Azidopine (BioDeep_00000008576)

 

Secondary id: BioDeep_00001876731

human metabolite blood metabolite


代谢物信息卡片


3-{2-[(4-azidophenyl)formamido]ethyl} 5-ethyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid

化学式: C27H26F3N5O5 (557.1885942)
中文名称:
谱图信息: 最多检出来源 Astragalus membranaceus(plant) 66.67%

分子结构信息

SMILES: CCOC(=O)C1=C(C)NC(=C(C1c1ccccc1C(F)(F)F)C(=O)OCCNC(=O)c1ccc(cc1)N=[N+]=[N-])C
InChI: InChI=1S/C27H26F3N5O5/c1-4-39-25(37)21-15(2)33-16(3)22(23(21)19-7-5-6-8-20(19)27(28,29)30)26(38)40-14-13-32-24(36)17-9-11-18(12-10-17)34-35-31/h5-12,23,33H,4,13-14H2,1-3H3,(H,32,36)

描述信息

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D000345 - Affinity Labels

同义名列表

4 个代谢物同义名

3-{2-[(4-azidophenyl)formamido]ethyl} 5-ethyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylic acid; 3-{2-[(4-azidophenyl)formamido]ethyl} 5-ethyl 2,6-dimethyl-4-[2-(trifluoromethyl)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate; Azidopine; Azidopine



数据库引用编号

13 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

  • Francisco Muñoz-Martínez, Peihua Lu, Fernando Cortés-Selva, José María Pérez-Victoria, Ignacio A Jiménez, Angel G Ravelo, Frances J Sharom, Francisco Gamarro, Santiago Castanys. Celastraceae sesquiterpenes as a new class of modulators that bind specifically to human P-glycoprotein and reverse cellular multidrug resistance. Cancer research. 2004 Oct; 64(19):7130-8. doi: 10.1158/0008-5472.can-04-1005. [PMID: 15466210]
  • Henrietta Venter, Richard A Shilling, Saroj Velamakanni, Lekshmy Balakrishnan, Hendrik W Van Veen. An ABC transporter with a secondary-active multidrug translocator domain. Nature. 2003 Dec; 426(6968):866-70. doi: 10.1038/nature02173. [PMID: 14685244]
  • Cheppail Ramachandran, Thangaiyan Rabi, Hugo B Fonseca, Steven J Melnick, Enrique A Escalon. Novel plant triterpenoid drug amooranin overcomes multidrug resistance in human leukemia and colon carcinoma cell lines. International journal of cancer. 2003 Jul; 105(6):784-9. doi: 10.1002/ijc.11180. [PMID: 12767063]
  • Shuzhong Zhang, Marilyn E Morris. Effects of the flavonoids biochanin A, morin, phloretin, and silymarin on P-glycoprotein-mediated transport. The Journal of pharmacology and experimental therapeutics. 2003 Mar; 304(3):1258-67. doi: 10.1124/jpet.102.044412. [PMID: 12604704]
  • Qin Qu, Joseph W K Chu, Frances J Sharom. Transition state P-glycoprotein binds drugs and modulators with unchanged affinity, suggesting a concerted transport mechanism. Biochemistry. 2003 Feb; 42(5):1345-53. doi: 10.1021/bi0267745. [PMID: 12564938]
  • P Mistry, A J Stewart, W Dangerfield, S Okiji, C Liddle, D Bootle, J A Plumb, D Templeton, P Charlton. In vitro and in vivo reversal of P-glycoprotein-mediated multidrug resistance by a novel potent modulator, XR9576. Cancer research. 2001 Jan; 61(2):749-58. doi: . [PMID: 11212278]
  • K Takara, Y Tanigawara, F Komada, K Nishiguchi, T Sakaeda, K Okumura. The novel anticancer drug KRN5500 interacts with, but is hardly transported by, human P-glycoprotein. Japanese journal of cancer research : Gann. 2000 Feb; 91(2):248-54. doi: 10.1111/j.1349-7006.2000.tb00938.x. [PMID: 10761713]
  • K Takara, Y Tanigawara, F Komada, K Nishiguchi, T Sakaeda, K Okumura. Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs. Biological & pharmaceutical bulletin. 1999 Dec; 22(12):1355-9. doi: 10.1248/bpb.22.1355. [PMID: 10746169]
  • F J Sharom, X Yu, P Lu, R Liu, J W Chu, K Szabó, M Müller, C D Hose, A Monks, A Váradi, J Seprôdi, B Sarkadi. Interaction of the P-glycoprotein multidrug transporter (MDR1) with high affinity peptide chemosensitizers in isolated membranes, reconstituted systems, and intact cells. Biochemical pharmacology. 1999 Aug; 58(4):571-86. doi: 10.1016/s0006-2952(99)00139-2. [PMID: 10413294]
  • N Sonveaux, C Vigano, A B Shapiro, V Ling, J M Ruysschaert. Ligand-mediated tertiary structure changes of reconstituted P-glycoprotein. A tryptophan fluorescence quenching analysis. The Journal of biological chemistry. 1999 Jun; 274(25):17649-54. doi: 10.1074/jbc.274.25.17649. [PMID: 10364203]
  • A Wallstab, M Koester, M Böhme, D Keppler. Selective inhibition of MDR1 P-glycoprotein-mediated transport by the acridone carboxamide derivative GG918. British journal of cancer. 1999 Mar; 79(7-8):1053-60. doi: 10.1038/sj.bjc.6690169. [PMID: 10098736]
  • Y Naoe, M Inami, S Takagaki, S Matsumoto, I Kawamura, F Nishigaki, S Tsujimoto, T Manda, K Shimomura. Different effects of FK317 on multidrug-resistant tumor in vivo and in vitro. Japanese journal of cancer research : Gann. 1998 Oct; 89(10):1047-54. doi: 10.1111/j.1349-7006.1998.tb00495.x. [PMID: 9849584]
  • M H Charuk, A A Grey, R A Reithmeier. Identification of the synthetic surfactant nonylphenol ethoxylate: a P-glycoprotein substrate in human urine. The American journal of physiology. 1998 06; 274(6):F1127-39. doi: 10.1152/ajprenal.1998.274.6.f1127. [PMID: 9841506]
  • Y Zhang, X Guo, E T Lin, L Z Benet. Overlapping substrate specificities of cytochrome P450 3A and P-glycoprotein for a novel cysteine protease inhibitor. Drug metabolism and disposition: the biological fate of chemicals. 1998 Apr; 26(4):360-6. doi: . [PMID: 9531525]
  • G Toffoli, G Corona, R Sorio, A Bertola, M Boiocchi. Reversal activity of cyclosporin A and its metabolites M1, M17 and M21 in multidrug-resistant cells. International journal of cancer. 1997 May; 71(5):900-6. doi: 10.1002/(sici)1097-0215(19970529)71:5<900::aid-ijc32>3.0.co;2-8. [PMID: 9180163]
  • J S Gilsdorf, J F Rebbeor, P D Holohan. Evidence that the organic cation/H+ exchanger in the brush border membrane of dog kidney is a 41-kDa protein. The Journal of pharmacology and experimental therapeutics. 1997 Feb; 280(2):1043-50. doi: NULL. [PMID: 9023322]
  • S Nakamura, T Minamino, M Nomura, S Wakusawa, K Miyamoto, H Hidaka. Inhibition of P-glycoprotein-dependent multidrug resistance by an isoquinolinesulfonamide compound H-87 in rat ascites hepatoma AH66 cells. Biological & pharmaceutical bulletin. 1996 Jun; 19(6):886-9. doi: 10.1248/bpb.19.886. [PMID: 8799494]
  • C L Lanning, R L Fine, C W Sachs, U S Rao, J J Corcoran, M B Abou-Donia. Chlorpyrifos oxon interacts with the mammalian multidrug resistance protein, P-glycoprotein. Journal of toxicology and environmental health. 1996 Mar; 47(4):395-407. doi: 10.1080/009841096161726. [PMID: 8600291]
  • J Bentley, S E Bell, D M Quinn, G L Kellett, J R Warr. 2-deoxy-D-glucose toxicity and transport in human multidrug-resistant KB carcinoma cell lines. Oncology research. 1996; 8(2):77-84. doi: NULL. [PMID: 8859778]
  • K S Schumaker, M J Gizinski. 1,4-Dihydropyridine binding sites in moss plasma membranes. Properties of receptors for a calcium channel antagonist. The Journal of biological chemistry. 1995 Oct; 270(40):23461-7. doi: 10.1074/jbc.270.40.23461. [PMID: 7559508]
  • M Kawada, K Umezawa. Inostamycin, an inhibitor of P-glycoprotein function, interacts specifically with phosphatidylethanolamine. Japanese journal of cancer research : Gann. 1995 Sep; 86(9):873-8. doi: 10.1111/j.1349-7006.1995.tb03099.x. [PMID: 7591966]
  • L Y Wei, M J Stutts, M M Hoffman, P D Roepe. Overexpression of the cystic fibrosis transmembrane conductance regulator in NIH 3T3 cells lowers membrane potential and intracellular pH and confers a multidrug resistance phenotype. Biophysical journal. 1995 Sep; 69(3):883-95. doi: 10.1016/s0006-3495(95)79962-3. [PMID: 8519988]
  • J F Eliason, H Ramuz, T Yoshikubo, T Ishikawa, T Yamamoto, T Tsuruo. Novel dithiane analogues of tiapamil with high activity to overcome multidrug resistance in vitro. Biochemical pharmacology. 1995 Jul; 50(2):187-96. doi: 10.1016/0006-2952(95)00115-g. [PMID: 7632162]
  • J H Charuk, P Y Wong, R A Reithmeier. Differential interaction of human renal P-glycoprotein with various metabolites and analogues of cyclosporin A. The American journal of physiology. 1995 Jul; 269(1 Pt 2):F31-9. doi: 10.1152/ajprenal.1995.269.1.f31. [PMID: 7631829]
  • F J Sharom, G DiDiodato, X Yu, K J Ashbourne. Interaction of the P-glycoprotein multidrug transporter with peptides and ionophores. The Journal of biological chemistry. 1995 Apr; 270(17):10334-41. doi: 10.1074/jbc.270.17.10334. [PMID: 7730340]
  • I L Urbatsch, A E Senior. Effects of lipids on ATPase activity of purified Chinese hamster P-glycoprotein. Archives of biochemistry and biophysics. 1995 Jan; 316(1):135-40. doi: 10.1006/abbi.1995.1020. [PMID: 7840607]
  • J Drímal, L Bohácik. The effect of photogenerated site-directed free radicals on surface dihydropyridine binding sites identified with photoaffinity probe (-)-[3H]-azidopine on cultured monkey renal cells. Methods and findings in experimental and clinical pharmacology. 1994 Jul; 16(6):397-404. doi: . [PMID: 7530790]
  • M S Poruchynsky, V Ling. Detection of oligomeric and monomeric forms of P-glycoprotein in multidrug resistant cells. Biochemistry. 1994 Apr; 33(14):4163-74. doi: 10.1021/bi00180a009. [PMID: 7908829]
  • J Drímal. Identification of dihydropyridine (DHP) binding sites on cultured monkey renal cells (GMRC) with a photoaffinity probe (-)-[3H]-azidopine. General physiology and biophysics. 1994 Apr; 13(2):137-48. doi: . [PMID: 7528701]
  • T W Loo, D M Clarke. Functional consequences of glycine mutations in the predicted cytoplasmic loops of P-glycoprotein. The Journal of biological chemistry. 1994 Mar; 269(10):7243-8. doi: 10.1016/s0021-9258(17)37274-5. [PMID: 7907326]
  • J H Charuk, T W Loo, D M Clarke, R A Reithmeier. Interaction of rat kidney P-glycoprotein with a urinary component and various drugs including cyclosporin A. The American journal of physiology. 1994 Jan; 266(1 Pt 2):F66-75. doi: 10.1152/ajprenal.1994.266.1.f66. [PMID: 7905714]
  • T Zordan-Nudo, V Ling, Z Liu, E Georges. Effects of nonionic detergents on P-glycoprotein drug binding and reversal of multidrug resistance. Cancer research. 1993 Dec; 53(24):5994-6000. doi: ". [PMID: 7903200]
  • K Nishiyama, T Shirahama, A Yoshimura, T Sumizawa, T Furukawa, M Ichikawa-Haraguchi, S Akiyama, Y Ohi. Expression of the multidrug transporter, P-glycoprotein, in renal and transitional cell carcinomas. Cancer. 1993 Jun; 71(11):3611-9. doi: 10.1002/1097-0142(19930601)71:11<3611::aid-cncr2820711124>3.0.co;2-t. [PMID: 8098269]
  • G Chen, C Ramachandran, A Krishan. Thaliblastine, a plant alkaloid, circumvents multidrug resistance by direct binding to P-glycoprotein. Cancer research. 1993 Jun; 53(11):2544-7. doi: . [PMID: 8098661]
  • K Miyamoto, K Inoko, S Wakusawa, S Kajita, T Hasegawa, K Takagi, M Koyama. Inhibition of multidrug resistance by a new staurosporine derivative, NA-382, in vitro and in vivo. Cancer research. 1993 Apr; 53(7):1555-9. doi: . [PMID: 8095855]
  • T W Loo, D M Clarke. Functional consequences of proline mutations in the predicted transmembrane domain of P-glycoprotein. The Journal of biological chemistry. 1993 Feb; 268(5):3143-9. doi: NULL. [PMID: 8094081]
  • E Friche, E J Demant, M Sehested, N I Nissen. Effect of anthracycline analogs on photolabelling of p-glycoprotein by [125I]iodomycin and [3H]azidopine: relation to lipophilicity and inhibition of daunorubicin transport in multidrug resistant cells. British journal of cancer. 1993 Feb; 67(2):226-31. doi: 10.1038/bjc.1993.44. [PMID: 8094288]
  • S Léonce, A Pierré, M Anstett, V Pérez, A Genton, J P Bizzari, G Atassi. Effects of a new triazinoaminopiperidine derivative on adriamycin accumulation and retention in cells displaying P-glycoprotein-mediated multidrug resistance. Biochemical pharmacology. 1992 Nov; 44(9):1707-15. doi: 10.1016/0006-2952(92)90063-o. [PMID: 1360210]
  • S Wakusawa, K Takeda, K Miyamoto, H Hidaka. Increase of vinblastine accumulation by inhibitors of calmodulin-dependent cell functions in rat ascites hepatoma AH66 cells. Anticancer research. 1992 Nov; 12(6B):2021-4. doi: . [PMID: 1363514]
  • E Friche, M K Danks, W T Beck. Characterization of tumor cell resistance to 4'-deoxy-4'-iododoxorubicin developed in Ehrlich ascites cells in vivo. Cancer research. 1992 Oct; 52(20):5701-6. doi: . [PMID: 1356619]
  • J H Charuk, R A Reithmeier. Interaction of P-glycoprotein with a hydrophobic component of rat urine. Biochemical and biophysical research communications. 1992 Jul; 186(2):796-802. doi: 10.1016/0006-291x(92)90816-4. [PMID: 1353959]
  • P D Holohan, K E White, P P Sokol, J Rebbeor. Photoaffinity labeling of the organic cation/H+ exchanger in renal brush border membrane vesicles. The Journal of biological chemistry. 1992 Jul; 267(19):13513-9. doi: 10.1016/s0021-9258(18)42241-7. [PMID: 1352295]
  • K Miyamoto, S Wakusawa, K Inoko, K Takagi, M Koyama. Reversal of vinblastine resistance by a new staurosporine derivative, NA-382, in P388/ADR cells. Cancer letters. 1992 Jun; 64(2):177-83. doi: 10.1016/0304-3835(92)90079-b. [PMID: 1351792]
  • T Saeki, A M Shimabuku, K Ueda, T Komano. Specific drug binding by purified lipid-reconstituted P-glycoprotein: dependence on the lipid composition. Biochimica et biophysica acta. 1992 Jun; 1107(1):105-10. doi: 10.1016/0005-2736(92)90334-i. [PMID: 1352129]
  • I Tamai, A R Safa. Azidopine noncompetitively interacts with vinblastine and cyclosporin A binding to P-glycoprotein in multidrug resistant cells. The Journal of biological chemistry. 1991 Sep; 266(25):16796-800. doi: . [PMID: 1679434]
  • T Saeki, A M Shimabuku, Y Azuma, Y Shibano, T Komano, K Ueda. Expression of human P-glycoprotein in yeast cells--effects of membrane component sterols on the activity of P-glycoprotein. Agricultural and biological chemistry. 1991 Jul; 55(7):1859-65. doi: NULL. [PMID: 1369463]
  • S E Bates, C Y Shieh, L A Mickley, H L Dichek, A Gazdar, D L Loriaux, A T Fojo. Mitotane enhances cytotoxicity of chemotherapy in cell lines expressing a multidrug resistance gene (mdr-1/P-glycoprotein) which is also expressed by adrenocortical carcinomas. The Journal of clinical endocrinology and metabolism. 1991 Jul; 73(1):18-29. doi: 10.1210/jcem-73-1-18. [PMID: 1675220]
  • W Sato, N Fukazawa, T Suzuki, K Yusa, T Tsuruo. Circumvention of multidrug resistance by a newly synthesized quinoline derivative, MS-073. Cancer research. 1991 May; 51(9):2420-4. doi: . [PMID: 1673087]
  • M Ichikawa, A Yoshimura, T Furukawa, T Sumizawa, Y Nakazima, S Akiyama. Glycosylation of P-glycoprotein in a multidrug-resistant KB cell line, and in the human tissues. Biochimica et biophysica acta. 1991 Mar; 1073(2):309-15. doi: 10.1016/0304-4165(91)90136-5. [PMID: 1672608]
  • Y Miyamoto, H Maeda. Enhancement by verapamil of neocarzinostatin action on multidrug-resistant Chinese hamster ovary cells: possible release of nonprotein chromophore in cells. Japanese journal of cancer research : Gann. 1991 Mar; 82(3):351-6. doi: 10.1111/j.1349-7006.1991.tb01853.x. [PMID: 1673676]
  • M Ichikawa, A Yoshimura, T Sumizawa, N Shudo, Y Kuwazuru, T Furukawa, S Akiyama. Interaction of organic chemicals with P-glycoprotein in the adrenal gland, kidney, and a multidrug-resistant KB cell. The Journal of biological chemistry. 1991 Jan; 266(2):903-8. doi: . [PMID: 1670776]
  • M Horio, E Lovelace, I Pastan, M M Gottesman. Agents which reverse multidrug-resistance are inhibitors of [3H]vinblastine transport by isolated vesicles. Biochimica et biophysica acta. 1991 Jan; 1061(1):106-10. doi: 10.1016/0005-2736(91)90274-c. [PMID: 1671642]
  • M Sehested, T Skovsgaard, P B Jensen, E J Demant, E Friche, N Bindslev. Transport of the multidrug resistance modulators verapamil and azidopine in wild type and daunorubicin resistant Ehrlich ascites tumour cells. British journal of cancer. 1990 Jul; 62(1):37-41. doi: 10.1038/bjc.1990.225. [PMID: 1975202]
  • M Ichikawa, A Yoshimura, T Furukawa, T Sumizawa, S Akiyama. Modulators of the multidrug-transporter, P-glycoprotein, exist in the human plasma. Biochemical and biophysical research communications. 1990 Jan; 166(1):74-80. doi: 10.1016/0006-291x(90)91913-d. [PMID: 1967939]
  • E Friche, P B Jensen, M Sehested, E J Demant, N N Nissen. The solvents cremophor EL and Tween 80 modulate daunorubicin resistance in the multidrug resistant Ehrlich ascites tumor. Cancer communications. 1990; 2(9):297-303. doi: . [PMID: 1976341]
  • A Yoshimura, Y Kuwazuru, T Sumizawa, M Ichikawa, S Ikeda, T Uda, S Akiyama. Cytoplasmic orientation and two-domain structure of the multidrug transporter, P-glycoprotein, demonstrated with sequence-specific antibodies. The Journal of biological chemistry. 1989 Sep; 264(27):16282-91. doi: . [PMID: 2476441]
  • E P Bruggemann, U A Germann, M M Gottesman, I Pastan. Two different regions of P-glycoprotein [corrected] are photoaffinity-labeled by azidopine. The Journal of biological chemistry. 1989 Sep; 264(26):15483-8. doi: . [PMID: 2475500]