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Chlormethine

Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a682223
Pregnancy category	D (US)
Routes of administration	IV, intracavitary, intrapericardially, topical
ATC code	L01AA05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	?
Metabolism	Rapid hydrolysis and demethylation, possibly in plasma
Elimination half-life	< 1 minute
Excretion	Urine (50% as metabolites, <0.01% as unchanged drug)
Identifiers
IUPAC name 2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine
CAS Number	51-75-2
PubChem CID	4033
DrugBank	APRD00249
ChemSpider	3893
UNII	50D9XSG0VR
ChEBI	CHEBI:28925
ChEMBL	ChEMBL427
CompTox Dashboard (EPA)	DTXSID2020975
ECHA InfoCard	100.000.110
Chemical and physical data
Formula	C5H11Cl2N
Molar mass	156.055 g mol g·mol
3D model (JSmol)	Interactive image
SMILES ClCCN(CCCl)C
InChI InChI=1S/C5H11Cl2N/c1-8(4-2-6)5-3-7/h2-5H2,1H3 Key:HAWPXGHAZFHHAD-UHFFFAOYSA-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.

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.

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

• Nitrogen mustards
  • HN1
  • HN3

References

1. Rappeneau S, Baeza-Squiban A, Jeulin C, Marano F (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. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
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

• British Columbia Cancer Agency profile

• Amines
• Organochlorides
• Alkylating antineoplastic agents
• Nitrogen mustards