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

General Information of Drug (ID: DR5092)
Drug Name
Spironolactone
Synonyms
Abbolactone; Acelat; Aldace; Aldactazide; Aldactide; Aldactone; Alderon; Aldopur; Almatol; Altex; Aquareduct; Deverol; Diatensec; Dira; Duraspiron; Espironolactona; Euteberol; Flumach; Frumikal; Jenaspiron; Lacalmin; Lacdene; Laractone; Melarcon; Nefurofan; NovoSpiroton; Osyrol; Practon; SNL; Sagisal; Sincomen; Spiractin; Spiresis; Spiretic; Spiridon; Spirobeta; Spiroctan; Spiroctanie; Spiroderm; Spirogamma; Spirolactone; Spirolakton; Spirolang; Spirolone; Spirone; Spironocompren; Spironolactonum; Spironolattone; Spironone; Spirospare; Sprioderm; Suracton; Uractone; Urusonin; Veroshpiron; Verospiron; Verospirone; Xenalon; Aldactone A; Alphapharm Brand of Spironolactone; Alpharma Brand of Spironolactone; Alter Brand of Spironolactone; Ashbourne Brand of Spironolactone; Azupharma Brand of Spironolactone; Betapharm Brand of Spironolactone; Cardel Brand of Spironolactone; Ct Arzneimittel Brand of Spironolactone; Dexo Brand of Spironolactone; Espironolactona Alter; Espironolactona Mundogen; Generosan Brand of Spironolactone; Hormosan Brand of Spironolactone; Jenapharm Brand of Spironolactone; Merck dura Brand of Spironolactone; Mundogen Brand of Spironolactone; Novo Spiroton; Novopharm Brand of Spironolactone; Pfizer Brand of Spironolactone; Pharmafrid Brand of Spironolactone; Roche Brand of Spironolactone; Searle Brand of Spironolactone; Spiro von ct; Spirono Isis; Spironolactone A; Spironolattone [DCIT]; Verospirone Opianin; Worwag Brand of Spironolactone; LT00772287; SC 9420; SC9420; Aldactazide (TN); Aldactone (TN); Berlactone (TN); Ct-Arzneimittel Brand of Spironolactone; Espironolactona [INN-Spanish]; Mayoly-Spindler Brand of Spironolactone; Novo-Spiroton; SC-9420; Spiractin (TN); Spiro-Tablinen; Spirono-Isis; Spironolactonum [INN-Latin]; Spirotone (TN); Supra-puren; Verospiron (TN); Von ct, spiro; Novo-Spiroton (TN); Spironolactone [BAN:INN:JAN]; Spironolactone [INN:BAN:JAN]; Spiro L.U.T.; Spironolactone (JP15/USP/INN); Spiro[17H-cyclopenta[a]phenauthrene-17,2'-(3'H)-furan]; Spiro(17H-cyclopenta(a)phenauthrene-17,2'-(3'H)-furan); 4-Pregnen-21-oic acid-17alpha-ol-3-one-7alpha-thiol gamma-lactone 7-acetate; 7-alpha-Acetylthio-3-oxo-17-alpha-pregn-4-ene-21,17-beta-carbolactone; 7alpha-(acetylsulfanyl)-3-oxo-17alpha-pregn-4-ene-21,17-carbolactone
Indication Congestive heart failure [ICD11: BD10-BD1Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 416.6 Topological Polar Surface Area 85.7
Heavy Atom Count 29 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5833
ChEBI ID
CHEBI:9241
CAS Number
52-01-7
TTD Drug ID
D0EP0C
Formula
C24H32O4S
Canonical SMILES
CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
InChI
InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1
InChIKey
LXMSZDCAJNLERA-ZHYRCANASA-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
7alpha-thiospironolactone DM015132
119472
Oxidation - Deacetylation 1 [5] , [3]
7alpha-thiomethylSpirolactone DM016881 N. A. Hydrolysis - Hydrolysis 2 [6]
7alpha-thiomethylspironolactone DM015224
162325
Conjugation - S-methylation 2 [7]
Canrenone DM014959
13789
Other reaction - Elimination 2 [6]
15alpha-OH-canrenone DM016890 N. A. Unclear - Unclear 3 [6]
3alpha-hydroxythiomethylspironolactone DM016889 N. A. Reduction - Reduction 3 [7]
3beta-hydroxythiomethylspironolactone DM016888 N. A. Reduction - Reduction 3 [7]
6bate-OH-7alpha-thiomethylSpirolactone DM016882 N. A. Oxidation - Hydroxylation 3 [6]
7alpha-methylsulfinylSpirolactone DM016886 N. A. Conjugation - S-methylation 3 [6]
Canrenoate DM015336
656615
Unclear - Unclear 3 [6]
6bate-OH-7alpha-methylsulfinylSpironolactone DM016883 N. A. Oxidation - Hydroxylation 4 [6]
6bate-OH-7alpha-methylsulfinylSpironolactone DM016883 N. A. Conjugation - S-methylation 4 [6]
7alpha-methylsulfonylSpirolactone DM016887 N. A. Oxidation - S-oxidation 4 [6]
6bate-OH-7alpha-methylsulfonylSpirolactone DM016884 N. A. Oxidation - S-oxidation 5 [6]
Spironolactone metabolite XIV DM016885 N. A. Unclear - Unclear 6 [8]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007684 Spironolactone 7alpha-thiospironolactone Oxidation - Deacetylation Unclear [5], [3]
MR007685 7alpha-thiospironolactone 7alpha-thiomethylSpirolactone Hydrolysis - Hydrolysis Unclear [6]
MR007696 7alpha-thiospironolactone Canrenone Other reaction - Elimination Unclear [6]
MR007686 7alpha-thiomethylSpirolactone 6bate-OH-7alpha-thiomethylSpirolactone Oxidation - Hydroxylation Unclear [6]
MR007690 7alpha-thiomethylSpirolactone 7alpha-methylsulfinylSpirolactone Conjugation - S-methylation Unclear [6]
MR007694 7alpha-thiomethylspironolactone 3beta-hydroxythiomethylspironolactone Reduction - Reduction Unclear [7]
MR007695 7alpha-thiomethylspironolactone 3alpha-hydroxythiomethylspironolactone Reduction - Reduction Unclear [7]
MR007697 Canrenone Canrenoate Unclear - Unclear Unclear [6]
MR007698 Canrenone 15alpha-OH-canrenone Unclear - Unclear Unclear [6]
MR007687 6bate-OH-7alpha-thiomethylSpirolactone 6bate-OH-7alpha-methylsulfinylSpironolactone Conjugation - S-methylation Unclear [6]
MR007691 7alpha-methylsulfinylSpirolactone 6bate-OH-7alpha-methylsulfinylSpironolactone Oxidation - Hydroxylation Unclear [6]
MR007692 7alpha-methylsulfinylSpirolactone 7alpha-methylsulfonylSpirolactone Oxidation - S-oxidation Unclear [6]
MR007693 7alpha-methylsulfonylSpirolactone 7alpha-thiomethylspironolactone Conjugation - S-methylation Unclear [7]
MR007688 6bate-OH-7alpha-methylsulfinylSpironolactone 6bate-OH-7alpha-methylsulfonylSpirolactone Oxidation - S-oxidation Unclear [6]
MR007689 6bate-OH-7alpha-methylsulfonylSpirolactone Spironolactone metabolite XIV Unclear - Unclear Unclear [8]
⏷ Show the Full List of 15 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldosterone synthase (CYP11B2) DME0036 Homo sapiens
C11B2_HUMAN
1.14.15.4
[2]
Keto-steroid reductase (HSD17B7) DME0424 Homo sapiens
DHB7_HUMAN
1.1.1.270
[3]
Steroid 11-beta-hydroxylase (CYP11B1) DME0027 Homo sapiens
C11B1_HUMAN
1.14.15.4
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[4]
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: 2875).
2 Biotransformation of the mineralocorticoid receptor antagonists spironolactone and canrenone by human CYP11B1 and CYP11B2: Characterization of the products and their influence on mineralocorticoid receptor transactivation
3 Hepatic metabolism of spironolactone. Production of 3-hydroxy-thiomethyl metabolites
4 Spironolactone and canrenone inhibit UGT2B7-catalyzed human liver and kidney microsomal aldosterone 18beta-glucuronidation: a potential drug interaction
5 Conversion of spironolactone to 7 alpha-thiomethylspironolactone by hepatic and renal microsomes
6 The metabolism and biopharmaceutics of spironolactone in man
7 DrugBank(Pharmacology-Metabolism):Spironolactone
8 Spironolactone: disposition, metabolism, pharmacodynamics, and bioavailability

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