| Identification | Back Directory | [Name]
5-benzylacyclouridine | [CAS]
82857-69-0 | [Synonyms]
Benzylacyclouridine
5-benzylacyclouridine
5-Benzyl-1-(2-hydroxyethoxymethyl)uracil | [Molecular Formula]
C14H16N2O4 | [MDL Number]
MFCD00866330 | [MOL File]
82857-69-0.mol | [Molecular Weight]
276.29 |
| Chemical Properties | Back Directory | [Melting point ]
144-145 °C(Solv: ethanol (64-17-5)) | [density ]
1.290±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO : 100 mg/mL (361.94 mM; Need ultrasonic) | [form ]
Solid | [pka]
9.43±0.10(Predicted) | [color ]
White to light yellow |
| Hazard Information | Back Directory | [Uses]
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]. | [Definition]
ChEBI: A pyrimidone that is uracil which is substituted by a 2-hydroxyethoxymethyl group at position 1 and a benzyl group at position 5. | [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]. | [storage]
Store at -20°C | [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. PMID:9607574
[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. DOI:10.1016/0006-2952(83)90419-7
[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. DOI:10.1186/1472-6807-9-14 |
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