Ranimustine

Ranimustine

File:Ranimustine (Haworth).svg
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 checkY
PubChem CID	71741
ChemSpider	64785
UNII	RYH2T97J77
E number	{{#property:P628}}
CompTox Dashboard (EPA)	{{#property:P3117}}
ECHA InfoCard	{{#property:P2566}}
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, 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

File:Ranimustine synthesis.svg

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.

External links

• (in Japanese) Cymerin サイメリン (PDF) Mitsubishi Tanabe Pharma. October 2007.