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

General Information of Drug (ID: DR0946)
Drug Name
Levonorgestrel
Synonyms
Levonorgestrel; Levonorgestrelum; Levonova; Logynon ED; Microgest ED; Microgyn; Microgynon 21; Microgynon 28; Microgynon CD; Microlut; Microlution; Microval; Minivlar 30; D-Norgestrel; Follistrel; Jadelle; Levlen ED; Mirena; Monofeme 28; Monovar; NORPLANT; Neogest; Neogynon 21; Nordet; Nordette 21; Nordette 28; Norplant 2; Norplant II; Ovral-Lo; Ovranette; Ovrette; Plan B; Postinor; Stediril 30; Triagynon; Triciclor; Trigoa; Trinordiol 21; Trinordiol 28; Trivora; d(-)-Norgestrel; norgestrel; (-)-Norgestrel; 18-Methylnorethisterone; 797-63-7
Indication Menorrhagia [ICD11: GA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 312.4 Topological Polar Surface Area 37.3
Heavy Atom Count 23 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
13109
ChEBI ID
CHEBI:6443
CAS Number
797-63-7
TTD Drug ID
D0G6CT
Formula
C21H28O2
Canonical SMILES
CCC12CCC3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
InChI
1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChIKey
WWYNJERNGUHSAO-XUDSTZEESA-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
16beta-hydroxylevonorgestrel DM000308 N. A. Unclear 1 [6]
3alpha, 5beta-tetrahydrolevonorgestrel DM000306
71752466
Unclear 1 [6]
Glucuronide conjugates of levonorgestrel DM000310 N. A. Conjugation - Glucuronidation 1 [6]
Sulfate conjugates of levonorgestrel DM000311 N. A. Conjugation - Sulfation 1 [6]
Unclear DM009999 N. A. Unclear 1 [7]
16beta-hydroxylevonorgestrel glucuronide DM000309 N. A. Conjugation - Glucuronidation 2 [6]
3alpha, 5beta-tetrahydrolevonorgestrel sulfate DM000307 N. A. Conjugation - Sulfation 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001510 Levonorgestrel 3alpha, 5beta-tetrahydrolevonorgestrel Unclear Unclear [6]
MR001511 Levonorgestrel 16beta-hydroxylevonorgestrel Unclear Unclear [6]
MR001512 Levonorgestrel Glucuronide conjugates of levonorgestrel Conjugation - Glucuronidation Unclear [6]
MR001513 Levonorgestrel Sulfate conjugates of levonorgestrel Conjugation - Sulfation Unclear [6]
MR001514 Levonorgestrel . Unclear CYP3A4 [7]
MR001509 16beta-hydroxylevonorgestrel 16beta-hydroxylevonorgestrel glucuronide Conjugation - Glucuronidation Unclear [6]
MR001508 3alpha, 5beta-tetrahydrolevonorgestrel 3alpha, 5beta-tetrahydrolevonorgestrel sulfate Conjugation - Sulfation Unclear [6]
⏷ 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
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
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 [5]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1378 Bacteroides uniformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1447 Parabacteroides merdae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [5]
⏷ Show the Full List of 21  DME(s)
References
1 Levonorgestrel was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In?vitro assessment of the potential for dolutegravir to affect hepatic clearance of levonorgestrel
3 Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study. Biomedica. 2012 Oct-Dec;32(4):570-7.
4 [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study] Biomedica. 2012 Oct-Dec;32(4):570-7. doi: 10.1590/S0120-41572012000400012.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 DrugBank(Pharmacology-Metabolism)Levonorgestrel
7 [Influence of CYP3A4/5 polymorphisms in the pharmacokinetics of levonorgestrel: a pilot study]. Biomedica. 2012 Oct-Dec;32(4):570-7.

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