Tamibarotene (BioDeep_00000009397)
Secondary id: BioDeep_00001871423
human metabolite blood metabolite Chemicals and Drugs
代谢物信息卡片
4-((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid
化学式: C22H25NO3 (351.1834)
中文名称: 他米巴罗汀
谱图信息:
最多检出来源 Homo sapiens(blood) 2.8%
分子结构信息
SMILES: CC1(C)CCC(C)(C)C2=C1C=CC(NC(=O)C1=CC=C(C=C1)C(O)=O)=C2
InChI: InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
描述信息
Tamibarotene is only found in individuals that have used or taken this drug. It is a novel synthetic retinoid for acute promyelocytic leukaemia (APL). Tamibarotene is currently approved in Japan for treatment of recurrent APL, and is undergoing clinical trials in the United States.Tamibarotene is a specific agonist for retinoic acid receptor alpha/beta with possible binding to retinoid X receptors (RXR).
C274 - Antineoplastic Agent > C2122 - Cell Differentiating Agent > C1934 - Differentiation Inducer
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C804 - Retinoic Acid Agent
C308 - Immunotherapeutic Agent > C129820 - Antineoplastic Immunomodulating Agent
Same as: D01418
同义名列表
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:32181
- KEGG: C12864
- PubChem: 108143
- HMDB: HMDB0015605
- Metlin: METLIN69500
- DrugBank: DB04942
- ChEMBL: CHEMBL25202
- Wikipedia: Tamibarotene
- chemspider: 97231
- CAS: 94497-51-5
- PMhub: MS000023177
- PubChem: 583253
- PDB-CCD: A80
- NIKKAJI: J227.635F
- KNApSAcK: 32181
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
1 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Somdutt Mujwar. Computational repurposing of tamibarotene against triple mutant variant of SARS-CoV-2.
Computers in biology and medicine.
2021 09; 136(?):104748. doi:
10.1016/j.compbiomed.2021.104748. [PMID: 34388463] - Lixi Li, Ran Luo, Yi Yang, Yichun Cheng, Shuwang Ge, Gang Xu. Tamibarotene inhibit the accumulation of fibrocyte and alleviate renal fibrosis by IL-17A.
Renal failure.
2020 Nov; 42(1):1173-1183. doi:
10.1080/0886022x.2020.1847145. [PMID: 33213229] - Hiroshi Watanabe, Jing Bi, Ryota Murata, Rui Fujimura, Kento Nishida, Tadashi Imafuku, Yuka Nakamura, Hitoshi Maeda, Ayumi Mukunoki, Toru Takeo, Naomi Nakagata, Yuki Kurauchi, Hiroshi Katsuki, Motoko Tanaka, Kazutaka Matsushita, Masafumi Fukagawa, Toru Maruyama. A synthetic retinoic acid receptor agonist Am80 ameliorates renal fibrosis via inducing the production of alpha-1-acid glycoprotein.
Scientific reports.
2020 07; 10(1):11424. doi:
10.1038/s41598-020-68337-z. [PMID: 32651445] - Ping Leng, Zhao Yang, Baohua Ma, Jing Li, Jialin Sun, Yiming Xie, Yong Sun. Simultaneous determination of AM80 (tamibarotene) and WJD-A-1 in rat plasma by ultra high-performance liquid chromatography-tandem mass spectrometry and its application to a pharmacokinetic study.
Artificial cells, nanomedicine, and biotechnology.
2018; 46(sup1):1131-1137. doi:
10.1080/21691401.2018.1446443. [PMID: 29504426] - Ying Jin, Dixin Liu, Xu Fang, Kebei Gao, Xiaoping Lin. [Effect of tamibarotene on innate immune response in the model of Porphyromonas gingivalis induced periodontitis].
Zhonghua kou qiang yi xue za zhi = Zhonghua kouqiang yixue zazhi = Chinese journal of stomatology.
2015 Mar; 50(3):146-50. doi:
. [PMID: 26081852] - Xin Liu, Zhihua Zhang, Yuqi Jiang, Yue Hu, Zhonglan Wang, Junli Liu, Ruihua Feng, Jie Zhang, Guihua Huang. Novel PEG-grafted nanostructured lipid carrier for systematic delivery of a poorly soluble anti-leukemia agent Tamibarotene: characterization and evaluation.
Drug delivery.
2015 Feb; 22(2):223-9. doi:
10.3109/10717544.2014.885614. [PMID: 24559497] - Chia-Wen Hsu, Jinghua Zhao, Ruili Huang, Jui-Hua Hsieh, Jon Hamm, Xiaoqing Chang, Keith Houck, Menghang Xia. Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor.
Scientific reports.
2014 Sep; 4(?):6437. doi:
10.1038/srep06437. [PMID: 25257666] - M Richards, S Chiba, M Ninomiya, C Wakabayasi, H Kunugi. Inhibition of olanzapine-induced weight gain by the retinoid analog AM-80.
Pharmacopsychiatry.
2013 Nov; 46(7):267-73. doi:
10.1055/s-0033-1354406. [PMID: 24105080] - Xin Liu, Zhonglan Wang, Ruihua Feng, Yue Hu, Guihua Huang. A novel approach for systematic delivery of a hydrophobic anti-leukemia agent tamibarotene mediated by nanostructured lipid carrier.
Journal of biomedical nanotechnology.
2013 Sep; 9(9):1586-93. doi:
10.1166/jbn.2013.1656. [PMID: 23980506] - Chie Miyabe, Yoshishige Miyabe, Noriko N Miura, Kei Takahashi, Yuya Terashima, Etsuko Toda, Fumiko Honda, Tomohiro Morio, Naoko Yamagata, Naohito Ohno, Koichi Shudo, Jun-ichi Suzuki, Mitsuaki Isobe, Kouji Matsushima, Ryoji Tsuboi, Nobuyuki Miyasaka, Toshihiro Nanki. Am80, a retinoic acid receptor agonist, ameliorates murine vasculitis through the suppression of neutrophil migration and activation.
Arthritis and rheumatism.
2013 Feb; 65(2):503-12. doi:
10.1002/art.37784. [PMID: 23203767] - Osamu Yoshikawa, Yu Ebata, Hiroyuki Tsuchiya, Arisa Kawahara, Chihiro Kojima, Yoshito Ikeda, Susumu Hama, Kentaro Kogure, Koichi Shudo, Goshi Shiota. A retinoic acid receptor agonist tamibarotene suppresses iron accumulation in the liver.
Obesity (Silver Spring, Md.).
2013 Jan; 21(1):E22-5. doi:
10.1002/oby.20013. [PMID: 23404745] - Hideaki Muratake, Yohei Amano, Takahiro Toda, Kiyoshi Sugiyama, Koichi Shudo. Synthesis of Am80 (tamibarotene) prodrug candidates, congeners and metabolites.
Chemical & pharmaceutical bulletin.
2013; 61(8):846-52. doi:
10.1248/cpb.c13-00356. [PMID: 23902867] - Chao Yuan, Yu-Sheng Zhang, Yan-Na Cheng, Xia Xue, Wen-Fang Xu, Xian-Jun Qu. A112, a tamibarotene dimethylaminoethyl ester, may inhibit human leukemia cell growth more potently than tamibarotene.
Leukemia & lymphoma.
2012 Feb; 53(2):295-304. doi:
10.3109/10428194.2011.614707. [PMID: 21846186] - Huazhen Ye, Bin Qiu, Zhenyu Lin, Guonan Chen. Fluorescence spectrometric study on the interaction of tamibarotene with bovine serum albumin.
Luminescence : the journal of biological and chemical luminescence.
2011 Sep; 26(5):336-41. doi:
10.1002/bio.1234. [PMID: 22021245] - Kazuki Morohoshi, Katsumi Yoshida, Yoshinori Nakagawa, Saeko Hoshikawa, Hiroshi Ozaki, Yurie Takahashi, Sadayoshi Ito, Kouki Mori. Effects of synthetic retinoid Am80 on iodide-induced autoimmune thyroiditis in nonobese diabetic mice.
Cellular immunology.
2011; 270(1):1-4. doi:
10.1016/j.cellimm.2011.05.005. [PMID: 21601836] - Aya Sato, Kaori Watanabe, Kayoko Kaneko, Yousuke Murakami, Miwako Ishido, Nobuyuki Miyasaka, Toshihiro Nanki. The effect of synthetic retinoid, Am80, on T helper cell development and antibody production in murine collagen-induced arthritis.
Modern rheumatology.
2010 Jun; 20(3):244-51. doi:
10.1007/s10165-009-0265-y. [PMID: 20039185] - Megumi Sugitani, Rieko Abe, Nobutomo Ikarashi, Kiyomi Ito, Hideaki Muratake, Koichi Shudo, Kiyoshi Sugiyama. Disposition of a new tamibarotene prodrug in mice.
Biological & pharmaceutical bulletin.
2009 Dec; 32(12):1997-2001. doi:
10.1248/bpb.32.1997. [PMID: 19952418] - Naho Ohyanagi, Miwako Ishido, Fumihito Suzuki, Kayoko Kaneko, Tetsuo Kubota, Nobuyuki Miyasaka, Toshihiro Nanki. Retinoid ameliorates experimental autoimmune myositis, with modulation of Th cell differentiation and antibody production in vivo.
Arthritis and rheumatism.
2009 Oct; 60(10):3118-27. doi:
10.1002/art.24930. [PMID: 19790078] - Ishido Miwako, Koichi Shudo. Oral administration of synthetic retinoid Am80 inhibits the development of type 1 diabetes in non-obese diabetic (NOD) mice.
Biological & pharmaceutical bulletin.
2009 Jan; 32(1):157-9. doi:
10.1248/bpb.32.157. [PMID: 19122301] - Ishido Miwako, Hiroyuki Kagechika. Tamibarotene.
Drugs of today (Barcelona, Spain : 1998).
2007 Aug; 43(8):563-8. doi:
10.1358/dot.2007.43.8.1072615. [PMID: 17925887] - Takaomi Sanda, Shinsuke Iida, Satoshi Kayukawa, Ryuzo Ueda. Induction of class II major histocompatibility complex expression in human multiple myeloma cells by retinoid.
Haematologica.
2007 Jan; 92(1):115-20. doi:
10.3324/haematol.10300. [PMID: 17229644] - Norifumi Takeda, Ichiro Manabe, Takayuki Shindo, Hiroshi Iwata, Satoshi Iimuro, Hiroyuki Kagechika, Koichi Shudo, Ryozo Nagai. Synthetic retinoid Am80 reduces scavenger receptor expression and atherosclerosis in mice by inhibiting IL-6.
Arteriosclerosis, thrombosis, and vascular biology.
2006 May; 26(5):1177-83. doi:
10.1161/01.atv.0000214296.94849.1c. [PMID: 16484594] - Makoto Takeuchi. [Clinical experience with a new synthetic retinoid, tamibarotene (Am-80) for relapsed or refractory acute promyelocytic leukemia].
Gan to kagaku ryoho. Cancer & chemotherapy.
2006 Mar; 33(3):397-401. doi:
. [PMID: 16531727] - Shinichiro Orita, Masao Hirose, Satoru Takahashi, Katsumi Imaida, Nobuyuki Ito, Koichi Shudo, Hajime Ohigashi, Akira Murakami, Tomoyuki Shirai. Modifying effects of 1'-acetoxychavicol acetate (ACA) and the novel synthetic retinoids Re-80, Am-580 and Am-55P in a two-stage carcinogenesis model in female rats.
Toxicologic pathology.
2004 Mar; 32(2):250-7. doi:
10.1080/01926230490274425. [PMID: 15200164] - M Itoh, G Kominami. On-line immunoaffinity extraction followed by high-performance liquid chromatography and radioimmunoassay for a novel retinobenzoic acid, AM-80, in human plasma.
Journal of immunoassay & immunochemistry.
2001; 22(3):213-23. doi:
10.1081/ias-100104707. [PMID: 11506273] - K Mizojiri, H Okabe, K Sugeno, A Misaki, M Ito, G Kominami, Y Esumi, M Takaichi, T Harada, H Seki, A Inaba. Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl] benzoic acid. 4th communication: absorption, metabolism, excretion and plasma protein binding in various animals and man.
Arzneimittel-Forschung.
1997 Mar; 47(3):259-69. doi:
NULL. [PMID: 9105544] - K Mizojiri, H Okabe, K Sugeno, Y Esumi, M Takaichi, T Harada, H Seki, A Inaba. Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl]benzoic acid. 3rd communication: placental transfer and excretion into milk in rats.
Arzneimittel-Forschung.
1997 Feb; 47(2):201-8. doi:
. [PMID: 9079241] - K Mizojiri, H Okabe, K Sugeno, Y Esumi, M Takaichi, S Tsutsumi, T Harada, R Miyoshi, A Inaba. Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl] benzoic acid. 2nd communication: absorption, distribution and excretion after single and consecutive subcutaneous administration in rats.
Arzneimittel-Forschung.
1997 Feb; 47(2):195-200. doi:
NULL. [PMID: 9079240] - K Mizojiri, H Okabe, K Sugeno, Y Esumi, M Takaichi, T Miyake, H Seki, A Inaba. Studies on the metabolism and disposition of the new retinoid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)carbamoyl] benzoic acid. 1st communication: absorption, distribution, metabolism and excretion after topical application and subcutaneous administration in rats.
Arzneimittel-Forschung.
1997 Jan; 47(1):59-69. doi:
NULL. [PMID: 9037446] - K Kuwabara, K Shudo, Y Hori. Novel synthetic retinoic acid inhibits rat collagen arthritis and differentially affects serum immunoglobulin subclass levels.
FEBS letters.
1996 Jan; 378(2):153-6. doi:
10.1016/0014-5793(95)01440-3. [PMID: 8549823] - N Takahashi, T R Breitman. Induction of differentiation and covalent binding to proteins by the synthetic retinoids Ch55 and Am80.
Archives of biochemistry and biophysics.
1994 Oct; 314(1):82-9. doi:
10.1006/abbi.1994.1414. [PMID: 7944409]
