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65886-71-7, Fazarabine, CAS:65886-71-7

65886-71-7, Fazarabine,
CAS:65886-71-7
C8H12N4O5 / 244.205

Fazarabine, 法扎拉滨

Fazarabine is an orally-active pyrimidine analogue of an aza-substituted cytidine in which the ribose moiety is replaced by an arabinose sugar. Similar in action to cytarabine, fazarabine is phosphorylated by deoxycytidine kinase to a triphosphate form which competes with thymidine for incorporation into DNA; its incorporation into DNA inhibits DNA synthesis, resulting in tumor cell death and tumor necrosis. The presence of deoxycytidine kinase in a tumor is a determinant of tumor sensitivity to this drug. (NCI04)

Fazarabine is an N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-arabinofuranosyl residue via an N-glycosidic linkage. A synthetic analogue of cytosine arabinoside and 5-azacytidine that incorporates structural features of both compounds, it shows good activity against a variety of transplanted tumors. It has a role as an antineoplastic agent. It is a N-glycosyl-1,3,5-triazine and a nucleoside analogue. It derives from a beta-D-arabinofuranose.

Fazarabine is a nucleoside analog that has been shown to be a potent inhibitor of the enzyme fyn tyrosine kinase and to have cytotoxic effects on human leukemia HL-60 cells. The chemical stability of fazarabine has been demonstrated in methyltransferase inhibition studies. Fazarabine is also an anti-cancer compound with selective toxicity towards colorectal adenocarcinoma cells. Fazarabine inhibits cell proliferation by inhibiting protein synthesis, which may be due to its ability to act as a DNA template, or its receptor activity. Fazarabine also has immunosuppressive properties and can be used for the treatment of autoimmune diseases such as rheumatoid arthritis, Crohn's disease, and psoriasis.

CAS Number65886-71-7
Product NameFazarabine
IUPAC Name4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
Molecular FormulaC8H12N4O5
Molecular Weight244.205 g/mol
InChIInChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5+,6-/m1/s1
InChI KeyNMUSYJAQQFHJEW-ARQDHWQXSA-N
SMILESC1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
SolubilityWater > 16 (mg/mL)
Ethanol insoluble (mg/mL)
Dimethylsulfoxide > 165 (mg/mL)
Synonyms1-beta-D-arabinosyl-5-azacytosine, 5-azacytosine arabinoside, ara-5-aza-Cyd, ara-5-azacytosine, ara-AC, arabinofuranosyl-5-azacytosine, arabinosyl-5-azacytosine, fazarabine, NSC 281272, NSC-281272
Canonical SMILESC1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
Isomeric SMILESC1=NC(=NC(=O)N1[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O)N


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