Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR5171)
Drug Name
Penicillamine
Synonyms
D-Penicillamine; penicillamine; 52-67-5; Cuprimine; D-(-)-Penicillamine; 3-Mercapto-D-valine; Depen; Cuprenil; D-Penamine; (-)-Penicillamine; (2S)-2-Amino-3-methyl-3-sulfanylbutanoic acid; D-Mercaptovaline; Mercaptovaline; Perdolat; Penicillamin; Pendramine; Kuprenil; Depamine; Mercaptyl; Trolovol; Metalcaptase; Artamine; Cupripen; (S)-3,3-Dimethylcysteine; D-Valine, 3-mercapto-; Penicillaminum; Penicilamina; Sufirtan; beta-Thiovaline; Dimethylcysteine; D-beta,beta-Dimethylcysteine; D-3-Mercaptovaline; beta,beta-Dimethylcysteine; Penicillamina; Penicilllamine; Sufortan; Copper penicillaminate; D Penicillamine; Penicillamina [DCIT]; Reduced penicillamine; D 3 Mercaptovaline; TBB068824; Beta,beta Dimethylcysteine; Beta-Thiovaline; Cuprimine (TN); D-Penicilamine; D-Penicyllamine; Depen (TN); P-1280; Penicilamina [INN-Spanish]; Penicillaminate, Copper; Penicillaminum [INN-Latin]; Reduced D-penicillamine; Beta,beta-Dimethylcysteine; D,3-Mercaptovaline; D-beta-Mercaptovaline; Distamine (*Hydrochloride*); Metalcaptase (*Hydrochloride*); Penicillamine (JAN/USP/INN); Penicillamine [USAN:INN:BAN:JAN]; Alpha-Amino-beta-methyl-beta-mercaptobutyric acid; D-(-)-2-Amino-3-mercapto-3-methylbutanoic acid; (2S)-2-amino-3-methyl-3-sulfanyl-butanoic acid; (D)-PENICILLAMINE; (S)-Penicillamin; (S)-Penicillamine; 2-Amino-3-mercapto-3-methylbutanoic acid; 3,3-Dimethyl-D-cysteine; 3-Mercaptovaline; 3-sulfanyl-D-valine; D-penicillamine
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 149.21 Topological Polar Surface Area 64.3
Heavy Atom Count 9 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5852
ChEBI ID
CHEBI:7959
CAS Number
771431-20-0
TTD Drug ID
D08HZC
Formula
C5H11NO2S
Canonical SMILES
CC(C)([C@H](C(=O)O)N)S
InChI
InChI=1S/C5H11NO2S/c1-5(2,9)3(6)4(7)8/h3,9H,6H2,1-2H3,(H,7,8)/t3-/m0/s1
InChIKey
VVNCNSJFMMFHPL-VKHMYHEASA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Cysteine-penicillamine disulfide DM015217
161257
Unclear - Unclear 1 [7]
Free penicillamine DM014889
5852
Unclear - Unclear 1 [7]
N-Acetyl penicillamine DM014996
27372
Conjugation - N-acetylation 1 [8]
Penicillamine disulfide DM015264
258527
Unclear - Unclear 1 [7]
S-Methyl penicillamine DM015650
10329618
Conjugation - S-methylation 1 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007721 Penicillamine Free penicillamine Unclear - Unclear Unclear [7]
MR007722 Penicillamine Penicillamine disulfide Unclear - Unclear Unclear [7]
MR007723 Penicillamine Cysteine-penicillamine disulfide Unclear - Unclear Unclear [7]
MR007724 Penicillamine S-Methyl penicillamine Conjugation - S-methylation Unclear [8]
MR007725 Penicillamine N-Acetyl penicillamine Conjugation - N-acetylation Unclear [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
human erythrocyte membrane thiol methyltransferase (HMTMT) DMEN841 Homo sapiens Not Available Not Available [2]
penicillamine ADP transferase (NAD) DMEN838 . Not Available Not Available [3]
Skin sulfhydryl oxidase (Qsox1) DMEN842 Mus musculus
QSOX1_MOUSE
1.8.3.2
[4]
Thiol S-methyltransferase TMT1B (TMT1B) DMEN227 Homo sapiens
TMT1B_HUMAN
2.1.1.9
[5]
thiol-disulfide transhydrogenase (TDTHD) DMEN840 Bacteroides fragilis Not Available Not Available [6]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7264).
2 S-Methylation of D- and L-penicillamine by human erythrocyte membrane thiol methyltransferase
3 Purification and characterization of NAD:Penicillamine ADP transferase from Bacillus sphaericus. A novel NAD-dependent enzyme catalyzing phosphoramide bond formation
4 Skin sulfhydryl oxidase. Purification and some properties
5 Human METTL7B is an alkyl thiol methyltransferase that metabolizes hydrogen sulfide and captopril
6 Reversibility of disulfide formation. Comparison of chemical and enzyme-mediated reduction of penicillamine and captopril disulfides
7 The metabolism and pharmacology of D-penicillamine in man
8 The metabolism and disposition of D-penicillamine in the DA-strain rat

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