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the 4th letter of the Roman alphabet (同)d
a drug (trade name Cuprimine) used to treat heavy metal poisoning and Wilsons disease and severe arthritis (同)Cuprimine

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deuteriumの化学記号
(おもに人称代名詞・固有名詞(人名),thereの後で)had, wouldの短縮形 / (疑問文でwhere,what,whenの後で)didの短縮形;Where'd he go?=Where did he go?

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/18 19:10:47」(JST)

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Penicillamine is a pharmaceutical of the chelator class.^[1] It is 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]

Uses[edit]

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.^[4]

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.^[5]
Penicillamine has been used to treat scleroderma.^[6]
Penicillamine was the second line treatment for arsenic poisoning, after dimercaprol (BAL).^[7] It is no longer recommended.^[8]

Adverse effects[edit]

Bone marrow suppression, dysgeusia, anorexia, vomiting and diarrhea are the most common side effects, occurring in ~20-30% of the patients treated with penicillamine.^[4]^[9]

Other possible adverse effects include:

Nephropathy^[4]^[5]
Hepatotoxicity^[10]
Membranous glomerulonephritis ^[11]
Aplastic anemia (idiosyncratic) ^[10]
Antibody-mediated myasthenia gravis^[4] and Lambert-Eaton myasthenic syndrome, which may persist even after its withdrawal
Drug-induced systemic lupus erythematosus^[12]
Elastosis perforans serpiginosa ^[13]
Toxic myopathies^[14]
Unwanted breast growth.^[15]

Besides, people allergic to penicillin may have hypersensitivity to penicillamine.^[3]

History[edit]

Dr. John Walshe first described the use of penicillamine in Wilson's disease in 1956.^[16] 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 (Drs 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.^[17]

Penicillamine has been used in rheumatoid arthritis since the first successful case in 1964.^[18]

References[edit]

^ ^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. edit
^ Jaffe, I. A.; Altman, K.; Merryman, P. (1964). "The Antipyridoxine Effect of Penicillamine in Man*". Journal of Clinical Investigation 43 (10): 1869–1873. doi:10.1172/JCI105060. PMC 289631. PMID 14236210. edit
^ ^a ^b 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. PMC 2137514. PMID 14483916. edit
^ ^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. edit
^ ^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. edit
^ 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. PMID 7137731. edit
^ 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. edit
^ Hall, A. H. (2002). "Chronic arsenic poisoning". Toxicology Letters 128 (1–3): 69–72. doi:10.1016/S0378-4274(01)00534-3. PMID 11869818. edit
^ Grasedyck, K. (1988). "D-penicillamine--side effects, pathogenesis and decreasing the risks". Zeitschrift fur Rheumatologie. 47 Suppl 1: 17–19. PMID 3063003. edit
^ ^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. PMC 1003826. PMID 2774703. edit
^ 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. PMID 6958210. edit
^ 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. Cite uses deprecated parameters (help)
^ Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074. Cite uses deprecated parameters (help)
^ Jaffe, I. A. (1964). "Rheumatoid Arthritis with Arteritis; Report of a Case Treated with Penicillamine". Annals of internal medicine 61: 556–563. PMID 14218939. edit

External links[edit]

Penicillamine (Systemic) - Medlineplus.org
Penicillamine and Arthritis - Medicinenet.com

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. ウィルソン病：治療および予後 wilson disease treatment and prognosis
2. 免疫調節および抗線維化による全身性硬化症（強皮症）治療 immunomodulatory and antifibrotic approaches to the treatment of systemic sclerosis scleroderma
3. 小児期の鉛中毒：管理 childhood lead poisoning management
4. 関節リウマチにおける薬剤誘発性肺疾患 drug induced lung disease in rheumatoid arthritis
5. 薬物誘導性ミオパシー drug induced myopathies

English Journal

Metal Element Excretion in 24-h Urine in Patients with Wilson Disease under Treatment of D: -Penicillamine.

Huang L, Yu X, Zhang J, Liu X, Zhang Y, Jiao X, Yu X.SourceDepartment of Pediatrics, XinHua Hospital affiliated to Shanghai Jiao Tong University School of Medicine, 1665 Kongjiang Road, Shanghai, China.
Biological trace element research.Biol Trace Elem Res.2012 May;146(2):154-9. Epub 2011 Nov 11.
Wilson disease is an inherited autosomal recessive disorder causing copper accumulation and consequent toxicity. D: -Penicillamine, a potent metal chelator, is an important therapy for Wilson disease. To investigate the changes of metal elements under the treatment of D: -penicillamine, we determine
PMID 22076732

Peroxynitrite has potent pulmonary vasodilator activity in the rat.

Casey DB, Pankey EA, Badejo AM, Bueno FR, Bhartiya M, Murthy SN, Uppu RM, Nossaman BD, Kadowitz PJ.Sourcea Department of Pharmacology, Tulane University School of Medicine, 1430 Tulane Avenue, New Orleans, LA 70112-2699, USA.
Canadian journal of physiology and pharmacology.Can J Physiol Pharmacol.2012 Apr;90(4):485-500. Epub 2012 Mar 27.
Peroxynitrite (PN) worsens pathological conditions associated with oxidative stress. However, beneficial effects have also been reported. PN has been shown to demonstrate vasodilator as well as vasoconstrictor properties that are dependent upon the experimental conditions and the vascular bed studie
PMID 22452357

Japanese Journal

Disruption of elastic lamellae in the aorta by D-penicillamine and its effect on vaso-regulation in rats

Muto Takafumi,Miyajima Atsushi,Bamba Masaru [他]
The Journal of toxicological sciences : an official journal of the Japanese Society of Toxicology 38(5), 707-717, 2013-10
NAID 40019828975

Spectrophotometric Sequential Injection Determination of D-Penicillamine Based on a Complexation Reaction with Nickel Ion

MARTINOVIC-BEVANDA Anita,RADIC Njegomir
Analytical Sciences 29(6), 669-671, 2013-06
NAID 40019661082

P-0696 D-Penicillamineによるラット大動脈弾性繊維障害が血圧に及ぼす影響(一般演題ポスター発表,有害事象・副作用,Enjoy Pharmacists' Lifestyles)

武藤貴史,岡本将大,番場優,宮島篤志,廣田孝司
日本医療薬学会年会講演要旨集 21, 297, 2011-09-09
NAID 110008910162

Related Pictures

★リンクテーブル★

リンク元	「ペニシラミン」
拡張検索	「D-penicillamine(2,5)-enkephalin」
関連記事	「D」

「ペニシラミン」

Penicillamine
Systematic (IUPAC) name
	(2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid
Clinical data
Trade names	Cuprimine
AHFS/Drugs.com	monograph
Pregnancy cat.	D (AU) D (US)
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Bioavailability	Variable
Metabolism	Hepatic
Half-life	1 hour
Excretion	Renal
Identifiers
CAS number	52-67-5
ATC code	M01CC01
PubChem	CID 5852
DrugBank	DB00859
ChemSpider	5643
UNII	GNN1DV99GX
KEGG	D00496
ChEBI	CHEBI:7959
ChEMBL	CHEMBL1430
Chemical data
Formula	C5H11NO2S
Mol. mass	149.212 g/mol
	SMILES CC(C)([C@H](C(=O)O)N)S;
	InChI InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1 ; Key:VVNCNSJFMMFHPL-VKHMYHEASA-N ;
(what is this?) (verify)

　　[★]

英: penicillamine, D-penicillamine
同: D-ペニシラミン
商: メタルカプターゼ, Cuprimine, Depen

GOO. capter65(重金属拮抗剤)

キレート剤。金属解毒薬
アスピリンを投与された肝臓病患者の尿から見いだされた。

構造

D-β,β-dimethylcystein
システイン残基の炭素(-CH₃-SH)に結合している２つの水素原子がメチル基に置換された構造

作用機序

キレート薬

重金属をキレートして、尿として排泄する

薬理作用

重金属のキレート作用

動態

適応

銅、水銀、鉛、亜鉛の中毒 (GOO. 771)
cystiuria (GOO. 771)
Wilson's diease(hepatolenticular degeneration woing to an excess of copper) (GOO. 771)
関節リウマチ(稀) (GOO. 771)

「D-penicillamine(2,5)-enkephalin」

　　[★]

D-ペニシラミン(2

関: DPDPE

「D」

　　[★]

アスパラギン酸
ジヒドロウリジン
遠位の distal,
うつ病 depression
下行結腸 descending colon(大腸内視鏡検査の結果を記載するときに用いる)

[xl2-1] 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. edit

[2] Jaffe, I. A.; Altman, K.; Merryman, P. (1964). "The Antipyridoxine Effect of Penicillamine in Man*". Journal of Clinical Investigation 43 (10): 1869–1873. doi:10.1172/JCI105060. PMC 289631. PMID 14236210. edit

[sb-3] 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. PMC 2137514. PMID 14483916. edit

[xl3-4] 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. edit

[xl4-5] 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. edit

[6] 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. PMID 7137731. edit

[7] 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. edit

[8] Hall, A. H. (2002). "Chronic arsenic poisoning". Toxicology Letters 128 (1–3): 69–72. doi:10.1016/S0378-4274(01)00534-3. PMID 11869818. edit

[9] Grasedyck, K. (1988). "D-penicillamine--side effects, pathogenesis and decreasing the risks". Zeitschrift fur Rheumatologie. 47 Suppl 1: 17–19. PMID 3063003. edit

[xl-10] 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. PMC 1003826. PMID 2774703. edit

[Kumar8-5-11] 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.

[12] 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. PMID 6958210. edit

[13] Bolognia, Jean; et al (2007). Dermatology. Philadelphia: Elsevier. ISBN 1-4160-2999-0. 2nd edition.

[14] Underwood, J. C. E. (2009). General and systemic Pathology. Elsevier Limited. ISBN 978-0-443-06889-8.

[15] 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.

[Walshe1956-16] 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. Cite uses deprecated parameters (help)

[17] Walshe JM (August 2003). "The story of penicillamine: a difficult birth". Mov. Disord. 18 (8): 853–9. doi:10.1002/mds.10458. PMID 12889074. Cite uses deprecated parameters (help)

[18] Jaffe, I. A. (1964). "Rheumatoid Arthritis with Arteritis; Report of a Case Treated with Penicillamine". Annals of internal medicine 61: 556–563. PMID 14218939. edit

匿名

検索

案内

案内

D-penicillamine