Capecitabine (RO 09-1978) - Moligand™, 10mM in DMSO , Thymidylate synthase inhibitor, CAS No.154361-50-9, Thymidylate synthase inhibitor

CAS: 154361-50-9 Cat. No.: C407856 Peso molecular: 359.35 Número EC: 604-948-1

GRADE & PURITY Moligand™, 10mM in DMSO

Synonyms

pentyl 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoro-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Descripción general

Information

Capecitabine (RO 09-1978) Capecitabine (RO 09-1978) is a tumor-selective fluoropyrimidine carbamate, which achieves higher intratumoral 5-FU level with lower toxicity than 5-FU. Capecitabine treatment of HCT-15 cells causes condensation of DNA and induc
In vitro

Both LS174T WT and LS174T-c2 cells show significantly greater sensitivity to Capecitabine when cultivated in the same plates as HepG2 hepatoma with IC50 values of 890 and 630 μM in LS174T WT alone and cultivated with HepG2, respectively. In addition, for the LS174T-C2 subline, the IC50 falls from 330 ± 4 down to 89 ± 6 μm when cultivated in the same plates as hepatoma cells. Furthermore, Capecitabine induces apoptosis in a Fas-dependent manner, and shows a 7-fold higher cytotoxicity and markedly stronger apoptotic potential in thymidine phosphorylase (TP)-transfected LS174T-c2 cells.

In vivo

In the human cancer xenograft models studied, Capecitabine is more effective in a wider dose range and has a broader spectrum of antitumor activity than 5-FU, UFT or its intermediate metabolite 5\'-DFUR, which can be correlated with tumor dThdPase levels. Capecitabine inhibits tumor growth and metastatic recurrence after resection of human hepatocellular carcinoma (HCC) in highly metastatic nude mice model which is attributed to the high expression of platelet-derived endothelial cell growth factor in tumors.
Cell Data

cell lines：MV4-11 and RS4;11 cells

Concentrations：~1 mM

Incubation Time：72 hours

Powder Purity:≥99%

Specifications

Sinónimos

pentyl 1-((2R, 3R, 4S, 5R)-3, 4-dihydroxy-5-methyl-tetrahydrofuran-2-yl)-5-fluoro-2-oxo-1, 2-dihydropyrimidin-4-ylcarbamate

Especificaciones y pureza

Moligand™, 10mM in DMSO

Mecanismos bioquímicos y fisiológicos

Capecitabine (RO 09-1978) is a tumor-selective fluoropyrimidine carbamate, which achieves higher intratumoral 5-FU level with lower toxicity than 5-FU. Capecitabine treatment of HCT-15 cells causes condensation of DNA and induces apoptosis.

Condiciones de almacenamiento de almacenamiento

Store at -80°C

Enviado en

Dry ice packs + Cold packs

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Tipo de acción

INHIBITOR

Mecanismo de acción

Thymidylate synthase inhibitor

Propiedades del producto

• ALogP: 0.6

Nombres e identificadores

• Isómeros SMILES: CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O
• WGK Alemania: 3
• CAS alternativo: 154361-50-9
• Términos de entrada MeSH: capecitabine;N(4)-pentyloxycarbonyl-5'-deoxy-5-fluorocytidine;Xeloda
• Peso molecular: 359.35
• Reaxy-Rn: 12681864
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=12681864&ln=

Objetivos asociados (humanos)

TYMS Tclin Thymidylate synthase (0 Activities)

Discover Target: TYMS

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Propiedades químicas y físicas

• Rotación específica [α]: 98° (C=1,MeOH)
• Punto de fusión (°C): 123 °C(dec.)

Referencias

1. Wei Xie, Xue-Jian Li, Yu-Sen Zhong, Jie Fang, Hui Qi, Meng Yang, Hua-Zhong Ying, Chen-Huan Yu.  (2025)  Ginsenoside F4 inhibits colorectal cancer progression by boosting dendritic cell maturation and remodeling the tumor microenvironment.  World Journal of Gastrointestinal Oncology,  17  (9): (108892).  [PMID:40977662] [10.4251/wjgo.v17.i9.108892]

2. Zhu Yan, Ding Zhechun, Wang Yini, Wu Qing, Chen Dongmei, Wang Luanhong, Li Yuancheng, Yao Yao, Huang Jiman, Li Yun, Wang Xiaojing, Lin Yanchun, Guan Tian, Zeng Haoyu, Li Congzhu.  (2023)  BME-free primary patient-specific organoids obtained with a one-day mimicking method to replicate the corresponding tumor for personalized treatment options.  Frontiers in Oncology,      [PMID:38162496] [10.3389/fonc.2023.1239957]

3. Ming Liu, Ran Cen, Ji-Hong Lu, Tie-Hong Meng, Chun-Rong Li, Carl Redshaw, Timothy J. Prior, Zhu Tao, Xin Xiao.  (2022)  Cucurbit[6]uril-based carbon dots for recognizing L-tryptophan and capecitabine.  Materials Chemistry Frontiers,  6  (19): (2859-2868).  [PMID:] [10.1039/D2QM00589A]

4. Hanwen Liu, Ying Liu, Ting Zhou, Penghui Zhou, Jianguo Li, Anping Deng.  (2022)  Ultrasensitive and Specific Detection of Anticancer Drug 5-Fluorouracil in Blood Samples by a Surface-Enhanced Raman Scattering (SERS)-Based Lateral Flow Immunochromatographic Assay.  MOLECULES,  27  (13): (4019).  [PMID:35807264] [10.3390/molecules27134019]

5. Ting Zhou, Guangzhao He, Changjia Hu, Kang Wu, Ying Liu, Jianguo Li, Anping Deng.  (2022)  Development of a highly sensitive and specific monoclonal antibody-based ELISA coupled with immuno-affinity extraction for the detection of anticancer drug 5-fluorouracil in blood samples.  TALANTA,      [PMID:35696979] [10.1016/j.talanta.2022.123655]

6. Zhouxuan Xiang, Ting Liu, Huimin Wang, Genxin Chen, Xiongbin Zhu, Tonghui Hao, Jiabing Ran, Changying Yang.  (2022)  Rational design of a supramolecular hydrogel with customizable pH-responsiveness on the basis of pH-induced ionization/protonation transition of BSA.  Soft Matter,  18  (16): (3157-3167).  [PMID:35380147] [10.1039/D1SM01589C]

7. Shaoyu Tang, Lei Xu, Xiaolong Yu, Shuona Chen, Huanyong Li, Ying Huang, Junfeng Niu.  (2020)  Degradation of anticancer drug capecitabine in aquatic media by three advanced oxidation processes: Mechanisms, toxicity changes and energy cost evaluation.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2020.127489]

8. Yiren Yang, Pengyu Liu, Yue Jin, Huilin Zhu, Miao Wang, Xiaowen Jiang, Huiyuan Gao.  (2024)  A combined treatment with Ursolic acid and Solasodine inhibits colorectal cancer progression through the AKT1/ERK1/2-GSK-3β-β-catenin axis.  PHYTOMEDICINE,      [PMID:39515101] [10.1016/j.phymed.2024.156068]

9. Chensi Zeng, Yanfang Gong, Chenxi Qi, Xianghua Zeng, Ni Tan.  (2024)  A smart capecitabine imprinted nanocontainer with the dual-responsive performance to pH/NIR light.  Materials Today Communications,      [PMID:] [10.1016/j.mtcomm.2024.109940]

10. Shuliang Song, Xiao Zhang, Lei Cui, Yan Wang, Xiao Tian, Ke Wang, Kai Ji.  (2024)  Mechanisms of lipopolysaccharide protection in tumor drug–induced macrophage damage.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38522696] [10.1016/j.ijbiomac.2024.131006]

11. Yuteng Tang, Yuanhang Xiang, Yu Yang, Yuyuan Zhang, Binqi Wei, Xiaojie Qin, Min Fang, Qiqin Wang, Xinchun Li, Fan Yang.  (2024)  Nanostructured Bubbles-Enhanced Fluorescence for Ultrasensitive Portable MicroRNA Detection.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202413832]

12. Xinqi Qiu, Minhui Zhang, Yan Liu, Mingao Li, Quanzhou Wu, Jianfeng He.  (2024)  Novel water-compatible surface molecularly imprinted polymer microspheres based on boronate affinity and hydrophilic coating for efficient enrichment and separation of capecitabine from urine samples.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.111289]

13. Sai-Nan Qin, Yi-Xue Zhang, Yi-Jie Cao, Ting Wan, Yi-Yang Zhou, Shan-Shan Su, Yu-Qiong Guo, Jian-Jun Sun, Kalle Salminen.  (2026)  A self-assembled electrochemical aptasensor for one-step rapid detection of cisplatin in blood via aptamer conformational change.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2026.116962]