Troxacitabine

Title: Troxacitabine
CAS Registry Number: 145918-75-8
CAS Name: 4-Amino-1-[(2S,4S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]-2(1H)-pyrimidinone
Additional Names: (-)-2¢-deoxy-3¢-oxacytidine; b-L-(-) dioxolane cytidine; (-)-(2S,4S)-1-[2-(hydroxymethyl)-1,3-dioxolan-4-yl]cytosine; L-OddC
Manufacturers' Codes: (-)-BCH-204; BCH-4556
Trademarks: Troxatyl (Shire Biochem)
Molecular Formula: C8H11N3O4
Molecular Weight: 213.19
Percent Composition: C 45.07%, H 5.20%, N 19.71%, O 30.02%
Literature References: Synthetic nucleoside analog with stereochemically unnatural b-L configuration. Prepn: Y.-C. Cheng et al., WO 9218517 (1992 to Yale Univ. and Univ. Georgia Res. Found.); B. R. Belleau et al., Tetrahedron Lett. 33, 6949 (1992); H. O. Kim et al., J. Med. Chem. 36, 519 (1993). Resolution of enantiomers: M. P. DiMarco et al., J. Chromatogr. 645, 107 (1993). Structure activity study: T. S. Mansour et al., Nucleosid. Nucleotid. 14, 627 (1995). Clinical pharmacokinetics: J. S. deBono et al. J. Clin. Oncol. 20, 96 (2001). Population pharmacokinetics: C. K. K. Lee et al., Clin. Cancer Res. 12, 2158 (2006). Clinical evaluation in refractory leukemia: F. J. Giles et al., ibid. 20, 656 (2002); in imatinib-resistant chronic myelogenous leukemia: idem et al., Leukem. Res. 27, 1091 (2003); in pancreatic cancer: R. Lapointe et al., Ann. Oncol. 16, 289 (2005). Review of pharmacology and clinical development: idem, Expert Rev. Anticancer Ther. 2, 261-266 (2002); G. Ecker, Curr. Opin. Invest. Drugs 3, 1533-1538 (2002).
Properties: mp 176-177°. [a]D25 -38.33° (c = 0.43 in MeOH). uv max (water): 270.0 (pH 7), 278.0 (pH 2), 269.0 (pH 11) ( e 7770, 11970, 8380).
Melting point: mp 176-177°
Optical Rotation: [a]D25 -38.33° (c = 0.43 in MeOH).
Absorption maximum: uv max (water): 270.0 (pH 7), 278.0 (pH 2), 269.0 (pH 11) ( e 7770, 11970, 8380)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.
Troxipide Truxillic Acid Trypan Red Tryparsamide Trypsin

Troxacitabine
Troxacitabine.svg
Systematic (IUPAC) name
4-amino-1-[(2S,4S)-2-(hydroxymethyl)-1,3-dioxolan-4-yl]pyrimidin-2(1H)-one
Clinical data
Legal status  ?
Identifiers
CAS number 145918-75-8 N
ATC code  ?
PubChem CID 151173
ChemSpider 399955 YesY
UNII 60KQZ0388Y YesY
ChEMBL CHEMBL359164 YesY
Chemical data
Formula C8H11N3O4 
Mol. mass 213.19 g/mol
 N (what is this?)  (verify)

Troxacitabine (brand name Troxatyl) is a nucleoside analogue with anticancer activity. Its use is being studied in patients with refractory lymphoproliferative diseases.[1]