|
|
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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Antidotes
- Antirheumatic Agents
- Chelating Agent
- Chelating Agents
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Protective Agents
- Reproductive Effect
- Sequestering Agents
- Tumor Data
* denotes mobile formatted website
Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
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/s1InChIKey
VVNCNSJFMMFHPL-VKHMYHEASA-NSmiles
CC(C)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.