Mechlorethamine

Mechlorethamine
Systematic (IUPAC) name
2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a682223
Pregnancy cat. D (US)
Legal status ℞ Prescription only
Routes IV, intracavitary, intrapericardially, topical
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)
Identifiers
CAS number 51-75-2 Y
ATC code L01AA05
PubChem CID 4033
DrugBank APRD00249
ChemSpider 3893 Y
UNII 50D9XSG0VR Y
ChEBI CHEBI:28925 Y
ChEMBL CHEMBL427 Y
Chemical data
Formula C5H11Cl2N 
Mol. mass 156.055 g mol−1
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Mechlorethamine also known as chlormethine, mustine and HN2 is a nitrogen mustard sold under the brand name Mustargen. It is the prototype of alkylating agents, a group of anticancer chemotherapeutic drug. It works by binding to DNA, crosslinking two strands and preventing cell duplication. It binds to the N7 nitrogen on the DNA base guanine. As the chemical is a blister agent, its use is strongly restricted within the Chemical Weapons Convention where it is classified as a Schedule 1 substance.

Mechlorethamine belongs to the group of nitrogen mustard alkylating agents.[1][2]

Contents

History

Successful clinical use of mechlorethamine gave birth to the field of anticancer chemotherapy. The drug is an nitrogen-based analogue of mustard gas (which is sulfur-based) and was derived from chemical warfare research. Secret clinical trials of the agent for Hodgkin's disease and several other lymphomas and leukemias in humans began in December 1942. Because of wartime secrecy restrictions, it was not until 1946 that the results of these trials were published openly.[3]

Uses

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 a powerful vesicant.

See also

References

  1. ^ Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (March 2000). "Protection from cytotoxic effects induced by the nitrogen mustard mechlorethamine on human bronchial epithelial cells in vitro". Toxicol. Sci. 54 (1): 212–21. doi:10.1093/toxsci/54.1.212. PMID 10746948. http://toxsci.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=10746948. 
  2. ^ Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach. 11 ed. 2008.
  3. ^ Gilman A. (1963). "The initial clinical trial of nitrogen mustard". Am J Surg. 105 (5): 574–578. doi:10.1016/0002-9610(63)90232-0. PMID 13947966. 

External links