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1. Beta,beta Dimethylcysteine
2. Beta,beta-dimethylcysteine
3. Copper Penicillaminate
4. Cuprenil
5. Cuprimine
6. D 3 Mercaptovaline
7. D Penicillamine
8. D-3-mercaptovaline
9. D-penicillamine
10. Dimethylcysteine
11. Mercaptovaline
12. Metalcaptase
13. Penicillaminate, Copper
1. D-penicillamine
2. 52-67-5
3. Cuprimine
4. D-(-)-penicillamine
5. 3-mercapto-d-valine
6. Depen
7. Cuprenil
8. D-penamine
9. (-)-penicillamine
10. Artamine
11. (2s)-2-amino-3-methyl-3-sulfanylbutanoic Acid
12. D-valine, 3-mercapto-
13. Kuprenil
14. Mercaptyl
15. Perdolat
16. Trolovol
17. D-3-mercaptovaline
18. (s)-3,3-dimethylcysteine
19. Penicilamina
20. Penicillaminum
21. 3-sulfanyl-d-valine
22. D-beta,beta-dimethylcysteine
23. D-mercaptovaline
24. Penicillamin
25. Beta-thiovaline
26. Metalcaptase
27. (d)-penicillamine
28. Beta,beta-dimethylcysteine
29. D-penicilamine
30. (s)-2-amino-3-mercapto-3-methylbutanoic Acid
31. Penicillamina [dcit]
32. Distamine
33. Penicilamina [inn-spanish]
34. Penicillaminum [inn-latin]
35. Cupripen
36. Depamine
37. Pendramine
38. Chebi:7959
39. (s)-penicillamine
40. Penicillamine (cuprimine)
41. Reduced Penicillamine
42. Sufirtan
43. Gnn1dv99gx
44. Chembl1430
45. Reduced D-penicillamine
46. 3,3-dimethyl-d-cysteine
47. Nsc-81549
48. (s)-penicillamin
49. D,3-mercaptovaline
50. Ncgc00024359-04
51. Penicillamina
52. Mfcd00064302
53. Sufortan
54. Cuprimine (tn)
55. Valine, 3-mercapto-, D-
56. Ccris 2904
57. D-beta-mercaptovaline
58. Depen (tn)
59. Hsdb 3378
60. Sr-01000000262
61. Einecs 200-148-8
62. Unii-gnn1dv99gx
63. Nsc 81549
64. Alpha-amino-beta-methyl-beta-mercaptobutyric Acid
65. (2s)-2-amino-3-methyl-3-sulfanyl-butanoic Acid
66. Distamine (*hydrochloride*)
67. D-penicillamin
68. Penicillamine (jan/usp/inn)
69. Dimethyl Cysteine
70. Metalcaptase (*hydrochloride*)
71. Penicillamine-(d)
72. 3-thio-d-valine
73. Penicillamine,(s)
74. D-(-)-2-amino-3-mercapto-3-methylbutanoic Acid
75. Nsc81549
76. Penicillamine-(racemic)
77. Spectrum_000283
78. Penicillamine [usan:usp:inn:ban:jan]
79. Spectrum2_001029
80. Spectrum3_000541
81. Spectrum4_000470
82. Spectrum5_001196
83. Penicillamine [mi]
84. Epitope Id:113237
85. P-1280
86. Penicillamine [inn]
87. Penicillamine [jan]
88. Schembl4343
89. Dsstox_cid_17069
90. Dsstox_rid_79300
91. Penicillamine [hsdb]
92. Penicillamine [usan]
93. Dsstox_gsid_37069
94. Bspbio_002181
95. Kbiogr_000920
96. Kbioss_000763
97. Penicillamine [vandf]
98. Cid_92173
99. Divk1c_000314
100. Penicillamine [mart.]
101. Spbio_001217
102. D-penicillamine, 98-101%
103. Penicillamine [usp-rs]
104. Penicillamine [who-dd]
105. Gtpl7264
106. Dtxsid6037069
107. Bdbm39346
108. Kbio1_000314
109. Kbio2_000763
110. Kbio2_003331
111. Kbio2_005899
112. Kbio3_001681
113. Ninds_000314
114. Zinc114127
115. Penicillamine [ep Impurity]
116. Penicillamine [orange Book]
117. Bcp17247
118. Hy-b0300
119. Str02534
120. Penicillamine [ep Monograph]
121. Tox21_110899
122. Bdbm50217941
123. Penicillamine [usp Monograph]
124. S1853
125. Akos006237201
126. Zinc100509167
127. Am83710
128. Ccg-266197
129. Db00859
130. Cas-52-67-5
131. Idi1_000314
132. Smp1_000042
133. Ncgc00018283-01
134. Ncgc00024359-05
135. Ncgc00024359-06
136. P0147
137. En300-52608
138. C07418
139. D00496
140. M06142
141. P15236
142. 064p302
143. Q421239
144. Sr-01000000262-3
145. Sr-01000000262-4
146. (2s)-2-amino-3-mercapto-3-methyl-butyric Acid;hydrochloride
147. (2s)-2-amino-3-mercapto-3-methylbutanoic Acid;hydrochloride
148. (2s)-2-azanyl-3-methyl-3-sulfanyl-butanoic Acid;hydrochloride
149. Penicillamine, European Pharmacopoeia (ep) Reference Standard
150. (2s)-2-amino-3-methyl-3-sulfanylbutanoic Acid3-sulfanyl-d-valine
151. Penicillamine, United States Pharmacopeia (usp) Reference Standard
| Molecular Weight | 149.21 g/mol |
|---|---|
| Molecular Formula | C5H11NO2S |
| XLogP3 | -1.8 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Exact Mass | 149.05104977 g/mol |
| Monoisotopic Mass | 149.05104977 g/mol |
| Topological Polar Surface Area | 64.3 Ų |
| Heavy Atom Count | 9 |
| Formal Charge | 0 |
| Complexity | 124 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
| 1 of 4 | |
|---|---|
| Drug Name | Cuprimine |
| PubMed Health | Penicillamine (By mouth) |
| Drug Classes | Antirheumatic, Heavy Metal Chelator, Renal-Urologic Agent |
| Drug Label | 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 (see INDICATIO |
| Active Ingredient | Penicillamine |
| Dosage Form | Capsule |
| Route | Oral |
| Strength | 250mg |
| Market Status | Prescription |
| Company | Aton |
| 2 of 4 | |
|---|---|
| Drug Name | Depen |
| PubMed Health | Penicillamine (By mouth) |
| Drug Classes | Antirheumatic, Heavy Metal Chelator, Renal-Urologic Agent |
| Drug Label | DESCRIPTION - Penicillamine is 3-mercapto-D-valine, a disease modifying antirheumatic drug. It is a white or practically white, crystalline powder, freely soluble in water, slightly soluble in alcohol, and insoluble in ether, acetone, benzene, and ca... |
| Active Ingredient | Penicillamine |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 250mg |
| Market Status | Prescription |
| Company | Meda Pharms |
| 3 of 4 | |
|---|---|
| Drug Name | Cuprimine |
| PubMed Health | Penicillamine (By mouth) |
| Drug Classes | Antirheumatic, Heavy Metal Chelator, Renal-Urologic Agent |
| Drug Label | 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 (see INDICATIO |
| Active Ingredient | Penicillamine |
| Dosage Form | Capsule |
| Route | Oral |
| Strength | 250mg |
| Market Status | Prescription |
| Company | Aton |
| 4 of 4 | |
|---|---|
| Drug Name | Depen |
| PubMed Health | Penicillamine (By mouth) |
| Drug Classes | Antirheumatic, Heavy Metal Chelator, Renal-Urologic Agent |
| Drug Label | DESCRIPTION - Penicillamine is 3-mercapto-D-valine, a disease modifying antirheumatic drug. It is a white or practically white, crystalline powder, freely soluble in water, slightly soluble in alcohol, and insoluble in ether, acetone, benzene, and ca... |
| Active Ingredient | Penicillamine |
| Dosage Form | Tablet |
| Route | Oral |
| Strength | 250mg |
| Market Status | Prescription |
| Company | Meda Pharms |
Antidotes; Antirheumatic Agents; Chelating Agents
National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)
THE D ISOMER IS USED CLINICALLY, ALTHOUGH THE L ISOMER ALSO FORMS CHELATION COMPLEXES. PENICILLAMINE IS EFFECTIVE CHELATOR OF COPPER, MERCURY, ZINC, & LEAD & PROMOTES EXCRETION OF THESE METALS IN URINE.
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1610
THERE IS SOME PROMISE IN TREATMENT OF RHEUMATOID ARTHRITIS WITH PENICILLAMINE. ... BENEFICIAL EFFECT IS SEEN ONLY AFTER SEVERAL WK OF TREATMENT, & ARTHRITIC SYMPTOMS RETURN IF DRUG IS WITHDRAWN PREMATURELY.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 920
PENICILLAMINE HAS BECOME ESTABLISHED IN TREATMENT OF CYSTINURIA & ASSOC NEPHROLITHIASIS. IN DOSE OF 30 MG/KG/DAY, IT LOWERS OR ELIMINATES URINARY CYSTINE & PREVENTS FURTHER STONE DEVELOPMENT.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 920
For more Therapeutic Uses (Complete) data for (D)-PENICILLAMINE (11 total), please visit the HSDB record page.
VET: USE IN PREGNANCY IS CONTRAINDICATED BECAUSE OF ITS CHELATING EFFECT ON TRACE METALS.
Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 417
CROSS SENSITIVITY BETWEEN PENICILLIN & PENICILLAMINE DOES NOT ALWAYS OCCUR; THEREFORE, PENICILLAMINE CAN BE GIVEN CAUTIOUSLY TO PATIENTS WHO ARE HYPERSENSITIVE TO PENICILLIN.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 757
CAREFUL EXAM OF SKIN, AS WELL AS URINALYSIS, DIFFERENTIAL & WHITE BLOOD CELL COUNTS, DIRECT PLATELET COUNTS, & HEMOGLOBIN DETERMINATION SHOULD BE PERFORMED.
American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 757
EXPTL, TOXIC EFFECTS IN RATS GIVEN HIGH DOSES OF PENICILLAMINE RESEMBLE THOSE SEEN IN PYRIDOXINE DEFICIENCY, & EFFECTS ARE REVERSED BY FEEDING PYRIDOXINE. IN HUMAN BEINGS, PYRIDOXINE ANTAGONISM IS READILY DEMONSTRATED WITH L & DL FORMS, BUT RARELY WITH D FORM. ... INCR URINARY EXCRETION OF XANTHURENIC ACID & KYNURENINE.
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 919
For more Drug Warnings (Complete) data for (D)-PENICILLAMINE (11 total), please visit the HSDB record page.
For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.
FDA Label
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. Penicillamine inhibits macrophages, decreases IL-1 and the number of T-lymphocytes, and prevents collagen cross linkage. In Wilson's disease it binds copper, allowing it to be eliminated in the urine.
Antidotes
Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)
Chelating Agents
Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)
Antirheumatic Agents
Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)
M - Musculo-skeletal system
M01 - Antiinflammatory and antirheumatic products
M01C - Specific antirheumatic agents
M01CC - Penicillamine and similar agents
M01CC01 - Penicillamine
Absorption
rapidly but incompletely
Route of Elimination
Excretion is mainly renal, mainly as disulfides.
HUMAN SUBJECTS SUFFERING FROM WILSON'S DISEASE, RAPIDLY ABSORBED ORAL DOSE OF (35)S DL-PENICILLAMINE. PLASMA CONCN OF (35)S PEAKED WITHIN 60 MIN. (35)S WAS RAPIDLY EXCRETED, ALMOST COMPLETELY IN 24 HR URINE WHERE 73% OF ADMIN (35)S ... RECOVERED. THERE WAS INTERSUBJECT VARIATION IN EXTENT OF BINDING ... BY PLASMA PROTEINS. /DL-PENICILLAMINE/
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 135
FROM METABOLIC POINT OF VIEW, D-PENICILLAMINE IS VIRTUALLY INERT, & THIS OBSERVATION IS COMPATIBLE WITH FACT THAT EXTRACELLULAR WATER MAKES UP MAIN DISTRIBUTION VOL FOR D-PENICILLAMINE.
The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 153
PENICILLAMINE IS WELL ABSORBED (40% to70%) FROM GI TRACT &, THEREFORE, HAS DECIDED ADVANTAGE OVER OTHER CHELATING AGENTS. PEAK CONCN IN BLOOD ARE OBTAINED BETWEEN 1 AND 3 HR AFTER ADMINISTRATION. ... /IT/ IS SOMEWHAT RESISTANT TO ATTACK BY CYSTEINE DESULFHYDRASE OR L-AMINO ACID OXIDASE. AS A RESULT ... IS RELATIVELY STABLE IN VIVO. ... HEPATIC BIOTRANSFORMATION IS RESPONSIBLE FOR MOST OF THE DEGRADATION OF PENICILLAMINE, AND VERY LITTLE IS EXCRETED UNCHANGED. METABOLITES ARE FOUND IN BOTH URINE AND FECES.
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1610
The effects of chelating agents (citric acid, tartaric acid, penicillamine and ethylenediaminetetraacetic acid) and cysteine on the absorption of mercuric chloride were investigated in rats. Perfusion of the small intestine showed that the chelating agents and cysteine decreased the absorption of mercuric chloride depending on their stability of constants wtih Hg2+, under the predominant conditions of water absorption and secretion. The difference in absorption of mercuric chloride between both conditions was inversely correlated with their logarithmic stability constant values. These agents decreased the transport of mercuric chloride through the everted intestinal wall and the uptake of mercuric chloride by the intestinal brush border membrane in a similar manner. From these results, it is suggested that the chelating agents and cysteine decrease the absorption of mercuric chloride through the pores of the brush border membrane due to th solvent drag effect.
PMID:2057447 Endo T et al; Pharmacol Toxicol 68 (3): 171-6 (1991)
For more Absorption, Distribution and Excretion (Complete) data for (D)-PENICILLAMINE (7 total), please visit the HSDB record page.
Hepatic
The transformation of D-penicillamine was studied in orally and iv dosed rats and in human plasma in vitro. In each case, low molecular weight metabolites (previously identified as disulfides) and a mixed disulfide between D-penicillamine and albumin (D-penicillamine-protein) formed. The rates of D-penicillamine elimination, other than through protein conjugation, were comparable in the rat groups to the rate of oxidation to low molecula weight metabolites in vitro. The rates of transformation to D-penicillamine protein were also comparable in the in vitro preparations and in orally treated rats. These qualitative and quantitative similarities suggest blood plasma may be an important site of transformation in vivo. Extracellular oxidation of D-penicillamine may be linked to its antirheumatic action, either through reduction of oxygen species or through formation of D-penicillamine protein disulfides at surfaces of mononuclear leukocytes.
PMID:2085148 Joyce DA, Murphy BR; Agents Actions 31 (3-4): 353-7 (1990)
1 hour
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.
The rationale for ... use in cyctinuria is that penicillamine forms a relatively soluble disulfide compound with cysteine through a disulfide interchange mechanism and thereby decr the formation of cystine containing renal stones.
Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1610
Penicillamine chelates mercury, lead, copper, iron, and probably other heavy metals to form stable, soluble complexes that are readily excreted in the urine.
US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.I p.2158 (1992)
The mechanism of action of penicillamine in rheumatoid arthritis is not known, but may involve improvement of lymphocyte function. It markedly reduces IgM rheumatoid factor and immune complexes in serum and synovial fluid, but does not significantly lower absolute concentrations of serum immunoglobulins. In vitro, penicillamine depresses T-cell but not B-cell activity. However, the relationship of these effects to the activity of penicillamine in rheumatoid arthritis is not known.
US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.I p.2158 (1992)
Antiurolithic (cystine calculi) Penicillamine combines chemically with cystine (cysteine-cysteine disulfide) to form penicillamine cysteine disulfide, which is more soluble than cystine and is readily excreted. As a result, urinary cystine concentrations are lowered and the formation of cystine calculi is prevented. With prolonged treatment, existing cystine calculi may be gradually dissolved.
US Pharmacopeial Convention; US Pharmacopeia Dispensing Information (USP DI); Drug Information for the Health Care Professional 12th ed, V.I p.2158 (1992)
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