| Description | Nitrogen mustard (HN) was developed in three formulations: HN-1, HN-2, and HN-3. HN-1 was the first to be produced in the late 1920s and early 1930s. Originally, it was developed as a pharmaceutical and used to remove warts before it became a military agent. Agent H-2 was developed as a military agent and became a pharmaceutical. HN-3 was designed as a military mustard agent and is the only one that remains in military use. Therefore, this section will only cover the characteristics of HN-3 mustard agent. HN-3 is colorless to pale yellow with a butter-almond odor. The chemical formula for nitrogen mustard agent HN-3 is N(CH2CH2Cl)3. It will otherwise be ineffective against stopping the damage to the body. |
| Chemical Properties | White Solid |
| Chemical Properties | Highly toxic white to yellowish crystallinesolid or powder. May be available as an unstable aqueoussolution. Fish-like odor. |
| Uses | xanthine oxidase/dehydrogenase inhibitor |
| Uses | It has been used as an antineoplastic. A nitrogen mustard prepared by action of thionyl chloride on 2,2’(methylimino)-diethanol in trichloroethylene. |
| Uses | Mechlorethamine hydrochloride USP (Mustargen)is used to treat Hodgkin’s disease; non-Hodgkin’s lymphomas; lymphosarcoma; cancer of breast, ovary, lung; neoplastic effusion. |
| Definition | ChEBI: The hydrochloride salt of mechlorethamine. |
| Indications | Mechlorethamine (Mustargen) is a cytotoxic alkylatingagent. Topical application of freshly prepared aqueoussolutions are used in patients with early stages of cutaneousT-cell lymphoma. A major disadvantage to theuse of this drug is the rapid induction of allergic contactdermatitis in some patients. |
| Indications | Mechlorethamine (nitrogen mustard; Mustargen), a derivativeof the war gas sulfur mustard, is considered tobe the first modern anticancer drug. In the early 1940s itwas discovered to be effective in the treatment of humanlymphomas. |
| Brand name | Mustargen (Ovation). |
| Biological Functions | Mechlorethamine is still used in regimens for cancers of the blood (e.g., Hodgkin's disease, chronic myelocytic, or chronic lymphocytic leukemia); fortunately, however, safer and still highly potent antineoplastic agents are now available. |
| General Description | White to off-white crystals or powder with a fishy odor. Initial pH (2% aqueous solution) 3.0-4.0. |
| General Description | Mechlorethamine is available in 10-mg vials for intravenous(IV) administration in the treatment of Hodgkin’slymphoma. It is part of the MOPP regimen used in treatingthis condition, which is comprised of mechlorethamine,vincristine (Oncovin), procarbazine, and prednisone. Theagent is also used topically in the treatment of mycosis fungoides,a rare type of cancer but the most common type ofcutaneous T-cell lymphoma. Additional uses have includedtreatment of cancers that have resulted in pleural effusion.Although the compound is a potent alkylating agent, resistancemay develop as a result of increased inactivation bysulfhydryl containing proteins such as glutathione andincreased expression of DNA repair mechanisms. Adverseeffects include dose-limiting myelosuppression and nausea/vomiting. There is a significant risk of extravasationupon IV administration, and the agent may produce painat the injection site. Additional adverse effects include alopecia, azoospermia, amenorrhea, hyperuricemia, and anincreased risk of secondary cancers. |
| Air & Water Reactions | Hygroscopic. Water soluble. |
| Reactivity Profile | Dry crystals are stable at temperatures up to 104° F. Chlormethine hydrochloride is incompatible with strong oxidizing agents. . |
| Hazard | Highly toxic, vesicant, and strongly irritantto mucous membranes. |
| Fire Hazard | Flash point data for Chlormethine hydrochloride are not available. Chlormethine hydrochloride is probably combustible. |
| Mechanism of action | Mechlorethamine in aqueous solution loses a chlorideatom and forms a cyclic ethylenimmonium ion.Thiscarbonium ion interacts with nucleophilic groups, suchas the N7 and O6 of guanine, and leads to an interstrandcross-linking of DNA. Although there is great variationamong normal and tumor tissues in their sensitivity tomechlorethamine, the drug is generally more toxic toproliferating cells than to resting or plateau cells.Mechlorethamine has a chemical and biological half-lifein plasma of less than 10 minutes after intravenous injection.Little or no intact drug is excreted in urine.
The major indication for mechlorethamine isHodgkin’s disease; the drug is given in the MOPP regimen. Other less reactive nitrogenmustards are now preferred for the treatment of non-Hodgkin’s lymphomas, leukemias, and various solidtumors. |
| Clinical Use | Mechlorethamine is the only aliphatic nitrogen mustard currently on the U.S. market. Its use is limited by extremely high reactivity, which leads to rapid and nonspecific alkylation of cellular nucleophiles and excessive toxicity. It is a severe vesicant, and if accidental skin contact occurs, the drug must be inactivated with 2% sodium thiosulfate (Na2S2O3) solution. |
| Side effects | The dose-limiting toxicity of mechlorethamine ismyelosuppression; maximal leukopenia and thrombocytopeniaoccur 10 to 14 days after drug administration,and recovery is generally complete at 21 to 28 days.Lymphopenia and immunosuppression may lead to activationof latent herpes zoster infections, especially inpatients with lymphomas. Mechlorethamine will affectrapidly proliferating normal tissues and cause alopecia,diarrhea, and oral ulcerations. Nausea and vomiting mayoccur 1 to 2 hours after injection and can last up to 24hours. Since mechlorethamine is a potent blisteringagent, care should be taken to avoid extravasation intosubcutaneous tissues or even spillage onto the skin.Reproductive toxicity includes amenorrhea and inhibitionof oogenesis and spermatogenesis. About half ofpremenopausal women and almost all men treated for 6months with MOPP chemotherapy become permanentlyinfertile. The drug is teratogenic and carcinogenicin experimental animals. |
| Safety Profile | Confirmed carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Deadly poison by ingestion,intravenous, subcutaneous, intraperitoneal, and parenteralroutes. Experimental teratogenic and reproductive effects.Human systemic eff |
| Synthesis | Mechlorethamine, bis-(2-chloroethyl)methylamine (30.2.1.2), is madeby reacting methylamine with ethylene oxide, forming bis-(2-hydroxyethyl)methylamine(30.2.1.1), which upon reaction with thionyl chloride turns into the desired mechlorethamine. |
| Carcinogenicity | Nitrogen mustard hydrochloride is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals. In the literature, the names“nitrogen mustard” and “nitrogen mustard hydrochloride” are used interchangeably. Only nitrogen mustard hydrochloride is produced commercially, so it is assumed that nitrogen mustard hydrochloride was used in all cancer studies in animals reported below. |
| Shipping | UN2928 Toxic solids, corrosive, organic, n.o.s.,Hazard Class: 6.1; Labels: 6.1-Poisonous materials,8-Corrosive material, Technical Name Required. UN2811Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels:6.1-Poisonous materials, Technical Name Required. |
| Waste Disposal | It is not appropriate to disposeof expired or waste product such as lab chemicals byflushing them down the toilet or discarding them to thetrash. Larger quantities shall carefully take into considerationapplicable EPA, and FDA regulations. If possiblereturn the lab chemicals to the manufacturer for proper disposalbeing careful to properly label and securely packagethe material. Alternatively, the waste lab chemicals shall belabeled, securely packaged and transported by a statelicensed medical waste contractor to dispose by burial in alicensed hazardous or toxic waste landfill or incinerator. |
