Mustine

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Mechlorethamine

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Identifiers
CAS number 51-75-2 YesY
PubChem 4033 YesY
ChemSpider 3893 YesY
UNII 50D9XSG0VR YesY
EC number 200-120-5
DrugBank DB00888
KEGG D0767 YesY
MeSH Mechlorethamine
ChEBI CHEBI:28925 YesY
ATC code AA05
Jmol-3D images Image 1
Properties
Molecular formula C5H11Cl2N
Molar mass 156.05 g mol−1
Appearance Colourless liquid
Odor Ichtyal, ammoniacal
log P 0.91
Pharmacology
Routes of
administration
  • Intracavitary
  • Intrapericardial
  • Intravenous
  • Topical
Elimination
half-life
<1 minute
Excretion 50% (renal)
Legal status


Prescription only

Pregnancy
category
D(US)
Related compounds
Related amines
Related compounds
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 drugs. 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 resulted in development of the field of anticancer chemotherapy. The drug is a 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

External links

  • British Columbia Cancer Agency profile
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