Details of the Drug

General Information of Drug (ID: DM78XFG)

Drug Name
Tibolone
Synonyms Livial (TN)
Indication
Disease Entry ICD 11 Status REF
Anabolic metabolism 5C50-5C8Z Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 312.4
Logarithm of the Partition Coefficient (xlogp) 2.4
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination
0% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 45 hours [3]
Metabolism
The drug is metabolized via the liver [3]
Chemical Identifiers
Formula
C21H28O2
IUPAC Name
(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
Canonical SMILES
C[C@@H]1CC2=C(CCC(=O)C2)[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C#C)O
InChI
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
Cross-matching ID
PubChem CID
444008
ChEBI ID
CHEBI:32223
CAS Number
5630-53-5
DrugBank ID
DB09070
TTD ID
D0W3OS
INTEDE ID
DR1590

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-HSD adrenal and gonadal type (HSD3B2) DEN0GVQ 3BHS2_HUMAN Substrate [4]
Sulfotransferase 1A1 (SULT1A1) DEYWLRK ST1A1_HUMAN Substrate [5]
Dihydrotestosterone oxidoreductase (HSD3B1) DERDQWN 3BHS1_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-reactive protein (CRP) OT0RFT8F CRP_HUMAN Gene/Protein Processing [6]
C-type lectin domain family 4 member E (CLEC4E) OT7P8ICY CLC4E_HUMAN Gene/Protein Processing [7]
E-selectin (SELE) OT33RZWY LYAM2_HUMAN Gene/Protein Processing [6]
Estrogen receptor (ESR1) OTKLU61J ESR1_HUMAN Gene/Protein Processing [8]
Estrogen receptor beta (ESR2) OTXNR2WQ ESR2_HUMAN Gene/Protein Processing [8]
Intercellular adhesion molecule 1 (ICAM1) OTTOIX77 ICAM1_HUMAN Gene/Protein Processing [6]
Interleukin-13 receptor subunit alpha-1 (IL13RA1) OT59OYXP I13R1_HUMAN Gene/Protein Processing [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [9]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [9]
Peptidyl-prolyl cis-trans isomerase FKBP5 (FKBP5) OT404F9K FKBP5_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS applied to over 900 drugs
3 Tibolone for Postmenopausal Women: Systematic Review of Randomized Trials
4 Tibolone: a unique version of hormone replacement therapy. Ann Pharmacother. 2004 May;38(5):874-81.
5 Sulfation of tibolone metabolites by human postmenopausal liver and small intestinal sulfotransferases (SULTs). Steroids. 2006 May;71(5):343-51.
6 Effects of hormone treatment on hemostasis variables. Climacteric. 2007 Oct;10 Suppl 2:32-7. doi: 10.1080/13697130701598548.
7 A microarray study on the effect of four hormone therapy regimens on gene transcription in whole blood from healthy postmenopausal women. Thromb Res. 2012 Jul;130(1):45-51. doi: 10.1016/j.thromres.2011.12.009. Epub 2012 Jan 2.
8 Estrogenic effects of natural and synthetic compounds including tibolone assessed in Saccharomyces cerevisiae expressing the human estrogen alpha and beta receptors. FASEB J. 2006 Jul;20(9):1552-4. doi: 10.1096/fj.05-5413fje. Epub 2006 May 23.
9 Tibolone and its metabolites induce antimitogenesis in human coronary artery smooth muscle cells: role of estrogen, progesterone, and androgen receptors. J Clin Endocrinol Metab. 2004 Feb;89(2):852-9. doi: 10.1210/jc.2003-031272.