Ranimustine
Chemical compound
- L01AD07 (WHO)
- In general: ℞ (Prescription only)
- Methyl 6-({[(2-chloroethyl)(nitroso)amino]carbonyl}amino)-6-deoxy-α-D-glucopyranoside
- 58994-96-0
Y
- 71741
- 64785
- RYH2T97J77
- DTXSID501015584
- Interactive image
- CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CNC(=O)N(CCCl)N=O)O)O)O
InChI
- 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
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
![](http://upload.wikimedia.org/wikipedia/commons/thumb/f/f5/Ranimustine_synthesis.svg/400px-Ranimustine_synthesis.svg.png)
- o-nitrophenyl N-(2-chloroethyl)N-nitrosocarbamate, PC13231923 (1)
- (2R,3S,4S,5R,6S)-2-(aminomethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol [5155-47-5] (2)
References
- ^ Kitajima K, Adachi T, Takahashi I, 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 (in Japanese). 16 (11): 3573–9. PMID 2817908.
- ^ Nagai M, Tasaka T, Kamano H, et al. (December 1988). "[Therapeutic effect of ranimustine (MCNU) on essential thrombocythemia and polycythemia vera]". Gan To Kagaku Ryoho (in Japanese). 15 (12): 3267–70. PMID 3196045.
- ^ Prous, J.; Castaer, J.; Ranimustine. Drugs Fut 1986, 11, 9, 762.
- ^ Goro Kimura, U.S. patent 4,156,777 (1979 to Tokyo Tanabe Co Ltd).
- ^ Sosnovsky, George; Rao, Nuti Uma Maheshwara (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.
- (in Japanese) Cymerin サイメリン (PDF) Mitsubishi Tanabe Pharma. October 2007.
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(M phase)
Block microtubule assembly | |
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Block microtubule disassembly |
inhibitor
DNA precursors/ antimetabolites (S phase) |
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Topoisomerase inhibitors (S phase) |
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Crosslinking of DNA (CCNS) |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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