penicillamine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2081 52-67-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • penicillamine
  • cuprenil
  • cuprimine
  • cupripen
  • D-Mercaptovaline
  • D-Penicillamine
  • depamine
  • pendramine
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.
  • Molecular weight: 149.21
  • Formula: C5H11NO2S
  • CLOGP: -1.73
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 63.32
  • ALOGS: -1.51
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.50 g O

ADMET properties:

PropertyValueReference
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:

DateAgencyCompanyOrphan
Dec. 4, 1970 FDA ATON

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 130.21 57.42 36 114 46607 2311328
Anti-neutrophil cytoplasmic antibody positive vasculitis 122.29 57.42 16 134 324 2357611
Proteinuria 88.29 57.42 16 134 2834 2355101
Vasculitis 65.08 57.42 12 138 2306 2355629
Acute kidney injury 65.01 57.42 19 131 28103 2329832
Drug intolerance 58.27 57.42 15 135 13702 2344233

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC M01CC01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
SPECIFIC ANTIRHEUMATIC AGENTS
Penicillamine and similar agents
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:35842 antirheumatic drug
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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
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 levelDissociation constantType (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:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
copper Inorganic material CHELATING AGENT DRUG LABEL DRUG LABEL
Succinyl-diaminopimelate desuccinylase Enzyme IC50 4.30 CHEMBL

External reference:

IDSource
4017940 VUID
N0000146290 NUI
C0030817 UMLSCUI
D00496 KEGG_DRUG
387235007 SNOMEDCT_US
4219002 SNOMEDCT_US
52894 MMSL
4017940 VANDF
7975 RXNORM
5243 MMSL
d00333 MMSL
001088 NDDF
5852 PUBCHEM_CID
CHEBI:7959 CHEBI
CHEMBL1430 ChEMBL_ID
DB00859 DRUGBANK_ID
GNN1DV99GX UNII
1121 INN_ID
D010396 MESH_DESCRIPTOR_UI
7264 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Depen HUMAN PRESCRIPTION DRUG LABEL 1 0037-4401 TABLET 250 mg ORAL NDA 11 sections
penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 0254-2000 TABLET, FILM COATED 250 mg ORAL ANDA 10 sections
D-Penamine HUMAN PRESCRIPTION DRUG LABEL 1 0378-0709 TABLET 125 mg ORAL Unapproved drug for use in drug shortage 2 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 0591-4171 CAPSULE 250 mg ORAL ANDA 11 sections
Cuprimine HUMAN PRESCRIPTION DRUG LABEL 1 25010-705 CAPSULE 250 mg ORAL NDA 12 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 43975-309 CAPSULE 250 mg ORAL ANDA 11 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 49884-146 CAPSULE 250 mg ORAL ANDA 11 sections
penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 68682-020 CAPSULE 250 mg ORAL NDA authorized generic 12 sections