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Chemistry

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Also known as: D-penicillamine, 52-67-5, Cuprimine, D-(-)-penicillamine, 3-mercapto-d-valine, Depen
Molecular Formula
C5H11NO2S
Molecular Weight
149.21  g/mol
InChI Key
VVNCNSJFMMFHPL-VKHMYHEASA-N
FDA UNII
GNN1DV99GX

Penicillamine
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.
Penicillamine is an Antirheumatic Agent.
1 2D Structure

Penicillamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
2.1.2 InChI
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
2.1.3 InChI Key
VVNCNSJFMMFHPL-VKHMYHEASA-N
2.1.4 Canonical SMILES
CC(C)(C(C(=O)O)N)S
2.1.5 Isomeric SMILES
CC(C)([C@H](C(=O)O)N)S
2.2 Other Identifiers
2.2.1 UNII
GNN1DV99GX
2.3 Synonyms
2.3.1 MeSH Synonyms

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

2.3.2 Depositor-Supplied Synonyms

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

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 149.21 g/mol
Molecular Formula C5H11NO2S
XLogP3-1.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass149.05104977 g/mol
Monoisotopic Mass149.05104977 g/mol
Topological Polar Surface Area64.3 Ų
Heavy Atom Count9
Formal Charge0
Complexity124
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameCuprimine
PubMed HealthPenicillamine (By mouth)
Drug ClassesAntirheumatic, Heavy Metal Chelator, Renal-Urologic Agent
Drug LabelPenicillamine 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 IngredientPenicillamine
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyAton

2 of 4  
Drug NameDepen
PubMed HealthPenicillamine (By mouth)
Drug ClassesAntirheumatic, Heavy Metal Chelator, Renal-Urologic Agent
Drug LabelDESCRIPTION - 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 IngredientPenicillamine
Dosage FormTablet
RouteOral
Strength250mg
Market StatusPrescription
CompanyMeda Pharms

3 of 4  
Drug NameCuprimine
PubMed HealthPenicillamine (By mouth)
Drug ClassesAntirheumatic, Heavy Metal Chelator, Renal-Urologic Agent
Drug LabelPenicillamine 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 IngredientPenicillamine
Dosage FormCapsule
RouteOral
Strength250mg
Market StatusPrescription
CompanyAton

4 of 4  
Drug NameDepen
PubMed HealthPenicillamine (By mouth)
Drug ClassesAntirheumatic, Heavy Metal Chelator, Renal-Urologic Agent
Drug LabelDESCRIPTION - 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 IngredientPenicillamine
Dosage FormTablet
RouteOral
Strength250mg
Market StatusPrescription
CompanyMeda Pharms

4.2 Therapeutic Uses

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.


4.3 Drug Warning

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.


4.4 Drug Indication

For treatment of Wilson's disease, cystinuria and active rheumatoid arthritis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 MeSH Pharmacological Classification

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PENICILLAMINE
5.3.2 FDA UNII
GNN1DV99GX
5.3.3 Pharmacological Classes
Antirheumatic Agent [EPC]
5.4 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01C - Specific antirheumatic agents

M01CC - Penicillamine and similar agents

M01CC01 - Penicillamine


5.5 Absorption, Distribution and Excretion

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.


5.6 Metabolism/Metabolites

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)


5.7 Biological Half-Life

1 hour


5.8 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.


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)


API Reference Price

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16-Jan-2021
28-Aug-2024
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