GLPG-0492 (GLPG0492) is a novel and potent androgen receptor modulator with anabolic activity on muscle. It has the potential to be used for muscle atrophy. GLPG0492 treatment partially prevents immobilization-induced muscle atrophy with a trend to promote muscle fiber hypertrophy in a dose-dependent manner.
Physicochemical Properties
| Molecular Formula | C19H14F3N3O3 |
| Molecular Weight | 389.3342 |
| Exact Mass | 389.098 |
| CAS # | 1215085-92-9 |
| Related CAS # | GLPG0492 (R enantiomer);1215085-93-0 |
| PubChem CID | 59317190 |
| Appearance | White to off-white solid powder |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 544.0±60.0 °C at 760 mmHg |
| Flash Point | 282.8±32.9 °C |
| Vapour Pressure | 0.0±1.5 mmHg at 25°C |
| Index of Refraction | 1.627 |
| LogP | 2.07 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 28 |
| Complexity | 683 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CN1C(=O)N(C(=O)[C@@]1(CO)C2=CC=CC=C2)C3=CC(=C(C=C3)C#N)C(F)(F)F |
| InChi Key | VAJGULUVTFDTAS-GOSISDBHSA-N |
| InChi Code | InChI=1S/C19H14F3N3O3/c1-24-17(28)25(14-8-7-12(10-23)15(9-14)19(20,21)22)16(27)18(24,11-26)13-5-3-2-4-6-13/h2-9,26H,11H2,1H3/t18-/m1/s1 |
| Chemical Name | 4-[(4S)-4-(hydroxymethyl)-3-methyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile |
| Synonyms | GLPG0492 GLPG 0492 GLPG-0492 |
| 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
| References |
[1]. Identification of a 4-(hydroxymethyl)diarylhydantoin as a selective androgen receptor modulator. J Med Chem. 2012 Oct 11;55(19):8236-47. [2]. GLPG0492, a novel selective androgen receptor modulator, improves muscle performance in the exercised-mdx mouse model of muscular dystrophy. Pharmacol Res. 2013 Jun;72:9-24. [3]. Characterization of GLPG0492, a selective androgen receptor modulator, in a mouse model of hindlimb immobilization. BMC Musculoskelet Disord. 2014 Sep 3;15:291. |
| Additional Infomation | Glpg0492 is under investigation in clinical trial NCT01130818 (First-in-Human Single Ascending Dose of GLPG0492). |
Solubility Data
| Solubility (In Vitro) | DMSO : ≥ 50 mg/mL (~128.43 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.42 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 (6.42 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 (6.42 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 | 2.5685 mL | 12.8426 mL | 25.6852 mL | |
| 5 mM | 0.5137 mL | 2.5685 mL | 5.1370 mL | |
| 10 mM | 0.2569 mL | 1.2843 mL | 2.5685 mL |