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| Targets |
4-Amino-5-bromopyrimidin-2(1H)-one is a synthetic intermediate and pyrimidine analog rather than a direct pharmacological agent. As a building block, it does not have specific biological receptors as its primary targets. The brominated cytosine scaffold is a privileged structure in medicinal chemistry, and the compound has been shown to be a potent anti-HIV agent as a 5-bromocytosine derivative. The amino and bromo substituents provide handles for diverse chemical transformations, including cross-coupling reactions and nucleophilic substitution. Its primary applications are as a synthetic intermediate for antiviral drug discovery.
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| ln Vitro |
In vitro, 4-amino-5-bromopyrimidin-2(1H)-one is used as a biochemical reagent and organic compound for biomedical research. The compound is a 5-bromocytosine derivative that has been shown to be a potent anti-HIV agent. Cellular assays are typically performed on the final compounds synthesized from this building block. The compound's brominated pyrimidine scaffold allows for various chemical transformations, making it valuable for drug discovery, particularly for antiviral agents.
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| ln Vivo |
In vivo data for 4-amino-5-bromopyrimidin-2(1H)-one is limited, as it is primarily a research reagent and synthetic intermediate. The compound is classified for research use only and is not intended for human or veterinary therapeutic applications. However, anti-HIV agents synthesized using this building block have been investigated for their therapeutic potential. The compound's primary value lies in its use as a synthetic intermediate. Specific in vivo data for the parent compound is not available in the public literature.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for 4-amino-5-bromopyrimidin-2(1H)-one are not typically performed, as it is primarily a synthetic intermediate. The compound is used as a building block in the synthesis of antiviral agents. A typical assay involves using the compound in chemical reactions, such as cross-coupling or nucleophilic substitution, to prepare final compounds. The compound is dissolved in organic solvents such as DMSO or ethanol. The resulting products can be evaluated for biological activity. Antiviral assays against HIV or other viruses can be performed on the final synthesized compounds. IC₅₀ values are calculated from dose-response curves.
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| Cell Assay |
Cellular assays for 4-amino-5-bromopyrimidin-2(1H)-one derivatives typically evaluate antiviral activity. A standard protocol involves culturing virus-susceptible cell lines in growth medium at 37°C with 5% CO₂. Cells are infected with virus and treated with synthesized compounds at varying concentrations. Viral replication is assessed by measuring viral antigens or cytopathic effect. Cytotoxicity is evaluated using MTT or similar assays. EC₅₀ and CC₅₀ values are calculated from dose-response curves. The selectivity index is determined.
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| Animal Protocol |
In vivo animal studies for 4-amino-5-bromopyrimidin-2(1H)-one are not standard, as it is a synthetic intermediate rather than a therapeutic candidate. The compound is classified for research use only and is not intended for human or veterinary applications. Any animal studies would typically be conducted on the final antiviral agents synthesized using this building block. These studies would evaluate efficacy in animal models, pharmacokinetics, and safety. The compound's primary value lies in its use as a synthetic intermediate.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 4-amino-5-bromopyrimidin-2(1H)-one is limited, as it is primarily a research reagent. The compound has a molecular weight of 189.99 g/mol and a molecular formula of C₄H₄BrN₃O. It appears as a solid at room temperature. As a brominated pyrimidine, it may undergo metabolic dehalogenation and oxidation. Specific ADME data is not available. The compound is stored in a dry, cool place.
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| Toxicity/Toxicokinetics |
4-Amino-5-bromopyrimidin-2(1H)-one is classified for research use only and is not intended for human or veterinary applications. Standard safety precautions include handling with appropriate personal protective equipment (gloves, lab coat, safety goggles) in a well-ventilated area. The compound should be stored in a dry, cool place away from incompatible materials. Acute toxicity data is not readily available in the public literature. As with all research chemicals, appropriate laboratory safety practices should be followed. No specific LD₅₀ values are available in the public domain.
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| References | |
| Additional Infomation |
4-Amino-5-bromopyrimidin-2(1H)-one (5-Bromocytosine, CAS 2240-25-7) is a biochemical reagent with the molecular formula C₄H₄BrN₃O and a molecular weight of 189.99 g/mol. It is a 5-bromocytosine derivative that has been shown to be a potent anti-HIV agent. The compound is classified as a research-use-only reagent and is available from multiple commercial suppliers.
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| Molecular Formula |
C4H4BRN3O
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|---|---|
| Molecular Weight |
190.00
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| Exact Mass |
263.071
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| CAS # |
2240-25-7
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| PubChem CID |
75233
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
359.5±42.0 °C at 760 mmHg
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| Melting Point |
240-243ºC
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| Flash Point |
171.2±27.9 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.583
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| LogP |
3.14
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
9
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| Complexity |
208
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| Defined Atom Stereocenter Count |
0
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| SMILES |
BrC1C([H])=NC(N([H])C=1N([H])[H])=O
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| InChi Key |
QFVKLKDEXOWFSL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C4H4BrN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
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| Chemical Name |
6-amino-5-bromo-1H-pyrimidin-2-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~12.5 mg/mL (~65.8 mM; with ultrasonication)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (6.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 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 DMSO stock solution (12.5 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and 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: ≥ 1.25 mg/mL (6.58 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 DMSO stock solution (12.5 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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: ≥ 1.25 mg/mL (6.58 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 DMSO stock solution (12.5 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.2632 mL | 26.3158 mL | 52.6316 mL | |
| 5 mM | 1.0526 mL | 5.2632 mL | 10.5263 mL | |
| 10 mM | 0.5263 mL | 2.6316 mL | 5.2632 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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