen mustards form cyclic aminium ions (aziridinium rings) by intramolecular displacement of the chloride by the amine nitrogen. This azidirium group then alkylates basic centers on the DNA. Alkylated DNA malfunctions in replication. The therapeutically useful alkylating agents have more than one alkylating group per molecule, i.e. they are di- or polyalkylating agent. The effects are "radiomimetic," i.e. the DNA damage is similar to that which is seen when genetic material is exposed to radiation.
In the early 1960s, NMs were reported to form interstrand crosslinks (ICLs). At that time it was proposed that the ICLs were formed between N-7 atom of guanine residue in a 5’-d(GC) sequence.[1][2] Later was it clearly demonstrated that NM form a 1,3 ICL in the 5’-d(GNC) sequence.[3][4][5]
References
- ^ Geiduschek EP: "Reversible" DNA. Proc Natl Acad Sci U S A 1961, 47:950-955.
- ^ Brookes P, Lawley PD: The reaction of mono- and di-functional alkylating agents with nucleic acids. Biochem J 1961, 80(3):496-503.
- ^ Rink SM, Solomon MS, Taylor MJ, Rajur SB, McLaughlin LW, Hopkins PB: 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 1993, vol. 115, pp.2551-2557.
- ^ Dong Q, Barskt D, Colvin ME, Melius CF, Ludeman SM, Moravek JF, Colvin OM, Bigner DD, Modrich P, Friedman HS: A structural basis for a phosphoramide mustard-induced DNA interstrand cross-link at 5?-d(GAC). Proceedings of the National Academy of Sciences of the United States of America 1995, 92(26):12170-12174.
- ^ Bauer GB, Povirk LF: Specificity and kinetics of interstrand and intrastrand bifunctional alkylation by nitrogen mustards at a G-G-C sequence. Nucleic Acids Res 1997, volume 25, pages 1211-1218.
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| melphalan |
| mustine hydrochloride |
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