Pirarubicin (BioDeep_00000765989)

   

Chemicals and Drugs


代谢物信息卡片


(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2S)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

化学式: C32H37NO12 (627.2315642000001)
中文名称: 吡柔比星
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)OC6CCCCO6
InChI: InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1

描述信息

L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01D - Cytotoxic antibiotics and related substances > L01DB - Anthracyclines and related substances
D000970 - Antineoplastic Agents
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent

同义名列表

3 个代谢物同义名

Pirarubicin; (7S,9S)-7-[(2R,4S,5S,6S)-4-amino-6-methyl-5-[(2S)-oxan-2-yl]oxyoxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; 7-[4-amino-6-methyl-5-(oxan-2-yloxy)oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione



数据库引用编号

10 个数据库交叉引用编号

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)

0 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

  • Mengying Wu, Wei Zhang, Xueru Zhou, Zijun Wang, Sha Li, Chenqi Guo, Yuping Yang, Rongping Zhang, Zhirong Zhang, Xun Sun, Tao Gong. An in situ forming gel co-loaded with pirarubicin and celecoxib inhibits postoperative recurrence and metastasis of breast cancer. International journal of pharmaceutics. 2024 Mar; 653(?):123897. doi: 10.1016/j.ijpharm.2024.123897. [PMID: 38360289]
  • Hongwei Shi, Yue Yan, Hong Yang, Peng Pu, Heng Tang. Schisandrin B Diet Inhibits Oxidative Stress to Reduce Ferroptosis and Lipid Peroxidation to Prevent Pirarubicin-Induced Hepatotoxicity. BioMed research international. 2022; 2022(?):5623555. doi: 10.1155/2022/5623555. [PMID: 36060128]
  • O A El-Kawy, G Abdelaziz. Preparation, characterization and evaluation of [125I]-pirarubicin: A new therapeutic agent for urinary bladder cancer with potential for use as theranostic agent. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine. 2022 Jan; 179(?):110007. doi: 10.1016/j.apradiso.2021.110007. [PMID: 34736111]
  • Li-Rui Sun, Qiu-Shi Guo, Wei Zhou, Min Li. Extract from Dioscorea bulbifera L. rhizomes aggravate pirarubicin-induced cardiotoxicity by inhibiting the expression of P-glycoprotein and multidrug resistance-associated protein 2 in the mouse liver. Scientific reports. 2021 10; 11(1):19720. doi: 10.1038/s41598-021-99264-2. [PMID: 34611244]
  • Nobuhiko Yamauchi, Dai Maruyama, Ilseung Choi, Yoshiko Atsuta, Rika Sakai, Kazuho Miyashita, Yukiyoshi Moriuchi, Hideki Tsujimura, Nobuko Kubota, Go Yamamoto, Tadahiko Igarashi, Koji Izutsu, Shinichiro Yoshida, Kensuke Kojima, Toshiki Uchida, Yoshiko Inoue, Norifumi Tsukamoto, Eiichi Ohtsuka, Sachiko Suzuki, Yoko Inaguma, Satoshi Ichikawa, Hiroshi Gomyo, Yoko Ushijima, Kisato Nosaka, Mio Kurata, Yasuhito Tanaka, Ryuzo Ueda, Masashi Mizokami, Shigeru Kusumoto. Prophylactic antiviral therapy for hepatitis B virus surface antigen-positive patients with diffuse large B-cell lymphoma treated with rituximab-containing chemotherapy. Cancer science. 2021 May; 112(5):1943-1954. doi: 10.1111/cas.14846. [PMID: 33576088]
  • Sajid Ali, Muhammad Umair Amin, Imran Tariq, Muhammad Farhan Sohail, Muhammad Yasir Ali, Eduard Preis, Ghazala Ambreen, Shashank Reddy Pinnapireddy, Jarmila Jedelská, Jens Schäfer, Udo Bakowsky. Lipoparticles for Synergistic Chemo-Photodynamic Therapy to Ovarian Carcinoma Cells: In vitro and in vivo Assessments. International journal of nanomedicine. 2021; 16(?):951-976. doi: 10.2147/ijn.s285950. [PMID: 33603362]
  • Yang Li, Chuchu Feng, Yantao Chen, Ke Huang, Chunmou Li, Xilin Xiong, Peng Li, Dunhua Zhou, Xiaomin Peng, Wenjun Weng, Xiaogeng Deng, Yaohao Wu, Jianpei Fang. Improved Outcomes with Induction Chemotherapy Combined with Arsenic Trioxide in Stage 4 Neuroblastoma: A Case Series. Technology in cancer research & treatment. 2021 Jan; 20(?):15330338211041454. doi: 10.1177/15330338211041454. [PMID: 34569870]
  • Feng Wang, Lixin Wang, Yue Jiao, Zhirong Wang. Qishen Huanwu capsule reduces pirarubicin-induced cardiotoxicity in rats by activating the PI3K/Akt/mTOR pathway. Annals of palliative medicine. 2020 Sep; 9(5):3453-3461. doi: 10.21037/apm-20-1746. [PMID: 33065796]
  • Eva Randárová, Hideaki Nakamura, Rayhanul Islam, Martin Studenovský, Haratake Mamoru, Jun Fang, Petr Chytil, Tomáš Etrych. Highly effective anti-tumor nanomedicines based on HPMA copolymer conjugates with pirarubicin prepared by controlled RAFT polymerization. Acta biomaterialia. 2020 04; 106(?):256-266. doi: 10.1016/j.actbio.2020.02.011. [PMID: 32058082]
  • Chuchu Zhou, Xu Song, Chenqi Guo, Yulu Tan, Juan Zhao, Qin Yang, Dan Chen, Tiantian Tan, Xun Sun, Tao Gong, Zhirong Zhang. Alternative and Injectable Preformed Albumin-Bound Anticancer Drug Delivery System for Anticancer and Antimetastasis Treatment. ACS applied materials & interfaces. 2019 Nov; 11(45):42534-42548. doi: 10.1021/acsami.9b11307. [PMID: 31479235]
  • Bin Huang, Jiabo Zheng, Zhijun Yao, Wenzhe Fan, Shaopeng Qiu, Lingwu Chen, Junxing Chen. Efficacy of intra-arterial chemotherapy combined with intravesical chemotherapy in T1G3 bladder cancer when compared with intravesical chemotherapy alone after bladder-sparing surgery: a retrospective study. World journal of urology. 2019 May; 37(5):823-829. doi: 10.1007/s00345-018-2437-x. [PMID: 30191393]
  • Jin-Hu Wang, Min-Ju Li, Da-Xing Tang, Shan Xu, Jun-Qing Mao, Jia-Bin Cai, Min He, Qiang Shu, Can Lai. Neoadjuvant transcatheter arterial chemoembolization and systemic chemotherapy for treatment of clear cell sarcoma of the kidney in children. Journal of pediatric surgery. 2019 Mar; 54(3):550-556. doi: 10.1016/j.jpedsurg.2018.09.012. [PMID: 30318310]
  • Yang Zhang, Xiao-Yan Ma, Tong Zhang, Meng Qin, Bo Sun, Qi Li, Dian-Wen Hu, Li-Qun Ren. Protective Effects of Apocynum venetum Against Pirarubicin-Induced Cardiotoxicity. The American journal of Chinese medicine. 2019; 47(5):1075-1097. doi: 10.1142/s0192415x19500551. [PMID: 31311298]
  • Yoshio Naya, Kazuya Mikami, Natsuki Takaha, Yuuta Inoue, Atsuko Fujihara, Motohiro Kanazawa, Hiroyuki Nakanishi, Hiroaki Miyashita, Osamu Ukimura. Randomized study of intravesical pirarubicin chemotherapy with low and intermediate-risk nonmuscle-invasive bladder cancer in Japan: Comparison of a single immediate postoperative intravesical instillation with short-term adjuvant intravesical instillations after transurethral resection. Medicine. 2018 Oct; 97(42):e12740. doi: 10.1097/md.0000000000012740. [PMID: 30334959]
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  • Qiongli Su, Ting Tao, Lei Tang, Jun Deng, Kwame Oteng Darko, Sichun Zhou, Mei Peng, Shanping He, Qing Zeng, Alex F Chen, Xiaoping Yang. Down-regulation of PKM2 enhances anticancer efficiency of THP on bladder cancer. Journal of cellular and molecular medicine. 2018 05; 22(5):2774-2790. doi: 10.1111/jcmm.13571. [PMID: 29512924]
  • Ya-Di Wang, Yang Zhang, Bo Sun, Xiao-Wei Leng, Ya-Juan Li, Li-Qun Ren. Cardioprotective effects of rutin in rats exposed to pirarubicin toxicity. Journal of Asian natural products research. 2018 Apr; 20(4):361-373. doi: 10.1080/10286020.2017.1394292. [PMID: 29078725]
  • Waliul Islam, Jun Fang, Tomas Etrych, Petr Chytil, Karel Ulbrich, Akihiro Sakoguchi, Katsuki Kusakabe, Hiroshi Maeda. HPMA copolymer conjugate with pirarubicin: In vitro and ex vivo stability and drug release study. International journal of pharmaceutics. 2018 Jan; 536(1):108-115. doi: 10.1016/j.ijpharm.2017.11.011. [PMID: 29133205]
  • Tomáš Etrych, Kenji Tsukigawa, Hideaki Nakamura, Petr Chytil, Jun Fang, Karel Ulbrich, Masaki Otagiri, Hiroshi Maeda. Comparison of the pharmacological and biological properties of HPMA copolymer-pirarubicin conjugates: A single-chain copolymer conjugate and its biodegradable tandem-diblock copolymer conjugate. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2017 Aug; 106(?):10-19. doi: 10.1016/j.ejps.2017.05.031. [PMID: 28528285]
  • Shimpei Sugiura, Noriaki Noto, Mitsuyuki Koizumi, Daiji Takamoto, Naoya Fujikawa, Ichiro Ikeda. [Post-Operative Single Immediate Intravesical Instillation Chemotherapy as Prophylaxis for Reccurence after Transurethral Resection of Low Risk Non-Muscle-Invasive Bladder Cancer]. Hinyokika kiyo. Acta urologica Japonica. 2017 May; 63(5):183-187. doi: 10.14989/actauroljap_63_5_183. [PMID: 28625024]
  • Elisabetta Teodori, Silvia Dei, Marcella Coronnello, Elisa Floriddia, Gianluca Bartolucci, Dina Manetti, Maria Novella Romanelli, Diego Santo Domingo Porqueras, Milena Salerno. N-alkanol-N-cyclohexanol amine aryl esters: Multidrug resistance (MDR) reversing agents with high potency and efficacy. European journal of medicinal chemistry. 2017 Feb; 127(?):586-598. doi: 10.1016/j.ejmech.2017.01.019. [PMID: 28113128]
  • Caifeng Deng, Mengdi Jia, Guangfei Wei, Tiantian Tan, Yao Fu, Huile Gao, Xun Sun, Quan Zhang, Tao Gong, Zhirong Zhang. Inducing Optimal Antitumor Immune Response through Coadministering iRGD with Pirarubicin Loaded Nanostructured Lipid Carriers for Breast Cancer Therapy. Molecular pharmaceutics. 2017 01; 14(1):296-309. doi: 10.1021/acs.molpharmaceut.6b00932. [PMID: 27936775]
  • Hideaki Nakamura, Eva Koziolová, Petr Chytil, Kenji Tsukigawa, Jun Fang, Mamoru Haratake, Karel Ulbrich, Tomáš Etrych, Hiroshi Maeda. Pronounced Cellular Uptake of Pirarubicin versus That of Other Anthracyclines: Comparison of HPMA Copolymer Conjugates of Pirarubicin and Doxorubicin. Molecular pharmaceutics. 2016 12; 13(12):4106-4115. doi: 10.1021/acs.molpharmaceut.6b00697. [PMID: 27934482]
  • Wan-Jun Sun, Jia-Jia Zhang, Na An, Men Shen, Zhong-Xia Huang, Xin Li. Clinical analysis of 40 multiple myeloma patients with extramedullary plasmacytoma of the head. The Journal of international medical research. 2016 Dec; 44(6):1462-1473. doi: 10.1177/0300060516664820. [PMID: 28322099]
  • Yanping Li, Qinhui Liu, Wenyao Li, Ting Zhang, Hanmei Li, Rui Li, Lei Chen, Shiyun Pu, Jiangying Kuang, Zhiguang Su, Zhirong Zhang, Jinhan He. Design and Validation of PEG-Derivatized Vitamin E Copolymer for Drug Delivery into Breast Cancer. Bioconjugate chemistry. 2016 08; 27(8):1889-99. doi: 10.1021/acs.bioconjchem.6b00292. [PMID: 27418000]
  • Lei Zhang, W F Drew Bennett, Tao Zheng, Ping-Kai Ouyang, Xinping Ouyang, Xueqing Qiu, Anqi Luo, Mikko Karttunen, P Chen. Effect of Cholesterol on Cellular Uptake of Cancer Drugs Pirarubicin and Ellipticine. The journal of physical chemistry. B. 2016 Mar; 120(12):3148-56. doi: 10.1021/acs.jpcb.5b12337. [PMID: 26937690]
  • Liansheng Ren, Xihua Yang, Lili Zhao, Hong Zhang, Jing Wang. Evaluation of Su Fu'ning Lotion's Inhibitory Effects on Bladder Cancer Cells In Vitro and In Vivo by Intravesical Instillation. Integrative cancer therapies. 2016 Mar; 15(1):80-6. doi: 10.1177/1534735415596569. [PMID: 26315609]
  • J-P Long, F Wan, F Zhang, J Zhou, L-F Don. DTC chemotherapy regimen is associated with higher incidence of premature ovarian failure in women of reproductive age with breast cancer. European review for medical and pharmacological sciences. 2016; 20(6):1087-92. doi: NULL. [PMID: 27049261]
  • Xiaoli Yi, Xianghong Lian, Jianxia Dong, Zhuoya Wan, Chunyu Xia, Xu Song, Yao Fu, Tao Gong, Zhirong Zhang. Co-delivery of Pirarubicin and Paclitaxel by Human Serum Albumin Nanoparticles to Enhance Antitumor Effect and Reduce Systemic Toxicity in Breast Cancers. Molecular pharmaceutics. 2015 Nov; 12(11):4085-98. doi: 10.1021/acs.molpharmaceut.5b00536. [PMID: 26422373]
  • Jurstine Daruwalla, Khaled Greish, Cathy Malcontenti-Wilson, Vijayaragavan Muralidharan, Hiroshi Maeda, Chris Christophi. Styrene maleic acid copolymer-pirarubicin induces tumor-selective oxidative stress and decreases tumor hypoxia as possible treatment of colorectal cancer liver metastases. Surgery. 2015 Jul; 158(1):236-47. doi: 10.1016/j.surg.2015.03.019. [PMID: 25999256]
  • Xiao-Rong Ma, Jin Wang, Wang-Gang Zhang, Yin-Xia Chen, Xing-Mei Cao, Ai-Li He, Jie Liu, Jian-Li Wang, Liu-Fang Gu, Bo Lei, Peng-Yu Zhang, Wan-Hong Zhao, Yun Yang, Fang-Xia Wang, Yan Xu. [Cohort Study on GHA and New Combined Priming Chemotherapeutic Regimens in Treatment of Refractory Acute Myeloid Leukemia and Myelodysplastic Syndrome]. Zhongguo shi yan xue ye xue za zhi. 2015 Apr; 23(2):369-74. doi: 10.7534/j.issn.1009-2137.2015.02.014. [PMID: 25948187]
  • Xin Hua Long, Zhen Hao Zhong, Ai Fen Peng, Liang Bo Zhu, Heng Wang, Guo Mei Zhang, Zhi Li Liu. LY294002 suppresses the malignant phenotype and sensitizes osteosarcoma cells to pirarubicin chemotherapy. Molecular medicine reports. 2014 Dec; 10(6):2967-72. doi: 10.3892/mmr.2014.2617. [PMID: 25310590]
  • 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]
  • Parisa Sadatmousavi, Eugene Kovalenko, P Chen. Thermodynamic characterization of the interaction between a peptide-drug complex and serum proteins. Langmuir : the ACS journal of surfaces and colloids. 2014 Sep; 30(37):11122-30. doi: 10.1021/la502422u. [PMID: 25166955]
  • Hideaki Nakamura, Tomas Etrych, Petr Chytil, Manami Ohkubo, Jun Fang, Karel Ulbrich, Hiroshi Maeda. Two step mechanisms of tumor selective delivery of N-(2-hydroxypropyl)methacrylamide copolymer conjugated with pirarubicin via an acid-cleavable linkage. Journal of controlled release : official journal of the Controlled Release Society. 2014 Jan; 174(?):81-7. doi: 10.1016/j.jconrel.2013.11.011. [PMID: 24269967]
  • Hiroaki Tanaka, Satoshi Ambiru, Shunta Nakamura, Terumi Itabashi, Seiji Furuya, Takenori Shimura, Yuhei Nagao, Chika Kawajiri, Yusuke Takeda, Shinichiro Hashimoto, Chiaki Nakaseko. Successful diagnosis of type II enteropathy-associated T-cell lymphoma using flow cytometry and the cell block technique of celomic fluid manifesting as massive pyoid ascites that could not be diagnosed via emergency laparotomy. Internal medicine (Tokyo, Japan). 2014; 53(2):129-33. doi: 10.2169/internalmedicine.53.1268. [PMID: 24429453]
  • Akihiro Ito, Ichiro Shintaku, Makoto Satoh, Naomasa Ioritani, Tatsuo Tochigi, Isao Numata, Takashige Namima, Koichi Kambe, Atsushi Kyan, Seiji Ueno, Shinnosuke Katoh, Hisanobu Adachi, Shinichi Yamashita, Takuhiro Yamaguchi, Yoichi Arai. Intravesical seeding of upper urinary tract urothelial carcinoma cells during nephroureterectomy: an exploratory analysis from the THPMG trial. Japanese journal of clinical oncology. 2013 Nov; 43(11):1139-44. doi: 10.1093/jjco/hyt129. [PMID: 24006504]
  • Jing Zhou, Xuanmiao Zhang, Mei Li, Wenqi Wu, Xun Sun, Ling Zhang, Tao Gong. Novel lipid hybrid albumin nanoparticle greatly lowered toxicity of pirarubicin. Molecular pharmaceutics. 2013 Oct; 10(10):3832-41. doi: 10.1021/mp400303w. [PMID: 23947777]
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