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]

ATC Code

G03CX01: Tibolone

G03CX: Other estrogens

G03C: ESTROGENS

G03: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM

G: GENITO URINARY SYSTEM AND SEX HORMONES

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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEMBL2103774
CAS Number: 5630-53-5
UNII: FF9X0205V2
DrugBank ID: DB09070
TTD ID: D0W3OS
INTEDE ID: DR1590

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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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]
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	[8]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[8]
Peptidyl-prolyl cis-trans isomerase FKBP5 (FKBP5)	OT404F9K	FKBP5_HUMAN	Gene/Protein Processing	[7]
Plasminogen activator inhibitor 1 (SERPINE1)	OTT0MPQ3	PAI1_HUMAN	Gene/Protein Processing	[9]
Protein phosphatase Mn(2+)-dependent 1K (PPM1K)	OTNZ4N4E	PPM1K_HUMAN	Gene/Protein Processing	[7]
Protein-tyrosine sulfotransferase 1 (TPST1)	OTDPQKEA	TPST1_HUMAN	Gene/Protein Processing	[7]
Stromal membrane-associated protein 2 (SMAP2)	OTPGVRKO	SMAP2_HUMAN	Gene/Protein Processing	[7]

Molecular Interaction Atlas (MIA)

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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	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.
9	Tibolone and its metabolites enhance tissue factor and PAI-1 expression in human endometrial stromal cells: Evidence of progestogenic effects. Steroids. 2005 Nov;70(12):840-5. doi: 10.1016/j.steroids.2005.04.010.