Benzylacyclouridine (BAU) is a potent and specific inhibitor of uridine phosphorylase, the first enzyme in uridine catabolism. Benzylcyclouridine can modulate the cytotoxic side effects of 5-fluorouracil (5-FU) and its analogues.

Physicochemical Properties

Molecular Formula	C14H16N2O4
Molecular Weight	276.29
Exact Mass	276.111
CAS #	82857-69-0
PubChem CID	54929
Appearance	White to light yellow solid powder
Density	1.29g/cm3
Index of Refraction	1.583
LogP	0.506
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	6
Heavy Atom Count	20
Complexity	389
Defined Atom Stereocenter Count	0
InChi Key	SPJAGILXQBHHSZ-UHFFFAOYSA-N
InChi Code	InChI=1S/C14H16N2O4/c17-6-7-20-10-16-9-12(13(18)15-14(16)19)8-11-4-2-1-3-5-11/h1-5,9,17H,6-8,10H2,(H,15,18,19)
Chemical Name	5-benzyl-1-(2-hydroxyethoxymethyl)pyrimidine-2,4-dione
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	uridine phosphorylase[1]
ln Vitro	In many human cancer cell lines, benzolacyclouridine boosts the cytotoxicity caused by 5-FU [1]. By infusing artificial oxygen carriers into isolated rat livers, benzolacyclouridine (20-100 μM) decreases the fast clearance of supraphysiological doses of unlabeled uridine or trace amounts of [14C]uridine [2].
ln Vivo	In dogs and pigs, benzocyclouridine (orally or intravenously) inhibits the fast breakdown of tracer doses of uridine to uracil [1]. When administered to dogs, benzylacyclouridine has a t1/2 of 1.8-3.6 hours and a bioavailability of 85% (30 mg/kg) and 42.5% (120 mg/kg) [1]. Pigs treated with 120 mg/kg of benzoylacyclouridine have a t1/2 of 1.6-2.3 h and a 40% bioavailability [1].
References	[1]. Phase I clinical and pharmacological studies of benzylacyclouridine, a uridine phosphorylase inhibitor. Clin Cancer Res. 1998 May;4(5):1165-75. [2]. 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]. 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.
Additional Infomation	5-benzyl-1-(2-hydroxyethoxymethyl)uracil is a pyrimidone that is uracil which is substituted by a 2-hydroxyethoxymethyl group at position 1 and a benzyl group at position 5. It is a primary alcohol, a hydroxyether and a pyrimidone. It is functionally related to a uracil.

Solubility Data

Solubility (In Vitro)

DMSO: 100 mg/mL (361.94 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (9.05 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.05 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (9.05 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.6194 mL	18.0969 mL	36.1939 mL
	5 mM	0.7239 mL	3.6194 mL	7.2388 mL
	10 mM	0.3619 mL	1.8097 mL	3.6194 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.