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

General Information of Drug (ID: DR0551)
Drug Name
Drospirenone
Synonyms
Dehydrospirorenone; Dihydrospirorenone; Drospirenona; Drospirenona [INN-Spanish]; Drospirenone; Drospirenonum; Drospirenonum [INN-Latin]; ZK 30595; ZK-30595; ZK30595; 1,2-Dihydrospirorenone; 6-beta,7-beta;15-beta,16-beta-Dimethylene-3-oxo-17-alpha-pregn-4-ene-21,17-carbolactone; 67392-87-4; 6beta,7beta,15beta,16beta-dimethylene-3-oxo-17alpha-pregn-4-ene-21,17 carbolactone; BRN 4765500; C24H30O3; CCRIS 6523; CHEBI:50838; DRSP; DSSTox_CID_26465; DSSTox_RID_81639; EINECS 266-679-2; MFCD00867350; N295J34A25; UNII-N295J34A25
Indication Contraception [ICD11: JA65] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 366.5 Topological Polar Surface Area 43.4
Heavy Atom Count 27 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
68873
PubChem SID
8192410 ; 12014580 ; 14828605 ; 14828606 ; 43125386 ; 46507653 ; 47205906 ; 50047046 ; 53786814 ; 56352945 ; 57317123 ; 71824971 ; 76786916 ; 99437122 ; 103558411 ; 104343291 ; 124757204 ; 125164008 ; 126669927 ; 134338446 ; 135026678 ; 135650211 ; 135692124 ; 136096480 ; 136367961 ; 137005552 ; 141721609 ; 143493317 ; 144115924 ; 144205769 ; 152034656 ; 152233275 ; 152343982 ; 160964668 ; 162176923 ; 164757002 ; 170464870 ; 172089115 ; 174549055 ; 175267473 ; 176484977 ; 179150909 ; 184552367 ; 198991367 ; 210279219 ; 210281542 ; 223678437 ; 224322273 ; 226517963 ; 251915642
ChEBI ID
ChEBI:50838
CAS Number
67392-87-4
TTD Drug ID
D0Z4ZT
Formula
C24H30O3
Canonical SMILES
CC12CCC(=O)C=C1C3CC3C4C2CCC5(C4C6CC6C57CCC(=O)O7)C
InChI
1S/C24H30O3/c1-22-6-3-12(25)9-17(22)13-10-14(13)20-16(22)4-7-23(2)21(20)15-11-18(15)24(23)8-5-19(26)27-24/h9,13-16,18,20-21H,3-8,10-11H2,1-2H3/t13-,14+,15-,16+,18+,20-,21+,22-,23+,24+/m1/s1
InChIKey
METQSPRSQINEEU-HXCATZOESA-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
4,5-dihydro-drospirenone-3-sulfate DM006254
131770037
Multi-steps Reaction - Reduction; sulfation 1 [4]
6beta,7beta,15beta,16beta-dimethylene-3,11-dioxo-17alpha-pregn-4-ene-21,17-carbolactone DM006256 N. A. Unclear 1 [5]
6beta,7beta,15beta,16beta-dimethylene-3,12-dioxo-17alpha-pregn-4-ene-21,17-carbolactone DM006257 N. A. Unclear 1 [5]
6beta,7beta,15beta,16beta-dimethylene-3-oxo-11alpha-dihydroxy-17alpha-pregn-4-ene-21,17-carbolactone DM006259 N. A. Unclear 1 [5]
6beta,7beta,15beta,16beta-dimethylene-3-oxo-11beta,14alpha-dihydroxy-17alpha-pregn-4-ene-21,17-carbolactone DM006258 N. A. Unclear 1 [5]
6beta,7beta,15beta,16beta-dimethylene-3-oxo-14alpha-hydroxy-17alpha-pregn-4-ene-21,17-carbolactone DM006255 N. A. Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006709 Drospirenone 4,5-dihydro-drospirenone-3-sulfate Multi-steps Reaction - Reduction; sulfation Unclear [4]
MR006710 Drospirenone 6beta,7beta,15beta,16beta-dimethylene-3-oxo-14alpha-hydroxy-17alpha-pregn-4-ene-21,17-carbolactone Unclear Unclear [5]
MR006711 Drospirenone 6beta,7beta,15beta,16beta-dimethylene-3,11-dioxo-17alpha-pregn-4-ene-21,17-carbolactone Unclear Unclear [5]
MR006712 Drospirenone 6beta,7beta,15beta,16beta-dimethylene-3,12-dioxo-17alpha-pregn-4-ene-21,17-carbolactone Unclear Unclear [5]
MR006713 Drospirenone 6beta,7beta,15beta,16beta-dimethylene-3-oxo-11beta,14alpha-dihydroxy-17alpha-pregn-4-ene-21,17-carbolactone Unclear Unclear [5]
MR006714 Drospirenone 6beta,7beta,15beta,16beta-dimethylene-3-oxo-11alpha-dihydroxy-17alpha-pregn-4-ene-21,17-carbolactone Unclear Unclear [5]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [3]
⏷ Show the Full List of 9  DME(s)
References
1 Drospirenone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Role of CYP3A in oral contraceptives clearance. Clin Transl Sci. 2018 May;11(3):251-260.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Drospirenone: pharmacology and pharmacokinetics of a unique progestogen
5 Biotransformation of drospirenone, a contraceptive drug, with Cunninghamella elegans

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