penicillamine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,ACVRL1,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3B,IKBKB,ITK,JAK1,JAK2,JAK3,KDR,MAP2K6,MAP3K14,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDK4,PIK3CB,PIK3CD,PIK3CG,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ZAP70 54
kinase-selectivity-class ACVR2B,AXL,BMX,BRAF,CDK9,EPHB4,GRK2,MAP2K6,MAP3K14,MAPK7,PIK3CD,PIK3CG,PRKDC,TEK,TGFBR1 15
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 258.60 52.64 49 2068 3944 90622386
Proteinuria 204.78 52.64 56 2061 23235 90603095
Vasculitis 138.20 52.64 41 2076 22652 90603678
Drug hypersensitivity 132.77 52.64 99 2018 463510 90162820
Inflammation 104.88 52.64 60 2057 178532 90447798
Joint swelling 88.24 52.64 81 2036 503219 90123111
Cardiovascular disorder 84.80 52.64 25 2092 13467 90612863
SLE arthritis 66.94 52.64 12 2105 705 90625625
Weber tuning fork test abnormal 63.77 52.64 9 2108 110 90626220
Arthralgia 63.76 52.64 84 2033 778438 89847892
Elastosis perforans 63.33 52.64 7 2110 6 90626324
Acute kidney injury 62.73 52.64 55 2062 320332 90305998
Treatment failure 59.12 52.64 52 2065 303876 90322454
Elbow deformity 58.02 52.64 12 2105 1499 90624831
Anaphylactic reaction 55.53 52.64 31 2086 87493 90538837
Chest pain 54.91 52.64 51 2066 319594 90306736

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 39.36 34.52 5 253 112 42620965

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 193.27 39.83 39 2049 5378 110581833
Proteinuria 136.04 39.83 44 2044 39974 110547237
Drug hypersensitivity 113.05 39.83 82 2006 454008 110133203
Vasculitis 108.01 39.83 36 2052 35837 110551374
Inflammation 106.80 39.83 58 2030 193180 110394031
Joint swelling 88.03 39.83 70 2018 442775 110144436
Elastosis perforans 74.56 39.83 8 2080 6 110587205
Cardiovascular disorder 73.11 39.83 24 2064 22736 110564475
Weber tuning fork test abnormal 65.68 39.83 9 2079 110 110587101
Arthralgia 61.08 39.83 74 2014 779558 109807653
SLE arthritis 57.27 39.83 10 2078 627 110586584
Anaphylactic reaction 53.97 39.83 31 2057 114269 110472942
Elbow deformity 48.65 39.83 10 2078 1500 110585711
Red blood cell sedimentation rate increased 44.49 39.83 24 2064 78278 110508933
Jaw fracture 41.31 39.83 10 2078 3146 110584065
Contraindicated product administered 40.28 39.83 35 2053 248232 110338979
Chest pain 40.02 39.83 42 2046 376333 110210878

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 D002614 Chelating Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D020011 Protective Agents
MeSH PA D064449 Sequestering Agents
FDA EPC N0000175713 Antirheumatic Agent
CHEBI has role CHEBI:35842 antirheumatic drug
CHEBI has role CHEBI:38161 chelator
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:166831 copper chelator

Related Drugs by ATC class:

M01CC Penicillamine and similar agents 1 drug
bucillamine

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
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 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 68475-201 CAPSULE 250 mg ORAL ANDA 16 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 70010-907 CAPSULE 250 mg ORAL ANDA 16 sections
AAGYLUR HUMAN PRESCRIPTION DRUG LABEL 1 70709-102 CAPSULE 250 mg ORAL ANDA 18 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 70748-153 TABLET 250 mg ORAL ANDA 13 sections
Penicillamine HUMAN PRESCRIPTION DRUG LABEL 1 71205-916 CAPSULE 250 mg ORAL ANDA 16 sections