AZ7550 Mesylate (AZ-7550), the mesylate salt of AZ 7550, is an active metabolite of AZD-9291 (Osimertinib) by removing one of the methyl groups from the ethyl diamine side chain. AZD 9291 (Osimertinib) was approved in 2015 for the treatment of non-small-cell lung cancer (NSCLC) in patients harboring sensitizing (or activating) mutations for a number of years.
Physicochemical Properties
| Molecular Formula | C28H35N7O5S |
| Molecular Weight | 581.686404466629 |
| Exact Mass | 773.218 |
| CAS # | 2319837-99-3 |
| Related CAS # | AZ7550;1421373-99-0;AZ7550 hydrochloride;2309762-40-9 |
| PubChem CID | 134611624 |
| Appearance | Light yellow to yellow solid powder |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 16 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 51 |
| Complexity | 817 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | S(O)(=O)(=O)C.CN1C2=CC=CC=C2C(C2C=CN=C(NC3C=C(NC(=O)C=C)C(N(C)CCNC)=CC=3OC)N=2)=C1 |
| InChi Key | AZRGPJKRGFXCLD-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C27H31N7O2.3CH4O3S/c1-6-26(35)30-21-15-22(25(36-5)16-24(21)33(3)14-13-28-2)32-27-29-12-11-20(31-27)19-17-34(4)23-10-8-7-9-18(19)23;3*1-5(2,3)4/h6-12,15-17,28H,1,13-14H2,2-5H3,(H,30,35)(H,29,31,32);3*1H3,(H,2,3,4) |
| Chemical Name | methanesulfonic acid;N-[4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-2-[methyl-[2-(methylamino)ethyl]amino]phenyl]prop-2-enamide |
| Synonyms | AZ7550 Mesylate; AZ 7550; AZ-7550 |
| 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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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 | In terms of potency and selectivity, AZ7550 (compound 28) seems to offer properties that are largely comparable to those of the parent molecule AZD9291. The DM cell line H1975, the AM cell line PC9, and the WT cell line LoVo are all inhibited by AZ7550, with IC50 values of 45, 26, and 786 nM, respectively. The anti-proliferative cell lines H1975 from DM, PC9 from AM, and Calu3 from WT are all inhibited by AZ7550, with GI50 values of 19, 15, and 537 nM, respectively[1]. |
| References |
[1]. Discovery of a potent and selective EGFR inhibitor (AZD9291) of both sensitizing and T790M resistance mutations that spares the wild type form of the receptor. J Med Chem. 2014 Oct 23;57(20):8249-67. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~25 mg/mL (~32.30 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (3.23 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 (3.23 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7191 mL | 8.5956 mL | 17.1913 mL | |
| 5 mM | 0.3438 mL | 1.7191 mL | 3.4383 mL | |
| 10 mM | 0.1719 mL | 0.8596 mL | 1.7191 mL |