Penicillamine
Basic information
- CAS
52-67-5- Standard SMILES
CC(C)(S)[C@@H](N)C(=O)O- InChIKey
VVNCNSJFMMFHPL-VKHMYHEASA-N- Molecular formula
- C5H11NO2S
- Average molar mass
- 149.21 g/mol
- Monoisotopic mass
- 149.05104977
Overview
Penicillamine can cause developmental toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Penicillamine
- IUPAC
- (2S)-2-amino-3-methyl-3-sulfanylbutanoic acid
- English name
- D-Penicillamine
- Molecular formula
- C5H11NO2S
- Molecular weight
- 149.21
Names & synonyms
D-Penicillaminepenicillamine52-67-5CuprimineD-(-)-Penicillamine3-Mercapto-D-valine(2S)-2-Amino-3-methyl-3-sulfanylbutanoic acidDepenCuprenilCupripenD-Valine, 3-mercapto-(-)-Penicillamine
Show more names
Penicillamin2-Amino-3-mercapto-3-methylbutanoic acid(S)-2-aMino-3-Mercapto-3-Methylbutanoic acidPencillamineusanH-D-PEN-OHD-Pen-OH
KuprenilTrolovol(S)-3,3-DimethylcysteineMercaptovalinePenicilaminaD-3-MercaptovalinePenicillaminumDimethylcysteine
Database identifiers
- CAS
52-67-5、771431-20-0- PubChem CID
- 5852
- DTXSID
DTXSID6037069- ChEMBL
CHEMBL1430- ChEBI
CHEBI:7959- UNII
- GNN1DV99GX
- EC Number
- 200-148-8
- Nikkaji
- J9.116B
Properties
Computed structural properties
- XLogP
- -1.8
- Topological polar surface area
- 64.3 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 124
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Pharmaceuticals
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
OdorSLIGHT CHARACTERISTIC ODOR
TasteSLIGHTLY BITTER
Color/FormFINE, WHITE OR PRACTICALLY WHITE, CRYSTALLINE POWDER
Solubility
CRYSTALS; DECOMP 177.5 °C; SPECIFIC OPTICAL ROTATION: -63 DEG @ 25 °C/D (1N SODIUM HYDROXIDE); HYGROSCOPIC; FREELY SOL IN WATER, SOL IN ETHANOL. /D-PENICILLAMINE HYDROCHLORIDE/
FREELY SOL IN WATER; SLIGHTLY SOL IN ALC; INSOL IN ETHER, CHLOROFORM.
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antirheumatic Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Antidotes and other substances used in poisonings > Specific
DecompositionWhen heated to decomposition it emits very toxic fumes of oxides of nitrogen and oxides of sulfur.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (90.4%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationHazard Traits - Developmental Toxicity
Hazards Summary
Asthma reported in a pharmaceutical worker; [Malo] Penicillamine is a drug used to treat several diseases. Many side effects have been reported after ingestion of therapeutic doses, including bone marrow suppression and drug-induced hepatitis. [HSDB]
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl penicillamine, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.
Special Reports
HUSKISSON EC; EUR J RHEUMATOL INFLAMMATION 3 (2): 156 (1979); REVIEW ARTICLE ON THE RENAL TOXICITY OF PENICILLAMINE.
JELLUM E, MUNTHE E; NAT SULFUR CMPD, (PROC INT MEET) 3RD: 375 (1980); CLINICAL EFFECTS OF PENICILLAMINE IN THE TREATMENT OF RHEUMATOID ARTHRITIS ARE DISCUSSED.
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system
QM - Musculo-skeletal system
M01CC01
Protein Binding>80% (bound to plasma proteins)
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. 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.
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.
Penicillamine chelates mercury, lead, copper, iron, and probably other heavy metals to form stable, soluble complexes that are readily excreted in the urine.
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.
Related reactions
63 records
Compound notes
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