1204-68-8

Usage

Uses

Used in Oncology:
Mechlorethamine is used as a chemotherapeutic agent for the treatment of various types of cancer, such as Hodgkin’s disease, non-Hodgkin’s lymphoma, and leukemia. It functions by alkylating DNA, which results in the disruption of normal cellular processes and ultimately induces cell death. Due to its high reactivity and toxicity, strict safety measures are necessary when handling this substance in medical settings.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, mechlorethamine is used as an active pharmaceutical ingredient in the formulation of drugs intended for cancer treatment. Its application is carefully managed to maximize therapeutic benefits while minimizing the risk of adverse effects associated with its toxic nature.
As a Hazardous Substance:
Mechlorethamine is classified as a hazardous substance due to its potential to cause severe damage to tissues and organs if mishandled. It requires special handling, storage, and disposal protocols to ensure the safety of patients, healthcare professionals, and the environment.

InChI:InChI=1/C11H15Cl2N/c1-10-2-4-11(5-3-10)14(8-6-12)9-7-13/h2-5H,6-9H2,1H3

Upstream product

• 3077-12-1 N,N-bis-(2-hydroxyethyl)-P-toluidine 
• 106-49-0 p-toluidine 

Downstream Products

• 90254-19-6 N-(4-methylphenyl)thiomorpholine 

Relevant academic research and scientific papers

Hypoxia-Selective Antitumor Agents. 3. Relationships between Structure and Cytotoxicity against Cultured Tumor Cells for Substituted N,N-Bis(2-chloroethyl)anilines

A series of aniline mustards with a wide range of electron-donating and -withdrawing substituents in the 3- and 4-positions has been synthesized and evaluated for cytotoxicity in cell culture to examine the potential of using nitro group deactivated nitrogen mustards for the design of novel hypoxia-selective anticancer drugs (Denny, W.A.; Wilson, W.R.J.Med Chem. 1986, 29, 879).Hydrolytic half-lives in tissue culture media, determined by bioassay against a cell line (UV4) defective in the repair of DNA interstrand cross-links showed the expected dependence on the Hammett electronic parameter, ?, varying from 0.13 h for the 4-amino analogue to >100 h for analogues with strongly electron-withdrawing substituents.Cytotoxic potencies in aerobic UV4 cultures showed a similar dependence on ?.This dependence predicted that the 4-nitroaniline mustard would be 7200-fold less potent than its potential six-electron reduction product, the 4-amino compound, in growth inhibition assays using a 1-h drug exposure.The measured differential was much lower (225-fold) because of the instability of the latter compound, but a differential of 17500-fold was observed in the initial rate of killing by using a clonogenic assay.The potential for formation of reactive mustards by reduction to the amine or hydroxylamine was demonstrated by the 4-nitroso compound, which had an aerobic toxicity similar to that of the amine.Although these features confirmed the original rationale, the 3-nitro- and 4-nitroaniline mustards had only minimal hypoxic selectivity against UV cells.Toxicity to hypoxic cells appears to be limited by the low reduction potentials of these compounds and consequent lack of enzymatic nitroreduction.However, this study has demonstrated that nitro groups can be used to latentiate aromatic nitrogen mustards and indicates that examples with higher reduction potentials could provide useful hypoxia-selective therapeutic agents.