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

Stem definition	Drug id	CAS RN
	2081	52-67-5

Description:

Molecule	Description
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

Molecule

Description

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:

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
S (Water solubility)	111 mg/mL	Bocci G, Oprea TI, Benet LZ

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	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 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
Cutis laxa	40.28	36.79	5	210	91	34956625

FDA Adverse Event Reporting System (Geriatric)

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	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:

Source	Code	Description
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|

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

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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
Succinyl-diaminopimelate desuccinylase	Enzyme		DAPE_HAEIN		IC50	4.30		CHEMBL

External reference:

ID	Source
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:

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	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