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

General Information of Drug (ID: DR0269)
Drug Name
Captopril
Synonyms
Capoten; Captolane; Captoprilum; Captoprilum [INN-Latin]; Captopryl; Captoril; Cesplon; Alopresin; Apopril; Asisten; Dilabar; Garranil; Hipertil; Hypertil; Isopresol; L-Captopril; Lopirin; Lopirin [Switzerland]; Lopril; SA 333; SQ 14,225; SQ 14225; SQ-14225; Tenosbon; Tensobon; Tensoprel; captopril; (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid; 62571-86-2; Acediur; Aceplus; Acepress; Acepril; D-2-Methyl-3-mercaptopropanoyl-L-proline; D-3-Mercapto-2-methylpropanoyl-L-proline; D-3-Mercapto-2-methylpropionylproline
Indication Essential hypertension [ICD11: BA00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 217.29 Topological Polar Surface Area 58.6
Heavy Atom Count 14 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
44093
PubChem SID
823180 ; 855925 ; 3154070 ; 7847317 ; 7978852 ; 8149632 ; 8178487 ; 10321204 ; 11110941 ; 11335383 ; 11360622 ; 11363582 ; 11366144 ; 11368706 ; 11372295 ; 11374460 ; 11376868 ; 11461594 ; 11484758 ; 11489027 ; 11491203 ; 11492626 ; 11494502 ; 11533495 ; 12013747 ; 14797867 ; 15195876 ; 17404865 ; 22391411 ; 24278149 ; 24893111 ; 26612024 ; 26679590 ; 26747043 ; 26747044 ; 26751563 ; 26758381 ; 34709396 ; 46392259 ; 46487953 ; 46506879 ; 47365058 ; 47440133 ; 47515193 ; 47515194 ; 47515195 ; 47736347 ; 47736348 ; 47959603 ; 49698307
ChEBI ID
ChEBI:3380
CAS Number
62571-86-2
TTD Drug ID
D0I0EG
Formula
C9H15NO3S
Canonical SMILES
CC(CS)C(=O)N1CCCC1C(=O)O
InChI
1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
InChIKey
FAKRSMQSSFJEIM-RQJHMYQMSA-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
Captopril s-methyl DM000712
21121673
Unclear 1 [5]
Captopril-cysteine disulfide DM000715
44146831
Unclear 1 [5]
Captopril-disulfide DM000717
10002934
Unclear 1 [5]
Captopril-glutathione DM000714 N. A. Conjugation - Glutathione Conjugation 1 [5]
Captopril-plasma prote DM000716 N. A. Unclear 1 [5]
Captopril s-methyl sulfoxide DM000713 N. A. Unclear 2 [5]
Captopril-cysteine disulfide DM000715
44146831
Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000557 Captopril Captopril s-methyl Unclear Unclear [5]
MR000558 Captopril Captopril-glutathione Conjugation - Glutathione Conjugation Unclear [5]
MR000559 Captopril Captopril-cysteine disulfide Unclear Unclear [5]
MR000560 Captopril Captopril-plasma prote Unclear Unclear [5]
MR000561 Captopril Captopril-disulfide Unclear Unclear [5]
MR000555 Captopril s-methyl Captopril s-methyl sulfoxide Unclear Unclear [5]
MR000556 Captopril-glutathione Captopril-cysteine disulfide Unclear Unclear [5]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
#NAME? DMEN252 Homo sapiens Not Available Not Available [2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A (CYP3A) DMEN065 . Not Available Not Available [2]
Thiopurine methyltransferase (TPMT) DME0014 Homo sapiens
TPMT_HUMAN
2.1.1.67
[4]
References
1 Captopril was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Absorption, metabolism and excretion of [(14)C]-sotorasib in healthy male subjects: characterization of metabolites and a minor albumin-sotorasib conjugate
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 S-methylation of captopril. Demonstration of captopril thiol methyltransferase activity in human erythrocytes and enzyme distribution in rat tissues. Biochem Pharmacol. 1983 May 15;32(10):1557-62.
5 Captopril: pharmacology, metabolism and disposition Drug Metab Rev. 1984;15(4):841-69. doi: 10.3109/03602538409041080.

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