# Ranimustine

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Chemical compound

Pharmaceutical compound

Ranimustine Clinical data Trade names Cymerin Other names 1-(2-chloroethyl)-1-nitroso-3-([(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl)urea AHFS/Drugs.com International Drug Names Routes of administration IV ATC code L01AD07 (WHO) Legal status Legal status In general: ℞ (Prescription only) Identifiers IUPAC name Methyl 6-({[(2-chloroethyl)(nitroso)amino]carbonyl}amino)-6-deoxy-α-D-glucopyranoside CAS Number 58994-96-0 Y PubChem CID 71741 ChemSpider 64785 UNII RYH2T97J77 CompTox Dashboard (EPA) DTXSID501015584 Chemical and physical data Formula C10H18ClN3O7 Molar mass 327.72 g·mol−1 3D model (JSmol) Interactive image SMILES 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 (verify)

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

It has never been filed for [FDA](/source/Food_and_Drug_Administration) evaluation in the [United States](/source/United_States), where it is not marketed.

## Synthesis

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

## References

1. **[^](#cite_ref-pmid2817908_1-0)** 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](/source/PMID_(identifier)) [2817908](https://pubmed.ncbi.nlm.nih.gov/2817908).

1. **[^](#cite_ref-pmid3196045_2-0)** 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](/source/PMID_(identifier)) [3196045](https://pubmed.ncbi.nlm.nih.gov/3196045).

1. **[^](#cite_ref-3)** [US patent 4156777](https://worldwide.espacenet.com/textdoc?DB=EPODOC&IDX=US4156777), Goro Kimura, "Process for producing glucopyranose-nitrosourea compounds and novel compounds included therein", issued 1979-05-29, assigned to Tokyo Tanabe Co Ltd

1. **[^](#cite_ref-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](/source/Doi_(identifier)):[10.1002/jps.2600800717](https://doi.org/10.1002%2Fjps.2600800717). [PMID](/source/PMID_(identifier)) [1658297](https://pubmed.ncbi.nlm.nih.gov/1658297).

## External links

- (in Japanese) [Cymerin サイメリン](https://web.archive.org/web/20110814142718/http://di.mt-pharma.co.jp/file/dc/cmr_a.pdf) (PDF) Mitsubishi Tanabe Pharma. October 2007.

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Adapted from the Wikipedia article [Ranimustine](https://en.wikipedia.org/wiki/Ranimustine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Ranimustine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.