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

General Information of Drug (ID: DR5150)
Drug Name
Norethindrone
Synonyms
Activella; Anhydrohydroxynorprogesterone; Anovulatorio; Anovule; Brevicon; Brevinor; Camila; Ciclovulan; Conceplan;Conludaf; Conludag; Demulen; Errin; Estrinor; Ethinylnortestosterone; Ethynylmortestosterone; Ethynylnortestosterone; Gencept; Genora; Gestest; Jenest; Loestrin; Menzol; Microneth; Micronett; Micronor; Micronovum; Milli; Minovlar; Nelova; Nodiol; Noraethisteronum; Noralutin; Norcept; Norcolut; Norcolute; Noresthisterone; Norethadrone; Norethin; Norethindirone; Norethisteron; Norethisterone; Norethisteronum; Norethyndron; Norethynodron; Norethynodrone; Noretisterona; Noretisterone; Norfor; Norgestin; Noriday; Norluten; Norlutin; Norluton; Normapause; Norpregneninlone; Norpregneninolone; Norpregneninotone; Orlest; Proluteasi; Synphase; Triella; Utovlan; Utovlar; Component of Noriday; Norethindrone Norethisterone; Norethindrone [USAN]; Norethisterone [Progestins]; Noretisterone [DCIT]; Primolut N; Brevinor 21; Brevinor 28; Noriday 28; Ortho 1 35; Ortho 7 7 7; Ovysmen 1 35; SC 4640; Synphasic 28; Trinovum 21; Brevinor-1 21; Brevinor-1 28; Camila (TN); Jenest-28; Micronor (TN); Mini-Pe; Mini-pill; Nor-QD; Nora-BE; Norcept-E; Norethin 1/35 E; Norethin 1/50 M; Norethindrone (USP); Norethisterone (JP15); Norethisteronum [INN-Latin]; Noretisterona [INN-Spanish]; Ortho-Novum 1 35; Ortho-Novum 1 50; Ortho-Novum 7 7 7; Ovysmen 0.5 35; Primolut-N; Tri-Norinyl; Ethinyl-19-nortestosterone; Nor-Q.D; Primolut-N (TN); Nor-Q.D.; 17-Ethinyl-19-nortestosterone; 17-Ethynyl-17-hydroxyestr-4-en-3-one; 17-alpha-Ethynyl-19-nortestosterone; 17-alpha-Ethynyl-4-estren-17-ol-3-one; 17-ethynyl-17beta-hydroxyestr-4-en-3-one; 17.alpha.-Ethinyl-19-nortestosterone; 17.alpha.-Ethynyl-19-nortestosterone; 17.alpha.-Ethynyl-4-estren-17-ol-3-one; 17alpha-Ethinyl-19-nortestosterone; 17alpha-Ethynyl-19-nortestosterone; 17alpha-Ethynyl-4-estren-17-ol-3-one; 19-Nor-17-alpha-ethynyltestosterone; 19-Nor-17-ethinyltestosterone; 19-Nor-17.alpha.-ethynyltestosterone; 19-Nor-17alpa-ethynyltestosterone; 19-Nor-17alpha-ethynyltestosterone; 19-Nor-ethindrone; 19-Nor-ethinyl-4,5-testosterone; 19-Norethindrone; 19-Norethinyltestosterone; 19-Norethisterone; 4-Estren-17alpha-ethynyl-17beta-ol-3-one
Indication Solid tumour/cancer [ICD11: 2A00-2F9Z] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 298.4 Topological Polar Surface Area 37.3
Heavy Atom Count 22 Rotatable Bond Count 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6230
ChEBI ID
CHEBI:7627
CAS Number
68-22-4
TTD Drug ID
D0GL7U
Formula
C20H26O2
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
InChI
InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
InChIKey
VIKNJXKGJWUCNN-XGXHKTLJSA-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
3alpha-NET DM018639 N. A. Unclear - Unclear 1 [3]
3beta-NET DM018646 N. A. Unclear - Unclear 1 [3]
5alpha-NET DM018642 N. A. Unclear - Unclear 1 [3]
5beta-NET DM018644 N. A. Unclear - Unclear 1 [3]
3alpha,5alpha-NET DM018640 N. A. Unclear - Unclear 2 [3]
3alpha,5beta-NET DM018641 N. A. Unclear - Unclear 2 [3]
3beta,5alpha-NET DM018643 N. A. Unclear - Unclear 2 [3]
3beta,5beta-NET DM018645 N. A. Unclear - Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010809 Norethindrone 3alpha-NET Unclear - Unclear Unclear [3]
MR010812 Norethindrone 5alpha-NET Unclear - Unclear Unclear [3]
MR010815 Norethindrone 5beta-NET Unclear - Unclear Unclear [3]
MR010818 Norethindrone 3beta-NET Unclear - Unclear Unclear [3]
MR010810 3alpha-NET 3alpha,5alpha-NET Unclear - Unclear Unclear [3]
MR010811 3alpha-NET 3alpha,5beta-NET Unclear - Unclear Unclear [3]
MR010819 3beta-NET 3beta,5alpha-NET Unclear - Unclear Unclear [3]
MR010820 3beta-NET 3beta,5beta-NET Unclear - Unclear Unclear [3]
MR010813 5alpha-NET 3alpha,5alpha-NET Unclear - Unclear HSD3A [3]
MR010814 5alpha-NET 3beta,5alpha-NET Unclear - Unclear HSD3A [3]
MR010816 5beta-NET 3alpha,5beta-NET Unclear - Unclear Unclear [3]
MR010817 5beta-NET 3beta,5beta-NET Unclear - Unclear Unclear [3]
⏷ Show the Full List of 12 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
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
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 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.
3 Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22.

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