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

General Information of Drug (ID: DR0667)
Drug Name
Etonogestrel
Synonyms
Etonogestrel (USAN/INN); Implanon; Implanon (TN); ORG 3236; Org-3236; etonogestrelum; nexplanon; (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one; 13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one; 17-Ethinyl-17-beta-hydroxy-18-methyl-11-methylene-4-estren-3-one; 3-Keto-desogestrel; 3-Ketodesogestrel; 3-Oxodesogestrel; 304GTH6RNH; 54048-10-1; CHEBI:50777; ETONOGESTREL; EINECS 258-936-2; UNII-304GTH6RNH
Indication Contraception [ICD11: JA65] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 324.5 Topological Polar Surface Area 37.3
Heavy Atom Count 24 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6917715
PubChem SID
12012881 ; 14752897 ; 14777213 ; 17194516 ; 43529146 ; 46505321 ; 47206056 ; 53789691 ; 56352980 ; 57371661 ; 74860218 ; 103565890 ; 114786833 ; 126686585 ; 135004061 ; 136314851 ; 137005554 ; 140504091 ; 144206191 ; 162262948 ; 164152391 ; 164826700 ; 175268832 ; 179150591 ; 193126307 ; 198993353 ; 210279789 ; 210282112 ; 223365925 ; 223673211 ; 226489730 ; 241094452 ; 249582869 ; 252349777
ChEBI ID
ChEBI:50777
CAS Number
54048-10-1
TTD Drug ID
D02KIU
Formula
C22H28O2
Canonical SMILES
CCC12CC(=C)C3C(C1CCC2(C#C)O)CCC4=CC(=O)CCC34
InChI
1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
InChIKey
GCKFUYQCUCGESZ-BPIQYHPVSA-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
10beta-hydroxy-etonogestrel DM000944 N. A. Unclear 1 [3]
11,22-epoxy-etonogestrel DM000942 N. A. Unclear 1 [3]
14alpha-hydroxy-etonogestrel DM000941 N. A. Oxidation - Hydroxylation 1 [3]
6beta-hydroxy-11,22-epoxy-etonogestrel DM000943 N. A. Unclear 1 [3]
6beta-hydroxy-etonogestrel DM000940 N. A. Oxidation - Hydroxylation 1 [3]
Etonogestrel glucuronide DM000946 N. A. Conjugation - Glucuronidation 1 [4]
Etonogestrel sulfate DM000945 N. A. Conjugation - Sulfation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000974 Etonogestrel 6beta-hydroxy-etonogestrel Oxidation - Hydroxylation Unclear [3]
MR000975 Etonogestrel 14alpha-hydroxy-etonogestrel Oxidation - Hydroxylation Unclear [3]
MR000976 Etonogestrel 11,22-epoxy-etonogestrel Unclear Unclear [3]
MR000977 Etonogestrel 6beta-hydroxy-11,22-epoxy-etonogestrel Unclear Unclear [3]
MR000978 Etonogestrel 10beta-hydroxy-etonogestrel Unclear Unclear [3]
MR000979 Etonogestrel Etonogestrel sulfate Conjugation - Sulfation Unclear [4]
MR000980 Etonogestrel Etonogestrel glucuronide Conjugation - Glucuronidation Unclear [4]
⏷ 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Etonogestrel was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75.
3 Microbial transformation of contraceptive drug etonogestrel into new metabolites with Cunninghamella blakesleeana and Cunninghamella echinulata Steroids. 2016 Nov;115:56-61. doi: 10.1016/j.steroids.2016.08.003.
4 DrugBank(Pharmacology-Metabolism)Etonogestrel

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