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Drug-Target Interaction

Drug

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PubChem ID:40973
Structure:
Synonyms:
(17alpha)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,1
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol
13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol
13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol
17alpha-ethynyl-11-methylidene-18a-homo-estr-4-en-17beta-ol
18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17-alpha)-
18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)-
54024-22-5
AC-308
AC1L24T4
AC1Q282A
alpha-pregn-4-en-20-yn-17-ol, 13-Ethyl-11-methylene-18,19-dinor-17
C07629
C22H30O
Cerazette
CHEBI:4453
CHEMBL1533
CYCLESSA
D017135
D02367
DB00304
Desogen
Desogestrel
Desogestrel (USAN/INN)
DESOGESTREL AND ETHINYL ESTRADIOL
Desogestrel [USAN:BAN:INN]
Desogestrelum
Desogestrelum [INN-Latin]
EINECS 258-929-4
HSDB 3593
KARIVA
LMST02030104
LS-62079
Marvelon
MIRCETTE
Mixture Name
NCGC00167449-01
ORG 2969
Org-2969
Org2969
Organon Brand of Desogestrel
ORTHO-CEPT
UNII-81K9V7M3A3
ZINC04097416
ATC-Codes:

Target

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Uniprot ID:CP2CJ_HUMAN
Synonyms:
(R)-limonene 6-monooxygenase
(S)-limonene 6-monooxygenase
(S)-limonene 7-monooxygenase
CYPIIC17
CYPIIC19
Cytochrome P450 2C19
Mephenytoin 4-hydroxylase
P450-11A
P450-254C
EC-Numbers:1.14.13.48
1.14.13.49
1.14.13.80
Organism:Homo sapiens
Human
PDB IDs:-

Binding Affinities:

Ki: Kd:Ic 50:Ec50/Ic50:
----

References:

9864282
The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel.. D M Gentile; C H Verhoeven; T Shimada; D J Back (1998) The Journal of pharmacology and experimental therapeutics display abstract
Desogestrel is a 3-deoxo progestogenic steroid that requires bioactivation to 3-ketodesogestrel. In these studies we have attempted to define the pathway of 3-ketodesogestrel formation and characterise the enzymes responsible for this biotransformation in vitro. Initial studies using deuterated desogestrel confirmed that desogestrel is metabolised by human liver microsomes via 3alpha-hydroxy and 3beta-hydroxydesogestrel to 3-ketodesogestrel. Metabolites were analysed by radiometric high-performance liquid chromatography and were identified by liquid chromatography-mass spectrometry and by cochromatography with authentic standards. Desogestrel was metabolised by microsomes from lymphoblasts containing cDNA-expressed CYP2C9 and CYP2C19 to 3alpha-hydroxydesogestrel with small amounts of 3beta-hydroxydesogestrel also being observed. The Km value for 3alpha-hydroxylation by CYP2C9 cell line microsomes was 6.5 microM and the corresponding Vmax value was 1269 pmole. mg-1. min-1. Sulfaphenazole potently inhibited 3alpha-hydroxydesogestrel formation by CYP2C9 microsomes with a Ki value of 0.91 microM. There was a significant negative correlation between 3-ketodesogestrel and CYP3A4 content/activity in a panel of human livers suggesting that the further metabolism of 3-ketodesogestrel is mediated by CYP3A4. Sulfaphenazole partially inhibited 3alpha-hydroxydesogestrel and 3-ketodesogestrel formation in human liver microsomes indicating a possible in vivo role for CYP2C9. In addition, when sulfaphenazole was combined with S-mephenytoin, further inhibition of 3alpha-hydroxydesogestrel formation was observed suggesting a possible role for CYP2C19. This was confirmed in incubations with inhibitory antibodies. Whereas an anti-CYP2C9/2C19 antibody completely abolished desogestrel metabolism, anti-CYP3A4 and anti-CYP2E1 were not inhibitory. We conclude that CYP2C9 and possibly CYP2C19 and important isoforms catalysing the initial hydroxylation of desogestrel.