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

General Information of Drug (ID: DR1590)
Drug Name
Tibolone
Synonyms
Tibolona; Tibolona [INN-Spanish]; Tibolonum; Tibolonum [INN-Latin]; Boltin; FF9X0205V2; Livial; Liviella; Org OD 14; WZDGZWOAQTVYBX-XOINTXKNSA-N; Xyvion; tibolone; (7R,8R,9S,13S,14S,17R)-17-ethynyl-17-hydroxy-7,13-dimethyl-1,2,4,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one; 17-Hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one; 17alpha-ethynyl-17beta-hydroxy-7alpha-methylestr-5(10)-en-3-one; 5630-53-5; CHEBI:32223; DSSTox_CID_3667; DSSTox_GSID_23667; DSSTox_RID_77135; UNII-FF9X0205V2
Indication Depression [ICD11: 6A71] Phase 4 [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 1
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
444008
PubChem SID
7848702 ; 7980791 ; 10299464 ; 12013759 ; 14776671 ; 14874367 ; 36887128 ; 46386825 ; 48416626 ; 49681624 ; 49833539 ; 50865117 ; 53788419 ; 57404588 ; 71821445 ; 91616275 ; 92308642 ; 92309026 ; 92717925 ; 92741022 ; 104631120 ; 119525094 ; 124659125 ; 124800021 ; 126621866 ; 126659581 ; 129655300 ; 134986859 ; 137129351 ; 137234453 ; 144205803 ; 152102616 ; 160692461 ; 162176925 ; 164234540 ; 170465874 ; 172080521 ; 176484484 ; 179150655 ; 198967371 ; 223817077 ; 226426261 ; 241108113 ; 250136780 ; 252159141 ; 252357550 ; 252457660
ChEBI ID
ChEBI:32223
CAS Number
5630-53-5
TTD Drug ID
D0W3OS
Formula
C21H28O2
Canonical SMILES
CC1CC2=C(CCC(=O)C2)C3C1C4CCC(C4(CC3)C)(C#C)O
InChI
1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,17-19,23H,5-12H2,2-3H3/t13-,17-,18+,19-,20+,21+/m1/s1
InChIKey
WZDGZWOAQTVYBX-XOINTXKNSA-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-OH-tibolone DM005792
101734273
Oxidation - Hydrolyzationn 1 [2] , [3] , [4]
3beta-OH-tibolone DM005788
101734274
Oxidation - Hydrolyzationn 1 [2] , [3] , [4]
Delta(4)-tibolone DM005790
22814761
Unclear 1 [2] , [3] , [4]
3alpha-sulfated-tibolone DM005793 N. A. Conjugation - Sulfation 2 [2] , [3] , [4]
3beta-sulfated-tibolone DM005789 N. A. Conjugation - Sulfation 2 [2] , [3] , [4]
Delta(4)-tibolone DM005790
22814761
Unclear 2 [2]
3alpha-17beta-disulfated-tibolone DM005791 N. A. Conjugation - Sulfation 3 [2] , [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006183 Tibolone 3beta-OH-tibolone Oxidation - Hydrolyzationn 3HSD [2], [3], [4]
MR006187 Tibolone 3alpha-OH-tibolone Oxidation - Hydrolyzationn 3HSD [2], [3], [4]
MR006189 Tibolone Delta(4)-tibolone Unclear Unclear [2], [3], [4]
MR006188 3alpha-OH-tibolone 3alpha-sulfated-tibolone Conjugation - Sulfation SULT1E1 ... [2], [3], [4]
MR006184 3beta-OH-tibolone 3beta-sulfated-tibolone Conjugation - Sulfation SULT1E1 ... [2], [3], [4]
MR006185 3beta-OH-tibolone Delta(4)-tibolone Unclear 3HSD-iso [2]
MR006186 3beta-sulfated-tibolone 3alpha-17beta-disulfated-tibolone Conjugation - Sulfation SULT1E1 ... [2], [3], [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
3-hydroxysteriod dehydrogenase (3HSD) DMEN311 Homo sapiens Not Available Not Available [2] , [3] , [4]
3-hydroxysteriod dehydrogenase (3HSD) DMEN290 Homo sapiens Not Available Not Available [2] , [3] , [4]
3-hydroxysteroid dehydrogenase/isomeras (3HSD-iso) DMEN289 Homo sapiens Not Available Not Available [2]
Beta-HSD adrenal and gonadal type (HSD3B2) DME0222 Homo sapiens
3BHS2_HUMAN
1.1.1.145
[5]
Dihydrotestosterone oxidoreductase (HSD3B1) DME0221 Homo sapiens
3BHS1_HUMAN
1.1.1.145
[5]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[3]
Sulfotransferase 1E1 (SULT1E1) DME0061 Homo sapiens
ST1E1_HUMAN
2.8.2.4
[2] , [3] , [4]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[2] , [3] , [4]
Sulfotransferase 2B1 (SULT2B1) DME0384 Homo sapiens
ST2B1_HUMAN
2.8.2.2
[2] , [3] , [4]
⏷ Show the Full List of 9  DME(s)
References
1 ClinicalTrials.gov (NCT01470092) Tibolone and Placebo in Adjunct to Antidepressant Medication for Women With Menopausal Depression.
2 Sulfation of tibolone and tibolone metabolites by expressed human cytosolic sulfotransferases. J Steroid Biochem Mol Biol. 2004 Apr;88(4-5):383-91.
3 Sulfation of tibolone metabolites by human postmenopausal liver and small intestinal sulfotransferases (SULTs). Steroids. 2006 May;71(5):343-51.
4 Antioxidant effect of the active metabolites of tibolone
5 Tibolone: a unique version of hormone replacement therapy. Ann Pharmacother. 2004 May;38(5):874-81.

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