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Mechlorethamine



Mechlorethamine
Systematic (IUPAC) name
2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine
Identifiers
CAS number 51-75-2
ATC code L01AA05
PubChem 4033
DrugBank APRD00249
Chemical data
Formula C5H11Cl2N 
Mol. mass 156.055 g mol−1
Pharmacokinetic data
Bioavailability  ?
Metabolism Rapid hydrolysis and demethylation, possibly in plasma
Half life < 1 minute
Excretion Urine (50% as metabolites, <0.01% as unchanged drug)
Therapeutic considerations
Pregnancy cat.

D (US)

Legal status

℞ Prescription only

Routes IV, intracavitary, intrapericardially, topical

Mechlorethamine also known as chlormethine, mustine, nitrogen mustard and HN2 and sold under the brand name Mustargen, is the prototype anticancer chemotherapeutic drug. Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an analogue of mustard gas and was derived from chemical warfare research, in particular a 1943 accident in Bari, Italy which exposed civilians and soldiers-- it was noted that white cell counts of exposed patients decreased, suggesting a possible therapy for the cancer Hodgkin's lymphoma. It belongs to the group of nitrogen mustard alkylating agents.

It has been combined with estrogen as estramustine, used to treat prostate cancer.

It can also be used in chemical warfare where it has the code-name HN2. This chemical is a form of nitrogen mustard gas and therefore a powerful vesicant.

v • d • e
Chemotherapeutic agents/Antineoplastic agents (L01)
Alkylating and alkylating-like agentsNitrogen mustards: (Chlorambucil, Chlormethine, Cyclophosphamide, Ifosfamide, Melphalan). Nitrosoureas:(Carmustine, Fotemustine, Lomustine, Streptozocin). Platinum (alkylating-like): (Carboplatin, Cisplatin, Oxaliplatin, BBR3464). Busulfan, Dacarbazine, Procarbazine, Temozolomide, ThioTEPA, Uramustine
AntimetabolitesFolic acid: (Aminopterin, Methotrexate, Pemetrexed, Raltitrexed). Purine:(Cladribine, Clofarabine, Fludarabine, Mercaptopurine, Pentostatin, Thioguanine). Pyrimidine:(Capecitabine, Cytarabine, Fluorouracil, Floxuridine, Gemcitabine)
Spindle poison/mitotic inhibitorTaxane: (Docetaxel, Paclitaxel). Vinca: (Vinblastine, Vincristine, Vindesine, Vinorelbine).
Cytotoxic/antitumor antibioticsAnthracycline family: (Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Mitoxantrone, Valrubicin) - streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin) - Hydroxyurea
Topoisomerase inhibitorsCamptotheca: (Camptothecin, Topotecan, Irinotecan), Podophyllum:(Etoposide, Teniposide)
CI monoclonal antibodiesReceptor tyrosine kinase (Cetuximab, Panitumumab, Trastuzumab) - CD20 (Rituximab, Tositumomab) - other (Alemtuzumab, Bevacizumab, Gemtuzumab)
PhotosensitizersAminolevulinic acid, Methyl aminolevulinate, Porfimer sodium, Verteporfin
Tyrosine kinase inhibitorsDasatinib, Erlotinib, Gefitinib, Imatinib, Lapatinib, Nilotinib, Sorafenib, Sunitinib
Otherretinoids (Alitretinoin, Tretinoin) - Altretamine, Amsacrine, Anagrelide, Arsenic trioxide, Asparaginase (Pegaspargase), Bexarotene, Bortezomib, Denileukin diftitox, Estramustine, Ixabepilone, Masoprocol, Mitotane
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Mechlorethamine". A list of authors is available in Wikipedia.
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