CB3717 (BioDeep_00000008838)
代谢物信息卡片
10-Propargyl-5,8-dideazafolic acid
化学式: C24H23N5O6 (477.1648)
中文名称:
谱图信息:
最多检出来源 Mentha canadensis(plant) 16.67%
分子结构信息
SMILES: C#CCN(CC1=CC2=C(C=C1)N=C(NC2=O)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O
InChI: InChI=1S/C24H23N5O6/c1-2-11-29(13-14-3-8-18-17(12-14)22(33)28-24(25)27-18)16-6-4-15(5-7-16)21(32)26-19(23(34)35)9-10-20(30)31/h1,3-8,12,19H,9-11,13H2,(H,26,32)(H,30,31)(H,34,35)(H3,25,27,28,33)/t19-/m0/s1
描述信息
D004791 - Enzyme Inhibitors > D005493 - Folic Acid Antagonists
D000970 - Antineoplastic Agents
同义名列表
2 个代谢物同义名
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:3258
- KEGG: C11737
- PubChem: 135438608
- Metlin: METLIN69187
- DrugBank: DB03541
- ChEMBL: CHEMBL389051
- CAS: 76849-19-9
- PMhub: MS000022540
- PubChem: 13902
- PDB-CCD: CB3
- NIKKAJI: J22.095G
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
- Cristina Müller, Joseph A Reddy, Christopher P Leamon, Roger Schibli. Effects of the antifolates pemetrexed and CB3717 on the tissue distribution of (99m)Tc-EC20 in xenografted and syngeneic tumor-bearing mice.
Molecular pharmaceutics.
2010 Apr; 7(2):597-604. doi:
10.1021/mp900296k. [PMID: 20199053] - Magdalena Dudkowska, Seweryn Bajer, Tomasz Jaworski, Joanna Zielińska, Małgorzata Manteuffel-Cymborowska, Barbara Grzelakowska-Sztabert. Antifolate/folate-activated HGF/c-Met signalling pathways in mouse kidneys-the putative role of their downstream effectors in cross-talk with androgen receptor.
Archives of biochemistry and biophysics.
2009 Mar; 483(1):111-9. doi:
10.1016/j.abb.2008.12.015. [PMID: 19135973] - B Grzelakowska-Sztabert, M Dudkowska, M Manteuffel-Cymborowska. Nuclear and membrane receptor-mediated signalling pathways modulate polyamine biosynthesis and interconversion.
Biochemical Society transactions.
2007 Apr; 35(Pt 2):386-90. doi:
10.1042/bst0350386. [PMID: 17371283] - Magdalena Dudkowska, Tomasz Jaworski, Barbara Grzelakowska-Sztabert, Małgorzata Manteuffel-Cymborowska. Androgen receptor and c-Myc transcription factors as putative partners in the in vivo cross-talk between androgen receptor-mediated and c-Met-mediated signalling pathways.
Acta biochimica Polonica.
2007; 54(2):253-9. doi:
10.18388/abp.2007_3245. [PMID: 17520086] - Magdalena Dudkowska, Agnieszka Stachurska, Barbara Grzelakowska-Sztabert, Małgorzata Manteuffel-Cymborowska. Up-regulation of spermidine/spermine N1-acetyltransferase (SSAT) expression is a part of proliferative but not anabolic response of mouse kidney.
Acta biochimica Polonica.
2002; 49(4):969-77. doi:
024904969. [PMID: 12545203] - M Dudkowska, A Stachurska, W Chmurzyska, B Grzelakowska-Sztabert, M Manteuffel-Cymborowska. Cross-talk between steroid-receptor-mediated and cell-membrane-receptor-mediated signalling pathways results in the in vivo modulation of c-Met and ornithine decarboxylase gene expression in mouse kidney.
The Biochemical journal.
2001 Jan; 353(Pt 2):317-23. doi:
10.1042/0264-6021:3530317. [PMID: 11139396] - N J Curtin, K J Bowman, R N Turner, B Huang, P J Loughlin, A H Calvert, B T Golding, R J Griffin, D R Newell. Potentiation of the cytotoxicity of thymidylate synthase (TS) inhibitors by dipyridamole analogues with reduced alpha1-acid glycoprotein binding.
British journal of cancer.
1999 Aug; 80(11):1738-46. doi:
10.1038/sj.bjc.6690591. [PMID: 10468290] - M Dudkowska, M Manteuffel-Cymborowska, W Chmurzyńska, B Grzelakowska-Sztabert. Catecholamines participate in the induction of ornithine decarboxylase gene expression in normal and hyperplastic mouse kidney.
Biochimica et biophysica acta.
1999 May; 1454(1):71-9. doi:
10.1016/s0925-4439(99)00028-9. [PMID: 10354516] - D R Newell. Clinical pharmacokinetics of antitumor antifolates.
Seminars in oncology.
1999 Apr; 26(2 Suppl 6):74-81. doi:
. [PMID: 10598559] - G R Westerhof, S Rijnboutt, J H Schornagel, H M Pinedo, G J Peters, G Jansen. Functional activity of the reduced folate carrier in KB, MA104, and IGROV-I cells expressing folate-binding protein.
Cancer research.
1995 Sep; 55(17):3795-802. doi:
. [PMID: 7641196] - M Manteuffel-Cymborowska, W Chmurzyńska, M Peska, B Grzelakowska-Sztabert. Arginine and ornithine metabolizing enzymes in testosterone-induced hypertrophic mouse kidney.
The international journal of biochemistry & cell biology.
1995 Mar; 27(3):287-95. doi:
10.1016/1357-2725(94)00070-r. [PMID: 7780833] - A Jackman, I Judson. Re: 'Oncology drug discovery and clinical trial testing: who's listening?'.
Cancer investigation.
1994; 12(1):105-8. doi:
10.3109/07357909409021400. [PMID: 8281460] - M Manteuffel-Cymborowska, W Chmurzyńska, B Grzelakowska-Sztabert. Polyamines in testosterone-induced hypertrophic and antifolate-induced hyperplastic mouse kidney. Differential effect of alpha-difluoromethylornithine.
Biochimica et biophysica acta.
1993 Sep; 1182(2):133-41. doi:
10.1016/0925-4439(93)90133-l. [PMID: 8357843] - D I Jodrell, D R Newell, S E Morgan, S Clinton, J P Bensted, L R Hughes, A H Calvert. The renal effects of N10-propargyl-5,8-dideazafolic acid (CB3717) and a non-nephrotoxic analogue ICI D1694, in mice.
British journal of cancer.
1991 Nov; 64(5):833-8. doi:
10.1038/bjc.1991.409. [PMID: 1931603] - M Manteuffel-Cymborowska, W Chmurzyńska, B Grzelakowska-Sztabert. Ornithine decarboxylase induction in mouse kidney as indicator of renal damage. Differential nephrotoxic effect of anticancer antifolate drugs.
Cancer letters.
1991 Sep; 59(3):237-41. doi:
10.1016/0304-3835(91)90147-a. [PMID: 1913620] - D I Jodrell, D R Newell, W Gibson, L R Hughes, A H Calvert. The pharmacokinetics of the quinazoline antifolate ICI D 1694 in mice and rats.
Cancer chemotherapy and pharmacology.
1991; 28(5):331-8. doi:
10.1007/bf00685685. [PMID: 1914075] - N J Curtin, D R Newell, A L Harris. Modulation of dipyridamole action by alpha 1 acid glycoprotein. Reduced potentiation of quinazoline antifolate (CB3717) cytotoxicity by dipyridamole.
Biochemical pharmacology.
1989 Oct; 38(19):3281-8. doi:
10.1016/0006-2952(89)90626-6. [PMID: 2818627] - J Galivan, M S Rhee, T B Johnson, R Dilwith, M G Nair, M Bunni, D G Priest. The role of cellular folates in the enhancement of activity of the thymidylate synthase inhibitor 10-propargyl-5,8-dideazafolate against hepatoma cells in vitro by inhibitors of dihydrofolate reductase.
The Journal of biological chemistry.
1989 Jun; 264(18):10685-92. doi:
10.1016/s0021-9258(18)81677-5. [PMID: 2525127] - K R Harrap, A L Jackman, D R Newell, G A Taylor, L R Hughes, A H Calvert. Thymidylate synthase: a target for anticancer drug design.
Advances in enzyme regulation.
1989; 29(?):161-79. doi:
10.1016/0065-2571(89)90099-x. [PMID: 2633608] - J Galivan, M S Rhee, T B Johnson, T C Chou, M G Nair, M Bunni, D Priest. The enhancement of the activity of 10-propargyl-5,8-dideazafolate and 5,10-dideazatetrahydrofolate by inhibitors of dihydrofolate reductase.
Advances in enzyme regulation.
1989; 28(?):13-21. doi:
10.1016/0065-2571(89)90060-5. [PMID: 2624172] - M Manteuffel-Cymborowska, B Kaminska, B Grzelakowska-Sztabert. Dose dependent retention and polyglutamation of N10-propargyl-5,8-dideazafolic acid (CB 3717) in the tumour-bearing mouse.
Anticancer research.
1988 Jul; 8(4):791-6. doi:
NULL. [PMID: 3178167] - N J Curtin, A L Harris. Potentiation of quinazoline antifolate (CB3717) toxicity by dipyridamole in human lung carcinoma, A549, cells.
Biochemical pharmacology.
1988 Jun; 37(11):2113-20. doi:
10.1016/0006-2952(88)90568-0. [PMID: 3377815] - P K Buamah, A W Skillen, A J Cassells-Smith, O F James, A L Harris. Intestinal alkaline phosphatase isoenzyme in patients with primary liver cancer during treatment with N10-propargyl 5, 8-dideazafolic acid (CB 3717).
Journal of surgical oncology.
1988 Jun; 38(2):83-7. doi:
10.1002/jso.2930380205. [PMID: 2898039] - C Sessa, M Zucchetti, M Ginier, Y Willems, M D'Incalci, F Cavalli. Phase I study of the antifolate N10-propargyl-5,8-dideazafolic acid, CB 3717.
European journal of cancer & clinical oncology.
1988 Apr; 24(4):769-75. doi:
10.1016/0277-5379(88)90313-6. [PMID: 3383977] - B M Cantwell, V Macaulay, A L Harris, S B Kaye, I E Smith, R A Milsted, A H Calvert. Phase II study of the antifolate N10-propargyl-5,8-dideazafolic acid (CB 3717) in advanced breast cancer.
European journal of cancer & clinical oncology.
1988 Apr; 24(4):733-6. doi:
10.1016/0277-5379(88)90307-0. [PMID: 3383974] - M F Bassendine, N J Curtin, H Loose, A L Harris, O F James. Induction of remission in hepatocellular carcinoma with a new thymidylate synthase inhibitor, CB3717. A phase II study.
Journal of hepatology.
1987 Jun; 4(3):349-56. doi:
10.1016/s0168-8278(87)80545-7. [PMID: 2439582] - P K Buamah, O F James, A W Skillen, A L Harris. Serum vitamin B12 levels in patients with primary hepatocellular carcinoma during treatment with CB3717.
Journal of surgical oncology.
1987 Feb; 34(2):100-3. doi:
10.1002/jso.2930340207. [PMID: 2433545] - A H Calvert, D R Newell, A L Jackman, L A Gumbrell, E Sikora, B Grzelakowska-Sztabert, J A Bishop, I R Judson, S J Harland, K R Harrap. Recent preclinical and clinical studies with the thymidylate synthase inhibitor N10-propargyl-5,8-dideazafolic acid (CB 3717).
NCI monographs : a publication of the National Cancer Institute.
1987; ?(5):213-8. doi:
NULL. [PMID: 3431591] - A H Calvert, D L Alison, S J Harland, B A Robinson, A L Jackman, T R Jones, D R Newell, Z H Siddik, E Wiltshaw, T J McElwain. A phase I evaluation of the quinazoline antifolate thymidylate synthase inhibitor, N10-propargyl-5,8-dideazafolic acid, CB3717.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
1986 Aug; 4(8):1245-52. doi:
10.1200/jco.1986.4.8.1245. [PMID: 3734849] - D R Newell, D L Alison, A H Calvert, K R Harrap, M Jarman, T R Jones, M Manteuffel-Cymborowska, P O'Connor. Pharmacokinetics of the thymidylate synthase inhibitor N10-propargyl-5,8-dideazafolic acid (CB3717) in the mouse.
Cancer treatment reports.
1986 Aug; 70(8):971-9. doi:
. [PMID: 3731153] - M Manteuffel-Cymborowska, E Sikora, B Grzelakowska-Sztabert. Polyglutamation of the antifolate anticancer drug N10-propargyl-5,8-dideazafolic acid (CB 3717) in the mouse.
Anticancer research.
1986 Jul; 6(4):807-12. doi:
NULL. [PMID: 2875688] - N J Curtin, A L Harris, O F James, M F Bassendine. Inhibition of the growth of human hepatocellular carcinoma in vitro and in athymic mice by a quinazoline inhibitor of thymidylate synthase, CB3717.
British journal of cancer.
1986 Mar; 53(3):361-8. doi:
10.1038/bjc.1986.60. [PMID: 3008799] - P K Buamah, C Cornell, O F James, A W Skillen, A L Harris. Serial serum AFP heterogeneity changes in patients with hepatocellular carcinoma during chemotherapy.
Cancer chemotherapy and pharmacology.
1986; 17(2):182-4. doi:
10.1007/bf00306751. [PMID: 2424626] - D L Alison, D R Newell, C Sessa, S J Harland, L I Hart, K R Harrap, A H Calvert. The clinical pharmacokinetics of the novel antifolate N10-propargyl-5,8-dideazafolic acid (CB 3717).
Cancer chemotherapy and pharmacology.
1985; 14(3):265-71. doi:
10.1007/bf00258131. [PMID: 3995686] - A L Jackman, G A Taylor, A H Calvert, K R Harrap. Modulation of anti-metabolite effects. Effects of thymidine on the efficacy of the quinazoline-based thymidylate synthetase inhibitor, CB3717.
Biochemical pharmacology.
1984 Oct; 33(20):3269-75. doi:
10.1016/0006-2952(84)90089-3. [PMID: 6487375] - F Sikora, B Grzelakowska-Sztabert. Quinazoline CB 3717 and CB 3703 inhibition of folate retention and metabolism in Ehrlich ascites carcinoma cells and some organs of the host-mouse.
Cancer letters.
1984 Jul; 23(3):289-95. doi:
10.1016/0304-3835(84)90096-x. [PMID: 6744253] - G A Taylor, A L Jackman, A H Calvert, K R Harrap. Plasma nucleoside and base levels following treatment with the new thymidylate synthetase inhibitor CB 3717.
Advances in experimental medicine and biology.
1984; 165 Pt B(?):379-82. doi:
10.1007/978-1-4757-0390-0_72. [PMID: 6720435]
