Ranimustine

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]

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)

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.^{[3] [4]}