Apatinib

한글명:Apatinib

카스 번호811803-05-1

상품명:Apatinib

CBNumberCB72561458

분자식C24H23N5O

포뮬러 무게397.47

MOL 파일811803-05-1.mol

화학적 성질

끓는 점	578.2±50.0 °C(Predicted)
밀도	1.27
저장 조건	Store at -20°C
용해도	>49.4mg/ml in DMSO
물리적 상태	가루
산도 계수 (pKa)	11.93±0.70(Predicted)

그림문자(GHS)

그림문자(GHS)
신호 어

Warning
유해·위험 문구

H302：삼키면 유해함

H315：피부에 자극을 일으킴

H319：눈에 심한 자극을 일으킴

H335：호흡 자극성을 일으킬 수 있음
예방조치문구

P261：분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.

P264：취급 후에는 손을 철저히 씻으시오.

P264：취급 후에는 손을 철저히 씻으시오.

P270：이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.

P271：옥외 또는 환기가 잘 되는 곳에서만 취급하시오.

P280：보호장갑/보호의/보안경/안면보호구를 착용하시오.

P301+P312：삼켜서 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.

P302+P352：피부에 묻으면 다량의 물로 씻으시오.

P304+P340：흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.

P305+P351+P338：눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.

P321：(…) 처치를 하시오.

P330：입을 씻어내시오.

P332+P313：피부 자극이 생기면 의학적인 조치· 조언을 구하시오.

P337+P313：눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.

P403+P233：용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.

P405：밀봉하여 저장하시오.

P501：...에 내용물 / 용기를 폐기 하시오.

Apatinib 화학적 특성, 용도, 생산

개요
Apatinib mesylate, discovered by Advenchen Laboratories (United States of America, USA) and co-developed by Jiangsu Hengrui Medicine Co. Ltd (China), was approved by the Chinese Food and Drug Administration (CFDA) in October 2014 for the treatment of metastatic gastric carcinoma. Apatinib mesylate is an oral tyrosine kinase inhibitor that selectively inhibits the vascular endothelial growth factor receptor 2 (VEGFR2), which prevents new blood vessel formation selectively in tumor tissue. Apatinib has shown inhibition of the VEGF signaling pathway with an IC50 value of 1 nM for VEGFR-2 in in vitro enzyme experiments. A multicenter phase II study of apatinib is underway with patients in non-triple-negative metastatic breast cancer trials. Non-clinical studies concluded that apatinib may reverse the ATP-binding cassette subfamily B member 1 and subfamily G member 2 (ABCB1- and ABCG2, respectively)-mediated multidrug resistance which allows cancer cells to circumvent certain conventional antineoplastic drugs, suggesting that apatinib could be effective as a combination therapy.
용도
Apatinib (YN968D1) is a small-molecule selective multitargeted tyrosine kinase inhibitor with an IC50 of 2.43 nM for the inhibition of VEGFR2.
Synthesis
The synthesis started with commercially available 1-phenyl cyclopentane carbonitrile (8), which was nitrated to provide nitrobenzene 9. Subsequent reduction of 9 gave aniline 10, which was coupled with 2-chloronicotinoyl chloride (11) to afford aryl amide 12. Subjection of the 2-pyridyl chloride within 12 to pyridin-4-ylmethanamine (13) in hot pentanol gave 14. The preparation of apatinib 14 from starting material 8 were reported on gram or milligram reaction scale with no yield. 170 g of 14 was mixed with methylsulfonic acid in 95% isopropanol¨CH2O solution to give 161.5 g of apatinib mesylate (II) in 77% yield.

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