≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C,Desiccated Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Avitinib (Abivertinib) maleate is a pyrrolopyrimidine-based irreversible epidermal growth factor receptor ( EGFR ) inhibitor with an IC 50 of 7.68 nM.
In Vitro
Avitinib is structurally distinct from previously reported pyrimidine-based irreversible EGFR inhibitors such as osimertinib and rociletinib. Avitinib is designed specifically to inhibit EGFR active mutations and the T790M acquired resistant mutation, while sparing wild type EGFR. Avitinib selectively inhibits EGFR active and T790M mutations with up to 298-fold increase in potency compared to wild-type EGFR. Avitinib exhibits potent inhibitory activity with IC 50 value of 0.18 nM against EGFR L858R/T790M double mutations, nearly 43-fold greater potency over wild-type EGFR (IC 50 =7.68 nM). Avitinib selectively inhibits mutant EGFR phosphorylation with IC 50 values of 7.3 nM and 2.8 nM in NCI-H1975 and NIH/3T3_TC32T8 cells, about 115- and 298-fold more sensitive than that of the inhibition of wild type EGFR in A431. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
Oral administration of avitinib at daily dose of 500 mg/kg results in complete remission of tumors with EGFR active and T790M mutations for over 143 days with no weight loss. Three major metabolites of avitinib are tested and show no wild-type EGFR inhibition and off-target effects such as inhibition of IGF-1R. Avitinib is safe in non-small cell lung cancer (NSCLC) patients at the dose range between 50 mg and 550 mg once per day and no hyperglycemia and other severe adverse effects are detected such as grade 3 QT prolongation . MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:EGFR 7.68 nM (IC 50 )
| Canonical Smiles | CN1CCN(CC1)C2=C(C=C(C=C2)NC3=NC4=C(C=CN4)C(=N3)OC5=CC=CC(=C5)NC(=O)C=C)F.C(=CC(=O)O)C(=O)O |
|---|---|
| IUPAC Name | (Z)-but-2-enedioic acid;N-[3-[[2-[3-fluoro-4-(4-methylpiperazin-1-yl)anilino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenyl]prop-2-enamide |
| InChIKey | VRHPZWLHPIENFW-BTJKTKAUSA-N |
| INCHI | 1S/C26H26FN7O2.C4H4O4/c1-3-23(35)29-17-5-4-6-19(15-17)36-25-20-9-10-28-24(20)31-26(32-25)30-18-7-8-22(21(27)16-18)34-13-11-33(2)12-14-34;5-3(6)1-2-4(7)8/h3-10,15-16H,1,11-14H2,2H3,(H,29,35)(H2,28,30,31,32);1-2H,(H,5,6)(H,7,8)/b;2-1- |
| Isomeric SMILES | CN1CCN(CC1)C2=C(C=C(C=C2)NC3=NC4=C(C=CN4)C(=N3)OC5=CC=CC(=C5)NC(=O)C=C)F.C(=C\C(=O)O)\C(=O)O |
| Alternate CAS | 1822357-78-7 |
| Molecular Weight | 603.60 |
| Reaxy-Rn | 35296846 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=35296846&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Diazinanes |
| Subclass | Piperazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylpiperazines |
| Alternative Parents | N-arylpiperazines Diarylethers Pyrrolo[2,3-d]pyrimidines Anilides Phenoxy compounds Phenol ethers N-arylamides Dialkylarylamines Aniline and substituted anilines N-methylpiperazines Fluorobenzenes Aminopyrimidines and derivatives Unsaturated fatty acids Dicarboxylic acids and derivatives Aryl fluorides Pyrroles Heteroaromatic compounds Acrylic acids and derivatives Trialkylamines Secondary carboxylic acid amides Amino acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organofluorides Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Not available |
| Substituents | N-arylpiperazine - Phenylpiperazine - Diaryl ether - Pyrrolo[2,3-d]pyrimidine - Anilide - Pyrrolopyrimidine - Phenoxy compound - Aniline or substituted anilines - Dialkylarylamine - N-arylamide - Tertiary aliphatic/aromatic amine - Phenol ether - N-alkylpiperazine - N-methylpiperazine - Halobenzene - Fluorobenzene - Aminopyrimidine - Fatty acyl - Fatty acid - Benzenoid - Unsaturated fatty acid - Pyrimidine - Dicarboxylic acid or derivatives - Monocyclic benzene moiety - Aryl halide - Aryl fluoride - Acrylic acid or derivatives - Heteroaromatic compound - Pyrrole - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Carboxamide group - Amino acid or derivatives - Azacycle - Ether - Carboxylic acid - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organofluoride - Organohalogen compound - Carbonyl group - Amine - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. |
| External Descriptors | Not available |
| Solubility | DMSO : ≥ 100 mg/mL (165.67 mM) H2O : <0.1 mg/mL (ultrasonic;warming;heat to 60°C) (insoluble) |
|---|---|
| Molecular Weight | 603.600 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 12 |
| Rotatable Bond Count | 9 |
| Exact Mass | 603.224 Da |
| Monoisotopic Mass | 603.224 Da |
| Topological Polar Surface Area | 173.000 Ų |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Complexity | 871.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 1 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 1 |
| Covalently-Bonded Unit Count | 2 |
