您当前所在的位置:首页 > 产品中心 > 产品详细信息
402957-28-2 分子结构
点击图片或这里关闭

3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide

ChemBase编号:72733
分子式:C36H53N7O6
平均质量:679.84932
单一同位素质量:679.40573245
SMILES和InChIs

SMILES:
[C@H]12[C@H](CN([C@@H]1C(=O)NC(CCC)C(=O)C(=O)NC1CC1)C(=O)[C@H](C(C)(C)C)NC(=O)[C@@H](NC(=O)c1nccnc1)C1CCCCC1)CCC2
Canonical SMILES:
CCCC(C(=O)C(=O)NC1CC1)NC(=O)[C@@H]1[C@H]2CCC[C@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C1CCCCC1)NC(=O)c1nccnc1
InChI:
InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25?,27-,28-,30+/m0/s1
InChIKey:
BBAWEDCPNXPBQM-IGSHNTALSA-N

引用这个纪录

CBID:72733 http://www.chembase.cn/molecule-72733.html

Collapse All Expand All

名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-octahydrocyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide
IUPAC传统名
3-{[(1S,3aR,6aS)-2-[(2S)-2-[(2S)-2-cyclohexyl-2-(pyrazin-2-ylformamido)acetamido]-3,3-dimethylbutanoyl]-hexahydro-1H-cyclopenta[c]pyrrol-1-yl]formamido}-N-cyclopropyl-2-oxohexanamide
telaprevir
别名
VX-950
Telaprevir
(1S,3aR,6aS)-(2S)-2-Cyclohexyl-N-(2-pyrazinylcarbonyl)glycyl-3-methyl-L-valyl-N-[(1S)-1-[2-(cyclopropylamino)-2-oxoacetyl]butyl]octahydrocyclopenta[c]pyrrole-1-carboxamide
LY 570310
MP 424
VRT 111950
VX 950
CAS号
402957-28-2
PubChem SID
162037654
PubChem CID
3088969

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 3088969 external link

理论计算性质

理论计算性质

JChem
Acid pKa 11.857239  质子受体
质子供体 LogD (pH = 5.5) 2.580292 
LogD (pH = 7.4) 2.5802789  Log P 2.5802922 
摩尔折射率 180.0403 cm3 极化性 70.54791 Å3
极化表面积 179.56 Å2 可自由旋转的化学键 14 
里宾斯基五规则 false 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
DMSO expand 查看数据来源
Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
221-224°C (dec.) expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer, Under Inert Atmosphere expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
作用靶点
HCV protease expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals -  S1538 external link
Research Area
Description Hepatitis C
Biological Activity
Description Telaprevir (VX-950) is a HCV NS3-4A serine protease inhibitor with IC50 of 0.35 μM.
Targets HCV NS3-4A serine protease
IC50 0.35 μM [1]
In Vitro Telaprevir inhibits the hepatitis C virus NS3-4A serine protease, leading to the block of viral polyprotein processing and subsequently decrease of viral RNA replication, total HCV RNA levels and protein levels in the Con1 (genotype 1b) subgenomic HCV replicon cells in a time- and dose-dependent manner. Telaprevir displays a significant time-dependent increase in inhibitory effect on the replication of HCV RNA with IC50 values of 0.574 μM, 0.488 μM, 0.210 μM and 0.139 μM for 24, 48, 72 and 120 hours incubation, respectively. Telaprevir displays an average IC50 of 0.354 μM and an average IC90 of 0.830 μM, respectively, from three independent experiments using the 48 hours incubation. Telaprevir has no significant cytotoxicity to HCV replicon cells, parental Huh-7 and HepG2 cells after 48 hours incubation. Telaprevir (17.5 μM) completely eradicates HCV RNA from replicon cells after 13 days incubation without rebound after Telaprevir is withdrawn. Telaprevir displays an additive to moderate synergistic effect on reduction of HCV RNA replication and suppression of resistance mutations without significant increase in cytotoxicity when in combination with IFN-α, compared to treatment with each agent alone. [1]
In Vivo Oral administration of Telaprevir reduces HCV protease-dependent cleavage and subsequent secretion of SEAP from the liver into the blood in the mice model to 18.7% and 18.4% at dosage of 10 and 25 mg/kg, respectively. [2] Administration of Telaprevir at 200 mg/kg for 1 week results in a 1.9 log reduction of HCV RNA in genotype 1b HCV-infected human hepatocyte chimeric mice, and when treatment in combination with MK-0608 (50 mg/kg) for 4 weeks, viruses are eliminated from mice. [3]
Clinical Trials Currently in Phase III clinical trials in patients with Hepatitis C.
Features Unlike BILN 2061 (a noncovalent inhibitor), Telaprevir is a covalent, reversible inhibitor of the NS3-4A protease with a slow-binding and slow-dissociation mechanism.
Protocol
Kinase Assay [1]
Determination of anti-HCV activity Stable Huh-7 cells containing the self-replicating, subgenomic HCV replicon, which is identical in sequence to the I377neo/NS3-3'/wt replicon are used for anti-HCV assays. Replicon cells are incubated at 37 °C for the indicated period of time with Telaprevir serially diluted in DMEM plus 2% FBS and 0.5% dimethyl sulfoxide (DMSO). Total cellular RNA is extracted using an RNeasy-96 kit, and the copy number of HCV RNA is determined using a quantitative RTPCR (QRT-PCR) assay for the assessment of 50% inhibitory concentration (IC50).
Cell Assay [1]
Cell Lines Huh-7, HepG2, and peripheral blood mononuclear cells (PBMC)
Concentrations Dissolved in DMSO, final concentration ~1 mM
Incubation Time 48 hours
Methods Cells are incubated with various concentrations of Telaprevir for 48 hours. Cell viability is determined by using a tetrazolium (MTS)-based cell viability assay.
Animal Study [2]
Animal Models SCID mice injected with recombinant adenovirus (Ad-WT-HCVpro-SEAP or Ad-MT-HCVpro-SEAP)
Formulation Formulated in polyvinylpyrrolidone (PVP) K-30 plus 2% sodium lauryl sulfate
Doses ~300 mg/kg
Administration Oral gavage
References
[1] Lin K, et al. Antimicrob Agents Chemother, 2006, 50(5), 1813-1822.
[2] Perni RB, et al. Antimicrob Agents Chemother, 2006, 50(3), 899-909.
[3] Ohara E, et al. J Hepatol, 2011, 54(5), 872-878.
Toronto Research Chemicals -  T015650 external link
Telaprevir is a peptidomimetic inhibitor of hepatitis C virus protease.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
正在搜索,请耐心等待...(如果遇到网页错误或者长时间没有结果,请刷新页面[F5])

专利

专利

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

互联网资源

互联网资源

百度图标百度 google iconGoogle