Identification

Name
Chlorotrianisene
Accession Number
DB00269  (APRD00715)
Type
Small Molecule
Groups
Investigational, Withdrawn
Description

A powerful synthetic, non-steroidal estrogen. [PubChem]

Structure
Thumb
Synonyms
  • Chloortrianisestrol
  • Chlorestrolo
  • Chlorotrianisenum
  • Chlorotrianisine
  • Chlorotrianizen
  • Chlortrianisen
  • Chlortrianisestrol
  • Chlortrianisoestrolum
  • Chlortrianizen
  • Clorotrianiseno
External IDs
NSC-10108
International/Other Brands
Merbentul (Merrell) / Tace (Merrell) / Tace FN (Merrell) / Triagen (Gentili)
Categories
UNII
6V5034L121
CAS number
569-57-3
Weight
Average: 380.864
Monoisotopic: 380.117922245
Chemical Formula
C23H21ClO3
InChI Key
BFPSDSIWYFKGBC-UHFFFAOYSA-N
InChI
InChI=1S/C23H21ClO3/c1-25-19-10-4-16(5-11-19)22(17-6-12-20(26-2)13-7-17)23(24)18-8-14-21(27-3)15-9-18/h4-15H,1-3H3
IUPAC Name
1-[1-chloro-2,2-bis(4-methoxyphenyl)ethenyl]-4-methoxybenzene
SMILES
COC1=CC=C(C=C1)C(Cl)=C(C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1

Pharmacology

Indication

Used to treat symptoms of menopause, deficiencies in ovary function (including underdevelopment of female sexual characteristics and some types of infertility), and in rare cases, prostate cancer. Chlorotrianisene may also be used to prevent breast engorgement following childbirth.

Pharmacodynamics

Chlorotrianisene is a nonsteroidal synthetic estrogen. After menopause, when the body no longer produces estrogen, chlorotrianisene is used as a simple replacement of estrogen. The estrogen-stimulated endometrium may bleed within 48-72 hours after discontinuance of estrogen therapy. Paradoxically, prolonged estrogen therapy may cause shrinkage of the endometrium and an increase in size of the myometrium. Estrogens have a weak anabolic effect and may cause sodium retention with associated fluid retention and edema. Estrogens may also decrease elevated blood cholesterol and phospholipid concentrations. Estrogens affect bone by increasing calcium deposition and accelerating epiphyseal closure, following initial growth stimulation. During the preovulatory or nonovulatory phase of the menstrual cycle, estrogen is the principal determinant in the onset of menstruation. A decline of estrogenic activity at the end of the menstrual cycle also may induce menstruation; however, the cessation of progesterone secretion is the most important factor during the mature ovulatory phase of the menstrual cycle. The benefit derived from estrogen therapy in the prevention of postpartum breast engorgement must be carefully weighed against the potential increased risk of puerperal thromboembolism associated with the use of large doses of estrogens.

Mechanism of action

Chlorotrianisene binds to the estrogen receptor on various estrogen receptor bearing cells. Target cells include cells in the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Human
Absorption

Absorption following oral administration is rapid.

Volume of distribution
Not Available
Protein binding

50-80%

Metabolism

Metabolized principally in the liver, although the kidneys, gonads, and muscle tissues may be involved to some extent. The metabolic fate of the synthetic estrogens has not been fully elucidated.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Acute overdosage of large doses of oral contraceptives in chidren reportedly produces almost no toxicity except nausea and vomiting. Acute overdosage of estrogens may cause nausea, and withdrawal bleeding may occur in females.

Affected organisms
  • Humans and other mammals
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 Chlorotrianisene.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Chlorotrianisene.Experimental, Illicit
5-androstenedioneThe serum concentration of 5-androstenedione can be increased when it is combined with Chlorotrianisene.Experimental, Illicit
AbciximabChlorotrianisene may decrease the anticoagulant activities of Abciximab.Approved
AceclofenacAceclofenac may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
AcenocoumarolChlorotrianisene may decrease the anticoagulant activities of Acenocoumarol.Approved, Investigational
AcetaminophenAcetaminophen may increase the thrombogenic activities of Chlorotrianisene.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Chlorotrianisene.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
Acetylsalicylic acidAcetylsalicylic acid may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Chlorotrianisene.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Chlorotrianisene.Experimental, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Chlorotrianisene.Experimental, Investigational
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Chlorotrianisene.Approved
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Chlorotrianisene.Approved
Aminosalicylic AcidAminosalicylic Acid may increase the thrombogenic activities of Chlorotrianisene.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
AncestimThe risk or severity of cytotoxicity can be increased when Ancestim is combined with Chlorotrianisene.Approved, Investigational, Withdrawn
AncrodChlorotrianisene may decrease the anticoagulant activities of Ancrod.Approved, Investigational
AndrostenedioneThe serum concentration of Androstenedione can be increased when it is combined with Chlorotrianisene.Experimental, Illicit
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Chlorotrianisene.Investigational
anecortave acetateThe serum concentration of anecortave acetate can be increased when it is combined with Chlorotrianisene.Investigational
Anthrax immune globulin humanChlorotrianisene may increase the thrombogenic activities of Anthrax immune globulin human.Approved
AntipyrineAntipyrine may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
Antithrombin III humanChlorotrianisene may decrease the anticoagulant activities of Antithrombin III human.Approved
AntrafenineAntrafenine may increase the thrombogenic activities of Chlorotrianisene.Approved
ApixabanChlorotrianisene may decrease the anticoagulant activities of Apixaban.Approved
ArdeparinChlorotrianisene may decrease the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanChlorotrianisene may decrease the anticoagulant activities of Argatroban.Approved, Investigational
AtamestaneThe serum concentration of Atamestane can be increased when it is combined with Chlorotrianisene.Investigational
BalsalazideBalsalazide may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
BecaplerminChlorotrianisene may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Chlorotrianisene.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Chlorotrianisene.Approved, Investigational
BivalirudinChlorotrianisene may decrease the anticoagulant activities of Bivalirudin.Approved, Investigational
BromfenacBromfenac may increase the thrombogenic activities of Chlorotrianisene.Approved
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Chlorotrianisene.Approved
BufexamacBufexamac may increase the thrombogenic activities of Chlorotrianisene.Approved, Experimental
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Chlorotrianisene.Approved
Capromab pendetideChlorotrianisene may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CapsaicinCapsaicin may increase the thrombogenic activities of Chlorotrianisene.Approved
CarprofenCarprofen may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved, Withdrawn
CelecoxibCelecoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
CertoparinChlorotrianisene may decrease the anticoagulant activities of Certoparin.Approved, Investigational
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Chlorotrianisene.Approved
ChlorphenesinChlorphenesin may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved, Withdrawn
Choline magnesium trisalicylateCholine magnesium trisalicylate may increase the thrombogenic activities of Chlorotrianisene.Approved
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Chlorotrianisene.Approved, Investigational
CimicoxibCimicoxib may increase the thrombogenic activities of Chlorotrianisene.Investigational
CisplatinCisplatin may increase the thrombogenic activities of Chlorotrianisene.Approved
Citric AcidChlorotrianisene may decrease the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Chlorotrianisene.Approved, Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Chlorotrianisene.Approved
ClobetasoneThe serum concentration of Clobetasone can be increased when it is combined with Chlorotrianisene.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Chlorotrianisene.Approved
Clodronic AcidClodronic Acid may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Vet Approved
Conestat alfaChlorotrianisene 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 Chlorotrianisene.Investigational
CorticosteroneThe serum concentration of Corticosterone can be increased when it is combined with Chlorotrianisene.Experimental
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Chlorotrianisene.Approved, Investigational
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Chlorotrianisene.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
Dabigatran etexilateChlorotrianisene may decrease the anticoagulant activities of Dabigatran etexilate.Approved
DalteparinChlorotrianisene may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidChlorotrianisene may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanChlorotrianisene may decrease the anticoagulant activities of Darexaban.Investigational
DeflazacortThe serum concentration of Deflazacort can be increased when it is combined with Chlorotrianisene.Approved, Investigational
DesirudinChlorotrianisene may decrease the anticoagulant activities of Desirudin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Chlorotrianisene.Approved
DesonideThe serum concentration of Desonide can be increased when it is combined with Chlorotrianisene.Approved, Investigational
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Chlorotrianisene.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Chlorotrianisene.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Chlorotrianisene.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Chlorotrianisene.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Chlorotrianisene.Vet Approved
DexibuprofenDexibuprofen may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
DexketoprofenDexketoprofen may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
DextranChlorotrianisene may decrease the anticoagulant activities of Dextran.Approved, Investigational, Vet Approved
DiclofenacDiclofenac may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
DicoumarolChlorotrianisene may decrease the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Chlorotrianisene.Approved
DiflunisalDiflunisal may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Chlorotrianisene.Approved, Investigational, Withdrawn
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Chlorotrianisene.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Chlorotrianisene.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Chlorotrianisene.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Chlorotrianisene.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Chlorotrianisene.Approved, Investigational
DrospirenoneDrospirenone may increase the thrombogenic activities of Chlorotrianisene.Approved
DroxicamDroxicam may increase the thrombogenic activities of Chlorotrianisene.Withdrawn
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Chlorotrianisene.Approved
Edetic AcidChlorotrianisene may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanChlorotrianisene may decrease the anticoagulant activities of Edoxaban.Approved
EnoxaparinChlorotrianisene may decrease the anticoagulant activities of Enoxaparin.Approved
EquileninThe serum concentration of Equilenin can be increased when it is combined with Chlorotrianisene.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Chlorotrianisene.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Chlorotrianisene.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Chlorotrianisene.Approved
EtanerceptEtanercept may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
Ethyl biscoumacetateChlorotrianisene may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
FenoprofenFenoprofen may increase the thrombogenic activities of Chlorotrianisene.Approved
Ferulic acidChlorotrianisene may decrease the anticoagulant activities of Ferulic acid.Experimental
Fish oilFish oil may increase the thrombogenic activities of Chlorotrianisene.Approved, Nutraceutical
FluasteroneThe serum concentration of Fluasterone can be increased when it is combined with Chlorotrianisene.Investigational
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Chlorotrianisene.Approved, Investigational
FluindioneChlorotrianisene may decrease the anticoagulant activities of Fluindione.Approved, Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Chlorotrianisene.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Chlorotrianisene.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Chlorotrianisene.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Chlorotrianisene.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Chlorotrianisene.Approved, Investigational
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Chlorotrianisene.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Chlorotrianisene.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Chlorotrianisene.Approved
FlurbiprofenFlurbiprofen may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
FluticasoneThe serum concentration of Fluticasone can be increased when it is combined with Chlorotrianisene.Approved, Experimental, Investigational
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Chlorotrianisene.Approved
Fluticasone propionateThe serum concentration of Fluticasone propionate can be increased when it is combined with Chlorotrianisene.Approved
FondaparinuxChlorotrianisene may decrease the anticoagulant activities of Fondaparinux.Approved, Investigational
Fondaparinux sodiumChlorotrianisene may decrease the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Chlorotrianisene.Approved, Investigational, Withdrawn
GabexateChlorotrianisene may decrease the anticoagulant activities of Gabexate.Investigational
GinsengGinseng may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Nutraceutical
GitoformateGitoformate may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
HalcinonideThe serum concentration of Halcinonide can be increased when it is combined with Chlorotrianisene.Approved, Investigational, Withdrawn
HE3286The serum concentration of HE3286 can be increased when it is combined with Chlorotrianisene.Investigational
HeparinChlorotrianisene may decrease the anticoagulant activities of Heparin.Approved, Investigational
Human C1-esterase inhibitorChlorotrianisene may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
IbuprofenIbuprofen may increase the thrombogenic activities of Chlorotrianisene.Approved
IcosapentIcosapent may increase the thrombogenic activities of Chlorotrianisene.Approved, Nutraceutical
IdraparinuxChlorotrianisene may decrease the anticoagulant activities of Idraparinux.Investigational
IndomethacinIndomethacin may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Chlorotrianisene.Investigational
KetoprofenKetoprofen may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
KetorolacKetorolac may increase the thrombogenic activities of Chlorotrianisene.Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
LenalidomideChlorotrianisene may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinChlorotrianisene may decrease the anticoagulant activities of Lepirudin.Approved
LetaxabanChlorotrianisene may decrease the anticoagulant activities of Letaxaban.Investigational
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Chlorotrianisene.Approved
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Chlorotrianisene.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Chlorotrianisene.Approved
LornoxicamLornoxicam may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
LoteprednolThe serum concentration of Loteprednol can be increased when it is combined with Chlorotrianisene.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
Magnesium salicylateMagnesium salicylate may increase the thrombogenic activities of Chlorotrianisene.Approved
ME-609The serum concentration of ME-609 can be increased when it is combined with Chlorotrianisene.Investigational
Meclofenamic acidMeclofenamic acid may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Chlorotrianisene.Approved
Mefenamic acidMefenamic acid may increase the thrombogenic activities of Chlorotrianisene.Approved
MelagatranChlorotrianisene may decrease the anticoagulant activities of Melagatran.Experimental
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Chlorotrianisene.Vet Approved
MeloxicamMeloxicam may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
MesalazineMesalazine may increase the thrombogenic activities of Chlorotrianisene.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
MorniflumateMorniflumate may increase the thrombogenic activities of Chlorotrianisene.Approved
NabumetoneNabumetone may increase the thrombogenic activities of Chlorotrianisene.Approved
NadroparinChlorotrianisene may decrease the anticoagulant activities of Nadroparin.Approved, Investigational
NafamostatChlorotrianisene may decrease the anticoagulant activities of Nafamostat.Approved, Investigational
NaproxenNaproxen may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Chlorotrianisene.Investigational
NepafenacNepafenac may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
Niflumic AcidNiflumic Acid may increase the thrombogenic activities of Chlorotrianisene.Approved
NimesulideNimesulide may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Withdrawn
OleandrinOleandrin may decrease the cardiotoxic activities of Chlorotrianisene.Experimental, Investigational
Oleoyl-estroneThe serum concentration of Oleoyl-estrone can be increased when it is combined with Chlorotrianisene.Investigational
OspemifeneThe risk or severity of adverse effects can be increased when Chlorotrianisene is combined with Ospemifene.Approved, Investigational
OtamixabanChlorotrianisene may decrease the anticoagulant activities of Otamixaban.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Chlorotrianisene.Approved
OxaprozinOxaprozin may increase the thrombogenic activities of Chlorotrianisene.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Chlorotrianisene.Approved, Vet Approved
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Chlorotrianisene.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Chlorotrianisene.Approved
Pentaerythritol TetranitrateChlorotrianisene may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Pentosan PolysulfateChlorotrianisene may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
PhenindioneChlorotrianisene may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonChlorotrianisene may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenylbutazonePhenylbutazone may increase the thrombogenic activities of Chlorotrianisene.Approved, Vet Approved
PiroxicamPiroxicam may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
PomalidomidePomalidomide may increase the thrombogenic activities of Chlorotrianisene.Approved
Potassium CitrateChlorotrianisene may decrease the anticoagulant activities of Potassium Citrate.Approved, Investigational, Vet Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Chlorotrianisene.Approved, Investigational, Nutraceutical
Prasterone sulfateThe serum concentration of Prasterone sulfate can be increased when it is combined with Chlorotrianisene.Investigational
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Chlorotrianisene.Approved, Investigational
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Chlorotrianisene.Approved, Experimental, Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Chlorotrianisene.Experimental
Protein CChlorotrianisene may decrease the anticoagulant activities of Protein C.Approved
Protein S humanChlorotrianisene may decrease the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeChlorotrianisene may decrease the anticoagulant activities of Protocatechualdehyde.Approved
ResveratrolResveratrol may increase the thrombogenic activities of Chlorotrianisene.Approved, Experimental, Investigational
ReviparinChlorotrianisene may decrease the anticoagulant activities of Reviparin.Approved, Investigational
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Chlorotrianisene.Approved
RivaroxabanChlorotrianisene may decrease the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Chlorotrianisene.Approved, Investigational
Salicylic acidSalicylic acid may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Vet Approved
SalsalateSalsalate may increase the thrombogenic activities of Chlorotrianisene.Approved
SeliciclibSeliciclib may increase the thrombogenic activities of Chlorotrianisene.Investigational
Sodium CitrateChlorotrianisene may decrease the anticoagulant activities of Sodium Citrate.Approved, Investigational
SomatotropinThe therapeutic efficacy of Somatotropin can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
SulfasalazineSulfasalazine may increase the thrombogenic activities of Chlorotrianisene.Approved
SulindacSulindac may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
SulodexideChlorotrianisene may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
SuprofenSuprofen may increase the thrombogenic activities of Chlorotrianisene.Approved, Withdrawn
TalniflumateTalniflumate may increase the thrombogenic activities of Chlorotrianisene.Approved
TenoxicamTenoxicam may increase the thrombogenic activities of Chlorotrianisene.Approved
ThalidomideChlorotrianisene may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Chlorotrianisene.Approved
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Chlorotrianisene.Approved
Tiaprofenic acidTiaprofenic acid may increase the thrombogenic activities of Chlorotrianisene.Approved
TipranavirChlorotrianisene may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Chlorotrianisene.Approved, Withdrawn
TolmetinTolmetin may increase the thrombogenic activities of Chlorotrianisene.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Chlorotrianisene.Approved, Investigational
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
Trolamine salicylateTrolamine salicylate may increase the thrombogenic activities of Chlorotrianisene.Approved
TroxerutinChlorotrianisene may decrease the anticoagulant activities of Troxerutin.Investigational
UlobetasolThe serum concentration of Ulobetasol can be increased when it is combined with Chlorotrianisene.Approved
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational, Withdrawn
Vitamin CThe serum concentration of Chlorotrianisene can be increased when it is combined with Vitamin C.Approved, Nutraceutical
WarfarinChlorotrianisene may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranChlorotrianisene may decrease the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Shelton, R.S. and Van Campen, M.G. Jr.; U S . Patent 2,430,891; November 18,1947; assigned to the Wm. S. Merrell Company.

General References
Not Available
External Links
Human Metabolome Database
HMDB0014414
KEGG Drug
D00269
PubChem Compound
11289
PubChem Substance
46508811
ChemSpider
10815
ChEBI
3641
ChEMBL
CHEMBL1200761
Therapeutic Targets Database
DAP001012
PharmGKB
PA164768822
Drugs.com
Drugs.com Drug Page
Wikipedia
Chlorotrianisene
ATC Codes
G03CA06 — Chlorotrianisene

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2Not Yet RecruitingTreatmentPrimary Liver Carcinoma1
1, 2RecruitingTreatmentHepatocellular,Carcinoma1
2CompletedTreatmentHepatocellular,Carcinoma2
2CompletedTreatmentLiver Cancer1
2Not Yet RecruitingTreatmentHepatocellular,Carcinoma1
2Not Yet RecruitingTreatmentPrimary Hepatocellular Carcinoma1
2RecruitingPreventionAdvanced Adult Hepatocellular Carcinoma1
2RecruitingTreatmentHepatocellular,Carcinoma2
2TerminatedTreatmentHepatocellular,Carcinoma1
3RecruitingTreatmentHepatocellular,Carcinoma1
3RecruitingTreatmentLiver Cancer1
3Unknown StatusTreatmentHepatocellular,Carcinoma1
4CompletedTreatmentHepatocellular,Carcinoma1
4CompletedTreatmentUnresectable Hepatocellular Carcinoma1
Not AvailableCompletedTreatmentHepatocellular,Carcinoma1
Not AvailableRecruitingTreatmentHepatocellular,Carcinoma / Transcatheter Arterial Chemoembolization1

Pharmacoeconomics

Manufacturers
  • Banner pharmacaps inc
  • Sanofi aventis us llc
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)113-114REM p.988 Shelton, R.S. and Van Campen, M.G. Jr.; U S . Patent 2,430,891; November 18,1947; assigned to the Wm. S. Merrell Company.
logP6.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000199 mg/mLALOGPS
logP5.95ALOGPS
logP5.43ChemAxon
logS-6.3ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.69 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.17 m3·mol-1ChemAxon
Polarizability41.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.651
Caco-2 permeable+0.8218
P-glycoprotein substrateNon-substrate0.6283
P-glycoprotein inhibitor IInhibitor0.5266
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.8102
CYP450 2C9 substrateNon-substrate0.7764
CYP450 2D6 substrateNon-substrate0.8599
CYP450 3A4 substrateSubstrate0.6053
CYP450 1A2 substrateNon-inhibitor0.8094
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.5072
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8625
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6402
BiodegradationNot ready biodegradable0.9562
Rat acute toxicity1.9303 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8429
hERG inhibition (predictor II)Non-inhibitor0.8456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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/MSsplash10-0012-1495000000-9f658a59776206767e09

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Diphenylmethanes / Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / Vinyl chlorides / Chloroalkenes / Organochlorides / Hydrocarbon derivatives
Substituents
Stilbene / Diphenylmethane / Phenoxy compound / Anisole / Methoxybenzene / Phenol ether / Alkyl aryl ether / Monocyclic benzene moiety / Benzenoid / Chloroalkene
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
chloroalkene (CHEBI:3641)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
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. Kupfer D, Bulger WH: Inactivation of the uterine estrogen receptor binding of estradiol during P-450 catalyzed metabolism of chlorotrianisene (TACE). Speculation that TACE antiestrogenic activity involves covalent binding to the estrogen receptor. FEBS Lett. 1990 Feb 12;261(1):59-62. [PubMed:2307235]
  2. Jordan VC, Gosden B: Inhibition of the uterotropic activity of estrogens and antiestrogens by the short acting antiestrogen LY117018. Endocrinology. 1983 Aug;113(2):463-8. [PubMed:6872937]
  3. Wang JY, Xu BH, Tian LJ, Wang Y: [Clinical characteristics and potential prognostic factors of breast cancer patients with liver metastases]. Zhonghua Zhong Liu Za Zhi. 2006 Aug;28(8):612-6. [PubMed:17236558]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Adashi EY, Hsueh AJ: Estrogens augment the stimulation of ovarian aromatase activity by follicle-stimulating hormone in cultured rat granulosa cells. J Biol Chem. 1982 Jun 10;257(11):6077-83. [PubMed:6804461]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 06:32