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| Other Sizes |
| Targets |
The primary target of this compound is the androgen receptor (AR), as it contains the 3-fluoro-4-(methylcarbamoyl)phenyl motif which serves as the core AR-binding element in nonsteroidal androgen receptor antagonists. The compound is structurally related to Enzalutamide, a well-known AR antagonist used in prostate cancer treatment. The 3-fluoro-4-(methylcarbamoyl)phenyl group is critical for binding to the androgen receptor's ligand-binding domain, where it competes with endogenous androgens such as testosterone and dihydrotestosterone. By blocking AR signaling, compounds with this pharmacophore can inhibit androgen-dependent tumor growth.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
In vitro studies on this compound are limited as it is primarily characterized as an impurity standard for Enzalutamide rather than a therapeutic agent. However, related compounds containing the 3-fluoro-4-(methylcarbamoyl)phenyl motif have demonstrated potent androgen receptor antagonism in cell-based assays. Standard in vitro assays include AR binding studies using radiolabeled ligands, reporter gene assays measuring AR transcriptional activity, and proliferation assays using androgen-dependent prostate cancer cell lines such as LNCaP or VCaP. Its role as an impurity standard means it is used primarily in analytical method development and quality control. |
| ln Vivo |
In vivo studies on this compound are limited as it is primarily characterized as an impurity standard for Enzalutamide rather than a therapeutic agent. Related compounds containing the 3-fluoro-4-(methylcarbamoyl)phenyl motif have been evaluated in xenograft models of prostate cancer, where they demonstrate inhibition of tumor growth through AR antagonism. The compound's role as an impurity standard means it is used primarily in analytical method development and quality control rather than in pharmacological studies.
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| Enzyme Assay |
Non-cell-based enzyme or receptor binding assays for this compound typically involve competitive binding studies using purified androgen receptor protein. Standard protocols include incubating varying concentrations of the test compound with the AR ligand-binding domain and a radiolabeled androgen (e.g., [³H]-R1881 or [³H]-DHT) in appropriate buffer systems, followed by separation of bound from free ligand via filtration or charcoal adsorption. Binding affinity (Ki or IC₅₀ values) is calculated using nonlinear regression analysis. Surface plasmon resonance (SPR) or isothermal titration calorimetry (ITC) may also be employed to measure direct binding interactions.
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| Cell Assay |
Cell-based assays for this compound typically utilize androgen receptor-positive prostate cancer cell lines such as LNCaP or VCaP. Standard protocols involve culturing cells in androgen-depleted media at 37°C in 5% CO₂, followed by treatment with varying concentrations of the compound (typically 0.01-100 μM) for 24-72 hours. AR transcriptional activity is measured using luciferase reporter gene assays, while cell proliferation is assessed using MTT or CellTiter-Glo assays. The compound's effects on AR target gene expression (e.g., PSA, TMPRSS2) can be evaluated by qPCR. As an impurity standard, the compound is used primarily in analytical method development and quality control.
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| Animal Protocol |
In vivo animal studies for this compound would typically involve xenograft models of prostate cancer in athymic nude mice. Standard protocols include subcutaneous implantation of AR-positive prostate cancer cells (e.g., LNCaP or VCaP), followed by administration of the test compound via oral gavage at doses ranging from 1-50 mg/kg body weight. Tumor volume is measured twice weekly using calipers, and body weight is monitored for toxicity assessment. As an impurity standard, the compound is used primarily in analytical method development and quality control rather than in pharmacological studies.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties for this compound can be inferred from structurally related AR antagonists such as Enzalutamide. As a small molecule with moderate lipophilicity, it is expected to have reasonable oral bioavailability. The compound shows moderate solubility in organic solvents and can be formulated for in vitro and in vivo studies. For in vivo administration, formulations using suitable co-solvent systems may be employed. The compound should be stored as powder at -20°C for long-term preservation. Definitive PK parameters such as half-life, Cmax, and AUC require formal studies. As an impurity standard, PK data may not be available.
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| Toxicity/Toxicokinetics |
Toxicological data for this specific compound are limited as it is primarily used as an impurity standard for Enzalutamide rather than as a therapeutic agent. Related AR antagonists have been extensively studied and show manageable toxicity profiles, including fatigue, hypertension, and hepatotoxicity at therapeutic doses. Appropriate safety precautions should be observed during handling, including the use of personal protective equipment and work in well-ventilated areas. The compound may cause skin and eye irritation upon contact. Acute toxicity studies in animal models would be required to establish LD₅₀ values and no-observed-adverse-effect levels (NOAEL).
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| References | |
| Additional Infomation |
2-((3-Fluoro-4-(methylcarbamoyl)phenyl)amino)-2-methylpropanoic acid is a carboxylic acid derivative and known impurity of Enzalutamide, a nonsteroidal androgen receptor antagonist used in the treatment of prostate cancer. The compound contains the 3-fluoro-4-(methylcarbamoyl)phenyl motif, which serves as the core AR-binding element in nonsteroidal androgen receptor antagonists. As an impurity standard, it is supplied with detailed characterization data compliant with regulatory guidelines for analytical method development and quality control applications. It is not an approved drug and has not undergone clinical trials as a therapeutic agent; it is strictly for research purposes.
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| Molecular Formula |
C12H15FN2O3
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|---|---|
| Molecular Weight |
254.26
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| Exact Mass |
254.106
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| CAS # |
1289942-66-0
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| PubChem CID |
67106897
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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 |
455.1±45.0 °C at 760 mmHg
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| Flash Point |
229.0±28.7 °C
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| Vapour Pressure |
0.0±1.2 mmHg at 25°C
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| Index of Refraction |
1.571
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| LogP |
0.46
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
18
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| Complexity |
333
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(NC1=CC=C(C(NC)=O)C(F)=C1)C(O)=O
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| InChi Key |
IAAHEGARPMZSTJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H15FN2O3/c1-12(2,11(17)18)15-7-4-5-8(9(13)6-7)10(16)14-3/h4-6,15H,1-3H3,(H,14,16)(H,17,18)
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| Chemical Name |
2-[3-fluoro-4-(methylcarbamoyl)anilino]-2-methylpropanoic acid
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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 |
| 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: 100 mg/mL (393.30 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9330 mL | 19.6649 mL | 39.3298 mL | |
| 5 mM | 0.7866 mL | 3.9330 mL | 7.8660 mL | |
| 10 mM | 0.3933 mL | 1.9665 mL | 3.9330 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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