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Drugs and Medicinal Substances

Nitrogen mustard

Antineoplastic and Immunomodulating Agents

Nitrogen mustards are cytotoxic organic compounds sharing a bis(2-chloroethyl)amino functional group that act as DNA alkylating agents in cancer treatment. They were originally developed as chemical warfare agents, then became the first chemotherapy drugs used against cancer following studies at Yale during the Second World War. The compounds work by forming cross links between strands of DNA, which triggers the death of malignant cells such as those of lymphoma. Early nitrogen mustard drugs like mustine are rarely used today because of their toxicity, but derivatives including cyclophosphamide and bendamustine remain important chemotherapy medicines, and the parent compounds remain tightly regulated under the Chemical Weapons Convention.

Facts
Drug Class
Cytotoxic alkylating agent (nitrogen mustard compound) 1
Mechanism of Action
Forms an aziridinium ion that alkylates DNA at the guanine N-7 position 1
Approved Use
Historically the first chemotherapy drug (mustine, HN2), trialled against lymphoma; no longer commonly used because of excessive toxicity 1
First Approved / Isolated Year
1949 3
Significant Risk
Powerful, persistent blister (vesicant) agents 1
Classification
Approval Status
Approved 1
ATC ClassSourced to the subject's own account
L: Antineoplastic and Immunomodulating Agents 2
Route of Administration
Intravenous 1
Route of Administration
Topical 1
Connections

Long-Form Articles

Sources
1. Nitrogen mustard (Wikipedia)
  • Lead section
    Nitrogen mustards (NMs) are cytotoxic organic compounds with the bis(2-chloroethyl)amino ((ClC2H4)2NR) functional group.
  • Mechanism of action section
    This aziridinium group then alkylates DNA once it is attacked by the N-7 nucleophilic center on the guanine base.
  • Safety section
    Nitrogen mustards are powerful and persistent blister agents.
  • Other mustards section, first sentence
    The nitrogen mustard drug mustine (HN2), is no longer commonly in use because of excessive toxicity.
  • Regulatory approval status
  • Route of administration
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2. Anatomical Therapeutic Chemical Classification System (Wikipedia)
WikipediaFirst-level anatomical group codes, Code L
Quote, First-level anatomical group codes, Code L
Antineoplastic and immunomodulating agents
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3. MDedge: First FDA-Approved Chemo Agent Turns 60
Article text
Quote, Article text
On March 15, 1949, mechlorethamine (Mustargen) became the first chemical agent to receive FDA approval for the treatment of cancer
View the Source
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