Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C5H11NO2S |
| Molecular Weight | 149.211 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(S)[C@@H](N)C(O)=O
InChI
InChIKey=VVNCNSJFMMFHPL-VKHMYHEASA-N
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
| Molecular Formula | C5H11NO2S |
| Molecular Weight | 149.211 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Penicillamine, sold under the trade names of Cuprimine among others, is a medication primarily used for treatment of Wilson's disease, cystinuria and active rheumatoid arthritis. 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363057 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CUPRIMINE Approved UseCUPRIMINE is indicated in the treatment of Wilson's disease, cystinuria, and in patients with severe, active
rheumatoid arthritis who have failed to respond to an adequate trial of conventional therapy. Launch Date2.9116801E10 |
|||
| Primary | CUPRIMINE Approved UseCUPRIMINE is indicated in the treatment of Wilson's disease, cystinuria, and in patients with severe, active
rheumatoid arthritis who have failed to respond to an adequate trial of conventional therapy. Launch Date2.9116801E10 |
|||
| Primary | CUPRIMINE Approved UseCUPRIMINE is indicated in the treatment of Wilson's disease, cystinuria, and in patients with severe, active
rheumatoid arthritis who have failed to respond to an adequate trial of conventional therapy. Launch Date2.9116801E10 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.36 μg/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENICILLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
8.04 μg/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENICILLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
73.19 μg × h/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENICILLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
83.97 μg × h/mL |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENICILLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.37 h |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENICILLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
5.01 h |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
PENICILLAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
Disc. AE: Proteinuria, Rash... AEs leading to discontinuation/dose reduction: Proteinuria (10.6%) Sources: Page: p.1200Rash Myasthenia gravis (1.5%) Thrombocytopenia Flu-like illness Stomatitis |
4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
Disc. AE: Leukopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Leukopenia (5%) Sources: Page: p.4Thrombocytopenia (5%) Proteinuria Hematuria Glomerulonephritis membranous Nephrotic syndrome Goodpasture's syndrome (rare) Obliterative bronchiolitis (rare) Myasthenia gravis Pemphigus vulgaris Pemphigus foliaceus |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Myasthenia gravis | 1.5% Disc. AE |
1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
| Proteinuria | 10.6% Disc. AE |
1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
| Flu-like illness | Disc. AE | 1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
| Rash | Disc. AE | 1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
| Stomatitis | Disc. AE | 1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
| Thrombocytopenia | Disc. AE | 1 g 1 times / day multiple, oral (max) Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: Page: p.1200 |
unhealthy, 45+/-12 n = 66 Health Status: unhealthy Condition: Diffuse systemic sclerosis Age Group: 45+/-12 Sex: M+F Population Size: 66 Sources: Page: p.1200 |
| Leukopenia | 5% Disc. AE |
4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Thrombocytopenia | 5% Disc. AE |
4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Glomerulonephritis membranous | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Hematuria | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Myasthenia gravis | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Nephrotic syndrome | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Pemphigus foliaceus | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Pemphigus vulgaris | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Proteinuria | Disc. AE | 4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Goodpasture's syndrome | rare Disc. AE |
4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
| Obliterative bronchiolitis | rare Disc. AE |
4 g 1 times / day multiple, oral (max) Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Wilson's disease|Cystinuria Sources: Page: p.4 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Myasthenia gravis associated with penicillamine treatment for rheumatoid arthritis. | 1975 Mar 15 |
|
| Rapidly progressive glomerulonephritis with D-penicillamine. | 2000 Dec |
|
| Drug treatment of scleroderma. | 2001 |
|
| D-Penicillamine for preventing retinopathy of prematurity in preterm infants. | 2001 |
|
| Nitric oxide in the afferent synaptic transmission of the axolotl vestibular system. | 2001 |
|
| Mechanisms of nitric oxide-induced cytotoxicity in normal human hepatocytes. | 2001 |
|
| Nitric oxide differentially regulates induction of type II nitric oxide synthase in rat vascular smooth muscle cells versus macrophages. | 2001 Apr |
|
| Interaction of co-expressed mu- and delta-opioid receptors in transfected rat pituitary GH(3) cells. | 2001 Apr |
|
| Opposing actions of nitric oxide on synaptic inputs of identified interneurones in the central nervous system of the crayfish. | 2001 Apr |
|
| Induction of a non-rhythmic motor pattern by nitric oxide in hatchling Rana temporaria embryos. | 2001 Apr |
|
| Nitric oxide increases fluid extravasation from the splenic circulation of the rat. | 2001 Apr |
|
| Effect of NO donors on protein phosphorylation in intact vascular and nonvascular smooth muscles. | 2001 Apr |
|
| Cyclooxygenase-2 protein and prostaglandin E(2) production are up-regulated in a rat bladder inflammation model. | 2001 Apr 13 |
|
| Enantiomeric analysis of pharmaceutical compounds by ion/molecule reactions. | 2001 Apr 15 |
|
| The effect of various capacitation active compounds and capacitation time on the in vitro fertility and protein tyrosine phosphorylation profiles of bovine sperm. | 2001 Feb |
|
| Paracrine neuroprotective effect of nitric oxide in the developing retina. | 2001 Feb |
|
| Analysis of S-nitroso-N-acetylpenicillamine effects on dopamine release in the striatum of freely moving rats: role of endogenous ascorbic acid and oxidative stress. | 2001 Feb |
|
| Treatment of Wilson's disease: what are the relative roles of penicillamine, trientine, and zinc supplementation? | 2001 Feb |
|
| Coexistence of zinc and iron augmented oxidative injuries in the nigrostriatal dopaminergic system of SD rats. | 2001 Feb 1 |
|
| Pharmacological effects of naltriben as a ligand for opioid mu and kappa receptors in rat cerebral cortex. | 2001 Feb 2 |
|
| Role of copper ions and cytochrome P450 in the vasodilator actions of the nitroxyl anion generator, Angeli's salt, on rat aorta. | 2001 Feb 2 |
|
| Ligand binding profiles of delta-opioid receptor in human cerebral cortex membranes: evidence of delta-opioid receptor heterogeneity. | 2001 Feb 23 |
|
| The metabolic evidence of synergistic effect between ohmefentanyl and [D-Pen2, D-Pen5] enkephalin on differentiated SH-SY5Y cells in humans. | 2001 Feb 9 |
|
| Nitric oxide donors regulate nitric oxide synthase in bovine pulmonary artery endothelium. | 2001 Jan |
|
| Vascular endothelial growth factor receptor-2-mediated mitogenesis is negatively regulated by vascular endothelial growth factor receptor-1 in tumor epithelial cells. | 2001 Jan |
|
| Endothelial nitric oxide synthase gene-deficient mice demonstrate marked retardation in postnatal bone formation, reduced bone volume, and defects in osteoblast maturation and activity. | 2001 Jan |
|
| Structure, function, and regulation of human cystine/glutamate transporter in retinal pigment epithelial cells. | 2001 Jan |
|
| Nitric oxide attenuates H(2)O(2)-induced endothelial barrier dysfunction: mechanisms of protection. | 2001 Jan |
|
| Estradiol-induced attenuation of pulmonary hypertension is not associated with altered eNOS expression. | 2001 Jan |
|
| Interference of biocytin with opioid-evoked hyperpolarization and membrane properties of rat spinal substantia gelatinosa neurons. | 2001 Jan 12 |
|
| Osteopontin is a negative feedback regulator of nitric oxide synthesis in murine macrophages. | 2001 Jan 15 |
|
| Nitric oxide in the potassium-induced response of the rat middle cerebral artery: a possible permissive role. | 2001 Jan 19 |
|
| The regulation of NMDA-evoked dopamine release by nitric oxide in the frontal cortex and raphe nuclei of the freely moving rat. | 2001 Jan 19 |
|
| [Drug-induced taste disorders: analysis of the French Pharmacovigilance Database and literature review]. | 2001 Jan-Feb |
|
| Stimulation by nitric oxide of gastric acid secretion in bullfrog fundic mucosa in vitro. | 2001 Mar |
|
| Involvement of cyclooxygenase-derived prostaglandin E2 and nitric oxide in the protection of rat pancreas afforded by low dose of lipopolysaccharide. | 2001 Mar |
|
| The Disability Index of the Health Assessment Questionnaire is a predictor and correlate of outcome in the high-dose versus low-dose penicillamine in systemic sclerosis trial. | 2001 Mar |
|
| IL-4 gene expression up-regulated by mercury in rat mast cells: a role of oxidant stress in IL-4 transcription. | 2001 Mar |
|
| Induction of radioresistance by a nitric oxide-mediated bystander effect. | 2001 Mar |
|
| Tissue plasminogen activator protects hippocampal neurons from oxygen-glucose deprivation injury. | 2001 Mar 1 |
|
| Nitric oxide-dependent pro-oxidant and pro-apoptotic effect of metallothioneins in HL-60 cells challenged with cupric nitrilotriacetate. | 2001 Mar 1 |
|
| The metabolic evidence of synergistic interaction between DAMGO and DPDPE on undifferentiated SH-SY5Y cells. | 2001 Mar 26 |
|
| Cyclooxygenase-1 participates in selected vasodilator responses of the cerebral circulation. | 2001 Mar 30 |
|
| Evidence for an endocannabinoid system in the central nervous system of the leech Hirudo medicinalis. | 2001 Mar 5 |
|
| The role of delta-opioid receptor subtypes in neuropathic pain. | 2001 Mar 9 |
|
| Scleroderma in a child after chemotherapy for cancer. | 2001 Mar-Apr |
|
| Old and new drugs used in rheumatoid arthritis: a historical perspective. Part 1: the older drugs. | 2001 Mar-Apr |
|
| Glutamate release via NO production evoked by NMDA in the NTS enhances hypotension and bradycardia in vivo. | 2001 May |
|
| Endothelial nitric oxide synthase plays an essential role in regulation of renal oxygen consumption by NO. | 2001 May |
Sample Use Guides
In all patients receiving penicillamine, it is important that CUPRIMINE be given on an empty stomach, at least one hour before meals or two hours after meals, and at least one hour apart from any other drug, food, or milk.
Wilson's Disease: In the absence of any drug reaction, a dose between 0.75 and 1.5 g that results in an initial
24-hour cupriuresis of over 2 mg should be continued for about three months, by which time the most reliable
method of monitoring maintenance treatment is the determination of free copper in the serum. In patients who cannot tolerate as much as 1 g/day initially, initiating dosage with 250 mg/day, and
increasing gradually to the requisite amount, gives closer control of the effects of the drug and may help to
reduce the incidence of adverse reactions.
Cystinuria:The usual dosage of CUPRIMINE in the treatment of cystinuria is 2 g/day for adults, with a range of 1 to
4 g/day. For pediatric patients, dosage can be based on 30 mg/kg/day. The total daily amount should be divided
into four doses. If four equal doses are not feasible, give the larger portion at bedtime. If adverse reactions
necessitate a reduction in dosage, it is important to retain the bedtime dose.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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Wed Jul 05 22:41:21 UTC 2023
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| Record UNII |
GNN1DV99GX
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Validated (UNII)
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WHO-ESSENTIAL MEDICINES LIST |
4.2
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NDF-RT |
N0000175713
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NCI_THESAURUS |
C1971
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WHO-ESSENTIAL MEDICINES LIST |
2.4
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WHO-VATC |
QM01CC01
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LIVERTOX |
NBK548246
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WHO-ATC |
M01CC01
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52-67-5
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DB00859
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200-148-8
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GNN1DV99GX
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M8467
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7264
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CHEMBL1430
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GNN1DV99GX
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D010396
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Penicillamine
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PENICILLAMINE
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7975
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SUB127001
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2081
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BINDING
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
