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Nitrogen Mustard: DNA Cross-Linking Alkylating Agent in Cancer Chemotherapy
Nitrogen mustard (mechlorethamine) is the prototypical alkylating agent — first chemotherapy drug (1940s).
Mechanism
- Forms reactive aziridinium ion → covalent bonds with DNA (N7-guanine).
- Creates interstrand cross-links → prevents DNA separation → blocks replication/transcription.
- Triggers apoptosis via p53, DNA damage response.
Clinical Use
- Hodgkin/non-Hodgkin lymphoma (MOPP regimen)
- Chronic lymphocytic leukemia
- Mycosis fungoides (cutaneous T-cell lymphoma) — topical
- Palliative effusion control (intracavitary)
Toxicity
- Myelosuppression (nadir 2–3 weeks)
- Nausea/vomiting (high emetogenicity)
- Mucositis, alopecia, infertility
- Secondary AML (dose-related)
- Vesicant — extravasation causes severe necrosis
Historical Note
Derived from sulfur mustard (chemical warfare agent). Yale trials (1942) launched cancer chemotherapy era.
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