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Compound Detail

CHEMBL1430

PENICILLAMINE
💊 Approved Drug
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💊 Approved Drug
CC(C)(S)[C@@H](N)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1430
Name PENICILLAMINE
Phase Approved
Structure Type MOL
InChI Key VVNCNSJFMMFHPL-VKHMYHEASA-N
Therapeutic ✓ Yes

Known Names

Cuprimine D mercaptovaline D penicillamine D-3-mercaptovaline Depen Dimethylcysteine Distamine NSC-758421 NSC-81549 Penicilamina Penicillamine Trolovol
3
Targets
7
Activities
1
Assay Types
0
PK Parameters
20
Publications
12
Known Names
9
Indications
1
Mechanisms

Molecular Properties

149.2
MW (Da)
0.11
ALogP
3
HBA
3
HBD
63.3
PSA (Ų)
0.49
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1970
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Year 1963

Extended Properties

Molecular Formula C5H11NO2S
MW 149.21
Aromatic Rings 0
Heavy Atoms 9
NP-Likeness 1.17

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Copper chelating agent CHELATING AGENT Copper ✓ ✓

Indications

Arthritis, Rheumatoid Cystinuria Hepatolenticular Degeneration Hepatolenticular Degeneration Inflammation Rheumatic Diseases Spondylitis Central Nervous System Neoplasms Head and Neck Neoplasms

ATC Classification

M01CC01
penicillamine
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 7 meas. best 5.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.48 5.42 3300.0 2
Unchecked
CHEMBL612545
 IC50 5.31 5.31 4900.0 1
Succinyl-diaminopimelate desuccinylase
CHEMBL1075192
 IC50 4.3 4.3 50000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 3300.0 nM 5.48 Antioxidant activity assessed as authentic peroxynitrite free radical scavenging... 15844957
NON-PROTEIN TARGET IC50 = 4400.0 nM 5.36 Antioxidant activity assessed as 3-morpholinosydnonimine-derived peroxynitrite f... 15844957
Unchecked IC50 = 4900.0 nM 5.31 Singlet oxygen scavenging activity by assessed as inhibition of DHR oxidation 17624791
Succinyl-diaminopimelate desuccinylase IC50 = 50000.0 nM 4.3 Inhibition of Haemophilus influenzae recombinant DapE 19822427

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1383
- 10.6019/CHEMBL3885881 Rattus norvegicus 432
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
364061 10.1021/jm00210a019 Rattus norvegicus 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
3086558 10.1021/jm00156a032 Rattus norvegicus 6
17918925 10.1021/jm070803y Carboxypeptidase A1 4
16581247 10.1016/j.bmcl.2006.03.026 Rattus norvegicus 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
18834112 10.1021/jm800656v Amine oxidase [flavin-containing] A 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.1016/S0960-894X(01)80249-3 Rattus norvegicus 3
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
15844957 10.1021/np0495985 NON-PROTEIN TARGET 2
- 10.1039/C2MD20020A Serine palmitoyltransferase 2
22652051 10.1016/j.bmcl.2012.05.017 NON-PROTEIN TARGET 2
11229767 10.1016/s0960-894x(00)00718-6 ADMET 2
21657271 10.1021/jm2001663 NON-PROTEIN TARGET 2

Data from ChEMBL 36 via Core Engine