5-benzylacyclouridine

Modify Date: 2024-01-09 17:30:19

5-benzylacyclouridine Structure
5-benzylacyclouridine structure
Common Name 5-benzylacyclouridine
CAS Number 82857-69-0 Molecular Weight 276.28800
Density 1.29g/cm3 Boiling Point N/A
Molecular Formula C14H16N2O4 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of 5-benzylacyclouridine


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].

 Names

Name 5-benzyl-1-(2-hydroxyethoxymethyl)pyrimidine-2,4-dione
Synonym More Synonyms

 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
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

~%

5-benzylacyclouridine Structure

5-benzylacyclou...

CAS#:82857-69-0

Literature: Orr, G. Faye; Musso, David L.; Kelley, James L.; Joyner, Suzanne S.; Davis, Stephen T.; Baccanari, David P. Journal of Medicinal Chemistry, 1997 , vol. 40, # 8 p. 1179 - 1185

~70%

5-benzylacyclouridine Structure

5-benzylacyclou...

CAS#:82857-69-0

Literature: Lin, Tai-Shun; Liu, Mao-Chin Synthetic Communications, 1988 , vol. 18, # 9 p. 931 - 936

~%

5-benzylacyclouridine Structure

5-benzylacyclou...

CAS#:82857-69-0

Literature: Lin, Tai-Shun; Liu, Mao-Chin Synthetic Communications, 1988 , vol. 18, # 9 p. 931 - 936

~%

5-benzylacyclouridine Structure

5-benzylacyclou...

CAS#:82857-69-0

Literature: Orr; Musso; Boswell; Kelley; Joyner; Davis; Baccanari Journal of Medicinal Chemistry, 1995 , vol. 38, # 19 p. 3850 - 3856

~%

5-benzylacyclouridine Structure

5-benzylacyclou...

CAS#:82857-69-0

Literature: Orr; Musso; Boswell; Kelley; Joyner; Davis; Baccanari Journal of Medicinal Chemistry, 1995 , vol. 38, # 19 p. 3850 - 3856

 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%

 Synonyms

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