Carmofur (BioDeep_00000177049)

Main id: BioDeep_00000009435

 

human metabolite blood metabolite Volatile Flavor Compounds


代谢物信息卡片


5-fluoro-N-hexyl-4-hydroxy-2-oxo-1,2-dihydropyrimidine-1-carboximidic acid

化学式: C11H16FN3O3 (257.11756379999997)
中文名称: 氟脲己胺
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCCCN=C(O)N1C=C(F)C(O)=NC1=O
InChI: InChI=1S/C11H16FN3O3/c1-2-3-4-5-6-13-10(17)15-7-8(12)9(16)14-11(15)18/h7H,2-6H2,1H3,(H,13,17)(H,14,16,18)

描述信息

L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01B - Antimetabolites > L01BC - Pyrimidine analogues
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
D000970 - Antineoplastic Agents
Carmofur (HCFU) is a rat recombinant acid ceramidase inhibitor with an IC50 of 29 nM. Carmofur is also a protease inhibitor of SARS-CoV-2 main protease (Mpro), fatty acid amide hydrolase (FAAH) and N-acylethanolamine acid amidase (NAAA). Carmofur has anti-cancer, anti-inflammatory and anti-virus activities, and can be used for the study of COVID-19 and acute lung injury (ALI)[1][2][3].

同义名列表

8 个代谢物同义名

5-fluoro-N-hexyl-4-hydroxy-2-oxo-1,2-dihydropyrimidine-1-carboximidic acid; 5-Fluoro-N-hexyl-4-hydroxy-2-oxo-1,2-dihydropyrimidine-1-carboximidate; 1-Hexylcarbamoyl-5-fluorouracil; N-Hexylcarbamoyl-5-fluorouracil; carmofur; Mifurol; HCFU; Carmofur



数据库引用编号

12 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)

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

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Carmen Gil, Tiziana Ginex, Inés Maestro, Vanesa Nozal, Lucía Barrado-Gil, Miguel Ángel Cuesta-Geijo, Jesús Urquiza, David Ramírez, Covadonga Alonso, Nuria E Campillo, Ana Martinez. COVID-19: Drug Targets and Potential Treatments. Journal of medicinal chemistry. 2020 11; 63(21):12359-12386. doi: 10.1021/acs.jmedchem.0c00606. [PMID: 32511912]
  • Zhenming Jin, Yao Zhao, Yuan Sun, Bing Zhang, Haofeng Wang, Yan Wu, Yan Zhu, Chen Zhu, Tianyu Hu, Xiaoyu Du, Yinkai Duan, Jing Yu, Xiaobao Yang, Xiuna Yang, Kailin Yang, Xiang Liu, Luke W Guddat, Gengfu Xiao, Leike Zhang, Haitao Yang, Zihe Rao. Structural basis for the inhibition of SARS-CoV-2 main protease by antineoplastic drug carmofur. Nature structural & molecular biology. 2020 06; 27(6):529-532. doi: 10.1038/s41594-020-0440-6. [PMID: 32382072]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Jose Antonio Ortega, Jose M Arencibia, Giuseppina La Sala, Marco Borgogno, Inga Bauer, Luca Bono, Clarissa Braccia, Andrea Armirotti, Stefania Girotto, Anand Ganesan, Marco De Vivo. Pharmacophore Identification and Scaffold Exploration to Discover Novel, Potent, and Chemically Stable Inhibitors of Acid Ceramidase in Melanoma Cells. Journal of medicinal chemistry. 2017 07; 60(13):5800-5815. doi: 10.1021/acs.jmedchem.7b00472. [PMID: 28603987]
  • Namrata Sengupta, Delaney C Reardon, Patrick D Gerard, William S Baldwin. Exchange of polar lipids from adults to neonates in Daphnia magna: Perturbations in sphingomyelin allocation by dietary lipids and environmental toxicants. PloS one. 2017; 12(5):e0178131. doi: 10.1371/journal.pone.0178131. [PMID: 28542405]
  • Debojit Bhattacherjee, Krishna Pada Bhabak. Atom based 3D-QSAR studies on 2,4-dioxopyrimidine-1-carboxamide analogs: Validation of experimental inhibitory potencies towards acid ceramidase. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2016 Feb; 83(?):8-18. doi: 10.1016/j.ejps.2015.12.005. [PMID: 26658266]
  • Daniela Pizzirani, Chiara Pagliuca, Natalia Realini, Davide Branduardi, Giovanni Bottegoni, Marco Mor, Fabio Bertozzi, Rita Scarpelli, Daniele Piomelli, Tiziano Bandiera. Discovery of a new class of highly potent inhibitors of acid ceramidase: synthesis and structure-activity relationship (SAR). Journal of medicinal chemistry. 2013 May; 56(9):3518-30. doi: 10.1021/jm301879g. [PMID: 23614460]
  • Natalia Realini, Carlos Solorzano, Chiara Pagliuca, Daniela Pizzirani, Andrea Armirotti, Rosaria Luciani, Maria Paola Costi, Tiziano Bandiera, Daniele Piomelli. Discovery of highly potent acid ceramidase inhibitors with in vitro tumor chemosensitizing activity. Scientific reports. 2013; 3(?):1035. doi: 10.1038/srep01035. [PMID: 23301156]
  • Anita Kamra Verma, A Chanchal, A Maitra. Co-polymeric hydrophilic nanospheres for drug delivery: release kinetics, and cellular uptake. Indian journal of experimental biology. 2010 Oct; 48(10):1043-52. doi: . [PMID: 21299047]
  • Ken Morimoto, Masae Koh. [Postoperative changes in serum lipid levels of breast cancer and adjuvant chemotherapy]. Gan to kagaku ryoho. Cancer & chemotherapy. 2004 Oct; 31(10):1517-24. doi: . [PMID: 15508443]
  • Ken Morimoto, Masae Koh. Postoperative adjuvant use of carmofur for early breast cancer. Osaka city medical journal. 2003 Dec; 49(2):77-83. doi: . [PMID: 15179836]
  • P Osterlund, A Orpana, I Elomaa, H Repo, H Joensuu. Raltitrexed treatment promotes systemic inflammatory reaction in patients with colorectal carcinoma. British journal of cancer. 2002 Sep; 87(6):591-9. doi: 10.1038/sj.bjc.6600520. [PMID: 12237767]
  • A Ooi, T Ohkubo, M Higashigawa, H Kawasaki, H Kakito, Y Kagawa, M Kojima, M Sakurai. Plasma, intestine and tumor levels of 5-fluorouracil in mice bearing L1210 ascites tumor following oral administration of 5-fluorouracil, UFT (mixed compound of tegafur and uracil), carmofur and 5'-deoxy-5-fluorouridine. Biological & pharmaceutical bulletin. 2001 Nov; 24(11):1329-31. doi: 10.1248/bpb.24.1329. [PMID: 11725974]
  • K Sasaki, H Takasaka, H Kawasaki, T Matsunaga, N Nakagawa, K Shibata, T Yabana, T Yasojima, T Furuhata, F Hata, K Hirata. [Weekly low-dose CPT-11 and HCFU for advanced colorectal cancer on an outpatient treatment basis]. Gan to kagaku ryoho. Cancer & chemotherapy. 2000 Jun; 27(6):915-9. doi: . [PMID: 10897221]
  • T Matsuda, K Mabuchi, H Kitaoka, N Hirata, U Kitaoka. [A case of multiple liver metastases showing good response by administration of carmofur alone in an aged patient with colorectal cancer]. Gan to kagaku ryoho. Cancer & chemotherapy. 1999 Feb; 26(3):357-9. doi: . [PMID: 10065100]
  • K Sakurai, K Yoshiga, M Tsumura, K Takada. Effects of thermochemotherapy [1-hexylcarbamoyl-5-fluorouracil (HCFU) combined with hyperthermia]: a basic study on the most effective timing and sequence in vivo. Anticancer research. 1996 Sep; 16(5A):2729-33. doi: . [PMID: 8917379]
  • S Akaishi, M Kobari, T Yusa, H Yamanami, T Furukawa, S Matsuno. [Transfer of carmofur (HCFU) to the serum, bile, pancreatic juice and pancreatic tumor tissue in the cases of peri-pancreatic head cancer]. Gan to kagaku ryoho. Cancer & chemotherapy. 1995 Apr; 22(5):659-64. doi: . [PMID: 7717718]
  • Y Kuroda, R Ohkuma, K Ohsato. [Serum concentration of HCFU and 5-FU after oral administration of HCFU in postoperative digestive cancer patients]. Gan to kagaku ryoho. Cancer & chemotherapy. 1992 Sep; 19(11):1831-6. doi: NULL. [PMID: 1519925]
  • T Kubota, S Fujita, S Kodaira, T Yamamoto, K Josui, Y Arisawa, A Suto, K Ishibiki, O Abe, K Mabuchi. Antitumor activity of fluoropyrimidines and thymidylate synthetase inhibition. Japanese journal of cancer research : Gann. 1991 Apr; 82(4):476-82. doi: 10.1111/j.1349-7006.1991.tb01873.x. [PMID: 1904428]
  • M Tsubono, Y Nio, S Imai, T Shiraishi, H Morimoto, C C Tseng, T Tobe. [Chemotherapy with fluoropyrimidines for MOPC-104E plasmacytoma transplanted in mice with CCl4 induced chronic liver dysfunction]. Nihon Gan Chiryo Gakkai shi. 1990 Mar; 25(3):640-7. doi: . [PMID: 2141051]
  • K Fukushima. [Antitumor effects of 5-fluorouracil-bound organic silicon compound]. Gan to kagaku ryoho. Cancer & chemotherapy. 1989 Sep; 16(9):3243-50. doi: NULL. [PMID: 2782916]
  • K Takenaka, T Kanematsu, M Shimada, K Sugimachi. Low dose 1-hexylcarbamoyl-5-fluorouracil (HCFU) recommended for cirrhotic patients with hepatocellular carcinoma. European journal of cancer & clinical oncology. 1989 Aug; 25(8):1191-5. doi: 10.1016/0277-5379(89)90414-8. [PMID: 2548869]
  • H Komeda, M Horie, Y Takahashi, S Kobayashi, S Yamada, M Kuriyama, Y Kawada. [A case of renal cell carcinoma with lung metastases successfully treated by interferon-beta]. Hinyokika kiyo. Acta urologica Japonica. 1989 Apr; 35(4):637-41. doi: . [PMID: 2735268]
  • Y Kanda, S Akazawa, K Futatsugi, T Fujiki, K Saifuku, K Yamamoto, F Suzuki, T Nakajima, Y Naoi, M Muraoka. [A case of hepatocellular carcinoma (HCC) with lung metastasis which responded to chemotherapy with a single use of 1-hexylcarbamoyl-5-fluorouracil (HCFU)]. Gan to kagaku ryoho. Cancer & chemotherapy. 1989 Feb; 16(2):269-72. doi: . [PMID: 2537606]
  • H Taniguchi, Y Shioaki, A Itoh, K Seiki, M Shimotsuma, T Yamaguchi, K Sawai, T Takahashi, S Kitai, Y Shimamura. [Trans-arterial embolization or transarterial infusion of anti-cancer drugs suspended in a lipid contrast medium against unresectable metastatic liver cancer]. Gan to kagaku ryoho. Cancer & chemotherapy. 1988 Aug; 15(8 Pt 2):2568-72. doi: ". [PMID: 2843125]
  • M Suenaga. [5-FU and HCFU concentrations in serum and tissues in hepatocellular carcinoma after HCFU oral administration]. Gan no rinsho. Japan journal of cancer clinics. 1988 May; 34(6):744-8. doi: . [PMID: 2837592]
  • H Anai, Y Maehara, H Kusumoto, T Kusumoto, K Sugimachi. Sensitivity test for 5-fluorouracil and its analogues, 1-(2-tetrahydrofuryl)-5-fluorouracil, uracil/1-(2-tetrahydrofuryl)-5-fluorouracil (4:1) and 1-hexylcarbamoyl-5-fluorouracil, using the subrenal capsule assay. Oncology. 1988; 45(3):144-7. doi: 10.1159/000226551. [PMID: 3130595]
  • Y Maehara, H Anai, H Kusumoto, T Kusumoto, K Sugimachi. Colorectal carcinoma in vitro is more sensitive to 1-hexylcarbamoyl-5-fluorouracil compared with six other antitumor drugs: carboquone, Adriamycin, mitomycin C, aclacinomycin A, cisplatin, 5-fluorouracil. Diseases of the colon and rectum. 1988 Jan; 31(1):62-7. doi: 10.1007/bf02552573. [PMID: 3130239]
  • H Higashi, K Takenaka, T Kanematsu, T Matsumata, Y Yoshida, K Sugimachi. [1-Hexylcarbamoyl-5-fluorouracil (HCFU) effective in hepatocellular carcinoma metastatic to the lungs--a case report]. Gan to kagaku ryoho. Cancer & chemotherapy. 1987 Oct; 14(10):2956-9. doi: . [PMID: 2821925]
  • S Nishio, T Kishimoto, M Maekawa, J Kawakita, Y Morikawa, K Funai, N Hayahara, K Yuki, T Nishijima, R Yasumoto. [Study on effectiveness of carmofur (Mifurol) in urogenital carcinoma, especially bladder cancer, as a post-operative adjuvant chemotherapeutic agent]. Hinyokika kiyo. Acta urologica Japonica. 1987 Feb; 33(2):295-303. doi: . [PMID: 3591594]
  • K Sakakibara, K Mizuno, T Kano, M Ohta, Y Tomita, G Yoshio, Y Tokuhashi, Y Nishida, E Okamoto, M Hori. [The determination of thymidylate synthetase inhibition for testing fluoropyrimidines--pharmacokinetics and metabolism of carmofur (HCFU) in patients with gynecologic malignancies--Tokai HCFU Study Group for Gynecologic Malignancies]. Gan no rinsho. Japan journal of cancer clinics. 1986 Nov; 32(14):1841-8. doi: . [PMID: 2948036]
  • S Takashima, Y Kinami, M Kiriyama, F Tomita, K Ueno, I Miyazaki. [Distribution of 1-hexycarbamoyl-5-fluorouracil in rats and human patients, and clinical results in patients with colorectal cancer]. Gan to kagaku ryoho. Cancer & chemotherapy. 1986 Mar; 13(3 Pt 1):549-55. doi: NULL. [PMID: 3954377]
  • K Ueda, H Jinno, H Watanabe, K Ohtaguro. [Combination effects of CDDP, ACR and HCFU on progressive urothelial tumors]. Gan to kagaku ryoho. Cancer & chemotherapy. 1985 Jun; 12(6):1318-22. doi: . [PMID: 3859251]
  • H Nakazato, T Kito, M Yasue, Y Yamamura, T Kobari, T Hirakawa, M Hatta. [Influence of immunopotentiators on the activation of 5-FU derivatives]. Gan to kagaku ryoho. Cancer & chemotherapy. 1985 Apr; 12(4):867-74. doi: . [PMID: 3920971]
  • H Ueoka, S Kuroda, T Ohnoshi, I Kimura, A Numoto, I Hino, M Takahashi, M Tsuji. [Intraarterial Adriamycin for patients with hepatocellular carcinoma and metastatic liver carcinoma]. Gan to kagaku ryoho. Cancer & chemotherapy. 1984 Dec; 11(12 Pt 1):2579-84. doi: NULL. [PMID: 6095763]
  • R Okeda, T Karakama, S Kimura, S Toizumi, T Mitsushima, Y Yokoyama. Neuropathologic study on chronic neurotoxicity of 5-fluorouracil and its masked compounds in dogs. Acta neuropathologica. 1984; 63(4):334-43. doi: 10.1007/bf00687342. [PMID: 6433643]
  • M Sawada, Y Matsui, Y Okudaira. Concentrations of a new antitumor agent, 1-hexylcarbamoyl-5-fluorouracil in serum and gynecologic tumor tissue. Nihon Sanka Fujinka Gakkai zasshi. 1983 Dec; 35(12):2421-6. doi: NULL. [PMID: 6663150]
  • Y Hara, A Kono, M Tanaka. [Evaluation of the optimum method of administration of a new antineoplastic agent, HCFU, based on the serum 5-FU concentration following oral administration]. Gan to kagaku ryoho. Cancer & chemotherapy. 1982 Feb; 9(2):293-300. doi: NULL. [PMID: 7184403]
  • O Nakajima, Y Yoshida, T Isoda, Y Takemasa, Y Imamura, Y Koyama. Quantitative determination of 1-hexylcarbamoyl-5-fluorouracil and its metabolites in man. Journal of chromatography. 1981 Sep; 225(1):91-7. doi: 10.1016/s0378-4347(00)80247-9. [PMID: 7298763]
  • M Iigo, A Nakamura, K Kuretani, A Hoshi. Excretion of 1-hexylcarbamoyl-5-fluorouracil in urine of mice. Journal of pharmacobio-dynamics. 1981 Jul; 4(7):490-6. doi: 10.1248/bpb1978.4.490. [PMID: 6795334]
  • M Iigo, K Kuretani, A Hoshi. Metabolic fate on 1-hexylcarbamoyl-5-fluorouracil and 5-fluorouracil in mice bearing ascites sarcoma 180. Journal of the National Cancer Institute. 1981 Feb; 66(2):345-9. doi: . [PMID: 6935483]
  • T Kobari, Y Iguro, A Ujiie, H Namekawa. Metabolism of 1-hexylcarbamoyl-5-fluorouracil (HCFU), a new antitumour agent, in rats, rabbits and dogs. Xenobiotica; the fate of foreign compounds in biological systems. 1981 Jan; 11(1):57-62. doi: 10.3109/00498258109045272. [PMID: 7222730]
  • M Iigo, A Nakamura, K Kuretani, A Hoshi. Metabolic fate of 1-hexylcarbamoyl-5-fluorouracil after oral administration in mice. Xenobiotica; the fate of foreign compounds in biological systems. 1980 Nov; 10(11):847-54. doi: 10.3109/00498258009033815. [PMID: 7467400]
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  • T Kobari, K Tan, M Kumakura, S Watanabe, I Shirakawa, H Kobayashi, A Ujiie, Y Miyama, H Namekawa, H Yamamoto. Metabolic fate of 1-hexylcarbamoyl-5-fluorouracil in rats. Xenobiotica; the fate of foreign compounds in biological systems. 1978 Sep; 8(9):547-56. doi: 10.3109/00498257809061254. [PMID: 695698]