Mechlorethamine

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 YesY
ATC code L01AA05
PubChem CID 4033
DrugBank APRD00249
ChemSpider 3893 YesY
UNII 50D9XSG0VR YesY
ChEBI CHEBI:28925 N
ChEMBL CHEMBL427 N
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


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Look at other dictionaries:

  • mechlorethamine — A drug used to treat some types of cancer and some precancerous skin conditions. It causes cancer cells to die by attaching to the DNA in the cells. Mechlorethamine is a type of alkylating agent. Also called mustine, mechlorethamine hydrochloride …   English dictionary of cancer terms

  • mechlorethamine hydrochloride — A drug used to treat some types of cancer and some precancerous skin conditions. It causes cancer cells to die by attaching to the DNA in the cells. Mechlorethamine hydrochloride is a type of alkylating agent. Also called mustine, mechlorethamine …   English dictionary of cancer terms

  • mechlorethamine — /me klawr eth euh meen , klohr /, n. Pharm. a nitrogen mustard, C5H11Cl2N, used in combination with other drugs in the treatment of Hodgkin s disease and certain other cancers. [ME(THYL) + CHLOR 2 + ETH(YL) + AMINE] * * * …   Universalium

  • mechlorethamine — noun A particular drug used in chemotherapy …   Wiktionary

  • mechlorethamine — mech·lor·eth·amine .mek .lōr eth ə .mēn, .lȯr n a nitrogen mustard administered by injection in the form of its hydrochloride C5H11Cl2N·HCl in the palliative treatment of neoplastic diseases (as Hodgkin s disease and leukemia) …   Medical dictionary

  • mechlorethamine — mech·lor·eth·amine …   English syllables

  • mechlorethamine — ˌmeˌklōrˈethəˌmēn, lȯr , mə̇n noun Etymology: methyl + chloroethyl + amine : a nitrogen mustard C5H11Cl2N used in the form of its hydrochloride in the palliative treatment of some neoplastic diseases * * * /me klawr eth euh meen , klohr /, n.… …   Useful english dictionary

  • mechlorethamine hydrochloride — It is cytotoxic for all cells, but with a special affinity for bone marrow, lymphatic tissues, and rapidly proliferating cells of certain neoplasms. Used for the palliative treatment of Hodgkin disease, lymphosarcoma, and certain chronic… …   Medical dictionary

  • MOPP — • mechlorethamine, Oncovin, pro carbazine, prednisone; • mission oriented protective posture [clothing] …   Dictionary of medical acronyms & abbreviations

  • MOPP — Acronym for mechlorethamine, oncovin (vincristine), procarbazine, and prednisone, a chemotherapy regimen used in the treatment of Hodgkin disease. * * * mechlorethamine, Oncovin, pro carbazine, prednisone; mission oriented protective posture… …   Medical dictionary

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