Mechlorethamine
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| Mechlorethamine
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| Systematic (IUPAC) name | |
| 2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine | |
| Identifiers | |
| CAS number | |
| ATC code | L01 |
| PubChem | |
| DrugBank | |
| 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 |
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Overview
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 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.
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