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Temsirolimus

Temsirolimus 구조식 이미지
카스 번호:
162635-04-3
상품명:
Temsirolimus
동의어(영문):
C15182;CCL-779;NSC 683864;TEMSIROLIMUS;Simultaneous;Temsirolimus, >=98%;TeMsiroliMus (~90%);Temsirolimus(CCI-779);TeMsiroliMus (Torisel);temsirolimus 162635-04-3
CBNumber:
CB3506811
분자식:
C56H87NO16
포뮬러 무게:
1030.29
MOL 파일:
162635-04-3.mol

Temsirolimus 속성

녹는점
99-101°C
끓는 점
1048.4±75.0 °C(Predicted)
밀도
1.21
인화점
587.8℃
저장 조건
-20°C Freezer
용해도
Soluble in chloroform, methanol.
산도 계수 (pKa)
10.40±0.70(Predicted)
물리적 상태
powder
색상
white to off-white
Merck
14,9142
InChIKey
CBPNZQVSJQDFBE-FUXHJELOSA-N

안전

안전지침서 24/25
WGK 독일 3
RTECS 번호 VE6257000
HS 번호 29349990

Temsirolimus C화학적 특성, 용도, 생산

개요

While renal cell carcinoma (RCC) accounts for only 2 3% of all cancers, the 5-year survival rate for advanced RCC disease is only 5 10%, with approximately 13,000 deaths occurring annually (US statistics only). Immunotherapeutic cytokine options, such as IFN-αand IL-2, have traditionally been frontline treatments, but these agents are not efficacious in all patients and can cause serious side effects. In addition, bevacizumab, a monoclonal antibody against VEGF, has also demonstrated prolongation of PFS. The newest entry for this indication focuses on targets that are downstream from VEGF. Temsirolimus is an inhibitor of the serine/threonine kinase mTOR, which is the mammalian target of rapamycin. mTOR has been implicated in cell replication through control of the cell cycle translation of specific mRNAs. Inhibition of mTOR prevents phosphorylation of the 4E binding protein-1 and the 40S ribosomal protein S6 kinase that are responsible for cell cycle protein translation initiation; cell cycle arrest occurs as the result of termination of cell division from the G1 to the S phase. Disruption of mTOR signaling also has antiangiogenic effects that could be deemed essential in combating RCC, which is driven by unregulated angiogenesis. Temsirolimus is the 2,2-bis(hydroxymethyl)propionate ester of rapamycin (sirolimus), a macrolide fungicide isolated from the bacteria Streptomyces hygroscopicus. Similar to its parent sirolimus, temsirolimus interacts with mTOR through its complex with FK-506 binding protein 12.

화학적 성질

White Solid

Originator

Wyeth (US)

용도

Ester analog of Rapamycin

용도

Temsirolimus (CCI-779) is a specific mTOR inhibitor with IC50 of 1.76 μM.

용도

Temsirolimus is a semisynthetic macrocyclic lactone prepared from rapamycin by selective alkylation of the 42-hydroxy group with a protected bis(dihydromethyl)propionic acid, followed by deprotection. Like all tacrolimus analogues, temsirolimus binds to receptor protein, FKBP12. The complex then binds to mTOR preventing it from interacting with target proteins. Temsirolimus is extensively cited in the literature with over 700 citations.

용도

Temsirolimus is a semisynthetic macrocyclic lactone prepared from rapamycin by selective acylation of the 42-hydroxy group with a protected bis(dihydromethyl)propionic acid, followed by deprotection. Like all tacrolimus analogues, temsirolimus binds to receptor protein, FKBP12. The complex then binds to mTOR preventing it from interacting with target proteins. Temsirolimus is extensively cited in the literature with over 700 citations.

상표명

Torisel

일반 설명

Temsirolimus is an esterified derivative of rapamycinand in a similar manner binds initially to the proteinFKBP-12(FK506-binding protein).This complexthen acts to inhibit the mammalian target of rapamycin(mTOR), a serine-threonine kinase that plays a crucial rolein cell division. It is somewhat unique in its method of kinaseinhibition, because it actually binds to an allostericmodulator of the kinase rather than just binding to theATP-binding site like most other kinase inhibitors.Temsirolimus is available as a 25-mg/mL injection forIV administration in the treatment of advanced RCC. Theagent is extensively metabolized and undergoes rapid hydrolysisof the ester function to give rapamycin that retainsactivity.Additional metabolism is mediated primarilyby CYP3A4 to give several hydroxylated and demethylatedmetabolites that are inactive. The agent and metabolites areeliminated primarily in the feces with half-lives of 17 and55 hours for temsirolimus and rapamycin, respectively.This agent, like rapamycin, possesses immunosuppressantproperties and there is an increased risk of infection.The most serious side effects are interstitial lung disease,perforation of the bowel, and acute renal failure althoughthese occur only rarely. The most commonly seen side effects are rash, weakness, mucositis, nausea, edema, andanorexia.

Chemical Synthesis

While rufinamide may be prepared by several related routes, the preferred starting material is 2,6-difluorobenzyl azide. Reaction with either 2-propynoic acid or 2-chloroacrylonitrile affords 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid or 1-(2,6-difluorobenzyl)- 1H-1,2,3-triazole-4-carbonitrile, respectively. For the carboxylic acid Shridhar Hegde and Michelle Schmidt intermediate, treatment with thionyl chloride followed by concentrated aqueous ammonium hydroxide or conversion to its methyl ester (methanol/sulfuric acid) with subsequent ammonolyis provides rufinamide.

Temsirolimus 준비 용품 및 원자재

원자재

준비 용품


Temsirolimus 공급 업체

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ATK CHEMICAL COMPANY LIMITED
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+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 24191 60
Henan DaKen Chemical CO.,LTD.
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Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 739 60
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29999 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 969 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23980 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 sales@jushengtech.com CHINA 28236 58
QUALITY CONTROL CHEMICALS INC.
(323) 306-3136
(626) 453-0409 orders@qcchemical.com United States 8407 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6372 58

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