penicillamine 🐶 Veterinary Use | 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
S (Water solubility) 111 mg/mL Bocci G, Oprea TI, Benet LZ

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
Anti-neutrophil cytoplasmic antibody positive vasculitis 252.24 50.57 48 1999 2851 63484124
Proteinuria 193.28 50.57 55 1992 19090 63467885
Drug hypersensitivity 137.45 50.57 98 1949 310589 63176386
Vasculitis 134.08 50.57 41 2006 18168 63468807
Inflammation 127.45 50.57 59 1988 82214 63404761
Joint swelling 93.72 50.57 80 1967 327586 63159389
Cardiovascular disorder 80.14 50.57 25 2022 11787 63475188
SLE arthritis 63.70 50.57 12 2035 669 63486306
Treatment failure 61.62 50.57 51 1996 198992 63287983
Arthralgia 61.59 50.57 83 1964 569627 62917348
Elastosis perforans 61.08 50.57 7 2040 6 63486969
Weber tuning fork test abnormal 60.87 50.57 9 2038 110 63486865
Overlap syndrome 60.42 50.57 12 2035 884 63486091
Chest pain 57.99 50.57 51 1996 215908 63271067
Acute kidney injury 54.89 50.57 54 1993 263361 63223614
Elbow deformity 54.13 50.57 12 2035 1503 63485472

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
Cutis laxa 40.28 36.79 5 210 91 34956625

FDA Adverse Event Reporting System (Geriatric)

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
Anti-neutrophil cytoplasmic antibody positive vasculitis 191.75 43.82 38 1909 3691 79738750
Proteinuria 129.93 43.82 43 1904 32459 79709982
Inflammation 129.32 43.82 57 1890 93696 79648745
Drug hypersensitivity 122.67 43.82 81 1866 298835 79443606
Vasculitis 111.57 43.82 36 1911 25066 79717375
Joint swelling 94.16 43.82 68 1879 288578 79453863
Cardiovascular disorder 72.56 43.82 24 1923 18001 79724440
Elastosis perforans 72.50 43.82 8 1939 6 79742435
Weber tuning fork test abnormal 63.37 43.82 9 1938 110 79742331
Arthralgia 60.95 43.82 72 1875 571731 79170710
SLE arthritis 55.42 43.82 10 1937 583 79741858
Red blood cell sedimentation rate increased 50.77 43.82 24 1923 45918 79696523
Anaphylactic reaction 50.14 43.82 29 1918 83714 79658727
Overlap syndrome 49.97 43.82 10 1937 1014 79741427
Elbow deformity 45.85 43.82 10 1937 1537 79740904
Contraindicated product administered 44.18 43.82 34 1913 157504 79584937

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01CC01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
SPECIFIC ANTIRHEUMATIC AGENTS
Penicillamine and similar agents
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 anti-rheumatic drugs
CHEBI has role CHEBI:38161 Chelating agent
CHEBI has role CHEBI:88188 allergenic drug
CHEBI has role CHEBI:166831 copper chelator
FDA EPC N0000175713 Antirheumatic Agent

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
Succinyl-diaminopimelate desuccinylase Enzyme IC50 4.30 CHEMBL

External reference:

IDSource
4017940 VUID
N0000146290 NUI
D00496 KEGG_DRUG
4017940 VANDF
4021767 VANDF
C0030817 UMLSCUI
CHEBI:7959 CHEBI
LEI PDB_CHEM_ID
CHEMBL1430 ChEMBL_ID
DB00859 DRUGBANK_ID
D010396 MESH_DESCRIPTOR_UI
5852 PUBCHEM_CID
1121 INN_ID
7264 IUPHAR_LIGAND_ID
GNN1DV99GX UNII
202724 RXNORM
198 MMSL
5243 MMSL
52894 MMSL
d00333 MMSL
001088 NDDF
387235007 SNOMEDCT_US
4219002 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 51991-974 CAPSULE 250 mg ORAL ANDA 20 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 60505-4696 CAPSULE 250 mg ORAL ANDA 11 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 60505-4696 CAPSULE 250 1 ORAL ANDA 11 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 62559-970 CAPSULE 250 mg ORAL ANDA 16 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 68475-201 CAPSULE 250 mg ORAL ANDA 16 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 68475-201 CAPSULE 250 mg ORAL ANDA 16 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 70010-907 CAPSULE 250 mg ORAL ANDA 16 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 70748-153 TABLET 250 mg ORAL ANDA 13 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 70748-153 TABLET 250 1 ORAL ANDA 13 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 71205-916 CAPSULE 250 mg ORAL ANDA 16 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 71205-916 CAPSULE 250 mg ORAL ANDA 16 sections