用户名： 密   码：
注册 | 忘记密码？
药品详细

Penicillamine(青霉胺)

化学结构式图
中文名
青霉胺
英文名
Penicillamine
分子式
C5H11NO2S
化学名
2-amino-3-methyl-3-sulfanylbutanoic acid
分子量
Average: 149.211
Monoisotopic: 149.051049291
CAS号
52-67-5
ATC分类
M01C 未知
药物类型
small molecule
阶段
approved
商品名
Artamine;Cuprenil;Cuprimine;Cupripen;Depamine;Depen;Distamine;Kuprenil;Mercaptovaline;Mercaptyl;Metalcaptase;Pendramine;Perdolat;Sufirtan;Trolovol;
同义名
beta-Thiovaline;beta,beta-Dimethylcysteine;D-Mercaptovaline;D-Penamine;D-Penicilamine;D-Penicillamine;D-Penicyllamine;Dimethylcysteine;L-Penicillamine;PCA;Penicilamina [INN-Spanish];Penicillamin;Penicillamina [DCIT];Penicillaminum [INN-Latin];Penicilllamine;
基本介绍

3-Mercapto-D-valine. The most characteristic degradation product of the penicillin antibiotics. It is used as an antirheumatic and as a chelating agent in Wilson's disease. [PubChem]

生产厂家
  • Aton pharma inc
  • Meda pharmaceuticals inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. WALSHE JM: Penicillamine, a new oral therapy for Wilson’s disease. Am J Med. 1956 Oct;21(4):487-95. Pubmed
  2. Walshe JM: The story of penicillamine: a difficult birth. Mov Disord. 2003 Aug;18(8):853-9. Pubmed
  3. Gong Y, Frederiksen SL, Gluud C: D-penicillamine for primary biliary cirrhosis. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004789. Pubmed
  4. Suarez-Almazor ME, Spooner C, Belseck E: Penicillamine for rheumatoid arthritis. Cochrane Database Syst Rev. 2000;(2):CD001460. Pubmed
  5. Munro R, Capell HA: Penicillamine. Br J Rheumatol. 1997 Jan;36(1):104-9. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
ANTIINFLAMMATORY AND ANTIRHEUMATIC 消炎抗风湿;
药理
Indication For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.
Pharmacodynamics Penicillamine is a chelating agent used in the treatment of Wilson's disease. It is also used to reduce cystine excretion in cystinuria and to treat patients with severe, active rheumatoid arthritis unresponsive to conventional therapy. 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. Its use in Wilson's disease, a rare genetic disorder of copper metabolism, relies on its binding to accumulated copper and elimination through urine.
Mechanism of action Penicillamine is a chelating agent recommended for the removal of excess copper in patients with Wilson's 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.
Absorption rapidly but incompletely
Volume of distribution Not Available
Protein binding >80% (bound to plasma proteins)
Metabolism
Hepatic
Route of elimination Excretion is mainly renal, mainly as disulfides.
Half life 1 hour
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 198.5 °C PhysProp
water solubility 1.11E+005 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -1.78 HANSCH,C ET AL. (1995)
logS -0.13 ADME Research, USCD
pKa 1.8 MERCK for CO; NH2-7.9; thiol-10.5
Predicted Properties
Property Value Source
water solubility 4.65e+00 g/l ALOGPS
logP -1.7 ALOGPS
logP -2.1 ChemAxon
logS -1.5 ALOGPS
pKa (strongest acidic) 2.56 ChemAxon
pKa (strongest basic) 9.09 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 63.32 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 37.23 ChemAxon
polarizability 14.88 ChemAxon
药物相互作用
Drug Interaction
Digoxin Penicillamine decreases the effect of digoxin
Iron Dextran The multivalent agent decreases the effect of penicillamine
食物相互作用
  • Drink liberally.
  • Food reduces availability, take on an empty stomach.

返回 | 收藏