Selumetinib

Base Information

• Chemical Name: Selumetinib
• CAS No.: 606143-52-6
• Deprecated CAS: 865610-79-3
• Molecular Formula: C17H15BrClFN4O3
• Molecular Weight: 457.687
• Hs Code.: 29349990
• European Community (EC) Number: 641-434-6
• NSC Number: 741078
• UNII: 6UH91I579U
• DSSTox Substance ID: DTXSID3048944
• Nikkaji Number: J2.516.155F
• Wikipedia: Selumetinib
• Wikidata: Q7448840
• NCI Thesaurus Code: C66939
• RXCUI: 2289380
• Pharos Ligand ID: T5L9Y2W2CV11
• Metabolomics Workbench ID: 152804
• ChEMBL ID: CHEMBL1614701
• Mol file: 606143-52-6.mol

Synonyms:ARRY 142886;ARRY-142886;ARRY142886;AZD 6244;AZD-6244;AZD6244;selumetinib

Chemical Property of Selumetinib

Chemical Property:

• Appearance/Colour: White or pale white solid.
• PKA: 14.20±0.10(Predicted)
• PSA: 88.41000
• Density: 1.692 g/cm³
• LogP: 3.98950
• Storage Temp.: -20°
• Solubility.: Soluble in DMSO (up to 50 mg/ml) or in Ethanol (up to 2 mg/ml)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 456.00001
• Heavy Atom Count: 27
• Complexity: 523

Purity/Quality:

99% ^*data from raw suppliers

Selumetinib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Genetic Disorder Agents, Antineoplastic Agents
• Canonical SMILES: CN1C=NC2=C1C=C(C(=C2F)NC3=C(C=C(C=C3)Br)Cl)C(=O)NOCCO
• Recent ClinicalTrials: Selumetinib in Chinese Paediatric With Post-operative NF1-PNs, PhaseⅡ, Double-Blinded, Placebo-Controlled Study
• Recent EU Clinical Trials: A Phase I/II, Single-Arm, Open label Study to Evaluate the Pharmacokinetics, Safety/Tolerability and Efficacy of the Selumetinib Granule Formulation in Children Aged ≥ 1 to < 7 Years with Neurofibromatosis Type 1 (NF1) Related Symptomatic, Inoperable Plexiform Neurofibromas (PN) (SPRINKLE)
• Recent NIPH Clinical Trials: A Phase III, Multicentre, International Study With a Parallel, Randomised, Double-blind, Placebo-controlled, 2 Arm Design to Assess the Efficacy and Safety of Selumetinib in Adult Participants With NF1 Who Have Symptomatic, Inoperable Plexiform Neurofibromas
• Description: Selumetinib (AZD6244; ARRY-142886) is an oral MEK inhibitor. In a randomized trial, NSCLC patients with wild-type KRAS were randomized to erlotinib alone or combination therapy with selumetinib, while mutant KRAS patients were randomized to selumetinib alone or combination therapy. The primary end points were PFS for the KRAS wild-type cohort and objective response rate (ORR) for the KRAS mutant cohort. Results were not impressive, with no PFS difference in the KRAS wild-type arm (2.4 vs. 2.1?months) and no ORR difference in the KRASmutated subgroup (0% vs. 10%). A planned trial of selumetinib in combination with the anti-PD-L1 antibody durvalumab has since been suspended (NCT03004105).
• Uses: It is a tight-binding, uncompetitive inhibitor of mitogen-activated protein kinase kinases (MEK) 1 and 2 currently in clinical development. It is useful as biomarker in human lung cancer cell. Potent MEK inhibitor. It is a tight-binding, uncompetitive inhibitor of mitogen-activated protein kinase kinases (MEK) 1 and 2 currently in clinical development.

Technology Process of Selumetinib

There total 10 articles about Selumetinib which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

5-[(4-bromo-2-chlorophenyl)amino]-N-[2-(ethenyloxy)ethoxy]-4-fluoro-1-methyl-1H-benzimidazole-6-carboxamide (606144-05-2) → selumetinib (606143-52-6)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 24h;

Reference yield: 100.0%

6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-vinyloxy-ethoxy)-amide → selumetinib (606143-52-6)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 24h;

Reference yield: 91.5%

5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylic acid (606144-04-1) + O-(2-hydroxyethyl)hydroxylamine (3279-95-6) → selumetinib (606143-52-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Temperature;

upstream raw materials:

5-[(4-bromo-2-chlorophenyl)amino]-N-[2-(ethenyloxy)ethoxy]-4-fluoro-1-methyl-1H-benzimidazole-6-carboxamide

methyl 5-[(4-bromophenyl)amino]-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylate

methyl 5-[(4-bromo-2-chlorophenyl)amino]-4-fluoro-1-methyl-1H-benzimidazole-6-carboxylate

4-Amino-3-fluoro-5-nitro-2-phenylamino-benzoic acid methyl ester

Downstream raw materials:

6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxy-ethoxy)-amide p-toluenesulfonate

6-(4-bromo-2-chlorophenylamino)-7-fluoro-3-methyl-3H-benzoimidazole-5-carboxylic acid (2-hydroxyethoxy)amide hydrogen sulphate

6-(4-bromo-2-chloroanilino)-7-fluoro-N-[2-(α-D-glucopyranosyloxy)ethoxy]-3-methylbenzimidazole-5-carboxamide

C₂₄H₂₆BrClF₃N₇O₃

Refernces

• 1、 -. "Synthesis method of semetinib". Paragraph 0056-0062. . Retrieved 2021/05/08.
• 2、 -. "NOVEL HYDROGEN SULFATE SALT". Page/Page column 21-22. . Retrieved 2008/06/13.