Amifostine thiol (BioDeep_00001868834)
Main id: BioDeep_00000006567
代谢物信息卡片
2-((3-Aminopropyl)amino)ethanethiol
化学式: C5H14N2S (134.0878)
中文名称: 2-(3-氨基丙基氨基)乙烷硫醇, 2-（（3-氨基丙基）氨基）乙硫醇
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C(CN)CNCCS
InChI: InChI=1S/C5H14N2S/c6-2-1-3-7-4-5-8/h7-8H,1-6H2
描述信息
D020011 - Protective Agents > D011837 - Radiation-Protective Agents
Amifostine thiol (WR-1065) is an active metabolite of the cytoprotector Amifostine (HY-B0639). Amifostine thiol is a cytoprotective agent with radioprotective abilities. Amifostine thiol activates p53 through a JNK-dependent signaling pathway[1][2][3].
同义名列表
数据库引用编号
10 个数据库交叉引用编号
- ChEBI: CHEBI:72583
- KEGG: C07651
- PubChem: 104807
- ChEMBL: CHEMBL1201382
- CAS: 31098-42-7
- PubChem: 9853
- PDB-CCD: UGH
- NIKKAJI: J248.022K
- medchemexpress: HY-137864
- KNApSAcK: 72583
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
- 7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
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
- Eric S Simon, Dawn Reyna, Richard J Lister, Cheryl Harteg, Elke Lipka. Evaluation of a method for measuring the radioprotective metabolite WR-1065 in plasma using chemical derivatization combined with UHPLC-MS/MS.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2018 Mar; 1080(?):82-89. doi:
10.1016/j.jchromb.2018.02.030. [PMID: 29482122] - Kavitha Ranganathan, Eric Simon, Jeremy Lynn, Alicia Snider, Yu Zhang, Noah Nelson, Alexis Donneys, Jose Rodriguez, Lauren Buchman, Dawn Reyna, Elke Lipka, Steven R Buchman. Novel Formulation Strategy to Improve the Feasibility of Amifostine Administration.
Pharmaceutical research.
2018 Mar; 35(5):99. doi:
10.1007/s11095-018-2386-5. [PMID: 29556791] - Afshin Kheradmand, Alireza M Nayebi, Masoumeh Jorjani, Solmaz Khalifeh, Rasool Haddadi. Effects of WR1065 on 6-hydroxydopamine-induced motor imbalance: Possible involvement of oxidative stress and inflammatory cytokines.
Neuroscience letters.
2016 08; 627(?):7-12. doi:
10.1016/j.neulet.2016.05.040. [PMID: 27222379] - Chia-Hung Chen, Min-Liang Kuo, Jen-Ling Wang, Wei-Chuan Liao, Li-Ching Chang, Leong-Perng Chan, Johnson Lin. CCM-AMI, a Polyethylene Glycol Micelle with Amifostine, as an Acute Radiation Syndrome Protectant in C57BL/6 Mice.
Health physics.
2015 Sep; 109(3):242-8. doi:
10.1097/hp.0000000000000326. [PMID: 26222219] - N Vidal, J P Cavaille, F Graziani, M Robin, O Ouari, S Pietri, P Stocker. High throughput assay for evaluation of reactive carbonyl scavenging capacity.
Redox biology.
2014; 2(?):590-8. doi:
10.1016/j.redox.2014.01.016. [PMID: 24688895] - Tung-Kwang Lee, Kevin F O'Brien, Weidong Wang, Roberta M Johnke, Chao Sheng, Sidi M Benhabib, Tao Wang, Ron R Allison. Radioprotective effect of American ginseng on human lymphocytes at 90 minutes postirradiation: a study of 40 cases.
Journal of alternative and complementary medicine (New York, N.Y.).
2010 May; 16(5):561-7. doi:
10.1089/acm.2009.0590. [PMID: 20491513] - Trevor McKibbin, John C Panetta, Maryam Fouladi, Amar Gajjar, Feng Bai, M Fatih Okcu, Clinton F Stewart. Clinical pharmacokinetics of amifostine and WR1065 in pediatric patients with medulloblastoma.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2010 Feb; 16(3):1049-57. doi:
10.1158/1078-0432.ccr-09-1997. [PMID: 20103669] - Zaki S Badawy, Abdul-Kader Souid. Inhibition of human sperm respiration by 4-hydroperoxycyclophosphamide and protection by mesna and WR-1065.
Fertility and sterility.
2009 Jan; 91(1):173-8. doi:
10.1016/j.fertnstert.2007.11.008. [PMID: 18206143] - Tung-Kwang Lee, Weidong Wang, Kevin F O'Brien, Roberta M Johnke, Tao Wang, Ron R Allison, Angelica L Diaz. Effect of North American ginseng on 137Cs-induced micronuclei in human lymphocytes: a comparison with WR-1065.
Phytotherapy research : PTR.
2008 Dec; 22(12):1614-22. doi:
10.1002/ptr.2533. [PMID: 18803249] - David R Cassatt, Christine A Fazenbaker, Christine M Bachy, Gizachew Kifle, Michael P McCarthy. Amifostine (ETHYOL) protects rats from mucositis resulting from fractionated or hyperfractionated radiation exposure.
International journal of radiation oncology, biology, physics.
2005 Mar; 61(3):901-7. doi:
10.1016/j.ijrobp.2004.10.032. [PMID: 15708273] - Christine M Bachy, Christine A Fazenbaker, Gizachew Kifle, Michael P McCarthy, David R Cassatt. Tissue levels of WR-1065, the active metabolite of amifostine (Ethyol), are equivalent following intravenous or subcutaneous administration in cynomolgus monkeys.
Oncology.
2004; 67(3-4):187-93. doi:
10.1159/000081316. [PMID: 15557777] - David R Cassatt, Christine A Fazenbaker, Gizachew Kifle, Christine M Bachy. Effects of dose and schedule on the efficacy of ethyol: preclinical studies.
Seminars in oncology.
2003 Dec; 30(6 Suppl 18):31-9. doi:
10.1053/j.seminoncol.2003.11.039. [PMID: 14727238] - Olivier Pluquet, Sophie North, Marie-Jeanne Richard, Pierre Hainaut. Activation of p53 by the cytoprotective aminothiol WR1065: DNA-damage-independent pathway and redox-dependent modulation of p53 DNA-binding activity.
Biochemical pharmacology.
2003 Apr; 65(7):1129-37. doi:
10.1016/s0006-2952(02)01655-6. [PMID: 12663048] - David R Cassatt, Christine A Fazenbaker, Gizachew Kifle, Christine M Bachy. Preclinical studies on the radioprotective efficacy and pharmacokinetics of subcutaneously administered amifostine.
Seminars in oncology.
2002 Dec; 29(6 Suppl 19):2-8. doi:
10.1053/sonc.2002.37355. [PMID: 12577236] - Edgar Ben-Josef, Sue Han, Martin Tobi, Leslie M Shaw, Heather S Bonner, Barbara J Vargas, Sharon Prokop, Beth Stamos, Laura Kelly, Sandra Biggar, Irving Kaplan. A pilot study of topical intrarectal application of amifostine for prevention of late radiation rectal injury.
International journal of radiation oncology, biology, physics.
2002 Aug; 53(5):1160-4. doi:
10.1016/s0360-3016(02)02883-3. [PMID: 12128116] - Feng Bai, Mark N Kirstein, Suzan K Hanna, Clinton F Stewart. New liquid chromatographic assay with electrochemical detection for the measurement of amifostine and WR1065.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2002 Jun; 772(2):257-65. doi:
10.1016/s1570-0232(02)00104-6. [PMID: 12007770] - William Michael Whiteside, Devin N Sears, Paul R Young, David B Rubin. Properties of selected S-nitrosothiols compared to nitrosylated WR-1065.
Radiation research.
2002 May; 157(5):578-88. doi:
10.1667/0033-7587(2002)157[0578:possnc]2.0.co;2. [PMID: 11966324] - Jean-Louis Merlin, Sophie Marchal, Carole Ramacci, Maryse Berlion, Marie-Gwenaelle Poullain. Enhancement of fotemustine (Muphoran) cytotoxicity by amifostine in malignant melanoma cell lines.
Anti-cancer drugs.
2002 Feb; 13(2):141-7. doi:
10.1097/00001813-200202000-00005. [PMID: 11901306] - David J Grdina, Yasushi Kataoka, Jeffrey S Murley, Nancy Hunter, Ralph R Weichselbaum, Luka Milas. Inhibition of spontaneous metastases formation by amifostine.
International journal of cancer.
2002 Jan; 97(2):135-41. doi:
10.1002/ijc.1592. [PMID: 11774255] - A K Souid, R C Fahey, M K Aktas, O A Sayin, S Karjoo, G L Newton, P D Sadowitz, R L Dubowy, M L Bernstein. Blood thiols following amifostine and mesna infusions, a pediatric oncology group study.
Drug metabolism and disposition: the biological fate of chemicals.
2001 Nov; 29(11):1460-6. doi:
NULL. [PMID: 11602522] - M Fouladi, D Stempak, J Gammon, J Klein, R Grant, M L Greenberg, G Koren, S Baruchel. Phase I trial of a twice-daily regimen of amifostine with ifosfamide, carboplatin, and etoposide chemotherapy in children with refractory carcinoma.
Cancer.
2001 Aug; 92(4):914-23. doi:
10.1002/1097-0142(20010815)92:4<914::aid-cncr1401>3.0.co;2-s. [PMID: 11550166] - H S Bonner, L M Shaw. Measurement of both protein-bound and total S-2-(3-aminopropylamino)ethanethiol (WR-1065) in blood by high-performance liquid chromatography.
Journal of chromatography. B, Biomedical sciences and applications.
2000 Mar; 739(2):357-62. doi:
10.1016/s0378-4347(99)00523-x. [PMID: 10755379] - A K Souid, G L Newton, R L Dubowy, R C Fahey, M L Bernstein. Determination of the cytoprotective agent WR-2721 (Amifostine, Ethyol) and its metabolites in human blood using monobromobimane fluorescent labeling and high-performance liquid chromatography.
Cancer chemotherapy and pharmacology.
1998; 42(5):400-6. doi:
10.1007/s002800050836. [PMID: 9771955] - A E Korst, C M Eeltink, J B Vermorken, W J van der Vijgh. Pharmacokinetics of amifostine and its metabolites in patients.
European journal of cancer (Oxford, England : 1990).
1997 Aug; 33(9):1425-9. doi:
10.1016/s0959-8049(97)00138-x. [PMID: 9337685] - A E Korst, J B Vermorken, W J van der Vijgh. High-performance liquid chromatographic assay using electrochemical detection for the combined measurement of amifostine, WR 1065 and the disulfides in plasma.
Journal of chromatography. B, Biomedical sciences and applications.
1997 May; 693(1):167-74. doi:
10.1016/s0378-4347(97)00016-9. [PMID: 9200531] - R T Dorr. Cytoprotective agents for anthracyclines.
Seminars in oncology.
1996 Aug; 23(4 Suppl 8):23-34. doi:
. [PMID: 8783663] - A F List, R Heaton, B Glinsmann-Gibson, R L Capizzi. Amifostine protects primitive hematopoietic progenitors against chemotherapy cytotoxicity.
Seminars in oncology.
1996 Aug; 23(4 Suppl 8):58-63. doi:
NULL. [PMID: 8783669] - L M Shaw, H Bonner, R Lieberman. Pharmacokinetic profile of amifostine.
Seminars in oncology.
1996 Aug; 23(4 Suppl 8):18-22. doi:
. [PMID: 8783662] - R T Dorr, K Lagel, S McLean. Cardioprotection of rat heart myocytes with amifostine (Ethyol) and its free thiol, WR-1065, in vitro.
European journal of cancer (Oxford, England : 1990).
1996; 32A Suppl 4(?):S21-5. doi:
10.1016/s0959-8049(96)00314-0. [PMID: 8976818] - A E Korst, H E Gall, J B Vermorken, W J van der Vijgh. Pharmacokinetics of amifostine and its metabolites in the plasma and ascites of a cancer patient.
Cancer chemotherapy and pharmacology.
1996; 39(1-2):162-6. doi:
10.1007/s002800050553. [PMID: 8995515] - T Meier, R D Issels. Degradation of 2-(3-aminopropylamino)-ethanethiol (WR-1065) by Cu-dependent amine oxidases and influence on glutathione status of Chinese hamster ovary cells.
Biochemical pharmacology.
1995 Aug; 50(4):489-96. doi:
10.1016/0006-2952(95)00164-u. [PMID: 7646554] - A J Mank, E J Molenaar, C Gooijer, H Lingeman, N H Velthorst, U A Brinkman. Determination of the anticancer drug metabolite WR1065 using pre-column derivatization and diode laser induced fluorescence detection.
Journal of pharmaceutical and biomedical analysis.
1995 Mar; 13(3):255-63. doi:
10.1016/0731-7085(95)01286-t. [PMID: 7619885] - G Horváth, A Takáts. Effect of radioprotectors on the aggregability, cAMP and thiol content of blood platelets.
Acta physiologica Hungarica.
1995; 83(4):389-402. doi:
. [PMID: 8863901] - L M Shaw, H S Bonner, D Q Brown. Metabolic pathways of WR-2721 (ethyol, amifostine) in the BALB/c mouse.
Drug metabolism and disposition: the biological fate of chemicals.
1994 Nov; 22(6):895-902. doi:
NULL. [PMID: 7895607] - P Bhanumathi, E D Saleesh, D M Vasudevan. WR-1065 as a chemoprotector in Adriamycin chemotherapy.
Cancer letters.
1994 Jun; 81(2):171-5. doi:
10.1016/0304-3835(94)90199-6. [PMID: 8012934] - P Jolliet, B Polla, A Donath, D Slosman. Early hydrogen peroxide-induced pulmonary endothelial cell dysfunction: detection and prevention.
Critical care medicine.
1994 Jan; 22(1):157-62. doi:
10.1097/00003246-199401000-00028. [PMID: 8124959] - D J Mangold, B K Huelle, M A Miller, R S Geary, D O Sanchez-Barona, N F Swynnerton, L Fleckenstein, T M Ludden. Pharmacokinetics and disposition of WR-1065 in the rhesus monkey.
Drug metabolism and disposition: the biological fate of chemicals.
1990 May; 18(3):281-7. doi:
NULL. [PMID: 1974187] - L Tretter, E Rónai, G Szabados, R Hermann, A Andó, I Horváth. The effect of the radioprotector WR-2721 and WR-1065 on mitochondrial lipid peroxidation.
International journal of radiation biology.
1990 Mar; 57(3):467-78. doi:
10.1080/09553009014552611. [PMID: 1968940] - R S Geary, N F Swynnerton, M A Miller, D J Mangold, T Ludden. Intraduodenal administration of ethiofos (WR-2721): dose proportionality study in the rhesus monkey.
Research communications in chemical pathology and pharmacology.
1989 Aug; 65(2):147-59. doi:
NULL. [PMID: 2555852] - P M Calabro-Jones, J A Aguilera, J F Ward, G D Smoluk, R C Fahey. Uptake of WR-2721 derivatives by cells in culture: identification of the transported form of the drug.
Cancer research.
1988 Jul; 48(13):3634-40. doi:
. [PMID: 2837319] - H I Tahsildar, J E Biaglow, M M Kligerman, M E Varnes. Factors influencing the oxidation of the radioprotector WR-1065.
Radiation research.
1988 Feb; 113(2):243-51. doi:
. [PMID: 3340731] - N F Swynnerton, B K Huelle, E P McGovern, D J Mangold, T M Ludden. Measurement of WR-1065 in plasma: preliminary pharmacokinetics in the beagle.
Research communications in chemical pathology and pharmacology.
1986 Nov; 54(2):255-69. doi:
NULL. [PMID: 3786948] - L M Shaw, A T Turrisi, D J Glover, H S Bonner, A L Norfleet, C Weiler, M M Kligerman. Human pharmacokinetics of WR-2721.
International journal of radiation oncology, biology, physics.
1986 Aug; 12(8):1501-4. doi:
10.1016/0360-3016(86)90203-8. [PMID: 3019968] - N F Swynnerton, B K Huelle, D J Mangold, T M Ludden. A method for the combined measurement of ethiofos and WR-1065 in plasma: application to pharmacokinetic experiments with ethiofos and its metabolites.
International journal of radiation oncology, biology, physics.
1986 Aug; 12(8):1495-9. doi:
10.1016/0360-3016(86)90202-6. [PMID: 3019967] - R C Fahey, G L Newton. Measurement of WR-2721, WR-1065, and WR-33278 in plasma.
International journal of radiation oncology, biology, physics.
1985 Jun; 11(6):1193-7. doi:
10.1016/0360-3016(85)90069-0. [PMID: 2987166] - J F Utley, N Seaver, G L Newton, R C Fahey. Pharmacokinetics of WR-1065 in mouse tissue following treatment with WR-2721.
International journal of radiation oncology, biology, physics.
1984 Sep; 10(9):1525-8. doi:
10.1016/0360-3016(84)90495-4. [PMID: 6090355] - A I Minchinton. Measurements of glutathione and other thiols in cells and tissues: a simplified procedure based on the HPLC separation of monobromobimane derivatives of thiols.
International journal of radiation oncology, biology, physics.
1984 Sep; 10(9):1503-6. doi:
10.1016/0360-3016(84)90490-5. [PMID: 6480442] - K W Anderson, K A Krohn, Z Grunbaum, R B Phillips, P A Mahler, T W Menard, A M Spence, J S Rasey. Analysis of S-35 labeled WR-2721 and its metabolites in biological fluids.
International journal of radiation oncology, biology, physics.
1984 Sep; 10(9):1511-5. doi:
10.1016/0360-3016(84)90492-9. [PMID: 6090353] - E P McGovern, N F Swynnerton, P D Steele, D J Mangold. HPLC assay for 2-(3-aminopropylamino)ethanethiol (WR-1065) in plasma.
International journal of radiation oncology, biology, physics.
1984 Sep; 10(9):1517-20. doi:
10.1016/0360-3016(84)90493-0. [PMID: 6480444] - P Blackburn, C M Peterson. Thiol-disulfide interchange between cystine and N-2-mercaptoethyl-1, 3-diaminopropane as a potential treatment for cystinuria.
Analytical biochemistry.
1984 Jan; 136(1):31-8. doi:
10.1016/0003-2697(84)90304-x. [PMID: 6324613] - T Mori, M Watanabe, M Horikawa, P Nikaido, H Kimura, T Aoyama, T Sugahara. WR-2721, its derivatives and their radioprotective effects on mammalian cells in culture.
International journal of radiation biology and related studies in physics, chemistry, and medicine.
1983 Jul; 44(1):41-53. doi:
10.1080/09553008314550851. [PMID: 6305861] - J W Purdie, E R Inhaber, H Schneider, J L Labelle. Interaction of cultured mammalian cells with WR-2721 and its thiol, WR-1065: implications for mechanisms of radioprotection.
International journal of radiation biology and related studies in physics, chemistry, and medicine.
1983 May; 43(5):517-27. doi:
10.1080/09553008314550611. [PMID: 6303973] - N F Tabachnik, P Blackburn, C M Peterson, A Cerami. Protein binding of N-2-mercaptoethyl-1,3-diaminopropane via mixed disulfide formation after oral administration of WR 2721.
The Journal of pharmacology and experimental therapeutics.
1982 Feb; 220(2):243-6. doi:
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