Ranimustine ( INN, marketed under the tradename Cymerin; also known as MCNU) is a nitrosourea

alkylating agent Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting ...

approved in

Japan Japan is an island country in East Asia. Located in the Pacific Ocean off the northeast coast of the Asia, Asian mainland, it is bordered on the west by the Sea of Japan and extends from the Sea of Okhotsk in the north to the East China Sea ...

for the treatment of chronic myelogenous

leukemia Leukemia ( also spelled leukaemia; pronounced ) is a group of blood cancers that usually begin in the bone marrow and produce high numbers of abnormal blood cells. These blood cells are not fully developed and are called ''blasts'' or '' ...

and polycythemia vera. It has never been filed for

FDA The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...

evaluation in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

, where it is not marketed.

Synthesis

Ranimustine is made by reacting the

primary amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...

of a

pyranose In organic chemistry, pyranose is a collective term for saccharides that have a chemical structure that includes a six-membered ring consisting of five carbon atoms and one oxygen atom (a heterocycle). There may be other carbons external to the ...

sugar (2) with ''o''-nitrophenyl N-(2-chloroethyl)-N-nitrosocarbamate (1) to form the nitrosourea group.

References

External links

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Cymerin サイメリン
(PDF) Mitsubishi Tanabe Pharma. October 2007. Alkylating antineoplastic agents Nitrosamines Nitrosoureas Ureas Chloroethyl compounds {{antineoplastic-drug-stub