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

General Information of Drug (ID: DR0556)
Drug Name
Dydrogesterone
Synonyms
Didrogesterone; Didrogesterone [DCIT]; Diphaston; Dufaston; Duphaston; Duvaron; Dydrogesterona; Dydrogesterona [INN-Spanish]; Dydrogesteronum; Dydrogesteronum [INN-Latin]; Gestatron; Gynorest; Hydrogesterone; Hydrogestrone; Isopregnenone; Prodel; Retro-6-dehydroprogesterone; Retrone; Retroprogesterone, 6-dehydro-; Terolut; delta(6)-Retroprogesterone; delta(sup 6)-Retroprogesterone; dydrogesterone; 10alpha-Isopregnenone; 152-62-5; 6-Dehydro-retro-progesterone; 9beta,10alpha-Pregna-4,6-diene-3,20-dione; UNII-90I02KLE8K
Indication Menorrhagia [ICD11: GA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 312.4 Topological Polar Surface Area 34.1
Heavy Atom Count 23 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
9051
PubChem SID
398384 ; 7848280 ; 7979141 ; 8156439 ; 11466699 ; 11467819 ; 11486418 ; 14898944 ; 15444771 ; 29227669 ; 46506195 ; 47365375 ; 47736654 ; 47736655 ; 48259427 ; 48415933 ; 49699132 ; 50019401 ; 50124160 ; 50751954 ; 53787025 ; 56394852 ; 56463092 ; 57325399 ; 71822875 ; 85788500 ; 87325136 ; 92125727 ; 103770836 ; 103914481 ; 104319423 ; 121363398 ; 124799336 ; 126653040 ; 126667084 ; 128271591 ; 134338445 ; 134973758 ; 135650214 ; 137005553 ; 139642162 ; 144203980 ; 152034951 ; 160963725 ; 162177763 ; 164178107 ; 170465104 ; 175611963 ; 179149345 ; 184546093
ChEBI ID
ChEBI:31527
CAS Number
152-62-5
TTD Drug ID
D0F1UL
Formula
C21H28O2
Canonical SMILES
CC(=O)C1CCC2C1(CCC3C2C=CC4=CC(=O)CCC34C)C
InChI
1S/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19+,20+,21+/m0/s1
InChIKey
JGMOKGBVKVMRFX-HQZYFCCVSA-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
16alpha-hydroxyprogesterone DM000557
243761
Unclear 1 [2]
20alpha-dihydroxydydrogesterone DM000556
131769931
Oxidation - Hydroxylation 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002843 Dydrogesterone 20alpha-dihydroxydydrogesterone Oxidation - Hydroxylation CYP3A4 ... [2]
MR002844 Dydrogesterone 16alpha-hydroxyprogesterone Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1C1 (AKR1C1) DME0197 Homo sapiens
AK1C1_HUMAN
1.1.1.149
[2]
Aldo-keto reductase 1C2 (AKR1C2) DME0233 Homo sapiens
AK1C2_HUMAN
1.1.1.357
[2]
Aldo-keto reductase 1C3 (AKR1C3) DME0118 Homo sapiens
AK1C3_HUMAN
1.1.1.357
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Dydrogesterone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes Xenobiotica. 2016 Oct;46(10):868-74. doi: 10.3109/00498254.2015.1134852.
3 Dydrogesterone metabolism in human liver by aldo-keto reductases and cytochrome P450 enzymes. Xenobiotica. 2016 Oct;46(10):868-74.

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