9-Aminocamptothecin (BioDeep_00000230946)

PANOMIX_OTCML-2023 Chemicals and Drugs Antitumor activity Cytotoxicity

代谢物信息卡片

(19S)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

化学式: C20H17N3O4 (363.1219002)
中文名称: 9-氨基喜树碱
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.32%

分子结构信息

SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=C(C=CC=C5N=C4C3=C2)N)O
InChI: InChI=1S/C20H17N3O4/c1-2-20(26)13-7-16-17-10(6-11-14(21)4-3-5-15(11)22-17)8-23(16)18(24)12(13)9-27-19(20)25/h3-7,26H,2,8-9,21H2,1H3/t20-/m0/s1

描述信息

9-Aminocamptothecin is a pyranoindolizinoquinoline.
Aminocamptothecin has been used in trials studying the treatment of Lymphoma, Gastric Cancer, Ovarian Cancer, Esophageal Cancer, and Ovarian Neoplasms, among others.
Aminocamptothecin is a water-insoluble camptothecin derivative. Aminocamptothecin binds to the nuclear enzyme topoisomerase I, thereby inhibiting repair of single-strand DNA breakages. Because the terminal lactone ring of aminocamptothecin required for the agents antitumor activity spontaneously opens under physiological conditions to an inactive carboxy form, the drug must be administered over an extended period of time to achieve effective cytotoxicity. (NCI04)
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor
D000970 - Antineoplastic Agents
9-Aminocamptothecin (9-Amino-CPT) is a topoisomerase I inhibitor with potent anticancer activity[1].

9-Aminocamptothecin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=91421-43-1 (retrieved 2024-10-18) (CAS RN: 91421-43-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

同义名列表

34 个代谢物同义名

(19S)-8-amino-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione; (S)-10-amino-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H)-dione; 1H-PYRANO(3,4:6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE, 10-AMINO-4-ETHYL-4-HYDROXY-, (4S)-; 1H-Pyrano(3;,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 10-amino-4-ethyl-4-hydroxy-, (S)-; (S)-10-Amino-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione; (S)-10-Amino-4-ethyl-4-hydroxy-1H-pyrano[3,4:6,7]-indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 10-amino-4(s)-4-ethyl-4-hydroxy-1h-pyrano(3,4:6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione; 10-Amino-4(S)-4-ethyl-4-hydroxy-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; (S)-10-Amino-4-ethyl-4-hydroxy-1H-pyrano(3;,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione; 1H-Pyrano[3,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 10-amino-4-ethyl-4-hydroxy-, (S)-; (S)-10-Amino-4-ethyl-4-hydroxy-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione; 10-Amino-4-ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione; 1H-Pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione,4-ethyl-4-hydroxy-9-nitro-; 9-amino-CPT;9-amino-20(S)-camptothecin; 9-amino-20-camptothecin, (R,S)-isomer; 9-amino-20-camptothecin, (+-)-isomer; 9-amino-CPT (9-Aminocamptothecin); 9-AMINOCAMPTOTHECIN [WHO-DD]; FUXVKZWTXQUGMW-FQEVSTJZSA-N; 9-Amino-20-(S)-camptothecin; 9-amino-20(S)-camptothecin; 9-amino-2(S)-camptothecin; 9-AMINOCAMPTOTHECIN [MI]; Camptothecin, 9-amino-; 9-amino camptothecin; 9-Amino-camptothecin; 9-aminocamptothecan; 9-Aminocamptothecin; 9-NH2-Camptothecin; aminocamptothecin; UNII-5MB77ICE2Q; NCI60_004578; 9-amino-CPT; 5MB77ICE2Q

数据库引用编号

11 个数据库交叉引用编号

ChEBI: CHEBI:80755
KEGG: C16822
PubChem: 72402
DrugBank: DB12515
ChEMBL: CHEMBL274070
MeSH: 9-aminocamptothecin
ChemIDplus: 0091421431
chemspider: 115975
CAS: 91421-43-1
medchemexpress: HY-100309
NIKKAJI: J360.571J

分类词条

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)

3 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

Zeljko M Prijovich, Pierre-Alain Burnouf, Hua-Cheng Chou, Ping-Ting Huang, Kai-Chuan Chen, Tian-Lu Cheng, Yu-Lin Leu, Steve R Roffler. Synthesis and Antitumor Properties of BQC-Glucuronide, a Camptothecin Prodrug for Selective Tumor Activation. Molecular pharmaceutics. 2016 Apr; 13(4):1242-50. doi: 10.1021/acs.molpharmaceut.5b00771. [PMID: 26824303]
Deval Patel, Shahidur Rahman, Michalakis Savva. Kinetic and thermodynamic studies of 9-aminocamptothecin hydrolysis at physiological pH in the presence of human serum albumin. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2013 Aug; 49(5):858-63. doi: 10.1016/j.ejps.2013.06.005. [PMID: 23791639]
Joanne Bero, Véronique Hannaert, Gabrielle Chataigné, Marie-France Hérent, Joëlle Quetin-Leclercq. In vitro antitrypanosomal and antileishmanial activity of plants used in Benin in traditional medicine and bio-guided fractionation of the most active extract. Journal of ethnopharmacology. 2011 Sep; 137(2):998-1002. doi: 10.1016/j.jep.2011.07.022. [PMID: 21782916]
Zhao Yan, Zhongling Zhu, Kai Li, Peng Chen, Liuchun Wang, Chun Huang, Jinhuai Xue, Meijun Liu. A phase I pharmacokinetics study of 9-nitrocamptothecin in patients with advanced solid tumors. Cancer chemotherapy and pharmacology. 2011 Apr; 67(4):955-61. doi: 10.1007/s00280-010-1546-z. [PMID: 21191594]
Yuangang Zu, Dan Wang, Xiuhua Zhao, Ru Jiang, Qi Zhang, Dongmei Zhao, Yong Li, Baishi Zu, Zhiqiang Sun. A novel preparation method for camptothecin (CPT) loaded folic acid conjugated dextran tumor-targeted nanoparticles. International journal of molecular sciences. 2011; 12(7):4237-49. doi: 10.3390/ijms12074237. [PMID: 21845075]
Katayoun Derakhshandeh, Marzieh Soheili, Simin Dadashzadeh, Reza Saghiri. Preparation and in vitro characterization of 9-nitrocamptothecin-loaded long circulating nanoparticles for delivery in cancer patients. International journal of nanomedicine. 2010 Aug; 5(?):463-71. doi: 10.2147/ijn.s11586. [PMID: 20957168]
Nancy L Bartlett, Jeffrey L Johnson, Nina Wagner-Johnston, Mark J Ratain, Bruce A Peterson. Phase II study of 9-aminocamptothecin in previously treated lymphomas: results of Cancer and Leukemia Group B 9551. Cancer chemotherapy and pharmacology. 2009 Apr; 63(5):793-8. doi: 10.1007/s00280-008-0803-x. [PMID: 18648813]
William C Zamboni, Sandra Strychor, Erin Joseph, Robert A Parise, Merrill J Egorin, Julie L Eiseman. Tumor, tissue, and plasma pharmacokinetic studies and antitumor response studies of docetaxel in combination with 9-nitrocamptothecin in mice bearing SKOV-3 human ovarian xenografts. Cancer chemotherapy and pharmacology. 2008 Aug; 62(3):417-26. doi: 10.1007/s00280-007-0620-7. [PMID: 17957368]
R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
Yu-Ling Leu, Chien-Shu Chen, Yih-Jang Wu, Ji-Wang Chern. Benzyl ether-linked glucuronide derivative of 10-hydroxycamptothecin designed for selective camptothecin-based anticancer therapy. Journal of medicinal chemistry. 2008 Mar; 51(6):1740-6. doi: 10.1021/jm701151c. [PMID: 18318465]
Song-Qi Gao, Yongen Sun, Pavla Kopecková, C Matthew Peterson, Jindrich Kopecek. Pharmacokinetic modeling of absorption behavior of 9-aminocamptothecin (9-AC) released from colon-specific HPMA copolymer-9-AC conjugate in rats. Pharmaceutical research. 2008 Jan; 25(1):218-26. doi: 10.1007/s11095-007-9465-3. [PMID: 17929146]
Zeljko M Prijovich, Yu-Lin Leu, Steve R Roffler. Effect of pH and human serum albumin on the cytotoxicity of a glucuronide prodrug of 9-aminocamptothecin. Cancer chemotherapy and pharmacology. 2007 Jun; 60(1):7-17. doi: 10.1007/s00280-006-0340-4. [PMID: 16983566]
Song-Qi Gao, Zheng-Rong Lu, Pavla Kopecková, Jindrich Kopecek. Biodistribution and pharmacokinetics of colon-specific HPMA copolymer--9-aminocamptothecin conjugate in mice. Journal of controlled release : official journal of the Controlled Release Society. 2007 Feb; 117(2):179-85. doi: 10.1016/j.jconrel.2006.10.024. [PMID: 17150276]
William C Zamboni, Ramesh K Ramanathan, Howard L McLeod, Sridhar Mani, Douglas M Potter, Sandra Strychor, Lauren J Maruca, Cristi R King, Laura L Jung, Robert A Parise, Merrill J Egorin, Todd A Davis, Sharon Marsh. Disposition of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite in relation to ABC transporter genotypes. Investigational new drugs. 2006 Sep; 24(5):393-401. doi: 10.1007/s10637-006-6335-5. [PMID: 16505951]
Sanjeev Sewak, Joan Sorich, James O'Leary. Phase I trial of continuous infusion 9-aminocamptothecin in patients with advanced solid tumors: 21-day infusion is an active well-tolerated regimen. Anti-cancer drugs. 2006 Jun; 17(5):571-9. doi: 10.1097/00001813-200606000-00012. [PMID: 16702815]
William C Zamboni, Sanjay Goel, Tahir Iqbal, Robert A Parise, Sandra Strychor, Trisha V W Repinski, Merrill J Egorin, Sridhar Mani. Clinical and pharmacokinetic study evaluating the effect of food on the disposition of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite in patients with solid tumors. Cancer chemotherapy and pharmacology. 2006 May; 57(5):631-9. doi: 10.1007/s00280-005-0084-6. [PMID: 16205924]
William C Zamboni, Laura L Jung, Merrill J Egorin, Deborah R Hamburger, Erin Joseph, Ruzhi Jin, Sandra Strychor, Ramesh K Ramanathan, Julie L Eiseman. Relationship between plasma exposure of 9-nitrocamptothecin and its 9-aminocamptothecin metabolite and antitumor response in mice bearing human colon carcinoma xenografts. Clinical cancer research : an official journal of the American Association for Cancer Research. 2005 Jul; 11(13):4867-74. doi: 10.1158/1078-0432.ccr-05-0144. [PMID: 16000585]
Laura L Jung, Ramesh K Ramanathan, Merrill J Egorin, Ruzhi Jin, Chandra P Belani, Douglas M Potter, Sandra Strychor, Donald L Trump, Christine Walko, Marwan Fakih, William C Zamboni. Pharmacokinetic studies of 9-nitrocamptothecin on intermittent and continuous schedules of administration in patients with solid tumors. Cancer chemotherapy and pharmacology. 2004 Dec; 54(6):487-96. doi: 10.1007/s00280-004-0835-9. [PMID: 15322760]
M J A de Jonge, S Kaye, J Verweij, C Brock, S Reade, M Scurr, L van Doorn, C Verheij, W Loos, C Brindley, P Mistry, M Cooper, I Judson. Phase I and pharmacokinetic study of XR11576, an oral topoisomerase I and II inhibitor, administered on days 1-5 of a 3-weekly cycle in patients with advanced solid tumours. British journal of cancer. 2004 Oct; 91(8):1459-65. doi: 10.1038/sj.bjc.6602178. [PMID: 15452551]
Patrick A Thompson, Stacey L Berg, Alexander Aleksic, Jody Z Kerr, Leticia McGuffey, Robert Dauser, Jed G Nuchtern, Fred Hausheer, Susan M Blaney. Plasma and cerebrospinal fluid pharmacokinetic study of BNP1350 in nonhuman primates. Cancer chemotherapy and pharmacology. 2004 Jun; 53(6):527-32. doi: 10.1007/s00280-004-0765-6. [PMID: 14997342]
Anita K Lalloo, Feng R Luo, Ailan Guo, Pankaj V Paranjpe, Sung-Hack Lee, Viral Vyas, Eric Rubin, Patrick J Sinko. Membrane transport of camptothecin: facilitation by human P-glycoprotein (ABCB1) and multidrug resistance protein 2 (ABCC2). BMC medicine. 2004 May; 2(?):16. doi: 10.1186/1741-7015-2-16. [PMID: 15125776]
Murugesan K Gounder, Show-Li Sun, Howard Sands, Yong Lin, Weichung J Shih, Zheming Gu, Samantha Charles-Williams, Moulakshi Roychowdhury, Rajeev Rajendra, Eric H Rubin. Development of a bioanalytical liquid chromatography method for quantitation of 9-nitrocamptothecin in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2004 Jan; 799(1):63-72. doi: 10.1016/j.jchromb.2003.10.010. [PMID: 14659436]
Junhong Zhang, Thomas G Burke, Lori J Latus. Determination of 9-nitrocamptothecin by precolumn derivatization and its metabolite 9-aminocamptothecin in a biological fluid using reversed-phase high-performance liquid chromatography with fluorescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Oct; 795(2):309-18. doi: 10.1016/s1570-0232(03)00599-3. [PMID: 14522035]
Zeljko M Prijovich, Yu-Lin Leu, Steve R Roffler. Stability of the new prodrug 9-aminocamptothecin glucuronide (9ACG) in the presence of human serum albumin. Biochemical pharmacology. 2003 Oct; 66(7):1181-7. doi: 10.1016/s0006-2952(03)00472-6. [PMID: 14505797]
Jorge Leguizamo, Mary Quinn, Chris H Takimoto, Michael D Liang, Abdel-Salam Attia Ismail, Janet Pang, William Dahut, Jean L Grem. A phase I study of 9-aminocamptothecin as a colloidal dispersion formulation given as a fortnightly 72-h infusion. Cancer chemotherapy and pharmacology. 2003 Oct; 52(4):333-8. doi: 10.1007/s00280-003-0657-1. [PMID: 12819941]
Rizk El-Galley, Thomas E Keane, Carrie Sun. Camptothecin analogues and vinblastine in the treatment of renal cell carcinoma: an in vivo study using a human orthotopic renal cancer xenograft. Urologic oncology. 2003 Jan; 21(1):49-57. doi: 10.1016/s1078-1439(02)00243-0. [PMID: 12684128]
Franco M Muggia, Leonard Liebes, Maitreyee Hazarika, Scott Wadler, Anne Hamilton, Gila Hornreich, Joan Sorich, Chung Chiang, Elliot Newman, Milan Potmesil, Howard Hochster. Phase I and pharmacologic study of i.p. 9-aminocamptothecin given as six fractions over 14 days. Anti-cancer drugs. 2002 Sep; 13(8):819-25. doi: 10.1097/00001813-200209000-00006. [PMID: 12394266]
Nadja E Schoemaker, Hilde Rosing, Sindy Jansen, Patrick Schöffski, Jinee Rizzo, Jan H M Schellens, Jos H Beijnen. Determination of 9-nitrocamptothecin and its metabolite 9-aminocamptothecin in human plasma using high-performance liquid chromatography with ultraviolet and fluorescence detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Aug; 775(2):231-7. doi: 10.1016/s1570-0232(02)00294-5. [PMID: 12113990]
E Raymond, M Campone, R Stupp, J Menten, P Chollet, T Lesimple, R Fety-Deporte, D Lacombe, X Paoletti, P Fumoleau. Multicentre phase II and pharmacokinetic study of RFS2000 (9-nitro-camptothecin) administered orally 5 days a week in patients with glioblastoma multiforme. European journal of cancer (Oxford, England : 1990). 2002 Jul; 38(10):1348-50. doi: 10.1016/s0959-8049(02)00070-9. [PMID: 12091065]
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M N Kirstein, P J Houghton, P J Cheshire, L B Richmond, A K Smith, S K Hanna, C F Stewart. Relation between 9-aminocamptothecin systemic exposure and tumor response in human solid tumor xenografts. Clinical cancer research : an official journal of the American Association for Cancer Research. 2001 Feb; 7(2):358-66. doi: NULL. [PMID: 11234891]
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J H Schellens, M Maliepaard, R J Scheper, G L Scheffer, J W Jonker, J W Smit, J H Beijnen, A H Schinkel. Transport of topoisomerase I inhibitors by the breast cancer resistance protein. Potential clinical implications. Annals of the New York Academy of Sciences. 2000; 922(?):188-94. doi: 10.1111/j.1749-6632.2000.tb07037.x. [PMID: 11193894]
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W J Loos, J Verweij, H J Gelderblom, M J de Jonge, E Brouwer, B K Dallaire, A Sparreboom. Role of erythrocytes and serum proteins in the kinetic profile of total 9-amino-20(S)-camptothecin in humans. Anti-cancer drugs. 1999 Sep; 10(8):705-10. doi: 10.1097/00001813-199909000-00003. [PMID: 10573202]
M J de Jonge, C J Punt, A H Gelderblom, W J Loos, V van Beurden, A S Planting, M E van der Burg, L W van Maanen, B K Dallaire, J Verweij, D J Wagener, A Sparreboom. Phase I and pharmacologic study of oral (PEG-1000) 9-aminocamptothecin in adult patients with solid tumors. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1999 Jul; 17(7):2219-26. doi: 10.1200/jco.1999.17.7.2219. [PMID: 10561279]
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V M Herben, R van Gijn, J H Schellens, M Schot, J Lieverst, M J Hillebrand, N E Schoemaker, M G Porro, J H Beijnen, W W ten Bokkel Huinink. Phase I and pharmacokinetic study of a daily times 5 short intravenous infusion schedule of 9-aminocamptothecin in a colloidal dispersion formulation in patients with advanced solid tumors. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1999 Jun; 17(6):1906-14. doi: 10.1200/jco.1999.17.6.1906. [PMID: 10561232]
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M J de Jonge, J Verweij, W J Loos, B K Dallaire, A Sparreboom. Clinical pharmacokinetics of encapsulated oral 9-aminocamptothecin in plasma and saliva. Clinical pharmacology and therapeutics. 1999 May; 65(5):491-9. doi: 10.1016/s0009-9236(99)70068-8. [PMID: 10340914]
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A M Langevin, D T Casto, P J Thomas, S D Weitman, C Kretschmar, H Grier, C Pratt, R Dubowy, M Bernstein, S Blaney, T Vietti. Phase I trial of 9-aminocamptothecin in children with refractory solid tumors: a Pediatric Oncology Group study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1998 Jul; 16(7):2494-9. doi: 10.1200/jco.1998.16.7.2494. [PMID: 9667269]
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