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 |
|
| 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 |
|
| Divergent effects of ischemia/reperfusion and nitric oxide donor on TNFalpha mRNA accumulation in rat organs. | 2001 Apr |
|
| Modulation of human platelet aggregation by the phosphodiesterase type 5 inhibitor sildenafil. | 2001 Apr |
|
| Effects of nitrovasodilators on the human fetal-placental circulation in vitro. | 2001 Apr |
|
| NF-kappaB stimulates inducible nitric oxide synthase to protect mouse hepatocytes from TNF-alpha- and Fas-mediated apoptosis. | 2001 Apr |
|
| Galpha(14) links a variety of G(i)- and G(s)-coupled receptors to the stimulation of phospholipase C. | 2001 Apr |
|
| Interaction of co-expressed mu- and delta-opioid receptors in transfected rat pituitary GH(3) cells. | 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 |
|
| Direct autocrine inhibition and cAMP-dependent potentiation of single L-type Ca2+ channels in bovine chromaffin cells. | 2001 Apr 1 |
|
| 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 |
|
| Effect of nitric oxide on basal and stretch-induced release of atrial natriuretic factor (ANF) from isolated perfused rat atria. | 2001 Apr 20 |
|
| Uptake and efflux of the peptidic delta-opioid receptor agonist. | 2001 Apr 6 |
|
| Nitric oxide inhibits norepinephrine stimulated contraction of human internal thoracic artery and rat aorta. | 2001 Feb |
|
| Superoxide inhibits neuronal nitric oxide synthase influences on afferent arterioles in spontaneously hypertensive rats. | 2001 Feb |
|
| Paracrine neuroprotective effect of nitric oxide in the developing retina. | 2001 Feb |
|
| Involvement of reactive oxygen species and nitric oxide radicals in activation and proliferation of rat hepatic stellate cells. | 2001 Feb |
|
| Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols. | 2001 Feb 12 |
|
| Pharmacological effects of naltriben as a ligand for opioid mu and kappa receptors in rat cerebral cortex. | 2001 Feb 2 |
|
| Ligand binding profiles of delta-opioid receptor in human cerebral cortex membranes: evidence of delta-opioid receptor heterogeneity. | 2001 Feb 23 |
|
| Ionophoretic studies on mixed metal--nitrilotriacetate--penicillamine complexes. | 2001 Feb 23 |
|
| Effects of nitric oxide on matrix metalloproteinase-2 production by rheumatoid synovial cells. | 2001 Jan 12 |
|
| A thermodynamic study of the temperature-dependent elution order of cyclic alpha-amino acid enantiomers on a copper(II)-D-penicillamine chiral stationary phase. | 2001 Jan 15 |
|
| Metabolic regulation of aldose reductase activity by nitric oxide donors. | 2001 Jan 30 |
|
| High-performance liquid chromatographic enantiomeric separation of an enzyme inhibitor which possesses both a chiral center and tautomeric moieties. | 2001 Jan 5 |
|
| [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 |
|
| Coincident signalling between the Gi/Go-coupled delta-opioid receptor and the Gq-coupled m3 muscarinic receptor at the level of intracellular free calcium in SH-SY5Y cells. | 2001 Mar |
|
| Transport of opioids from the brain to the periphery by P-glycoprotein: peripheral actions of central drugs. | 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 |
|
| L-arginine effects on Na+ transport in M-1 mouse cortical collecting duct cells--a cationic amino acid absorbing epithelium. | 2001 Mar 15 |
|
| Effect of redox modulation on xenogeneic target cells: the combination of nitric oxide and thiol deprivation protects porcine endothelial cells from lysis by IL-2-activated human NK cells. | 2001 Mar 15 |
|
| Nitric oxide augments voltage-activated calcium currents of crustacea (Idotea baltica) skeletal muscle. | 2001 Mar 16 |
|
| 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 |
|
| Nitric oxide reduces energy supply by direct action on the respiratory chain in isolated cardiomyocytes. | 2001 May |
|
| 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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on
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Fri Dec 15 15:09:34 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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C729
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D010396
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Penicillamine
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PENICILLAMINE
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100000082481
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3378
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1501006
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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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ACTIVE MOIETY |
