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 ClassCytotoxic alkylating agent (nitrogen mustard compound) 1 Mechanism of ActionForms an aziridinium ion that alkylates DNA at the guanine N-7 position 1 Approved UseHistorically the first chemotherapy drug (mustine, HN2), trialled against lymphoma; no longer commonly used because of excessive toxicity 1 First Approved / Isolated Year Significant RiskPowerful, persistent blister (vesicant) agents 1 Classification
Approval Status ATC ClassSourced to the subject's own accountL: Antineoplastic and Immunomodulating Agents 2 Route of Administration Route of Administration Connections
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
View the Source2. Anatomical Therapeutic Chemical Classification System (Wikipedia)
WikipediaFirst-level anatomical group codes, Code LQuote, First-level anatomical group codes, Code L
Antineoplastic and immunomodulating agents
View the Source 3. MDedge: First FDA-Approved Chemo Agent Turns 60
Article textQuote, 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 Reader Challenges (0)
No disputes yet. Spotted an error or a better source? Open the first one.
Sign in to dispute this or suggest a correction.