Jump to content

Enocitabine

From Wikipedia, the free encyclopedia
Enocitabine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
IV
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • N-[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]docosanamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H55N3O6
Molar mass565.796 g·mol−1
3D model (JSmol)
  • O=C(N/C/1=N/C(=O)N(\C=C\1)[C@@H]2O[C@@H]([C@@H](O)[C@@H]2O)CO)CCCCCCCCCCCCCCCCCCCCC
  • InChI=1S/C31H55N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(36)32-26-22-23-34(31(39)33-26)30-29(38)28(37)25(24-35)40-30/h22-23,25,28-30,35,37-38H,2-21,24H2,1H3,(H,32,33,36,39)/t25-,28-,29+,30-/m1/s1 ☒N
  • Key:SAMRUMKYXPVKPA-VFKOLLTISA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Enocitabine (INN, marketed under the brand name Sunrabin) is a nucleoside analog used as chemotherapy.

Sunrabin contains the emulsifier HCO-60, which can cause allergic reactions.[1]

Synthesis[edit]

ChemDrug Synthesis:[2][3] Patent:[4]
  • cytarabine [147-94-4] (1)
  • Palmitic anhydride [623-65-4] (2)
  • cytidine [65-46-3] (4)
  • N-Hexadecanoylcytidine [60107-19-9] (5)

References[edit]

  1. ^ Tatetsu H, Asou N, Nakamura M, et al. (July 2003). "[Allergic reaction against an emulsifier, HCO-60, contained in multamin and enocitabine]". Rinsho Ketsueki (in Japanese). 44 (7): 471–3. PMID 12931567.
  2. ^ Cabanillas, F.; Castaer, J.; Palmitoyl/Staroyl Ara-C. Drugs Fut 1980, 5, 12, 617.
  3. ^ Akiyama, M., Ohishi, J., Shirai, T., Akashi, K., Yoshida, K.-I., Nishikido, J., Hayashi, H., Usubuchi, Y., Nishimura, D., Itoh, H., Shibuya, C., Ishida, T. (1978). "The synthesis of new derivatives of 1-.BETA.-D-arabinofuranosylcytosine". Chemical and Pharmaceutical Bulletin. 26 (3): 981–984. doi:10.1248/cpb.26.981.
  4. ^ Kageyasu Akashi, et al. DE2426304 (1988 to Asahi Chemical Industry Co Ltd).