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Substance Name: Penicillamine [USAN:USP:INN:BAN:JAN]
RN: 52-67-5
UNII: GNN1DV99GX
InChIKey: VVNCNSJFMMFHPL-VKHMYHEASA-N

Note

  • 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.

Molecular Formula

  • C5-H11-N-O2-S

Molecular Weight

  • 149.2129
 

Classification Codes

  • Antidotes
  • Antirheumatic Agents
  • Chelating Agent
  • Chelating Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Protective Agents
  • Reproductive Effect
  • Sequestering Agents
  • Tumor Data
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Names and Synonyms

Name of Substance

  • (D)-Penicillamine
  • Penicillamine
  • Penicillamine [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Penicillamine

Synonyms

  • (-)-Penicillamine
  • (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid
  • (S)-3,3-Dimethylcysteine
  • (S)-Penicillamin
  • (S)-Penicillamine
  • 2-Amino-3-mercapto-3-methylbutanoic acid
  • 3-Mercapto-D-valine
  • alpha-Amino-beta-methyl-beta-mercaptobutyric acid
  • Artamine
  • beta,beta-Dimethylcysteine
  • beta-Thiovaline
  • CCRIS 2904
  • Cuprenil
  • Cuprimine
  • Cupripen
  • d,3-Mercaptovaline
  • D-(-)-Penicillamine
  • D-3-Mercaptovaline
  • D-Mercaptovaline
  • D-Penamine
  • D-Penicillamine
  • D-Valine, 3-mercapto-
  • Depamine
  • Depen
  • DPA
  • EINECS 200-148-8
  • Emtexate
  • HSDB 3378
  • Kuprenil
  • Mercaptovaline
  • Mercaptyl
  • Metalcaptase
  • NSC 81549
  • Pendramine
  • Penicilamina
  • Penicilamina [INN-Spanish]
  • Penicillamin
  • Penicillamina
  • Penicillamina [DCIT]
  • Penicillamine
  • Penicillaminum
  • Penicillaminum [INN-Latin]
  • Perdolat
  • Reduced D-penicillamine
  • Reduced penicillamine
  • Sufirtan
  • Trolovol
  • UNII-GNN1DV99GX
  • Valine, 3-mercapto-, D-

Systematic Names

  • D-Penicillamine
  • D-Valine, 3-mercapto-
  • Penicillamine
  • Valine, 3-mercapto-, D-

Superlist Names

  • D-Penicilamine
  • Penicillamine

Registry Numbers

CAS Registry Number

  • 52-67-5

FDA UNII

  • GNN1DV99GX

Other Registry Numbers

  • 16414-54-3
  • 937590-88-0

System Generated Number

  • 0000052675

Structure Descriptors

InChI

InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1

InChIKey

VVNCNSJFMMFHPL-VKHMYHEASA-N

Smiles

CC(C)(S)[C@@H](N)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 40mg/kg/1W-I (40mg/kg) BLOOD: LEUKOPENIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 Archives of Internal Medicine. Vol. 145, Pg. 2271, 1985.
human TDLo oral 21mg/kg/D (21mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA

KIDNEY, URETER, AND BLADDER: PROTEINURIS		 JAMA, Journal of the American Medical Association. Vol. 240, Pg. 1870, 1978.
human TDLo oral 893mg/kg/30W- (893mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

MUSCULOSKELETAL: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Journal of Rheumatology. Vol. 11, Pg. 251, 1984.
man TDLo oral 400mg/kg/4W-I (400mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BLOOD: HEMORRHAGE		 Journal of Rheumatology. Vol. 13, Pg. 963, 1986.
man TDLo oral 482mg/kg/19W- (482mg/kg) BLOOD: THROMBOCYTOPENIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 Archives of Internal Medicine. Vol. 143, Pg. 1487, 1983.
man TDLo unreported 3200mg/kg/84W (3200mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION		 British Medical Journal. Vol. 296, Pg. 1332, 1988.
mouse LD50 intraperitoneal 298mg/kg (298mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1419, 1974.
mouse LD50 intravenous 3840mg/kg (3840mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 162, 1975.
mouse LD50 oral 720mg/kg (720mg/kg)   Pharmaceutical Chemistry Journal Vol. 21, Pg. 842, 1987.
mouse LD50 subcutaneous 3810mg/kg (3810mg/kg)   Drugs in Japan Vol. 6, Pg. 758, 1982.
rat LD50 intraperitoneal 2080mg/kg (2080mg/kg)   Drugs in Japan Vol. 6, Pg. 758, 1982.
rat LD50 intravenous 2gm/kg (2000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1434, 1972.
rat LD50 oral 6170mg/kg (6170mg/kg)   Drugs in Japan Vol. 6, Pg. 758, 1982.
rat LD50 subcutaneous 4020mg/kg (4020mg/kg)   Drugs in Japan Vol. 6, Pg. 758, 1982.
women LDLo oral 150mg/kg/30D- (150mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)		 Annals of Internal Medicine. Vol. 98, Pg. 327, 1983.
women TDLo oral 105mg/kg/6W-I (105mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" British Medical Journal. Vol. 294, Pg. 1101, 1987.
women TDLo oral 112mg/kg/1W-I (112mg/kg) BLOOD: AGRANULOCYTOSIS

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"		 Archives of Internal Medicine. Vol. 145, Pg. 2271, 1985.
women TDLo oral 900mg/kg/26W- (900mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Journal of Rheumatology. Vol. 12, Pg. 583, 1985.
women TDLo oral 650gm/kg/81W- (650000mg/kg) MUSCULOSKELETAL: OTHER CHANGES

BEHAVIORAL: MUSCLE WEAKNESS		 Arthritis and Rheumatism. Vol. 29, Pg. 560, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 198.5 deg C   EXP
pKa Dissociation Constant 1.8 (none)   EXP
log P (octanol-water) -1.78E+00 (none)   EXP
Water Solubility 1.11E+05 mg/L 20 EXP
Vapor Pressure 6.27E-07 mm Hg 25 EST
Henry's Law Constant 9.33E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.10E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.