AZ7550 HCl, the hydrochloride salt of AZ-7550, is N-demethylated (one of the methyl groups is removed from the ethyl diamine side chain) and active metabolite of AZD9291 (Osimertinib), which is approved anticancer drug that inhibits IGF1R with an IC50 of 1.6 μM.
Physicochemical Properties
| Molecular Formula | C27H32CLN7O2 |
| Molecular Weight | 522.041684150696 |
| Exact Mass | 521.23 |
| CAS # | 2309762-40-9 |
| Related CAS # | AZ7550 Mesylate;2319837-99-3;AZ7550;1421373-99-0 |
| PubChem CID | 132274051 |
| Appearance | Light yellow to yellow solid powder |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 10 |
| Heavy Atom Count | 37 |
| Complexity | 724 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | Cl.O(C)C1=CC(=C(C=C1NC1=NC=CC(C2=CN(C)C3C=CC=CC=32)=N1)NC(C=C)=O)N(C)CCNC |
| InChi Key | BHYPVGSNUFXTCM-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C27H31N7O2.ClH/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;/h6-12,15-17,28H,1,13-14H2,2-5H3,(H,30,35)(H,29,31,32);1H |
| Chemical Name | N-[4-methoxy-5-[[4-(1-methylindol-3-yl)pyrimidin-2-yl]amino]-2-[methyl-[2-(methylamino)ethyl]amino]phenyl]prop-2-enamide;hydrochloride |
| Synonyms | AZ7550 HCl; 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 : ~1.88 mg/mL (~3.60 mM) |
| 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 | 1.9156 mL | 9.5778 mL | 19.1556 mL | |
| 5 mM | 0.3831 mL | 1.9156 mL | 3.8311 mL | |
| 10 mM | 0.1916 mL | 0.9578 mL | 1.9156 mL |