Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C5H11NO2S |
| Molecular Weight | 149.2126 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)([C@]([H])(C(=O)O)N)S
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 | 149.2126 |
| 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 Date29116800000 |
|||
| 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 Date29116800000 |
|||
| 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 Date29116800000 |
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 Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
Disc. AE: Proteinuria, Rash... AEs leading to discontinuation/dose reduction: Proteinuria (10.6%) Sources: Rash Myasthenia gravis (1.5%) Thrombocytopenia Flu-like illness Stomatitis |
4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Leukopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Leukopenia (5%) Sources: Thrombocytopenia (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 Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
| Proteinuria | 10.6% Disc. AE |
1 g 1 times / day multiple, oral Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
| Flu-like illness | Disc. AE | 1 g 1 times / day multiple, oral Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
| Rash | Disc. AE | 1 g 1 times / day multiple, oral Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
| Stomatitis | Disc. AE | 1 g 1 times / day multiple, oral Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
| Thrombocytopenia | Disc. AE | 1 g 1 times / day multiple, oral Recommended Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy, 45+/-12 |
| Leukopenia | 5% Disc. AE |
4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Thrombocytopenia | 5% Disc. AE |
4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Glomerulonephritis membranous | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hematuria | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Myasthenia gravis | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Nephrotic syndrome | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Pemphigus foliaceus | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Pemphigus vulgaris | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Proteinuria | Disc. AE | 4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Goodpasture's syndrome | rare Disc. AE |
4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Obliterative bronchiolitis | rare Disc. AE |
4 g 1 times / day multiple, oral Recommended Dose: 4 g, 1 times / day Route: oral Route: multiple Dose: 4 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
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 |
|
| 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 |
|
| NMDA-induced phosphorylation of the microtubule-associated protein MAP-2 is mediated by activation of nitric oxide synthase and MAP kinase. | 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 |
|
| Activity of mu- and delta-opioid agonists in vas deferens from mice deficient in MOR gene. | 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| [Induction of nitric oxide synthesis in mononuclear cells in culture using peritoneal fluid from women with endometriosis, in relation to the percentage of T lymphocytes and NK cells identified in an such environment]. | 2001 Jan |
|
| Metabolic regulation of aldose reductase activity by nitric oxide donors. | 2001 Jan 30 |
|
| [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 |
|
| Expression of functional mu-opioid receptors during T cell development. | 2001 Mar 1 |
|
| Tissue plasminogen activator protects hippocampal neurons from oxygen-glucose deprivation injury. | 2001 Mar 1 |
|
| 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 |
|
| 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 |
|
| 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.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 21:05:25 UTC 2021
by
admin
on
Fri Jun 25 21:05:25 UTC 2021
|
| Record UNII |
GNN1DV99GX
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Brand Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
WHO-ESSENTIAL MEDICINES LIST |
4.2
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
||
|
NDF-RT |
N0000175713
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
||
|
NCI_THESAURUS |
C1971
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
||
|
WHO-ESSENTIAL MEDICINES LIST |
2.4
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
||
|
WHO-VATC |
QM01CC01
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
||
|
LIVERTOX |
752
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
||
|
WHO-ATC |
M01CC01
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
52-67-5
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
DB00859
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
200-148-8
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
M8467
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | Merck Index | ||
|
1501006
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | USP-RS | ||
|
7264
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
CHEMBL1430
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
GNN1DV99GX
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
52-67-5
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
C729
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
5852
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
D010396
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
Penicillamine
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
PENICILLAMINE
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
3378
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
1121
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
SUB09667MIG
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
7975
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | RxNorm | ||
|
SUB127001
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY | |||
|
2081
Created by
admin on Fri Jun 25 21:05:25 UTC 2021 , Edited by admin on Fri Jun 25 21:05:25 UTC 2021
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
BINDER->LIGAND |
BINDING
|
||
|
|
SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
