| Size | Price | Stock | Qty |
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| Targets |
Bicalutamide sulfide targets the androgen receptor (AR), a nuclear hormone receptor that mediates the effects of androgens such as testosterone and dihydrotestosterone. As a nonsteroidal antiandrogen, it competitively binds to the AR ligand-binding domain, blocks androgen binding, prevents nuclear translocation and co-activator recruitment, thereby inhibiting AR-mediated transcriptional activation. This mechanism is the same as that of the parent drug Bicalutamide, though the sulfide may have different binding affinity or metabolic stability.
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| ln Vitro |
No specific in vitro activity data for Bicalutamide sulfide is available in the search results. However, as a structural analog of Bicalutamide (an FDA-approved AR antagonist used for prostate cancer), the sulfide derivative is expected to exhibit similar antiandrogenic activity, binding to the AR and inhibiting AR-dependent gene expression. The sulfide group may affect the compound's potency, selectivity, or off-target activity compared to the sulfone. Biological activity is inferred from its classification as an antiandrogen.
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| ln Vivo |
Bicalutamide sulfide has not been studied as a drug candidate in vivo. As an impurity of Bicalutamide (Casodex), the parent drug has well-documented in vivo efficacy. Bicalutamide (50 mg/day in humans) is used for the treatment of prostate cancer, often in combination with a GnRH agonist. In animal models, Bicalutamide (5-20 mg/kg, oral) inhibits tumor growth in androgen-dependent xenograft models (e.g., LNCaP prostate cancer). The sulfide impurity is not evaluated therapeutically but may be used as a reference standard.
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| Enzyme Assay |
Androgen receptor binding assay (competitive binding): Purified human AR ligand-binding domain (AR-LBD) is incubated in binding buffer (20 mM Tris-HCl pH 7.4, 150 mM KCl, 1 mM EDTA, 1 mM DTT, 0.1% BSA) with 1 nM [3H]-R1881 (synthetic androgen) and varying concentrations of Bicalutamide sulfide (0.1 nM to 100 microM) at 4degC for 16-20 h. Bound radioligand is separated from free using dextran-coated charcoal. Radioactivity is counted, and IC₅0 is calculated. Ki is determined using the Cheng-Prusoff equation. Bicalutamide sulfide is expected to inhibit binding with potency similar to bicalutamide (Ki ~100-200 nM).
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| Cell Assay |
AR transcriptional activity reporter assay: AR-positive LNCaP or CWR22Rv1 human prostate cancer cells are seeded in 96-well plates (2×10⁴ cells/well) in RPMI-1640 containing 10% charcoal-stripped FBS for 24 h. Cells are transfected with an androgen-responsive luciferase reporter plasmid (ARE-Luc) using Lipofectamine 3000. After 24 h, cells are treated with 1 nM R1881 (androgen agonist) and varying concentrations of Bicalutamide sulfide (0.1 nM to 100 microM) for 24-48 h. Luciferase activity is measured. The IC₅0 for inhibition of R1881-induced AR transactivation is calculated. The sulfide is expected to have an IC₅0 in the low nM to low microM range, similar to bicalutamide.
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| Animal Protocol |
Prostate cancer xenograft model (for Bicalutamide sulfide, not published; protocol for parent drug): Male athymic nude mice (6-8 wk) are subcutaneously inoculated with 5×10⁶ AR-positive LNCaP cells in 0.1 mL PBS/Matrigel (1:1). When tumors reach ~100-150 mm3, mice are randomized into treatment groups (n=8-10/group). Bicalutamide sulfide is formulated in 0.5% methylcellulose and administered orally at doses of 5-50 mg/kg once daily for 4-6 weeks. Tumor volume is measured every 3 days using digital calipers, and body weight is monitored. Serum prostate-specific antigen (PSA, a marker of AR activity) is measured by ELISA. This protocol would be used if the sulfide were being evaluated as a drug candidate, but no such studies are reported.
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| ADME/Pharmacokinetics |
No specific PK data for Bicalutamide sulfide is available. The parent drug Bicalutamide has a long half-life (~6-10 days in humans, ~1-3 days in rodents), high protein binding (>96%), and is slowly metabolized. The sulfide is an impurity and may have different pharmacokinetic properties, including faster clearance due to the less stable sulfide group, which is more susceptible to oxidation (which may convert it back to the sulfone). The compound may be metabolized by CYP3A4, as is the case for bicalutamide.
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| Toxicity/Toxicokinetics |
For Bicalutamide sulfide, no specific toxicology data is available. As an impurity of an approved drug, it is considered a reference standard and is manufactured in small quantities. The parent drug Bicalutamide is generally well-tolerated; common adverse effects include hot flashes, gynecomastia, breast tenderness, and fatigue. Hepatotoxicity is rare but serious. The sulfide impurity may have a different safety profile, but it is not administered to humans. Standard safety precautions apply: use PPE (gloves, lab coat, goggles), work in a fume hood, avoid inhalation and skin contact.
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| References | |
| Additional Infomation |
Bicalutamide sulfide (CAS# 90356-78-8) is a research-grade nonsteroidal antiandrogen and an impurity of the FDA-approved drug Bicalutamide (Casodex, used for prostate cancer). It is not an approved drug. The compound is used as a reference standard in pharmaceutical quality control and for research on androgen-responsive diseases. It is for research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C18H14F4N2O2S
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|---|---|
| Molecular Weight |
398.37
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| Exact Mass |
398.071
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| CAS # |
90356-78-8
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| Related CAS # |
N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)thio)-2-hydroxy-2-methylpropanamide
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| PubChem CID |
9800987
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
2
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
27
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| Complexity |
571
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(CSC1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
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| InChi Key |
GCGWWKKSGPETMI-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H14F4N2O2S/c1-17(26,10-27-14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
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| Chemical Name |
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfanyl-2-hydroxy-2-methylpropanamide
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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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 2.5102 mL | 12.5511 mL | 25.1023 mL | |
| 5 mM | 0.5020 mL | 2.5102 mL | 5.0205 mL | |
| 10 mM | 0.2510 mL | 1.2551 mL | 2.5102 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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