This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Tibolone
Accession Number
DB09070
Type
Small Molecule
Groups
Approved, Investigational
Description

Tibolone is a synthetic steroid hormone drug, which is mainly non-selective in its binding profile, acting as an agonist primarily at estrogen receptors (ER), with a preference for ER alpha [11].

Tibolone (Livial, Org OD 14), produced by Organon (West Orange, NJ), is a synthetic steroid that possesses estrogenic, androgenic and progestogenic properties. It has been used in Europe for almost 2 decades, primarily for the prevention of postmenopausal osteoporosis and the treatment of post-menopausal symptoms [4]. Tibolone is approved in 90 countries to manage menopausal symptoms and in 45 countries to prevent the development of osteoporosis [12].

In June 2006, Organon Pharmaceuticals announced the receipt of a Not Approvable Letter from the U.S. Food and Drug Administration (FDA), advising the company that the New Drug Application (NDA) for tibolone had not been approved [5].

Interestingly, the use of tibolone in the treatment cardiovascular disease has been studied with inconclusive results [2]. Tibolone has been to have anti-resorptive effects on bone [11].

Structure
Thumb
Synonyms
  • 17-hydroxy-7alpha-methyl-19-nor-17alpha-pregn-5(10)-en-20-yn-3-one
  • tibolona
  • tibolonum
External IDs
ORG OD 14
Categories
UNII
FF9X0205V2
CAS number
5630-53-5
Weight
Average: 312.453
Monoisotopic: 312.208930142
Chemical Formula
C21H28O2
InChI Key
WZDGZWOAQTVYBX-XOINTXKNSA-N
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
IUPAC Name
(1S,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-2(7)-en-5-one
SMILES
[H][[email protected]@]12CC[[email protected]@](O)(C#C)[[email protected]@]1(C)CC[[email protected]]1([H])C3=C(CC(=O)CC3)C[[email protected]@]([H])(C)[[email protected]@]21[H]

Pharmacology

Indication

For the relief of post-menopausal symptoms and for the prevention of osteoporosis [7].

Structured Indications
Not Available
Pharmacodynamics

Tibolone prevents bone loss and treating post-menopausal symptoms without stimulating the endometrial tissues, which may lead to malignancy. Typical, drugs that treat post-menopausal symptoms such as estrogen, have a proliferative effect on the endometrium, increasing the risk of endometrial carcinoma [8]. The effects on the bone, brain and vaginal tissues can be explained by the estrogenic activity of tibolone. It is important to note that activity is not expressed in the endometrium. Tibolone behaves differently from estrogen plus progesterone combinations on the breast. Therefore, tibolone can be characterized as a selective estrogen activity regulator [1].

Tibolone has been demonstrated to be an effective agent in treating symptoms associated with menopause. A 16 week trial in 1189 women examined the effect of tibolone 2.5 mg once daily on climacteric symptoms. Women treated with tibolone showed improvement from baseline in typical menopausal symptoms including hot flashes, sweating, insomnia, and anxiety [14].

Mechanism of action

This drug's effects are owed to the activity of its metabolites in various tissues [4].

Upon ingestion, tibolone is quickly converted into three major metabolites: 3 alpha- and 3 beta-hydroxy-tibolone, which have oestrogenic effects, and the Delta(4)-isomer, which has progestogenic and androgenic effects. The specific tissue-selective effects of tibolone occur due to the metabolism, regulation of enzymes and receptor activation that varies in different tissues of the body.

The bone-conserving effects occur due to estradiol receptor activation, while the progesterone and androgen receptors are not involved in this process. Breast tissue of monkeys is not found to be stimulated after tibolone administration, as occurs with estrogen plus progesterone used in combination. This is explained by the fact that tibolone and its metabolites inhibit sulphatase and 17 beta-hydroxysteroid dehydrogenase (HSD) type I and stimulate sulphotransferase and 17 beta-HSD type II. The combined effects of this process prevent the conversion to active estrogens.

In the uterus, the progestogenic activity of the Delta(4)-metabolite and the effect on estrogen-inactivating enzymes prevent estrogenic stimulation. The mammary gland is not stimulated in currently used animal models. Tibolone has been shown to regulate estrogenic activity in several tissue types by influencing the availability of estrogenic compounds for the estradiol receptor in a selective manner [2].

Additionally, tibolone modulates cellular homeostasis in the breast by preventing breast tissue proliferation and stimulating cell apoptosis. Tibolone does not stimulate the endometrium because of the action of its highly stable progestogenic metabolite (Delta(4)-isomer) in combination with an effect on the sulfatase (inhibition)-sulfotransferase (stimulation) system. The estrogenic metabolites of tibolone have direct, favorable effects on the cardiovascular system and, in animal models, this drug has shown no adverse consequences.

The tissue-selective effects of tibolone are the result of metabolism, enzyme regulation and receptor activation that vary in different tissues. The bone-preserving effects of tibolone are the result of estradiol receptor activation, while other steroid receptors, mainly the progesterone and androgen receptors, are not involved in this process.

In a study of monkeys, breast tissue was not stimulated, which occurs with estrogen and progesterone, because tibolone and its metabolites inhibit sulfatase and 17 beta-hydroxysteroid _dehydrogenase (HSD) type I and stimulate _sulfotransferase and 17 beta-HSD type II. The simultaneous effects of this process halt conversion to active estrogens. Additionally, tibolone affects cellular homeostasis in the breast by preventing proliferation and stimulating apoptosis. Tibolone does not stimulate the endometrium due to the action of the highly stable progestogenic metabolite (Delta(4)-isomer) in combination with an effect on the sulphatase (inhibition)-sulphotransferase (stimulation) pathway [1].

The levels of tibolone metabolites and the alteration of hormonal activities vary according to the tissue type. In endometrial tissue the Δ4-isomer functions as a progestagen, however, in the brain and liver, it shows androgenic effects. In breast tissue, the primary actions of tibolone are strong inhibition of sulfatase activity and weak inhibition of 17β-hydroxysteroid dehydrogenase activity, which leads to blocking the conversion estrone sulfate to E2 [4].

TargetActionsOrganism
AEstrogen receptor alpha
antagonist
agonist
Human
Absorption

Tibolone is extensively and rapidly absorbed after oral administration [14]. The parent drug undergoes extensive metabolism, with. Greater than 80% of a radioactive dose excreted from the body as metabolites, which suggests very low plasma concentrations of tibolone. Plasma concentrations of the metabolites appear within 30 minutes and peak within 1–1.5 hours.2,7 The plasma concentrations of the hydroxymetabolites are higher than those of the ∆4-isomer. Food does not appear to have an effect on the absorption of this drug [14].

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Tibolone is metabolized mainly in the liver [4].

The cytochrome P450 isoenzyme system is involved in minor hydroxylation of tibolone [14].

Tibolone is rapidly converted into three major metabolites: 3 alpha- and 3 beta-hydroxy-tibolone, which have oestrogenic effects, and the Delta(4)-isomer, which has both progestogenic and androgenic effects. The 3-hydroxy metabolites are present in the circulation, predominantly in their inactive sulfated form [1].

Route of elimination

Excreted in the urine and feces in the form of sulfated metabolites [4], [14].

The predominant route of elimination of tibolone is via the feces, although some excretion occurs via the urine [14].

Half life

The elimination half-life is approximately 45 h [4].

Clearance

Elimination of tibolone is not dependent renal function [14].

Toxicity

>2000 mg/kg [MSDS]

The Million Women Study (MWS), which had a prospective observational design, studied the use of hormone replacement therapy. The results indicated that the increase in the incidence of breast cancer with estrogen and progestogen (compared to estrogen alone) was greater than the reduction in occurrence of endometrial cancer associated with adding progestogen to estrogen therapy. The MWS also reported a marked increase in the incidence of breast cancer with tibolone and with implanted and transdermal estrogen-only preparations [6].

Tibolone treatment in rodent studies showed an increased association with the development of a range of tumors in long-term oral carcinogenicity studies. These tumors included pituitary adenomas, mammary carcinomas and fibroadenomas, hepatic adenomas, uterine carcinoma, stromal polyps and stromal sarcoma, and carcinomas of the urinary bladder and testes. Tibolone failed to show any evidence of genotoxicity in studies for gene mutations, chromosomal damage as well as DNA damage [9].

Other adverse effects these include dizziness, headache, nausea, abdominal pain, rashes, pruritus, weight gain, edema, and migraine [L1728].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe serum concentration of 16-Bromoepiandrosterone can be increased when it is combined with Tibolone.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Tibolone.Experimental, Illicit
5-androstenedioneThe serum concentration of 5-androstenedione can be increased when it is combined with Tibolone.Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Tibolone.Experimental
AbciximabTibolone may increase the anticoagulant activities of Abciximab.Approved
AcebutololAcebutolol may increase the hypotensive activities of Tibolone.Approved, Investigational
AcemetacinThe therapeutic efficacy of Tibolone can be decreased when used in combination with Acemetacin.Approved, Experimental, Investigational
AcenocoumarolTibolone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Tibolone.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Tibolone.Experimental
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Tibolone.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Tibolone.Experimental, Investigational
AlfuzosinAlfuzosin may increase the hypotensive activities of Tibolone.Approved, Investigational
AliskirenAliskiren may increase the hypotensive activities of Tibolone.Approved, Investigational
AlprenololAlprenolol may increase the hypotensive activities of Tibolone.Approved, Withdrawn
AmbrisentanTibolone may increase the hypotensive activities of Ambrisentan.Approved, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Tibolone.Experimental, Investigational
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Tibolone.Approved
AmifostineTibolone may increase the hypotensive activities of Amifostine.Approved, Investigational
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Tibolone.Approved
AmlodipineAmlodipine may increase the hypotensive activities of Tibolone.Approved
AmphetamineAmphetamine may increase the hypotensive activities of Tibolone.Approved, Illicit, Investigational
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Tibolone.Approved, Investigational
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Tibolone.Approved, Investigational, Withdrawn
AncrodTibolone may increase the anticoagulant activities of Ancrod.Approved, Investigational
AndrostenedioneThe serum concentration of Androstenedione can be increased when it is combined with Tibolone.Experimental, Illicit
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Tibolone.Investigational
anecortave acetateThe serum concentration of anecortave acetate can be increased when it is combined with Tibolone.Investigational
Anthrax immune globulin humanTibolone may increase the thrombogenic activities of Anthrax immune globulin human.Approved
Antithrombin III humanTibolone may increase the anticoagulant activities of Antithrombin III human.Approved
ApixabanTibolone may increase the anticoagulant activities of Apixaban.Approved
ArdeparinTibolone may increase the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanTibolone may increase the anticoagulant activities of Argatroban.Approved, Investigational
AtamestaneThe serum concentration of Atamestane can be increased when it is combined with Tibolone.Investigational
AtenololAtenolol may increase the hypotensive activities of Tibolone.Approved
AvanafilAvanafil may increase the antihypertensive activities of Tibolone.Approved
BarnidipineTibolone may increase the antihypertensive activities of Barnidipine.Approved
BecaplerminTibolone may increase the anticoagulant activities of Becaplermin.Approved, Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Tibolone.Approved, Investigational
BenazeprilBenazepril may increase the hypotensive activities of Tibolone.Approved, Investigational
BendroflumethiazideBendroflumethiazide may increase the hypotensive activities of Tibolone.Approved
BenmoxinBenmoxin may increase the hypotensive activities of Tibolone.Withdrawn
BepridilBepridil may increase the hypotensive activities of Tibolone.Approved, Withdrawn
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Tibolone.Approved, Vet Approved
BetaxololBetaxolol may increase the hypotensive activities of Tibolone.Approved, Investigational
BethanidineBethanidine may increase the hypotensive activities of Tibolone.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Tibolone.Approved, Investigational
BietaserpineBietaserpine may increase the hypotensive activities of Tibolone.Experimental
BimatoprostBimatoprost may increase the hypotensive activities of Tibolone.Approved, Investigational
BisoprololBisoprolol may increase the hypotensive activities of Tibolone.Approved
BivalirudinTibolone may increase the anticoagulant activities of Bivalirudin.Approved, Investigational
BosentanBosentan may increase the hypotensive activities of Tibolone.Approved, Investigational
BQ-123Tibolone may increase the hypotensive activities of BQ-123.Investigational
BretyliumBretylium may increase the hypotensive activities of Tibolone.Approved
BrimonidineBrimonidine may increase the antihypertensive activities of Tibolone.Approved
BrofaromineBrofaromine may increase the hypotensive activities of Tibolone.Experimental
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Tibolone.Approved
BupranololBupranolol may increase the hypotensive activities of Tibolone.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Tibolone.Approved
CadralazineCadralazine may increase the hypotensive activities of Tibolone.Experimental
CafedrineTibolone may increase the hypotensive activities of Cafedrine.Investigational
CandesartanTibolone may increase the hypotensive activities of Candesartan.Experimental
Candesartan cilexetilCandesartan cilexetil may increase the hypotensive activities of Tibolone.Approved
CandoxatrilCandoxatril may increase the hypotensive activities of Tibolone.Experimental
Capromab pendetideTibolone may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CaptoprilCaptopril may increase the hypotensive activities of Tibolone.Approved
CaroxazoneCaroxazone may increase the hypotensive activities of Tibolone.Withdrawn
CarteololCarteolol may increase the hypotensive activities of Tibolone.Approved
CarvedilolCarvedilol may increase the hypotensive activities of Tibolone.Approved, Investigational
CelecoxibCelecoxib may increase the thrombogenic activities of Tibolone.Approved, Investigational
CeliprololCeliprolol may increase the hypotensive activities of Tibolone.Approved, Investigational
CertoparinTibolone may increase the anticoagulant activities of Certoparin.Approved, Investigational
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Tibolone.Approved
ChlorothiazideChlorothiazide may increase the hypotensive activities of Tibolone.Approved, Vet Approved
ChlorthalidoneChlorthalidone may increase the hypotensive activities of Tibolone.Approved
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Tibolone.Approved, Investigational
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Tibolone.Approved, Investigational
CicletanineTibolone may increase the hypotensive activities of Cicletanine.Investigational
CilazaprilCilazapril may increase the hypotensive activities of Tibolone.Approved
Citric AcidTibolone may increase the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Tibolone.Approved, Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Tibolone.Approved
ClobetasoneThe serum concentration of Clobetasone can be increased when it is combined with Tibolone.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Tibolone.Approved
ClonidineClonidine may increase the hypotensive activities of Tibolone.Approved
CloranololTibolone may increase the hypotensive activities of Cloranolol.Experimental
Conestat alfaTibolone may increase the thrombogenic activities of Conestat alfa.Approved, Investigational
Cortexolone 17α-propionateThe serum concentration of Cortexolone 17α-propionate can be increased when it is combined with Tibolone.Investigational
CorticosteroneThe serum concentration of Corticosterone can be increased when it is combined with Tibolone.Experimental
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Tibolone.Approved, Investigational
CryptenamineCryptenamine may increase the hypotensive activities of Tibolone.Approved
CyclopenthiazideTibolone may increase the hypotensive activities of Cyclopenthiazide.Experimental
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Tibolone.Approved, Investigational
CyclothiazideCyclothiazide may increase the hypotensive activities of Tibolone.Approved
CymarinCymarin may decrease the cardiotoxic activities of Tibolone.Experimental
Dabigatran etexilateTibolone may increase the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinTibolone may increase the anticoagulant activities of Dalteparin.Approved
DanaparoidTibolone may increase the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanTibolone may increase the anticoagulant activities of Darexaban.Investigational
DebrisoquinDebrisoquin may increase the hypotensive activities of Tibolone.Approved, Investigational
DeflazacortThe serum concentration of Deflazacort can be increased when it is combined with Tibolone.Approved, Investigational
DelaprilTibolone may increase the hypotensive activities of Delapril.Experimental
DeserpidineTibolone may increase the hypotensive activities of Deserpidine.Approved
DesirudinTibolone may increase the anticoagulant activities of Desirudin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Tibolone.Approved
DesonideThe serum concentration of Desonide can be increased when it is combined with Tibolone.Approved, Investigational
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Tibolone.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Tibolone.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Tibolone.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Tibolone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Tibolone.Vet Approved
DextranTibolone may increase the anticoagulant activities of Dextran.Approved, Investigational, Vet Approved
Dextran 40Tibolone may increase the anticoagulant activities of Dextran 40.Approved
Dextran 70Tibolone may increase the anticoagulant activities of Dextran 70.Approved
Dextran 75Tibolone may increase the anticoagulant activities of Dextran 75.Approved
DiazoxideDiazoxide may increase the hypotensive activities of Tibolone.Approved
DicoumarolTibolone may increase the anticoagulant activities of Dicoumarol.Approved
DiethylnorspermineDiethylnorspermine may increase the hypotensive activities of Tibolone.Investigational
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Tibolone.Approved
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Tibolone.Approved, Investigational, Withdrawn
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Tibolone.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Tibolone.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Tibolone.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Tibolone.Approved
DihydralazineDihydralazine may increase the hypotensive activities of Tibolone.Approved, Investigational
DiltiazemDiltiazem may increase the hypotensive activities of Tibolone.Approved, Investigational
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Tibolone.Approved, Investigational
DorzolamideDorzolamide may increase the hypotensive activities of Tibolone.Approved
DoxazosinDoxazosin may increase the hypotensive activities of Tibolone.Approved
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Tibolone.Approved
Edetic AcidTibolone may increase the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanTibolone may increase the anticoagulant activities of Edoxaban.Approved
EfonidipineTibolone may increase the hypotensive activities of Efonidipine.Approved, Investigational
EnalaprilEnalapril may increase the hypotensive activities of Tibolone.Approved, Vet Approved
EnalaprilatTibolone may increase the hypotensive activities of Enalaprilat.Approved
EndralazineEndralazine may increase the hypotensive activities of Tibolone.Experimental
EnoxaparinTibolone may increase the anticoagulant activities of Enoxaparin.Approved
EpanololTibolone may increase the hypotensive activities of Epanolol.Experimental
EpoprostenolEpoprostenol may increase the hypotensive activities of Tibolone.Approved
EprosartanEprosartan may increase the hypotensive activities of Tibolone.Approved
EquileninThe serum concentration of Equilenin can be increased when it is combined with Tibolone.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Tibolone.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Tibolone.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Tibolone.Approved
Ethyl biscoumacetateTibolone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Tibolone.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Tibolone.Approved, Investigational
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Tibolone.Approved, Investigational
FelodipineFelodipine may increase the hypotensive activities of Tibolone.Approved, Investigational
FenoldopamFenoldopam may increase the hypotensive activities of Tibolone.Approved
Ferulic acidTibolone may increase the anticoagulant activities of Ferulic acid.Experimental
FluasteroneThe serum concentration of Fluasterone can be increased when it is combined with Tibolone.Investigational
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Tibolone.Approved, Investigational
FluindioneTibolone may increase the anticoagulant activities of Fluindione.Approved, Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Tibolone.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Tibolone.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Tibolone.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Tibolone.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Tibolone.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Tibolone.Approved, Investigational
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Tibolone.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Tibolone.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Tibolone.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Tibolone.Approved
Fluticasone propionateThe serum concentration of Fluticasone propionate can be increased when it is combined with Tibolone.Approved
FondaparinuxTibolone may increase the anticoagulant activities of Fondaparinux.Approved, Investigational
Fondaparinux sodiumTibolone may increase the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Tibolone.Approved, Investigational, Withdrawn
FosinoprilFosinopril may increase the hypotensive activities of Tibolone.Approved
FurazolidoneFurazolidone may increase the hypotensive activities of Tibolone.Approved, Investigational, Vet Approved
GabexateTibolone may increase the anticoagulant activities of Gabexate.Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Tibolone.Experimental
GuanabenzGuanabenz may increase the hypotensive activities of Tibolone.Approved, Investigational
GuanadrelGuanadrel may increase the hypotensive activities of Tibolone.Approved
GuanazodineTibolone may increase the hypotensive activities of Guanazodine.Experimental
GuanethidineGuanethidine may increase the hypotensive activities of Tibolone.Approved
GuanfacineGuanfacine may increase the hypotensive activities of Tibolone.Approved, Investigational
GuanoclorTibolone may increase the hypotensive activities of Guanoclor.Experimental
GuanoxabenzTibolone may increase the hypotensive activities of Guanoxabenz.Experimental
GuanoxanTibolone may increase the hypotensive activities of Guanoxan.Experimental
HalcinonideThe serum concentration of Halcinonide can be increased when it is combined with Tibolone.Approved, Investigational, Withdrawn
HarmalineHarmaline may increase the hypotensive activities of Tibolone.Experimental
HE3286The serum concentration of HE3286 can be increased when it is combined with Tibolone.Investigational
HeparinTibolone may increase the anticoagulant activities of Heparin.Approved, Investigational
HexamethoniumHexamethonium may increase the hypotensive activities of Tibolone.Experimental
Human C1-esterase inhibitorTibolone may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Tibolone.Approved, Investigational
HydracarbazineHydracarbazine may increase the hypotensive activities of Tibolone.Experimental
HydralazineHydralazine may increase the hypotensive activities of Tibolone.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypotensive activities of Tibolone.Approved, Vet Approved
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Tibolone.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypotensive activities of Tibolone.Approved, Investigational
IdraparinuxTibolone may increase the anticoagulant activities of Idraparinux.Investigational
IloprostIloprost may increase the hypotensive activities of Tibolone.Approved, Investigational
ImidaprilTibolone may increase the hypotensive activities of Imidapril.Investigational
IndapamideIndapamide may increase the hypotensive activities of Tibolone.Approved
IndenololIndenolol may increase the hypotensive activities of Tibolone.Withdrawn
IndoraminIndoramin may increase the hypotensive activities of Tibolone.Withdrawn
IproclozideIproclozide may increase the hypotensive activities of Tibolone.Withdrawn
IproniazidIproniazid may increase the hypotensive activities of Tibolone.Withdrawn
IrbesartanIrbesartan may increase the hypotensive activities of Tibolone.Approved, Investigational
IsocarboxazidIsocarboxazid may increase the hypotensive activities of Tibolone.Approved
IsradipineIsradipine may increase the hypotensive activities of Tibolone.Approved, Investigational
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Tibolone.Investigational
KetanserinKetanserin may increase the hypotensive activities of Tibolone.Investigational
LabetalolLabetalol may increase the hypotensive activities of Tibolone.Approved
LacidipineTibolone may increase the hypotensive activities of Lacidipine.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Tibolone.Experimental
LatanoprostLatanoprost may increase the hypotensive activities of Tibolone.Approved, Investigational
LenalidomideTibolone may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinTibolone may increase the anticoagulant activities of Lepirudin.Approved
LercanidipineLercanidipine may increase the hypotensive activities of Tibolone.Approved, Investigational
LetaxabanTibolone may increase the anticoagulant activities of Letaxaban.Investigational
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Tibolone.Approved
LinsidomineTibolone may increase the hypotensive activities of Linsidomine.Experimental
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Tibolone.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Tibolone.Approved
LisinoprilLisinopril may increase the hypotensive activities of Tibolone.Approved, Investigational
LofexidineLofexidine may increase the hypotensive activities of Tibolone.Approved, Investigational
LosartanLosartan may increase the hypotensive activities of Tibolone.Approved
LoteprednolThe serum concentration of Loteprednol can be increased when it is combined with Tibolone.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Tibolone.Approved, Investigational
MacitentanTibolone may increase the hypotensive activities of Macitentan.Approved
ManidipineTibolone may increase the hypotensive activities of Manidipine.Approved, Investigational
ME-609The serum concentration of ME-609 can be increased when it is combined with Tibolone.Investigational
MebanazineMebanazine may increase the hypotensive activities of Tibolone.Withdrawn
MecamylamineMecamylamine may increase the hypotensive activities of Tibolone.Approved, Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Tibolone.Approved
MelagatranTibolone may increase the anticoagulant activities of Melagatran.Experimental
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Tibolone.Vet Approved
MethoserpidineTibolone may increase the hypotensive activities of Methoserpidine.Experimental
MethyldopaMethyldopa may increase the hypotensive activities of Tibolone.Approved
Methylene blueMethylene blue may increase the hypotensive activities of Tibolone.Approved, Investigational
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Tibolone.Approved, Investigational
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Tibolone.Approved, Vet Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Tibolone.Experimental
MetipranololMetipranolol may increase the hypotensive activities of Tibolone.Approved
MetolazoneMetolazone may increase the hypotensive activities of Tibolone.Approved
MetoprololMetoprolol may increase the hypotensive activities of Tibolone.Approved, Investigational
MetyrosineTibolone may increase the hypotensive activities of Metyrosine.Approved
MibefradilMibefradil may increase the hypotensive activities of Tibolone.Investigational, Withdrawn
MinaprineMinaprine may increase the hypotensive activities of Tibolone.Approved
MinoxidilMinoxidil may increase the hypotensive activities of Tibolone.Approved, Investigational
MirodenafilMirodenafil may increase the antihypertensive activities of Tibolone.Investigational
MoclobemideMoclobemide may increase the hypotensive activities of Tibolone.Approved, Investigational
MoexiprilMoexipril may increase the hypotensive activities of Tibolone.Approved
MolsidomineMolsidomine may increase the hypotensive activities of Tibolone.Approved, Investigational
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Tibolone.Approved, Vet Approved
MoxonidineMoxonidine may increase the hypotensive activities of Tibolone.Approved, Investigational
MuzolimineTibolone may increase the hypotensive activities of Muzolimine.Experimental
NabumetoneNabumetone may increase the thrombogenic activities of Tibolone.Approved
NadololNadolol may increase the hypotensive activities of Tibolone.Approved
NadroparinTibolone may increase the anticoagulant activities of Nadroparin.Approved, Investigational
NafamostatTibolone may increase the anticoagulant activities of Nafamostat.Approved, Investigational
NaftopidilTibolone may increase the hypotensive activities of Naftopidil.Investigational
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Tibolone.Investigational
NebivololNebivolol may increase the hypotensive activities of Tibolone.Approved, Investigational
NialamideNialamide may increase the hypotensive activities of Tibolone.Withdrawn
NicardipineNicardipine may increase the hypotensive activities of Tibolone.Approved, Investigational
NicorandilTibolone may increase the hypotensive activities of Nicorandil.Approved, Investigational
NiguldipineTibolone may increase the hypotensive activities of Niguldipine.Experimental
NilvadipineNilvadipine may increase the hypotensive activities of Tibolone.Approved, Investigational
NimodipineNimodipine may increase the hypotensive activities of Tibolone.Approved, Investigational
NisoldipineNisoldipine may increase the hypotensive activities of Tibolone.Approved
NitrendipineNitrendipine may increase the hypotensive activities of Tibolone.Approved, Investigational
NitroprussideNitroprusside may increase the hypotensive activities of Tibolone.Approved, Investigational
ObinutuzumabTibolone may increase the hypotensive activities of Obinutuzumab.Approved, Investigational
OctamoxinOctamoxin may increase the hypotensive activities of Tibolone.Withdrawn
OleandrinOleandrin may decrease the cardiotoxic activities of Tibolone.Experimental, Investigational
Oleoyl-estroneThe serum concentration of Oleoyl-estrone can be increased when it is combined with Tibolone.Investigational
OlmesartanOlmesartan may increase the hypotensive activities of Tibolone.Approved, Investigational
OmapatrilatOmapatrilat may increase the hypotensive activities of Tibolone.Investigational
OspemifeneThe risk or severity of adverse effects can be increased when Tibolone is combined with Ospemifene.Approved, Investigational
OtamixabanTibolone may increase the anticoagulant activities of Otamixaban.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Tibolone.Approved
OxprenololOxprenolol may increase the hypotensive activities of Tibolone.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Tibolone.Approved, Vet Approved
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Tibolone.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Tibolone.Approved
PargylinePargyline may increase the hypotensive activities of Tibolone.Approved
PenbutololPenbutolol may increase the hypotensive activities of Tibolone.Approved, Investigational
Pentaerythritol TetranitrateTibolone may increase the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PentoliniumPentolinium may increase the hypotensive activities of Tibolone.Approved
Pentosan PolysulfateTibolone may increase the anticoagulant activities of Pentosan Polysulfate.Approved
PentoxifyllinePentoxifylline may increase the hypotensive activities of Tibolone.Approved, Investigational
PerindoprilPerindopril may increase the hypotensive activities of Tibolone.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Tibolone.Experimental
PhenelzinePhenelzine may increase the hypotensive activities of Tibolone.Approved
PhenindioneTibolone may increase the anticoagulant activities of Phenindione.Approved, Investigational
PheniprazinePheniprazine may increase the hypotensive activities of Tibolone.Withdrawn
PhenoxybenzaminePhenoxybenzamine may increase the hypotensive activities of Tibolone.Approved
PhenoxypropazinePhenoxypropazine may increase the hypotensive activities of Tibolone.Withdrawn
PhenprocoumonTibolone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhentolaminePhentolamine may increase the hypotensive activities of Tibolone.Approved
PinacidilPinacidil may increase the hypotensive activities of Tibolone.Approved
PindololPindolol may increase the hypotensive activities of Tibolone.Approved, Investigational
PirlindolePirlindole may increase the hypotensive activities of Tibolone.Approved
PivhydrazinePivhydrazine may increase the hypotensive activities of Tibolone.Withdrawn
Platelet Activating FactorPlatelet Activating Factor may increase the hypotensive activities of Tibolone.Experimental
PolythiazidePolythiazide may increase the hypotensive activities of Tibolone.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Tibolone.Approved, Investigational, Nutraceutical
Prasterone sulfateThe serum concentration of Prasterone sulfate can be increased when it is combined with Tibolone.Investigational
PrazosinPrazosin may increase the hypotensive activities of Tibolone.Approved
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Tibolone.Approved, Investigational
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Tibolone.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Tibolone.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Tibolone.Approved, Experimental, Investigational
ProcarbazineProcarbazine may increase the hypotensive activities of Tibolone.Approved, Investigational
PropranololPropranolol may increase the hypotensive activities of Tibolone.Approved, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Tibolone.Experimental
Protein CTibolone may increase the anticoagulant activities of Protein C.Approved
Protein S humanTibolone may increase the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeTibolone may increase the anticoagulant activities of Protocatechualdehyde.Approved
QuinaprilQuinapril may increase the hypotensive activities of Tibolone.Approved, Investigational
QuinineQuinine may increase the hypotensive activities of Tibolone.Approved
RamiprilRamipril may increase the hypotensive activities of Tibolone.Approved
RasagilineRasagiline may increase the hypotensive activities of Tibolone.Approved
RemikirenRemikiren may increase the hypotensive activities of Tibolone.Approved
RescinnamineTibolone may increase the hypotensive activities of Rescinnamine.Approved
ReserpineReserpine may increase the hypotensive activities of Tibolone.Approved, Investigational
ReviparinTibolone may increase the anticoagulant activities of Reviparin.Approved, Investigational
RilmenidineRilmenidine may increase the hypotensive activities of Tibolone.Approved, Investigational
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Tibolone.Approved
RiociguatTibolone may increase the hypotensive activities of Riociguat.Approved
RituximabTibolone may increase the hypotensive activities of Rituximab.Approved
RivaroxabanTibolone may increase the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Tibolone.Approved, Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Tibolone.Approved, Investigational
SafrazineSafrazine may increase the hypotensive activities of Tibolone.Withdrawn
SaprisartanSaprisartan may increase the hypotensive activities of Tibolone.Experimental
SelegilineSelegiline may increase the hypotensive activities of Tibolone.Approved, Investigational, Vet Approved
SelexipagTibolone may increase the hypotensive activities of Selexipag.Approved
SildenafilSildenafil may increase the antihypertensive activities of Tibolone.Approved, Investigational
SitaxentanTibolone may increase the hypotensive activities of Sitaxentan.Approved, Investigational, Withdrawn
SomatotropinThe therapeutic efficacy of Somatotropin can be decreased when used in combination with Tibolone.Approved, Investigational
SpiraprilSpirapril may increase the hypotensive activities of Tibolone.Approved
SulodexideTibolone may increase the anticoagulant activities of Sulodexide.Approved, Investigational
TadalafilTadalafil may increase the antihypertensive activities of Tibolone.Approved, Investigational
TalinololTibolone may increase the hypotensive activities of Talinolol.Investigational
TelmisartanTelmisartan may increase the hypotensive activities of Tibolone.Approved, Investigational
TemocaprilTemocapril may increase the hypotensive activities of Tibolone.Experimental, Investigational
TerlipressinTerlipressin may increase the hypotensive activities of Tibolone.Approved, Investigational
TetrahydropalmatineTibolone may increase the hypotensive activities of Tetrahydropalmatine.Investigational
ThalidomideTibolone may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheodrenalineTibolone may increase the hypotensive activities of Theodrenaline.Investigational
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Tibolone.Approved
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Tibolone.Approved
TicrynafenTicrynafen may increase the hypotensive activities of Tibolone.Withdrawn
TimololTimolol may increase the hypotensive activities of Tibolone.Approved
TipranavirTibolone may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Tibolone.Approved, Withdrawn
TolazolineTolazoline may increase the hypotensive activities of Tibolone.Approved, Vet Approved
TolonidineTibolone may increase the hypotensive activities of Tolonidine.Experimental
ToloxatoneToloxatone may increase the hypotensive activities of Tibolone.Approved
TorasemideTorasemide may increase the hypotensive activities of Tibolone.Approved
TrandolaprilTrandolapril may increase the hypotensive activities of Tibolone.Approved
TranylcypromineTranylcypromine may increase the hypotensive activities of Tibolone.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Tibolone.Approved, Investigational
TravoprostTravoprost may increase the hypotensive activities of Tibolone.Approved
TreprostinilTreprostinil may increase the hypotensive activities of Tibolone.Approved, Investigational
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Tibolone.Approved, Vet Approved
TrichlormethiazideTrichlormethiazide may increase the hypotensive activities of Tibolone.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Tibolone.Experimental
TrimethaphanTrimethaphan may increase the hypotensive activities of Tibolone.Approved, Investigational
TroxerutinTibolone may increase the anticoagulant activities of Troxerutin.Investigational
UdenafilUdenafil may increase the antihypertensive activities of Tibolone.Approved, Investigational
UlobetasolThe serum concentration of Ulobetasol can be increased when it is combined with Tibolone.Approved
UnoprostoneUnoprostone may increase the hypotensive activities of Tibolone.Approved, Investigational
UrapidilUrapidil may increase the hypotensive activities of Tibolone.Investigational
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Tibolone.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Tibolone.Approved, Investigational, Withdrawn
ValsartanValsartan may increase the hypotensive activities of Tibolone.Approved, Investigational
VardenafilVardenafil may increase the antihypertensive activities of Tibolone.Approved
VincamineTibolone may increase the hypotensive activities of Vincamine.Experimental
VinpocetineTibolone may increase the hypotensive activities of Vinpocetine.Investigational
Vitamin CThe serum concentration of Tibolone can be increased when it is combined with Vitamin C.Approved, Nutraceutical
WarfarinTibolone may increase the anticoagulant activities of Warfarin.Approved
XimelagatranTibolone may increase the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
XipamideTibolone may increase the hypotensive activities of Xipamide.Experimental
XylometazolineXylometazoline may increase the hypotensive activities of Tibolone.Approved, Investigational
YohimbineYohimbine may decrease the antihypertensive activities of Tibolone.Approved, Investigational, Vet Approved
ZofenoprilTibolone may increase the hypotensive activities of Zofenopril.Experimental
Food Interactions
Not Available

References

General References
  1. Kloosterboer HJ: Tissue-selectivity: the mechanism of action of tibolone. Maturitas. 2004 Aug 30;48 Suppl 1:S30-40. doi: 10.1016/j.maturitas.2004.02.012. [PubMed:15337246]
  2. Campisi R, Marengo FD: Cardiovascular effects of tibolone: a selective tissue estrogenic activity regulator. Cardiovasc Drug Rev. 2007 Summer;25(2):132-45. doi: 10.1111/j.1527-3466.2007.00007.x. [PubMed:17614936]
  3. Steckelbroeck S, Oyesanmi B, Jin Y, Lee SH, Kloosterboer HJ, Penning TM: Tibolone metabolism in human liver is catalyzed by 3alpha/3beta-hydroxysteroid dehydrogenase activities of the four isoforms of the aldo-keto reductase (AKR)1C subfamily. J Pharmacol Exp Ther. 2006 Mar;316(3):1300-9. doi: 10.1124/jpet.105.091587. Epub 2005 Dec 8. [PubMed:16339391]
  4. Tibolone for Postmenopausal Women: Systematic Review of Randomized Trials [Link]
  5. Tibolone Approval Status [Link]
  6. WHO DRUG INFORMATION [Link]
  7. Livial [Link]
  8. Postmenopausal hormonal therapy: Current status [Link]
  9. LIVIAL- Drug sheet NZ [Link]
  10. Tibolone Drug Monograph [Link]
  11. Tibolone inhibits bone resorption without secondary positive effects on cartilage degradation [Link]
  12. The Effects of Tibolone in Older Postmenopausal Women [Link]
  13. Tibolone Metabolism in Human Liver Is Catalyzed by 3α/3β-Hydroxysteroid Dehydrogenase Activities of the Four Isoforms of the Aldo-Keto Reductase (AKR)1C Subfamily [Link]
  14. Tibolone: A Unique Version of Hormone Replacement Therapy [Link]
  15. Cardiovascular Effects of Tibolone: A Selective Tissue Estrogenic Activity Regulator [Link]
External Links
KEGG Drug
D01639
PubChem Compound
444008
PubChem Substance
347827821
ChemSpider
392038
ChEBI
32223
ChEMBL
CHEMBL2103774
Wikipedia
Tibolone
ATC Codes
G03CX01 — Tibolone
MSDS
Download (91.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Unknown StatusTreatmentDepression / Major Depressive Disorder (MDD)1
2CompletedTreatmentCancer, Breast / Menopause / Postmenopausal Bone Loss1
3CompletedOtherPostmenopausal Women1
3CompletedTreatmentCancer, Breast1
3CompletedTreatmentCancer, Breast / Climacteric Symptoms1
3CompletedTreatmentSexual Dysfunctions1
3CompletedTreatmentBone destruction1
4CompletedPreventionCholesterol, HDL1
4CompletedTreatmentMenopause2
4CompletedTreatmentOsteopenia1
4CompletedTreatmentVasomotor Symptoms1
4CompletedTreatmentBone destruction / One to five years postmenopausal1
4Not Yet RecruitingTreatmentAmenorrhea / Endometriosis / Quality of Life1
4RecruitingTreatmentMenopausal Depression1
4RecruitingTreatmentMenopausal Syndromes1
4TerminatedTreatmentPerimenopausal Depression1
Not AvailableCompletedTreatmentFlow-mediated Dilation Evaluation of the Brachial Artery1
Not AvailableCompletedTreatmentMenopause1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility<0.1 g/LMSDS
Predicted Properties
PropertyValueSource
Water Solubility0.00722 mg/mLALOGPS
logP2.69ALOGPS
logP3.1ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)16.27ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity91.73 m3·mol-1ChemAxon
Polarizability36.77 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0971000000-09912161a9fdfe89ed83

Taxonomy

Description
This compound belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxosteroids
Direct Parent
Oxosteroids
Alternative Parents
3-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Cyclohexenone / Ynone / Cyclic alcohol / Tertiary alcohol / Ketone / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 17beta-hydroxy steroid (CHEBI:32223)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Escande A, Servant N, Rabenoelina F, Auzou G, Kloosterboer H, Cavailles V, Balaguer P, Maudelonde T: Regulation of activities of steroid hormone receptors by tibolone and its primary metabolites. J Steroid Biochem Mol Biol. 2009 Aug;116(1-2):8-14. doi: 10.1016/j.jsbmb.2009.03.008. Epub 2009 Apr 2. [PubMed:19464167]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sulfuric ester hydrolase activity
Specific Function
Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name
STS
Uniprot ID
P08842
Uniprot Name
Steryl-sulfatase
Molecular Weight
65491.72 Da
References
  1. Tibolone: A Unique Version of Hormone Replacement Therapy [Link]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Substrate
General Function
Steroid delta-isomerase activity
Specific Function
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
Gene Name
HSD3B1
Uniprot ID
P14060
Uniprot Name
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
Molecular Weight
42251.25 Da
References
  1. Tibolone: A Unique Version of Hormone Replacement Therapy [Link]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Substrate
General Function
Steroid delta-isomerase activity
Specific Function
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
Gene Name
HSD3B2
Uniprot ID
P26439
Uniprot Name
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
Molecular Weight
42051.845 Da
References
  1. Tibolone: A Unique Version of Hormone Replacement Therapy [Link]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estroge...
Gene Name
SULT1A1
Uniprot ID
P50225
Uniprot Name
Sulfotransferase 1A1
Molecular Weight
34165.13 Da
References
  1. Cardiovascular Effects of Tibolone: A Selective Tissue Estrogenic Activity Regulator [Link]

Drug created on May 14, 2015 09:49 / Updated on March 27, 2018 10:44