Penicillamine (BioDeep_00000004142)
Secondary id: BioDeep_00001867837
natural product human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs Antibiotics
描述信息
Penicillamine is only found in individuals that have used or taken this drug. It is the most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilsons disease. [PubChem]Penicillamine is a chelating agent recommended for the removal of excess copper in patients with Wilsons disease. From in vitro studies which indicate that one atom of copper combines with two molecules of penicillamine. Penicillamine also reduces excess cystine excretion in cystinuria. This is done, at least in part, by disulfide interchange between penicillamine and cystine, resulting in formation of penicillamine-cysteine disulfide, a substance that is much more soluble than cystine and is excreted readily. Penicillamine interferes with the formation of cross-links between tropocollagen molecules and cleaves them when newly formed. The mechanism of action of penicillamine in rheumatoid arthritis is unknown although it appears to suppress disease activity. Unlike cytotoxic immunosuppressants, penicillamine markedly lowers IgM rheumatoid factor but produces no significant depression in absolute levels of serum immunoglobulins. Also unlike cytotoxic immunosuppressants which act on both, penicillamine in vitro depresses T-cell activity but not B-cell activity.
M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01C - Specific antirheumatic agents > M01CC - Penicillamine and similar agents
C274 - Antineoplastic Agent > C1742 - Angiogenesis Inhibitor > C1971 - Angiogenesis Activator Inhibitor
D064449 - Sequestering Agents > D002614 - Chelating Agents
D020011 - Protective Agents > D000931 - Antidotes
D018501 - Antirheumatic Agents
Penicillamine (D-(-)-Penicillamine) is a penicillin metabolic degradation product, can be used as a heavy metal chelator. Penicillamine increases free copper and enhances oxidative stress. Penicillamine has effect of seizures through nitric oxide/NMDA pathways. Penicillamine is a potential immune modulator. Penicillamine can be used for the research of Wilson disease, rheumatoid arthritis, and cystinuria[1][2][3][4].
同义名列表
42 个代谢物同义名
2-amino-3-methyl-3-sulfanylbutanoic acid; 2-Amino-3-mercapto-3-methylbutyric acid; 2-Amino-3-mercapto-3-methylbutyrate; beta,beta Dimethylcysteine; beta,beta-Dimethylcysteine; Penicillaminate, copper; Copper penicillaminate; DL-beta-Mercaptovaline; 3,3-Dimethylcysteine; D-(-)-Penicillamine; DL-3-Mercaptovaline; L-(+)-Penicillamine; DL-b-Mercaptovaline; DL-Β-mercaptovaline; beta-Mercaptovaline; (+-)-Penicillamine; D 3 Mercaptovaline; D-3-Mercaptovaline; D,L-Penicillamine; D-Mercaptovaline; b-Mercaptovaline; DL-Penicillamine; Dimethylcysteine; Β-mercaptovaline; L-penicillamine; D Penicillamine; D-Penicyllamine; D-penicillamine; beta-Thiovaline; Penicilllamine; D-Penicilamine; Mercaptovaline; Penicillamine; Penicillamina; Metalcaptase; Penicillamin; D-Penamine; Cuprimine; Cuprenil; DL-Penicillamine; Penicillamine; Penicillamine
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:50868
- ChEBI: CHEBI:7959
- KEGG: C07418
- KEGGdrug: D00496
- PubChem: 4727
- PubChem: 5852
- HMDB: HMDB0014997
- Metlin: METLIN1726
- DrugBank: DB00859
- ChEMBL: CHEMBL13239
- ChEMBL: CHEMBL1430
- Wikipedia: Penicillamine
- MeSH: Penicillamine
- chemspider: 4565
- CAS: 771431-20-0
- CAS: 52-67-5
- CAS: 52-66-4
- MoNA: PS019601
- PMhub: MS000015906
- PubChem: 9622
- PDB-CCD: LEI
- NIKKAJI: J9.116B
- RefMet: Penicillamine
- medchemexpress: HY-B0300
- KNApSAcK: 7959
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
- Liangjie Zhang, Ling Zhu, Chunling Ci, Wenlong Ai, Yu Wang, Xun Wang. A case of Wilson's disease combined with intracranial lipoma and dysplasia of the corpus callosum with review of the literature.
BMC neurology.
2024 Jan; 24(1):44. doi:
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Journal of pharmaceutical and biomedical analysis.
2023 Mar; 229(?):115355. doi:
10.1016/j.jpba.2023.115355. [PMID: 37018958] - Kuiyu Chen, Limin Wu, Qianzhuo Liu, Fang Tan, Luyao Wang, Dan Zhao, Xinru Fang, Xiang Liu, Jiabo Liu, Hui Han. Glutathione improves testicular spermatogenesis through inhibiting oxidative stress, mitochondrial damage, and apoptosis induced by copper deposition in mice with Wilson disease.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2023 Feb; 158(?):114107. doi:
10.1016/j.biopha.2022.114107. [PMID: 36502753] - Milad Baghal Behyar, Fatemeh Farshchi, Mohammad Hasanzadeh. Sensitive recognition of prostate-specific antigen using biotinylated antibody encapsulated on D-penicillamine decorated wrinkled silicate nanoparticles (WSN): An innovative sandwich-type biosensor toward diagnosis of prostate cancer.
Journal of molecular recognition : JMR.
2022 08; 35(8):e2960. doi:
10.1002/jmr.2960. [PMID: 35426958] - Brock Brady, Wuwei Li, Nashwan Farooque, Christopher Ehrhardt, Mark E Meyerhoff, Xuewei Wang. S-Nitrosothiol-Impregnated Silicone Catheter for Colorimetric Sensing of Indole and E. coli: Toward On-Body Detection of Urinary Tract Infections.
ACS sensors.
2022 06; 7(6):1712-1719. doi:
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BMC neurology.
2022 May; 22(1):178. doi:
10.1186/s12883-022-02691-5. [PMID: 35578211] - Sabine Borchard, Stefanie Raschke, Krzysztof M Zak, Carola Eberhagen, Claudia Einer, Elisabeth Weber, Sandra M Müller, Bernhard Michalke, Josef Lichtmannegger, Albrecht Wieser, Tamara Rieder, Grzegorz M Popowicz, Jerzy Adamski, Martin Klingenspor, Andrew H Coles, Ruth Viana, Mikkel H Vendelbo, Thomas D Sandahl, Tanja Schwerdtle, Thomas Plitz, Hans Zischka. Bis-choline tetrathiomolybdate prevents copper-induced blood-brain barrier damage.
Life science alliance.
2022 03; 5(3):. doi:
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Analytical and bioanalytical chemistry.
2022 Feb; 414(4):1651-1662. doi:
10.1007/s00216-021-03789-4. [PMID: 34988586] - Sanjay Kumar, Biswa Ranjan Patra, Mohammed Irtaza, Praveen Kumar Rao, Suprabhat Giri, Harish Darak, Amrit Gopan, Aditya Kale, Akash Shukla. Adverse Events with D-penicillamine Therapy in Hepatic Wilson's Disease: A Single-Center Retrospective Audit.
Clinical drug investigation.
2022 Feb; 42(2):177-184. doi:
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2021 12; 34(12):e2936. doi:
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2021 10; 34(10):e2903. doi:
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Mikrochimica acta.
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Archives of toxicology.
2020 12; 94(12):4037-4041. doi:
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European journal of gastroenterology & hepatology.
2020 12; 32(12):1545-1552. doi:
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2020 12; 71(6):720-725. doi:
10.1097/mpg.0000000000002894. [PMID: 32804913] - Andreas F Lehner, Levent Dirikolu, Margaret Johnson, John P Buchweitz, Daniel K Langlois. Liquid chromatography/tandem mass spectrometric analysis of penicillamine for its pharmacokinetic evaluation in dogs.
Toxicology mechanisms and methods.
2020 Nov; 30(9):687-702. doi:
10.1080/15376516.2020.1814467. [PMID: 32854553] - Xiao-Qun Zhu, Liang-Yong Li, Wen-Ming Yang, Yu Wang. Combined dimercaptosuccinic acid and zinc treatment in neurological Wilson's disease patients with penicillamine-induced allergy or early neurological deterioration.
Bioscience reports.
2020 08; 40(8):. doi:
10.1042/bsr20200654. [PMID: 32809015] - Jing Zhang, Lulu Xiao, Wenming Yang. Combined sodium Dimercaptopropanesulfonate and zinc versus D-penicillamine as first-line therapy for neurological Wilson's disease.
BMC neurology.
2020 Jun; 20(1):255. doi:
10.1186/s12883-020-01827-9. [PMID: 32593295] - Xiangxue Zhou, Xia Xiao, Xun-Hua Li, Hao-Ling Qin, Xiao-Yong Pu, Ding-Bang Chen, Chao Wu, Li Feng, Xiu-Ling Liang. A study of susceptibility-weighted imaging in patients with Wilson disease during the treatment of metal chelator.
Journal of neurology.
2020 Jun; 267(6):1643-1650. doi:
10.1007/s00415-020-09746-y. [PMID: 32060651] - Xiong Zhang, Qiao Liu, Zong-Wen Wang, Hui Xu, Feng-Ping An, Qun Huang, Hong-Bo Song, Yi-Wei Wang. D-penicillamine modified copper nanoparticles for fluorometric determination of histamine based on aggregation-induced emission.
Mikrochimica acta.
2020 05; 187(6):329. doi:
10.1007/s00604-020-04271-1. [PMID: 32405710] - Paria Pashazadeh-Panahi, Mohammad Hasanzadeh, Reza Eivazzadeh-Keihan. A novel optical probe based on d-penicillamine-functionalized graphene quantum dots: Preparation and application as signal amplification element to minoring of ions in human biofluid.
Journal of molecular recognition : JMR.
2020 05; 33(5):e2828. doi:
10.1002/jmr.2828. [PMID: 32102110] - Qi Wang, Lingfang Li, Tingxuan Wu, Xiangpeng Kong, Qingguo Ma, Chunlei Ma. A graphene quantum dots-Pb2+ based fluorescent switch for selective and sensitive determination of D-penicillamine.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2020 Mar; 229(?):117924. doi:
10.1016/j.saa.2019.117924. [PMID: 31839577] - Marcia Leung, Jaimie Wu Lanzafame, Valentina Medici. Switching Pharmacological Treatment in Wilson Disease: Case Report and Recommendations.
Journal of investigative medicine high impact case reports.
2020 Jan; 8(?):2324709619896876. doi:
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Molecular human reproduction.
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Molecular pharmacology.
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BJU international.
2019 11; 124(5):849-861. doi:
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Luminescence : the journal of biological and chemical luminescence.
2019 Nov; 34(7):767-773. doi:
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Pediatric emergency care.
2019 Oct; 35(10):696-699. doi:
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Journal of gastroenterology and hepatology.
2019 Oct; 34(10):1824-1828. doi:
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2019 Sep; 59(9):565-569. doi:
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Journal of Korean medical science.
2019 Jun; 34(24):e173. doi:
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Analytica chimica acta.
2019 Jun; 1058(?):97-106. doi:
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Hepatology (Baltimore, Md.).
2019 04; 69(4):1835-1837. doi:
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Journal of inherited metabolic disease.
2019 03; 42(2):371-380. doi:
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Annals of hepatology.
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Journal of veterinary internal medicine.
2019 Mar; 33(2):874-878. doi:
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Chemical communications (Cambridge, England).
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The Journal of biological chemistry.
2018 12; 293(49):18944-18964. doi:
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Analytica chimica acta.
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Cold Spring Harbor molecular case studies.
2018 10; 4(5):. doi:
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Scientific reports.
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Current opinion in urology.
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European journal of dermatology : EJD.
2018 Aug; 28(4):476-481. doi:
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Analytical and bioanalytical chemistry.
2018 Apr; 410(10):2629-2636. doi:
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Environmental toxicology and pharmacology.
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Journal of separation science.
2018 Mar; 41(6):1240-1246. doi:
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Indian journal of gastroenterology : official journal of the Indian Society of Gastroenterology.
2018 01; 37(1):31-38. doi:
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Pharmaceutical biology.
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Journal of pediatric gastroenterology and nutrition.
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Journal of natural products.
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Toxicology and industrial health.
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Mymensingh medical journal : MMJ.
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Molecular human reproduction.
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Clinical toxicology (Philadelphia, Pa.).
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South African medical journal = Suid-Afrikaanse tydskrif vir geneeskunde.
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Andrology.
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Journal of veterinary emergency and critical care (San Antonio, Tex. : 2001).
2016 Nov; 26(6):825-830. doi:
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Clinical nephrology.
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Reproduction (Cambridge, England).
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Electrophoresis.
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Current neuropharmacology.
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Oxidative medicine and cellular longevity.
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Neuromolecular medicine.
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Analytica chimica acta.
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Functional neurology.
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Animal reproduction science.
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Biochemical and biophysical research communications.
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Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
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PloS one.
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Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS).
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Vojnosanitetski pregled.
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Mayo Clinic proceedings.
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Bioelectrochemistry (Amsterdam, Netherlands).
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Biopharmaceutics & drug disposition.
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Journal of nuclear medicine : official publication, Society of Nuclear Medicine.
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In vitro cellular & developmental biology. Animal.
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Pakistan journal of pharmaceutical sciences.
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Anaesthesia and intensive care.
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Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban.
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American journal of kidney diseases : the official journal of the National Kidney Foundation.
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