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

General Information of Drug (ID: DR1750)
Drug Name
Norethindrone acetate
Synonyms
Noresthisterone; Norethadrone; Norethisteron; Norethisterone; Norethisteronum; Norethyndron; Norethynodron; Norethynodrone; Noretisterona; Norfor; Norgestin; Noriday; Norluten; Norlutin; Norluton; Norpregneninlone; Norpregneninolone; Primolut-N; Proluteasi; Synphase; Triella; Utovlan; Utovlar; norethindrone; 19-Nor-ethindrone; 19-Norethisterone; 68-22-4; Anovulatorio; Anovule; Camila; Ciclovulan; Conludaf; Conludag; Ethinylnortestosterone; Gestest; Microneth; Micronett; Micronor; Micronovum; Mini-Pe; Mini-pill; Minovlar; Nor-QD; Noralutin; Norcolut; 1-(Ethylsulfonyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-3-azetidineacetonitrile
Indication Menorrhagia [ICD11: GA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 340.5 Topological Polar Surface Area 43.4
Heavy Atom Count 25 Rotatable Bond Count 3
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
5832
ChEBI ID
CHEBI:7628
CAS Number
51-98-9
Formula
C22H28O3
Canonical SMILES
CC(=O)OC1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)C#C
InChI
1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,13,17-20H,5-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
InChIKey
IMONTRJLAWHYGT-ZCPXKWAGSA-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
5alpha-dihydronorethisterone DM002259
63023
Reduction - Reduction 1 [7] , [3]
5beta-dihydronorethisteronee DM002262
14260703
Unclear 1 [3]
Norethindrone acetate metabolite M1,M2 DM002265 N. A. Oxidation - Hydroxylation 1 [4]
Norethindrone acetate metabolite M4 DM002267 N. A. Oxidation - Dehydrogenation 1 [4]
3alpha,5alpha-tetrahydronorethisterone DM002261
14260695
Reduction - Reduction 2 [7]
3alpha,5beta-tetrahydronorethisterone DM002264
14260696
Reduction - Reduction 2 [3]
3beta,5alpha-tetrahydronorethisterone DM002260
10402682
Reduction - Reduction 2 [7]
3beta,5beta-tetrahydronorethisterone DM002263
14260697
Reduction - Reduction 2 [3]
Norethindrone acetate metabolite M3 DM002266 N. A. Oxidation - Dihydroxylation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001781 Norethindrone acetate 5alpha-dihydronorethisterone Reduction - Reduction Unclear [7], [3]
MR001782 Norethindrone acetate 5beta-dihydronorethisteronee Unclear AKR1D1 [3]
MR001783 Norethindrone acetate Norethindrone acetate metabolite M1,M2 Oxidation - Hydroxylation CYP3A4 ... [4]
MR001784 Norethindrone acetate Norethindrone acetate metabolite M4 Oxidation - Dehydrogenation CYP3A4 [4]
MR001776 5alpha-dihydronorethisterone 3beta,5alpha-tetrahydronorethisterone Reduction - Reduction HSD3B2 [7]
MR001777 5alpha-dihydronorethisterone 3alpha,5alpha-tetrahydronorethisterone Reduction - Reduction AKR1C4 [7]
MR001778 5beta-dihydronorethisteronee 3beta,5beta-tetrahydronorethisterone Reduction - Reduction HSD3B2 [3]
MR001779 5beta-dihydronorethisteronee 3alpha,5beta-tetrahydronorethisterone Reduction - Reduction AKR1C4 [3]
MR001780 Norethindrone acetate metabolite M1,M2 Norethindrone acetate metabolite M3 Oxidation - Dihydroxylation CYP3A4 [4]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1C4 (AKR1C4) DME0198 Homo sapiens
AK1C4_HUMAN
1.1.1.357
[2]
Aldo-keto reductase 1D1 (AKR1D1) DME0400 Homo sapiens
AK1D1_HUMAN
1.3.1.3
[3]
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Homo sapiens
3BHS2_HUMAN
1.1.1.145
[3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1357 Alistipes indistinctus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1367 Bacteroides finegoldii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1460 Ruminococcus torques Not Available Not Available [6]
⏷ Show the Full List of 36  DME(s)
References
1 Norethindrone Acetate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Drug Interactions Flockhart Table
3 Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22.
4 Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66.
5 The interaction between St John's wort and an oral contraceptive. Clin Pharmacol Ther. 2003 Dec;74(6):525-35.
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Tibolone and its delta-4, 7alpha-methyl norethisterone metabolite are reversible inhibitors of human aromatase J Steroid Biochem Mol Biol. 2007 May;104(3-5):154-60. doi: 10.1016/j.jsbmb.2007.03.027.

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