Icotinib (Hydrochloride)

Product Name: Icotinib (Hydrochloride)
CAS No.: 1204313-51-8
Chemical Name: Icotinib (Hydrochloride)
Synonyms: CS-1906;CS-1016;Icotinib HCl;Icotinib (Hydrochloride);Icotinib Hydrochloride (BPI-2009);Icotinib (Hydrochloride) impurity;Icotinib Hydrochloride, 10 mM in DMSO;N-(3-Ethynylphenyl)-7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine hydrochloride;N-(3-Ethynylphenyl)-7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine hydrochloride Icotinib (Hydrochloride)
CBNumber: CB22624183
Molecular Formula: C22H22ClN3O4
Formula Weight: 427.89
MOL File: 1204313-51-8.mol

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Icotinib (Hydrochloride) Property

storage temp.: Store at -20°C
solubility: Soluble in DMSO
form: Powder
color: White to off-white
InChI: InChI=1S/C22H21N3O4.ClH/c1-2-16-4-3-5-17(12-16)25-22-18-13-20-21(14-19(18)23-15-24-22)29-11-9-27-7-6-26-8-10-28-20;/h1,3-5,12-15H,6-11H2,(H,23,24,25);1H
InChIKey: PNNGXMJMUUJHAV-UHFFFAOYSA-N
SMILES: N(C1C=CC=C(C#C)C=1)C1=NC=NC2C=C3OCCOCCOCCOC3=CC1=2.Cl

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

ChemScene

Product number: CS-0918
Product name: Icotinib(Hydrochloride)
Purity: 99.99%
Packaging: 5mg
Price: $70
Updated: 2021/12/16

ChemScene

Product number: CS-0918
Product name: Icotinib(Hydrochloride)
Purity: 99.99%
Packaging: 10mg
Price: $100
Updated: 2021/12/16

ApexBio Technology

Product number: A3482
Product name: IcotinibHydrochloride
Packaging: 5mg
Price: $190
Updated: 2021/12/16

ChemScene

Product number: CS-0918
Product name: Icotinib(Hydrochloride)
Purity: 99.99%
Packaging: 50mg
Price: $290
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: 110621
Product name: IcotinibHydrochloride
Packaging: 300mg
Price: $690
Updated: 2021/12/16

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Icotinib (Hydrochloride) Chemical Properties,Usage,Production

Uses

Icotinib Hydrochloride (BPI-2009) is a potent and specific EGFR inhibitor with an IC50 of 5 nM; also inhibits mutant EGFRL858R, EGFRL858R/T790M, EGFRT790M and EGFRL861Q. Icotinib (Hydrochloride) is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.

Clinical Use

Icotinib hydrochloride, developed by the Chinese pharmaceutical company Zhejiang Bata Pharma Inc., is a potent small molecule epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor for the treatment of non-small cell lung cancer (NSCLC). It was first approved by the SFDA of China, and launched under the brand name Conmana in the middle of 2011, representing an important milestone for Chinese pharmaceutical research and development. As the third EGFR-TKI drug targeting NSCLS therapy, icotinib hydrochloride possesses a similar structure to gefitinib (Iressa, AstraZeneca) and erlotinib (Tarceva, OST & Roche). Interestingly, a randomized, double-blind phase III clinical study of icotinib versus gefitinib in 399 patients with advanced NSCLC demonstrated that icotinib provides similar efficacy to gefitinib, but with better tolerability in NSCLC patients previously treated with one or two chemotherapy agents.

Synthesis

Icotinib was prepared by a similar process approach to that of erlotinib. Beginning from commercially available 2,20-(ethylenedioxy)diethanol (162), bis-tosylation to 163, followed by bis-alkylation with commercially available catechol derivative 164 provided crown-4-ether 165 in 96% yield. Nitration of polyether 165 using concentrated nitric acid and concentrated sulfuric acid provided nitroarene 166 in 65% yield. Reduction of the nitroarene under catalytic hydrogenation conditions gave amine 167 in 85% yield. Condensation of the amine 167 with formamide in the presence of ammonium formate afforded quinazolinone 168 in 80% yield. The chlorination of 168 using POCl3 furnished quinazolyl chloride 169 in 77% yield. The treatment of chloride 169 with amine 170 followed by the HCl salt formation produced icotinib hydrochloride (XIV) in good yield.

in vivo

Icotinib exhibits potent dose-dependent antitumor effects in nude mice carrying a variety of human tumor-derived xenografts. The drug is well tolerated at doses up to 120 mg/kg/day in mice without mortality or significant body weight loss during the treatment. Icotinib inhibits tumor growth at a rate of 25.2%, 45.6% and 51.5% in the A431 cell line groups; 3.4%, 25.9% and 31.0% in the A549 cell line groups; 49.4%, 52.6% and 67.4% in the H460 cell line groups, and 30.3%, 36.4% and 46.5% in the HCT8 cell line groups, at 30, 60 and 120 mg/kg/dose, respectively^[1].

target

EGFR

IC 50

EGFR: 5 nM (IC₅₀); EGFR^L861Q; EGFR^L858R/T790M; EGFR^L858R; EGFR^T790M

References

[1] Tan F, et al. Icotinib (BPI-2009H), a novel EGFR tyrosine kinase inhibitor, displays potent efficacy in preclinical studies. Lung Cancer. 2012 May;76(2):177-82. DOI:10.1016/j.lungcan.2011.10.023

Icotinib (Hydrochloride) Preparation Products And Raw materials

Raw materials

Preparation Products

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Icotinib (Hydrochloride) Suppliers

China 86 United States 10 Global 96

AdooQ BioScience, LLC

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Target molecule Corp.

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Musechem

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TargetMol Chemicals Inc.

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InvivoChem

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Cckinase, Inc.

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BOC Sciences

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Aladdin Scientific

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ApexBio Technology

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Creative Enzymes

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1204313-51-8, Icotinib (Hydrochloride)Related Search:

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CS-1906

CS-1016

Icotinib Hydrochloride (BPI-2009)

Icotinib (Hydrochloride)

N-(3-Ethynylphenyl)-7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine hydrochloride

N-(3-Ethynylphenyl)-7,8,10,11,13,14-hexahydro-[1,4,7,10]tetraoxacyclododecino[2,3-g]quinazolin-4-amine hydrochloride Icotinib (Hydrochloride)

Icotinib HCl

Icotinib (Hydrochloride) impurity

Icotinib Hydrochloride, 10 mM in DMSO

1204313-51-8

C22H21N3O4HCl

Inhibitors