- 同
- Cuprimine, Depen
- 関
- D-Penicillamine
WordNet
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- be contingent upon (something that is elided); "That depends"
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- 〈人が〉『頼る』,依存する,当てにする / 〈物事が〉…次第である,‘に'かかっている(受動態にできない)
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/11/01 02:38:31」(JST)
[Wiki en表示]
Penicillamine
|
|
| Systematic (IUPAC) name |
|
(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
|
| Clinical data |
| Trade names |
Cuprimine |
| AHFS/Drugs.com |
monograph |
Pregnancy
category |
- AU: D
- US: D (Evidence of risk)
|
| Legal status |
|
Routes of
administration |
Oral |
| Pharmacokinetic data |
| Bioavailability |
Variable |
| Metabolism |
Hepatic |
| Biological half-life |
1 hour |
| Excretion |
Renal |
| Identifiers |
| CAS Registry Number |
52-67-5 Y |
| ATC code |
M01CC01 |
| PubChem |
CID: 5852 |
| IUPHAR/BPS |
7264 |
| DrugBank |
DB00859 Y |
| ChemSpider |
5643 Y |
| UNII |
GNN1DV99GX Y |
| KEGG |
D00496 Y |
| ChEBI |
CHEBI:7959 Y |
| ChEMBL |
CHEMBL1430 Y |
| Chemical data |
| Formula |
C5H11NO2S |
| Molecular mass |
149.212 g/mol |
|
|
InChI
-
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1 Y
-
Key:VVNCNSJFMMFHPL-VKHMYHEASA-N Y
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| Y (what is this?) (verify) |
Penicillamine is a pharmaceutical of the chelator class.[1] It has been sold under the trade names of Cuprimine and Depen. The pharmaceutical form is D-penicillamine, as L-penicillamine is toxic (it inhibits the action of pyridoxine).[2] It is an α-amino acid metabolite of penicillin, although it has no antibiotic properties.[3]
It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[4]
Contents
- 1 Medical uses
- 2 Adverse effects
- 3 History
- 4 References
- 5 External links
Medical uses
Penicillamine is used as a form of immunosuppression to treat rheumatoid arthritis. It works by reducing numbers of T-lymphocytes, inhibiting macrophage function, decreasing IL-1, decreasing rheumatoid factor, and preventing collagen from cross-linking.[5]
It is used as a chelating agent:
- In Wilson's disease, a rare genetic disorder of copper metabolism, penicillamine treatment relies on its binding to accumulated copper and elimination through urine.[1]
- In cystinuria, a hereditary disorder featuring formation of cystine stones, penicillamine binds with cysteine to yield a mixed disulfide which is more soluble than cystine.[6]
- Penicillamine has been used to treat scleroderma.[7]
- Penicillamine was the second line treatment for arsenic poisoning, after dimercaprol (BAL).[8] It is no longer recommended.[9]
- Penicillamine can be used as DMARD (Disease-modifying antirheumatic drugs)[citation needed]
Adverse effects
Bone marrow suppression, dysgeusia, anorexia, vomiting and diarrhea are the most common side effects, occurring in ~20-30% of the patients treated with penicillamine.[5][10]
Other possible adverse effects include:
- Nephropathy[5][6]
- Hepatotoxicity[11]
- Membranous glomerulonephritis [12]
- Aplastic anemia (idiosyncratic) [11]
- Antibody-mediated myasthenia gravis[5] and Lambert-Eaton myasthenic syndrome, which may persist even after its withdrawal
- Drug-induced systemic lupus erythematosus[13]
- Elastosis perforans serpiginosa [14]
- Toxic myopathies[15]
- Unwanted breast growth.[16]
Despite the similar name, there is no cross sensitivity between penicillin and penicillamine. Those with penicillin allergies may take it safely.
History
John Walshe first described the use of penicillamine in Wilson's disease in 1956.[17] He had discovered the compound in the urine of patients (including himself) who had taken penicillin, and experimentally confirmed that it increased urinary copper excretion by chelation. He had initial difficulty convincing several world experts of the time (Denny Brown and Cumings) of its efficacy, as they held that Wilson's disease was not primarily a problem of copper homeostasis but of amino acid metabolism, and that dimercaprol should be used as a chelator. Later studies confirmed both the copper-centered theory and the efficacy of D-penicillamine. Walshe also pioneered other chelators in Wilson's such as triethylene tetramine, 2HCl, and tetrathiomolybdate.[18]
Penicillamine has been used in rheumatoid arthritis since the first successful case in 1964.[19] Cuprimine went out of production in 2003.
References
- ^ a b Peisach, J.; Blumberg, W. E. (1969). "A mechanism for the action of penicillamine in the treatment of Wilson's disease". Molecular pharmacology 5 (2): 200–209. PMID 4306792.
- ^ Aronson, J.K. (2010). Meyler's side effects of analgesics and anti-inflammatory drugs. Amsterdam: Elsevier Science. p. 613. ISBN 9780080932941.
- ^ Parker, C. W.; Shapiro, J.; Kern, M.; Eisen, H. N. (1962). "Hypersensitivity to penicillenic acid derivatives in human beings with penicillin allergy". The Journal of experimental medicine 115 (4): 821–838. doi:10.1084/jem.115.4.821. PMC 2137514. PMID 14483916.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ a b c d Camp, A. V. (1977). "Penicillamine in the treatment of rheumatoid arthritis". Proceedings of the Royal Society of Medicine 70 (2): 67–69. PMC 1542978. PMID 859814.
- ^ a b Rosenberg, L. E.; Hayslett, J. P. (1967). "Nephrotoxic Effects of Penicillamine in Cystinuria". JAMA: the Journal of the American Medical Association 201 (9): 698. doi:10.1001/jama.1967.03130090062021.
- ^ Steen, V. D.; Medsger Jr, T. A.; Rodnan, G. P. (1982). "D-Penicillamine therapy in progressive systemic sclerosis (scleroderma): A retrospective analysis". Annals of internal medicine 97 (5): 652–659. doi:10.7326/0003-4819-97-5-652. PMID 7137731.
- ^ Peterson, R. G.; Rumack, B. H. (1977). "D-Penicillamine therapy of acute arsenic poisoning". The Journal of Pediatrics 91 (4): 661–666. doi:10.1016/S0022-3476(77)80528-3. PMID 908992.
- ^ Hall, A. H. (2002). "Chronic arsenic poisoning". Toxicology Letters 128 (1–3): 69–72. doi:10.1016/S0378-4274(01)00534-3. PMID 11869818.
- ^ Grasedyck, K. (1988). "D-penicillamine--side effects, pathogenesis and decreasing the risks". Zeitschrift fur Rheumatologie. 47 Suppl 1: 17–19. PMID 3063003.
- ^ a b Fishel, B.; Tishler, M.; Caspi, D.; Yaron, M. (1989). "Fatal aplastic anaemia and liver toxicity caused by D-penicillamine treatment of rheumatoid arthritis". Annals of the rheumatic diseases 48 (7): 609–610. doi:10.1136/ard.48.7.609. PMC 1003826. PMID 2774703.
- ^ Table 14-2 in: Mitchell, Richard Sheppard; Kumar, Vinay; Abbas, Abul K.; Fausto, Nelson. Robbins Basic Pathology. Philadelphia: Saunders. ISBN 1-4160-2973-7. 8th edition.
- ^ Chalmers, A.; Thompson, D.; Stein, H. E.; Reid, G.; Patterson, A. C. (1982). "Systemic lupus erythematosus during penicillamine therapy for rheumatoid arthritis". Annals of internal medicine 97 (5): 659–663. doi:10.7326/0003-4819-97-5-659. PMID 6958210.
- ^ Bolognia, Jean; et al. (2007). Dermatology. Philadelphia: Elsevier. ISBN 1-4160-2999-0. 2nd edition.
- ^ Underwood, J. C. E. (2009). General and systemic Pathology. Elsevier Limited. ISBN 978-0-443-06889-8.
- ^ Taylor, Cumming, Corenblum (January 31, 1981). "Successful treatment of D-penicillamine-induced breast gigantism with danazol". Taylor, Cumming, Corenblum. Br Med J. Retrieved 2013-04-06.
- ^ Walshe JM (January 1956). "Wilson's disease; new oral therapy". Lancet 267 (6906): 25–6. doi:10.1016/S0140-6736(56)91859-1. PMID 13279157.
- ^ Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074.
- ^ Jaffe, I. A. (1964). "Rheumatoid Arthritis with Arteritis; Report of a Case Treated with Penicillamine". Annals of internal medicine 61: 556–563. doi:10.7326/0003-4819-61-3-556. PMID 14218939.
External links
- Penicillamine (Systemic) - Medlineplus.org
- Penicillamine and Arthritis - Medicinenet.com
|
Specific antirheumatic products / DMARDs (M01C)
|
|
| Quinolines |
|
|
| Gold preparations |
- Sodium aurothiomalate
- Sodium aurothiosulfate
- Auranofin
- Aurothioglucose
- Aurotioprol
|
|
| Other |
- Penicillamine #/Bucillamine
- Chloroquine #/Hydroxychloroquine
- Leflunomide
- Sulfasalazine #
- antifolate (Methotrexate #)
- thiopurine (Azathioprine) #
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
|
Index of joint
|
|
| Description |
- Anatomy
- head and neck
- cranial
- arms
- torso and pelvis
- legs
- bursae and sheathes
- Physiology
|
|
| Disease |
- Arthritis
- acquired
- back
- childhood
- soft tissue
- Congenital
- Injury
- Symptoms and signs
- Examination
|
|
| Treatment |
- Procedures
- Drugs
- rheumatoid arthritis
- gout
- topical analgesics
|
|
|
|
Chelating agents / chelation therapy (V03AC, others)
|
|
| Copper |
|
|
| Iron |
- Deferasirox
- Deferiprone
- Deferoxamine#
|
|
| Lead |
|
|
| Thallium |
|
|
| Other |
- ALA
- BAPTA
- DMPS
- DMSA
- DTPA
- EGTA
|
|
|
Index of toxicology
|
|
| Description |
|
|
| Disease |
|
|
| Treatment |
- Antidotes
- Chelating agents
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
English Journal
- Correlation between periodontal disease indices and lung cancer in Greek adults: a case - control study.
- Chrysanthakopoulos NA1.
- Experimental oncology.Exp Oncol.2016 Mar;38(1):49-53.
- The aim of the present case - control study was to examine the possible associations between periodontal disease indices and the risk of lung cancer development in a sample of Greek out-patients referred to a medical and a dental private practice.MATERIALS AND METHODS: A total of 200 individuals wer
- PMID 27031720
- [The Effect of the Disease Duration on the Changes of the Visual Evoked Potentials and Contrast Sensitivity in Multiple Sclerosis].
- Murav'eva SV, Bisaga GN, Pronin SV, Bryakileva TV, Shelepin YE.
- Zhurnal vyssheĭ nervnoĭ deiatelnosti imeni I P Pavlova.Zh Vyssh Nerv Deiat Im I P Pavlova.2015 Nov-Dec;65(6):711-9.
- The most sensitive methods to detect pathological changes in the visual system are the method of recording visual evoked potentials and the psychophysical method of measuring contrast sensitivity. Described in the literature features of functional disorders of the visual system in patients with mult
- PMID 26841659
- Cytotoxicity of 1-dodecyl-3-methylimidazolium bromide on HepG2 cells.
- Li TH1, Jing CQ1, Gao KL1, Yue WY1, Li SF2.
- Genetics and molecular research : GMR.Genet Mol Res.2015 Oct 27;14(4):13342-8. doi: 10.4238/2015.October.26.31.
- We evaluated the cytotoxicity of 1-dodecyl-3-methylimidazo-lium bromide ([C12mim][Br]) on HepG2 cells and its influence on plasma membrane permeability. The results showed that [C12mim][Br] inhibited HepG2 cell growth and decreased cell viability in a concentration-depen-dent manner. The results als
- PMID 26535648
Japanese Journal
- 腐食生成物層の厚さを用いた無塗装普通鋼材の腐食深さとその経時性の評価方法
- 貝沼 重信,山本 悠哉,伊藤 義浩 [他],林 秀幸,押川 渡
- 材料と環境 : zairyo-to-kankyo 61(12), 483-494, 2012-12-15
- 鋼構造物の腐食環境は，その部位レベルで著しく異なる場合が少なくない．したがって，鋼構造物を経済的に維持管理するためには，各部位レベルの腐食環境を適切に評価した上で，腐食損傷の進行性を予測する必要がある．本研究では塗装鋼構造物の部位レベルの腐食性を対象部位に設置した無塗装普通鋼板の平均腐食深さを用いて総合評価する手法に着目した．そのために，腐食環境が著しく異なる4地点で無塗装普通鋼板の大気暴露試験を …
- NAID 10031137247
- 1b08 二光束干渉顕微鏡を用いたブルー相液晶の電気光学特性測定(ソフトマター,口頭発表,2012年日本液晶学会討論会)
- 藪 修平,刀根 央樹,吉田 浩之,菊池 裕嗣,尾崎 雅則
- 日本液晶学会討論会講演予稿集 (2012), "1b08-1"-"1b08-2", 2012-08-20
- … We investigated the field intensity depen-dency, temperature dependency, and time response of the phase modulation and reflection spectra. …
- NAID 110009668784
- 甲村 雄一,稲田 善紀
- 材料 55(3), 323-328, 2006-03-15
- … Therefore, it is important to pay attention to the behavior of the circumferential strain when the time-depen-dency of stress-strain characteristics of rocks is examined. …
- NAID 110006570920
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- Find patient medical information for Depen Titratabs Oral on WebMD including its uses, side effects and safety, interactions, pictures, warnings and user ratings.
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