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

General Information of Drug (ID: DR1178)
Drug Name
Norgestimate
Synonyms
Norgestimato; Norgestimato [INN-Spanish]; Norgestimatum; Norgestimatum [INN-Latin]; ORF 10131; ORF-10131; Ortho-Prefest; RWJ 10131; Dexnorgestrel acetime; NORGESTIMATE; norgestrel oxime acetate; (+)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one oxime acetate (ester); (17-alpha)-17-(Acetyloxy)-13-ethyl-18,19-dinorpregn-4-en-20-yn-3-one 3-oxime; 35189-28-7; C291HFX4DY; CHEBI:50815; D 138; DSSTox_RID_82018; NCGC00181353-01; UNII-C291HFX4DY; d-13-beta-Ethyl-17-alpha-ethynyl-17-beta-acetoxygon-4-en-3-one oxime
Indication Acne vulgaris [ICD11: ED80] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 369.5 Topological Polar Surface Area 58.9
Heavy Atom Count 27 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
6540478
PubChem SID
12013307 ; 14828760 ; 14877333 ; 23948292 ; 43185588 ; 46507381 ; 47206928 ; 49963131 ; 50125945 ; 50406385 ; 53787279 ; 56352967 ; 57370933 ; 92712530 ; 99375924 ; 103770917 ; 114617529 ; 126630090 ; 126656639 ; 126670754 ; 131311636 ; 134338450 ; 135000359 ; 135046943 ; 137002813 ; 141484503 ; 144206364 ; 152056974 ; 160964296 ; 162174921 ; 170464733 ; 175267643 ; 176250054 ; 179150362 ; 196110215 ; 223396532 ; 223556630 ; 223668437 ; 226423899 ; 226423900 ; 241064393 ; 249822572 ; 252062710 ; 252355235
ChEBI ID
ChEBI:50815
CAS Number
35189-28-7
TTD Drug ID
D09QZI
Formula
C23H31NO3
Canonical SMILES
CCC12CCC3C(C1CCC2(C#C)OC(=O)C)CCC4=CC(=NO)CCC34
InChI
1S/C23H31NO3/c1-4-22-12-10-19-18-9-7-17(24-26)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)27-15(3)25/h2,14,18-21,26H,4,6-13H2,1,3H3/b24-17+/t18-,19+,20+,21-,22-,23-/m0/s1
InChIKey
KIQQMECNKUGGKA-NMYWJIRASA-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
17-desacetylnorgestimate DM002268
9568628
Oxidation - Deacetylation 1 [4] , [2]
Norgestrel DM002269
13109
Unclear 2 [5]
Norgestrel glucuronide metabolite DM002270 N. A. Conjugation - O-Glucuronidation 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001793 Norgestimate 17-desacetylnorgestimate Oxidation - Deacetylation CYP3A4 [4], [2]
MR001791 17-desacetylnorgestimate Norgestrel Unclear Unclear [5]
MR001792 Norgestrel Norgestrel glucuronide metabolite Conjugation - O-Glucuronidation UGT1A1 [5]
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) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
⏷ Show the Full List of 9  DME(s)
References
1 Norgestimate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Metabolite identification, reaction phenotyping, and retrospective drug-drug interaction predictions of 17-deacetylnorgestimate, the active component of the oral contraceptive norgestimate. Drug Metab Dispos. 2017 Jun;45(6):676-685.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Metabolism of norgestimate by human gastrointestinal mucosa and liver microsomes in vitro J Steroid Biochem Mol Biol. 1991 Apr;38(4):497-503. doi: 10.1016/0960-0760(91)90338-6.
5 DrugBank(Pharmacology-Metabolism)Norgestimate

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