Mechlorethamine
| 170px | |
| Systematic (IUPAC) name | |
|---|---|
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2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine | |
| Clinical data | |
| Pregnancy category |
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| Routes of administration | IV, intracavitary, intrapericardially, topical |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Rapid hydrolysis and demethylation, possibly in plasma |
| Biological half-life | < 1 minute |
| Excretion | Urine (50% as metabolites, <0.01% as unchanged drug) |
| Identifiers | |
| CAS Number | 51-75-2 |
| ATC code | L01AA05 (WHO) |
| PubChem | CID 4033 |
| DrugBank | APRD00249 |
| Chemical data | |
| Formula | C5H11Cl2N |
| Molar mass | 156.055 g mol−1[[Script error: No such module "String".]] |
| (verify) | |
Mechlorethamine also known as chlormethine, mustine and HN2 is a nitrogen mustard sold under the brand name Mustargen. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drug. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.
Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.[1][2]
History
Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an nitrogen-based analogue of mustard gas (which is sulphur based) and was derived from chemical warfare research. Secret clinical trials of the agent for Hodgkin's disease and several other lymphomas/leukemias in humans began in December of 1942. Because of wartime secrecy restrictions, it was not until 1946 that the results of these trials were published openly [3].
Uses
It has been derivatized into the estrogen analogue 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.
See also
References
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| 40px | This antineoplastic or immunomodulatory drug article is a stub. You can help ssf by expanding it. |
fr:Chlorméthine it:Mecloretamina nl:Chloormethine
ru:Мехлоретамин- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach. 11 ed. 2008.
- ↑ Gilman A. The initial clinical trial of nitrogen mustard. Am J Surg. 1963; 105:574-8.
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