Physicochemical Properties
| Molecular Formula | C23H28F4N3O8PS |
| Molecular Weight | 613.51609992981 |
| Exact Mass | 515.15 |
| CAS # | 1198784-72-3 |
| Related CAS # | BI 653048 phosphate;1198784-97-2 |
| PubChem CID | 44543970 |
| Appearance | White to off-white solid powder |
| LogP | 3.7 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 35 |
| Complexity | 879 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | S(CC)(C1=CC2=C(C=N1)NC(=C2)C[C@@](C(F)(F)F)(CC(C)(C)C1C=CC(=CC=1C(N)=O)F)O)(=O)=O.P(=O)(O)(O)O |
| InChi Key | AUIFRJWXYUNPPV-QFIPXVFZSA-N |
| InChi Code | InChI=1S/C23H25F4N3O4S/c1-4-35(33,34)19-8-13-7-15(30-18(13)11-29-19)10-22(32,23(25,26)27)12-21(2,3)17-6-5-14(24)9-16(17)20(28)31/h5-9,11,30,32H,4,10,12H2,1-3H3,(H2,28,31)/t22-/m0/s1 |
| Chemical Name | 2-[(4R)-4-[(5-ethylsulfonyl-1H-pyrrolo[2,3-c]pyridin-2-yl)methyl]-5,5,5-trifluoro-4-hydroxy-2-methylpentan-2-yl]-5-fluorobenzamide |
| Synonyms | BI 653048 BI-653,048 BI653,048 BI 653,048BI-653048 BI653048 BI-653048 phosphate |
| 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
| ln Vitro | BI 653048 represents better drug-like qualities and inhibits CP1A2, CYP2D6, CYP2C9, CYP2C19, and CYP3A4 with IC50 values of 50 µM, 41 µM, 12 µM, 9 µM, and 8 µM, respectively[2]. BI 653048 lowered the affinity to hERG ion channels, with IC50>30 μM, in recombinant HEK293 cells expressing human ERG potassium channels [2]. With an IC50 of 100 nM, BI 653048 suppresses the production of IL-6 in mouse RAW cells when stimulated by TNF[2]. |
| ln Vivo | The ED50 value for the total score is 14 mg/kg. BI 653048 (oral; 3, 10, and 30 mg/kg) treatment significantly reduced pannus and bone resorption (33%) as well as the total score (27%), but at high doses (30 mg/kg) all parameters were significantly reduced (87-96%). At 3 mg/kg, there was no significant reduction in any of the measured histological parameters (ankle joint inflammation, pannus formation, cartilage damage, and bone resorption). |
| Animal Protocol |
Animal/Disease Models: Mice[2] Doses: 3, 10 and 30 mg/kg Route of Administration: Oral Experimental Results: All measured histological parameters were Dramatically diminished at high doses. |
| References |
[1]. Development of a large scale asymmetric synthesis of the glucocorticoid agonist BI 653048 BS H3PO4.J Org Chem. 2013 Apr 19;78(8):3616-35. [2]. Optimization of drug-like properties of nonsteroidal glucocorticoid mimetics and identification of a clinical candidate.ACS Med Chem Lett. 2014 Nov 20;5(12):1318-23. [3]. Latest bibliographic data on file with the International Bureau. |
Solubility Data
| 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 |
| 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 (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *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). 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)] *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. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL 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). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6299 mL | 8.1497 mL | 16.2994 mL | |
| 5 mM | 0.3260 mL | 1.6299 mL | 3.2599 mL | |
| 10 mM | 0.1630 mL | 0.8150 mL | 1.6299 mL |