Chlormethine

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Chlormethine
Skeletal formula of mechlorethamine
Identifiers
CAS number 51-75-2 YesY
PubChem 4033
ChemSpider 3893 YesY
UNII 50D9XSG0VR YesY
EC number 200-120-5
DrugBank DB00888
KEGG D0767 N
MeSH Mechlorethamine
ChEBI CHEBI:28925 YesY
ChEMBL CHEMBL427 YesY
ATC code D08AX04,L01AA05
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)


Prescription only

Pregnancy
category
Related compounds
Related amines
Related compounds
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Chlormethine (INN, BAN), mechlorethamine (widely used in the US, not the USAN, however) also known as mustine and HN2 and in former USSR known as Embichin 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[edit]

Successful clinical use of chlormethine (mechlorethamine) resulted in development of the field of anticancer chemotherapy, led by Cornelius P. Rhoads at Memorial Sloan-Kettering. 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[edit]

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.

Synthesis[edit]

Mechlorethamine synthesis:[4][5][6]

See also[edit]

References[edit]

  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. 
  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. 
  4. ^ Prelog, V.; Štěpán, V. (1935). "Nouvele synthèse des pipérazines N-monoalcoylées (VIIième communication sur les bis-[β-halogénoéthyl]-amines)". Collection of Czechoslovak Chemical Communications 7: 93. doi:10.1135/cccc19350093.  edit
  5. ^ Hanby, W. E.; Rydon, H. N. (1947). "98. The chemistry of 2-chloroalkylamines. Part I. Preparation and general reactions". Journal of the Chemical Society (Resumed): 513. doi:10.1039/JR9470000513.  edit
  6. ^ Abrams, J. T.; Barker, R. L.; Jones, W. E.; Val-Lender, H. W.; Woodward, F. N. (1949). "The preparation of n-methyldiethanolamine and Nmethyl-2:2′- dichlorodiethylamine". Journal of the Society of Chemical Industry 68 (9): 280. doi:10.1002/jctb.5000680908.  edit

External links[edit]