Ranimustine

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 and polycythemia vera.

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

Synthesis

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.

References

  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.
  2. ↑ 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.
  3. ↑ 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
  4. ↑ 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.