Jump to content
 







Main menu
    


Navigation  


●Main page
 ●Contents
 ●Current events
 ●Random article
 ●About Wikipedia
 ●Contact us
 ●Donate
  



Contribute  


●Help
 ●Learn to edit
 ●Community portal
 ●Recent changes
 ●Upload file
  







Search  

































●Create account

●Log in
 









●Create account
 ● Log in
  



Pages for logged out editors learn more  


●Contributions
 ●Talk
  


















Contents

   



(Top)
  


1 Synthesis  




2 References  




3 External links  













Ranimustine






●فارسی
 ●日本語
 ●Русский
 ●Српски / srpski
 ●Srpskohrvatski / српскохрватски
 ●Tiếng Việt
  
Edit links
  








●Article
 ●Talk
  
















●Read
 ●Edit
 ●View history
  







Tools
    


Actions  


●Read
 ●Edit
 ●View history
  



General  


●What links here
 ●Related changes
 ●Upload file
 ●Special pages
 ●Permanent link
 ●Page information
 ●Cite this page
 ●Get shortened URL
 ●Download QR code
 ●Wikidata item
  



Print/export  


●Download as PDF
 ●Printable version
  



In other projects  


●Wikimedia Commons
  















Appearance
    

 





From Wikipedia, the free encyclopedia
  

Ranimustine
Clinical data
Trade namesCymerin
Other names1-(2-chloroethyl)-1-nitroso-3-([(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl)urea
AHFS/Drugs.comInternational Drug Names
Routes of
administration		IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers

  • Methyl 6-({[(2-chloroethyl)(nitroso)amino]carbonyl}amino)-6-deoxy-α-D-glucopyranoside

CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H18ClN3O7
Molar mass327.72 g·mol−1
3D model (JSmol)

  • CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CNC(=O)N(CCCl)N=O)O)O)O

  • InChI=1S/C10H18ClN3O7/c1-20-9-8(17)7(16)6(15)5(21-9)4-12-10(18)14(13-19)3-2-11/h5-9,15-17H,2-4H2,1H3,(H,12,18)/t5-,6-,7+,8-,9+/m1/s1

  • Key:AHHFEZNOXOZZQA-ZEBDFXRSSA-N

  (verify)

Ranimustine (INN, marketed under the tradename Cymerin; also known as MCNU) is a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia[1] and polycythemia vera.[2]

It has never been filed for FDA evaluation in the United States, where it is not marketed.

Synthesis

[edit]

Ranimustine is made by reacting the primary amine of a pyranose sugar (2) with o-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (1) to form the nitrosourea group.[3] [4]

References

[edit]
  1. ^ Kitajima K, Adachi T, Takahashi I, Nakada H, Osada K, Fukuda S, et al. (November 1989). "[Chemotherapy of chronic myelogenous leukemia--VP(M) regimen initiated during its chronic phase, and evaluation of MCNU in the phase of blastic crisis]". Gan to Kagaku Ryoho. Cancer & Chemotherapy (in Japanese). 16 (11): 3573–3579. PMID 2817908.
  • ^ Nagai M, Tasaka T, Kamano H, Ohnishi H, Taoka T, Ikeda K, et al. (December 1988). "[Therapeutic effect of ranimustine (MCNU) on essential thrombocythemia and polycythemia vera]". Gan to Kagaku Ryoho. Cancer & Chemotherapy (in Japanese). 15 (12): 3267–3270. PMID 3196045.
  • ^ US patent 4156777, Goro Kimura, "Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein", issued 1979-05-29, assigned to Tokyo Tanabe Co Ltd 
  • ^ Sosnovsky G, Rao NU (July 1991). "In the search for new anticancer drugs. XXIII: Exploration of a predictive design for anticancer drugs of carbohydrates containing N-nitrosochloroethylamino, N-nitrosomethyl, and N-nitrosoaminoxyl components". Journal of Pharmaceutical Sciences. 80 (7): 693–699. doi:10.1002/jps.2600800717. PMID 1658297.
    • [edit]
    Stub icon

    This antineoplasticorimmunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

  • t
  • e

    • Retrieved from "https://en.wikipedia.org/w/index.php?title=Ranimustine&oldid=1233500626"
    Categories: 
    ●Alkylating antineoplastic agents
     ●Nitrosamines
     ●Nitrosoureas
     ●Ureas
     ●Chloroethyl compounds
     ●Antineoplastic and immunomodulating drug stubs
     Hidden categories: 
    ●CS1 Japanese-language sources (ja)
     ●Articles with short description
     ●Short description matches Wikidata
     ●Drugs with non-standard legal status
     ●Articles without EBI source
     ●Chemical pages without DrugBank identifier
     ●Articles without KEGG source
     ●Articles with Japanese-language sources (ja)
     ●All stub articles
      


    ●This page was last edited on 9 July 2024, at 11:52 (UTC).
    ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.


    ●Privacy policy
    ●About Wikipedia
    ●Disclaimers
    ●Contact Wikipedia
    ●Code of Conduct
    ●Developers
    ●Statistics
    ●Cookie statement
    ●Mobile view


    Wikimedia Foundation
    Powered by MediaWiki