penicillamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| 2081 | 52-67-5 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.50 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 3 | Benet LZ, Broccatelli F, Oprea TI |
| EoM (Fraction excreted unchanged in urine) | 45 % | Benet LZ, Broccatelli F, Oprea TI |
| BA (Bioavailability) | 50 % | Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H |
| Vd (Volume of distribution) | 1.26 L/kg | Lombardo F, Berellini G, Obach RS |
| CL (Clearance) | 10.65 mL/min/kg | Lombardo F, Berellini G, Obach RS |
| fu (Fraction unbound in plasma) | 0.12 % | Lombardo F, Berellini G, Obach RS |
| t_half (Half-life) | 3.04 hours | Lombardo F, Berellini G, Obach RS |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| Dec. 4, 1970 | FDA | ATON |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Anti-neutrophil cytoplasmic antibody positive vasculitis | 186.40 | 46.78 | 36 | 1788 | 1899 | 46682339 |
| Proteinuria | 151.38 | 46.78 | 46 | 1778 | 16507 | 46667731 |
| Drug hypersensitivity | 118.90 | 46.78 | 88 | 1736 | 243737 | 46440501 |
| Inflammation | 112.62 | 46.78 | 49 | 1775 | 48732 | 46635506 |
| Vasculitis | 107.96 | 46.78 | 34 | 1790 | 13677 | 46670561 |
| Joint swelling | 106.53 | 46.78 | 71 | 1753 | 166002 | 46518236 |
| Cardiovascular disorder | 74.67 | 46.78 | 25 | 1799 | 12162 | 46672076 |
| Treatment failure | 64.80 | 46.78 | 42 | 1782 | 93045 | 46591193 |
| Arthralgia | 59.84 | 46.78 | 72 | 1752 | 364531 | 46319707 |
| Red blood cell sedimentation rate increased | 59.32 | 46.78 | 25 | 1799 | 22864 | 46661374 |
| Overlap syndrome | 50.49 | 46.78 | 10 | 1814 | 597 | 46683641 |
| SLE arthritis | 50.17 | 46.78 | 10 | 1814 | 617 | 46683621 |
| Drug intolerance | 49.68 | 46.78 | 43 | 1781 | 147006 | 46537232 |
| Anaphylactic reaction | 47.12 | 46.78 | 28 | 1796 | 53084 | 46631154 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Hepato-lenticular degeneration | 80.12 | 40.73 | 8 | 228 | 9 | 29952233 |
| Cutis laxa | 47.24 | 40.73 | 6 | 230 | 102 | 29952140 |
| Elastosis perforans | 43.04 | 40.73 | 4 | 232 | 0 | 29952242 |
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | M01CC01 | MUSCULO-SKELETAL SYSTEM ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS SPECIFIC ANTIRHEUMATIC AGENTS Penicillamine and similar agents |
| FDA EPC | N0000175713 | Antirheumatic Agent |
| MeSH PA | D000931 | Antidotes |
| MeSH PA | D018501 | Antirheumatic Agents |
| MeSH PA | D002614 | Chelating Agents |
| MeSH PA | D020011 | Protective Agents |
| MeSH PA | D064449 | Sequestering Agents |
| CHEBI has role | CHEBI:35842 | antirheumatic agent |
| CHEBI has role | CHEBI:38161 | chelating agent |
| CHEBI has role | CHEBI:88188 | allergenic drug |
| CHEBI has role | CHEBI:166831 | copper chelator |
Drug Use (View source of the data)
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Rheumatoid arthritis | indication | 69896004 | DOID:7148 |
| Cystinuria | indication | 85020001 | DOID:9266 |
| Wilson's disease | indication | 88518009 | |
| Cystine Renal Calculi | indication | ||
| Felty's syndrome | off-label use | 57160007 | DOID:11042 |
| Rheumatoid vasculitis | off-label use | 400054000 | |
| Bronchiolitis | contraindication | 4120002 | DOID:2942 |
| Agranulocytosis | contraindication | 17182001 | DOID:12987 |
| Proteinuria | contraindication | 29738008 | DOID:576 |
| Blood in urine | contraindication | 34436003 | |
| Glomerulonephritis | contraindication | 36171008 | DOID:2921 |
| Goodpasture's syndrome | contraindication | 50581000 | |
| Pemphigus | contraindication | 65172003 | DOID:9182 |
| Leukopenia | contraindication | 84828003 | DOID:615 |
| Iron deficiency anemia | contraindication | 87522002 | |
| Kidney disease | contraindication | 90708001 | DOID:557 |
| Myasthenia gravis | contraindication | 91637004 | DOID:437 |
| Liver function tests abnormal | contraindication | 166603001 | |
| Lupus erythematosus and erythema multiforme-like syndrome | contraindication | 238926009 | |
| Aplastic anemia due to drugs | contraindication | 267527002 | |
| Pregnancy, function | contraindication | 289908002 | |
| Thrombocytopenic disorder | contraindication | 302215000 | DOID:1588 |
| Aplastic anemia | contraindication | 306058006 | DOID:12449 |
| Breastfeeding (mother) | contraindication | 413712001 | |
| Aphthous ulcer of mouth | contraindication | 426965005 | DOID:9663 |
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 1.9 | acidic |
| pKa2 | 10.65 | acidic |
| pKa3 | 8.68 | Basic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| copper | Inorganic material | CHELATING AGENT | DRUG LABEL | DRUG LABEL | |||||
| Succinyl-diaminopimelate desuccinylase | Enzyme | IC50 | 4.30 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4017940 | VUID |
| N0000146290 | NUI |
| D00496 | KEGG_DRUG |
| 4017940 | VANDF |
| 4021767 | VANDF |
| C0699484 | UMLSCUI |
| CHEBI:7959 | CHEBI |
| LEI | PDB_CHEM_ID |
| CHEMBL1430 | ChEMBL_ID |
| DB00859 | DRUGBANK_ID |
| D010396 | MESH_DESCRIPTOR_UI |
| 5852 | PUBCHEM_CID |
| 7264 | IUPHAR_LIGAND_ID |
| 1121 | INN_ID |
| GNN1DV99GX | UNII |
| 202724 | RXNORM |
| 198 | MMSL |
| 5243 | MMSL |
| 52894 | MMSL |
| d00333 | MMSL |
| 001088 | NDDF |
| 387235007 | SNOMEDCT_US |
| 4219002 | SNOMEDCT_US |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| Depen | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0037-4401 | TABLET | 250 mg | ORAL | NDA | 15 sections |
| penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0254-2000 | TABLET, FILM COATED | 250 mg | ORAL | ANDA | 14 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 0591-4171 | CAPSULE | 250 mg | ORAL | ANDA | 19 sections |
| Cuprimine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 25010-705 | CAPSULE | 250 mg | ORAL | NDA | 20 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 43598-634 | CAPSULE, GELATIN COATED | 250 mg | ORAL | ANDA | 17 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 43975-309 | CAPSULE | 250 mg | ORAL | ANDA | 17 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 49884-146 | CAPSULE | 250 mg | ORAL | ANDA | 17 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 60505-4696 | CAPSULE | 250 1 | ORAL | ANDA | 11 sections |
| penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 68682-020 | CAPSULE | 250 mg | ORAL | NDA authorized generic | 20 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70010-907 | CAPSULE | 250 mg | ORAL | ANDA | 16 sections |
| Penicillamine | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70748-153 | TABLET | 250 1 | ORAL | ANDA | 13 sections |