5-benzylacyclouridine

Names

[ Name ]:
5-benzylacyclouridine

[Synonym ]:
2,4(1H,3H)-Pyrimidinedione,1-((2-hydroxyethoxy)methyl)-5-(phenylmethyl)
Benzylacyclouridine
1-((2-HYDROXYETHOXY)METHYL)-5-BENZYLPYRIMIDINE-2,4(1H,3H)-DIONE
5-Benzyl-1-(2'-hydroxyethoxymethyl)uracil
5-Bacu
BAU
5-Benzylacyclouridine

Biological Activity

[Description]:

Benzylacyclouridine (BAU) is a potent and specific inhibitor of uridine phosphorylase, the first enzyme in the catabolism of uridine. Benzylacyclouridine can modulate the cytotoxic side effects of 5-fluorouracil (5-FU) and its derivatives[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[Target]

uridine phosphorylase[1]

[In Vitro]

Benzylacyclouridine increases 5-FU-induced cytotoxicity in a number of human cancer cell lines[1]. Benzylacyclouridine (20-100 μM) reduces the rapid clearance of trace amounts of either [14C]uridine or hyperphysiologic concentrations of non-labeled uridine by the isolated rat liver perfused with an artificial oxygen carrier[2].

[In Vivo]

Benzylacyclouridine (p.o. or i.v.) arrests the rapid degradation of a tracer dose of uridine into uracil in dogs and pigs[1]. Benzylacyclouridine exhibits the t1/2 of 1.8-3.6 h in dogs, with bioavailability levels of 85% (30 mg/kg) and 42.5% (120 mg/kg)[1]. Benzylacyclouridine (120 mg/kg) exhibits the t1/2 of 1.6-2.3 h, with a bioavailability of 40% in pigs[1].

[References]

[1]. Pizzorno G, et, al. Phase I clinical and pharmacological studies of benzylacyclouridine, a uridine phosphorylase inhibitor. Clin Cancer Res. 1998 May;4(5):1165-75.

[2]. Monks A, et, al. Effect of 5-benzylacyclouridine, a potent inhibitor of uridine phosphorylase, on the metabolism of circulating uridine by the isolated rat liver. Biochem Pharmacol. 1983 Jul 1;32(13):2003-9.

[3]. Roosild TP, et, al. Implications of the structure of human uridine phosphorylase 1 on the development of novel inhibitors for improving the therapeutic window of fluoropyrimidine chemotherapy. BMC Struct Biol. 2009 Mar 16;9:14.

Chemical & Physical Properties

[ Density]:
1.29g/cm3

[ Molecular Formula ]:
C₁₄H₁₆N₂O₄

[ Molecular Weight ]:
276.28800

[ Exact Mass ]:
276.11100

[ PSA ]:
84.58000

[ LogP ]:
0.50610

[ Index of Refraction ]:
1.583

Safety Information

[ Hazard Codes ]:
Xi

[ HS Code ]:
2933599090

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2933599090

[ Summary ]:
2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%