Related CAS #: 939791-38-5 (besylate)   717907-75-0 (free base)   939791-39-6 (mesylate)   939791-41-0 (HCl)   939791-40-9 (tosylate)    

Synonym: PF562271; PF562271; PF-562271; PF-00562271; PF00562271; PF 00562271; PF562271 PhSO3H; PF562271 benzesulfonate salt; PF-271; PF562271 besylate.

IUPAC/Chemical Name: N-methyl-N-(3-(((2-((2-oxoindolin-5-yl)amino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)methyl)pyridin-2-yl)methanesulfonamide benzenesulfonate

InChi Key: LKLWTLXTOVZFAE-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H20F3N7O3S.C6H6O3S/c1-31(35(2,33)34)19-12(4-3-7-25-19)10-26-18-15(21(22,23)24)11-27-20(30-18)28-14-5-6-16-13(8-14)9-17(32)29-16;7-10(8,9)6-4-2-1-3-5-6/h4-8,11H,9-10H2,1-2H3,(H,29,32)(H2,26,27,28,30);1-5H,(H,7,8,9)

SMILES Code: CS(=O)(N(C)C1=NC=CC=C1CNC2=NC(NC3=CC4=C(NC(C4)=O)C=C3)=NC=C2C(F)(F)F)=O.O=S(C5=CC=CC=C5)(O)=O

Technical Data

Additional Information

Tips for making stock solution:
Due to its chemical nature, pure PF-562271 benzenesulfonate solid powder was found to have low solubility in common organic solvents and buffers. User may use the following information as reference when making stock solution:

1. PF562271 benzenesulfonate solubility data:(25°C): DMSO: ~ 0.4 mg/mL; Water ~ 0.8 mg/mL; Ethanol ~ 0.7 mg/mL. PBS (10 mM, pH 7.4) not soluble

2. Since PF562271 benzenesulfonate is not very soluble, when preparing stock solution, please always try small quantity first. After you get familiar with its solubility properties, you can scale up to make stock solution and do formulation.

3. The following method may help you to make high concentration stock solution: 5 mg PF562271 benzenesulfonate is mixed with 0.9 mL DMSO. The solution is sonicated for a few seconds till all big solid particles were disappeared. A cloudy solution was formed at this point. Then 0.1 mLwater was added and sonicated for a few seconds, which would give you a clear solution. The solution made by this method may be used as a stock solution. This stock solution can be diluted with water without precipitation. However, when it’s diluted with PBS buffer (10 mM, pH 7.4), the solution becomes cloudy, indicating that PF562271 was precipited from the solution.

4. Ward et al. had used 30% 2-hydroxypropyl-beta-cyclodextrin (HPCD) in 3 % dextrose to formulate PF562271. HPCD is a macrocyclic molecule, the inner core is more hydrophobic and would form complex with PF5622271. In other words, the PF562271 is encapsulated into the inner core of HPCD to form a complex, which would be more aqueous soluble. Many water insoluble drugs were formulated in this method. (reference: Ward et al. Clinical experimental metastasis June 2013, vol 30, 5:579-594).

5. The stock solution (12.5 mg/ml) was made by dissolving the drug in a solution of 50% DMSO, 50% PEG-400 (http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3087944.

6. PF562271 benzenesulfonate is less soluble in buffers with high pH (pH > 7). Therefore, we suggest to use water or acidic buffer for dilution.

7. Pure PF562271 has very low solubility, because of its chemical property, not because of the poor quality of our product. Molecule of PF562271 contains several basic nitrogen atoms, which will be porotonated in acdic media, and made the molecule more water soluble.

Related CAS#
CAS#939791-38-5 (PF-562271 benzenesulfonate salt);
CAS#717907-75-0 (PF-562271 free base).

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