Difference between revisions of "Mechlorethamine"

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Mechlorethamine
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Systematic (IUPAC) name
2-chloro-N-(2-chloroethyl)-N-methyl-ethanamine
Clinical data
Pregnancy
category
  • D (US)
Routes of
administration		 IV, intracavitary, intrapericardially, topical
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Bioavailability ?
Metabolism Rapid hydrolysis and demethylation, possibly in plasma
Biological half-life < 1 minute
Excretion Urine (50% as metabolites, <0.01% as unchanged drug)
Identifiers
CAS Number 51-75-2
ATC code L01AA05 (WHO)
PubChem CID 4033
DrugBank APRD00249
Chemical data
Formula C5H11Cl2N
Molar mass 156.055 g mol−1[[Script error: No such module "String".]]
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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]

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 sulphur based) and was derived from chemical warfare research. Secret clinical trials of the agent for Hodgkin's disease and several other lymphomas/leukemias in humans began in December of 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 therefore a powerful vesicant.

See also

References

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External links


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de:Mechlorethamin

fr:Chlorméthine it:Mecloretamina nl:Chloormethine

ru:Мехлоретамин
  1. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  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. The initial clinical trial of nitrogen mustard. Am J Surg. 1963; 105:574-8.
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