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Identification
NameChlorotrianisene
Accession NumberDB00269  (APRD00715)
TypeSmall Molecule
GroupsWithdrawn
DescriptionA powerful synthetic, non-steroidal estrogen. [PubChem]
Structure
Thumb
Synonyms
Chloortrianisestrol
Chlorestrolo
Chlorotrianisenum
Chlorotrianisine
Chlorotrianizen
Chlortrianisen
Chlortrianisestrol
Chlortrianisoestrolum
Chlortrianizen
Clorotrianiseno
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MerbentulMerrell
TaceMerrell
Tace FNMerrell
TriagenGentili
Brand mixturesNot Available
SaltsNot Available
Categories
UNII6V5034L121
CAS number569-57-3
WeightAverage: 380.864
Monoisotopic: 380.117922245
Chemical FormulaC23H21ClO3
InChI KeyBFPSDSIWYFKGBC-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
IndicationUsed 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.
Structured Indications Not Available
PharmacodynamicsChlorotrianisene 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 actionChlorotrianisene 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
agonist
HumanP03372 details
Related Articles
AbsorptionAbsorption following oral administration is rapid.
Volume of distributionNot Available
Protein binding50-80%
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 eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAcute 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Chlorotrianisene can be decreased when it is combined with 1,10-Phenanthroline.Experimental
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
3,4-DichloroisocoumarinThe serum concentration of Chlorotrianisene can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDEThe serum concentration of Chlorotrianisene can be decreased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
4-AndrostenedioneThe serum concentration of 4-Androstenedione 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
AcenocoumarolChlorotrianisene may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Chlorotrianisene.Approved
AcitretinThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Adapalene.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
AlitretinoinThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Alitretinoin.Approved, Investigational
AlogliptinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Chlorotrianisene can be decreased when it is combined with Alpha-1-proteinase inhibitor.Approved
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Chlorotrianisene.Experimental
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
AmobarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Amobarbital.Approved, Illicit
AmprenavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Amprenavir.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
AncrodChlorotrianisene may decrease the anticoagulant activities of Ancrod.Investigational
AnecortaveThe serum concentration of Anecortave 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
Antithrombin III humanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Antithrombin III human.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Chlorotrianisene.Investigational
ApixabanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Apixaban.Approved
AprepitantThe serum concentration of Chlorotrianisene can be decreased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Chlorotrianisene can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArdeparinChlorotrianisene may decrease the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Armodafinil.Approved, Investigational
ArtemetherThe serum concentration of Chlorotrianisene can be decreased when it is combined with Artemether.Approved
AsunaprevirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Atazanavir.Approved, Investigational
BarbexacloneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Barbital.Illicit
BatimastatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Batimastat.Experimental
BecaplerminChlorotrianisene may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
BeclomethasoneThe serum concentration of Beclomethasone can be increased when it is combined with Chlorotrianisene.Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Chlorotrianisene.Approved, Investigational
BenazeprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Chlorotrianisene can be decreased when it is combined with Benzamidine.Experimental
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
BexaroteneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Bexarotene.Approved, Investigational
BexaroteneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Bexarotene.Approved, Investigational
Bi201335The serum concentration of Chlorotrianisene can be decreased when it is combined with Bi201335.Investigational
BivalirudinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Boceprevir.Approved
BosentanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Bosentan.Approved, Investigational
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Chlorotrianisene.Approved
C1 Esterase Inhibitor (Human)Chlorotrianisene may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Chlorotrianisene may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Chlorotrianisene.Approved
CandoxatrilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Captopril.Approved
CarbamazepineThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Carbamazepine.Approved, Investigational
CelecoxibCelecoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
CertoparinChlorotrianisene may decrease the anticoagulant activities of Certoparin.Approved
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Chlorotrianisene.Approved
CholestyramineThe serum concentration of Chlorotrianisene can be decreased when it is combined with Cholestyramine.Approved
ChymostatinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Chymostatin.Experimental
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Chlorotrianisene.Approved, Investigational
CilastatinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Cilazapril.Approved
Citric AcidChlorotrianisene may decrease the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClobazamThe serum concentration of Chlorotrianisene can be decreased when it is combined with Clobazam.Approved, Illicit
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Chlorotrianisene.Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate 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
CobicistatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Chlorotrianisene can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Chlorotrianisene can be decreased when it is combined with Colestipol.Approved
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Chlorotrianisene.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Chlorotrianisene.Approved, Investigational
Dabigatran etexilateThe serum concentration of Chlorotrianisene can be decreased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Chlorotrianisene can be decreased when it is combined with Dabrafenib.Approved
DalteparinChlorotrianisene may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidChlorotrianisene may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarunavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Darunavir.Approved
dehydroepiandrosterone sulfateThe serum concentration of dehydroepiandrosterone sulfate can be increased when it is combined with Chlorotrianisene.Investigational
DesirudinChlorotrianisene may decrease the anticoagulant activities of Desirudin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Chlorotrianisene.Approved
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
DextranChlorotrianisene may decrease the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Chlorotrianisene may decrease the anticoagulant activities of Dextran 40.Approved
Dextran 70Chlorotrianisene may decrease the anticoagulant activities of Dextran 70.Approved
Dextran 75Chlorotrianisene may decrease the anticoagulant activities of Dextran 75.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
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Chlorotrianisene.Approved
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Chlorotrianisene.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Chlorotrianisene.Approved
DigoxinDigoxin 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
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Chlorotrianisene.Approved
EcabetThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ecabet.Approved, Investigational
Edetic AcidChlorotrianisene may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Elafin.Investigational
ElvitegravirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Elvitegravir.Approved
EnalaprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Chlorotrianisene can be decreased when it is combined with Enalkiren.Experimental
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
Eslicarbazepine acetateThe serum concentration of Chlorotrianisene can be decreased when it is combined with Eslicarbazepine acetate.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
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
ExenatideThe serum concentration of Chlorotrianisene can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Chlorotrianisene can be decreased when it is combined with Felbamate.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Chlorotrianisene.Approved
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
FluindioneChlorotrianisene may decrease the anticoagulant activities of Fluindione.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
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
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.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
FosamprenavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Chlorotrianisene can be decreased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Fosphenytoin.Approved
GabexateThe serum concentration of Chlorotrianisene can be decreased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Geldanamycin.Experimental
GM6001The serum concentration of Chlorotrianisene can be decreased when it is combined with GM6001.Experimental
GriseofulvinThe metabolism of Chlorotrianisene can be increased when combined with Griseofulvin.Approved, Vet Approved
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
HexobarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Hexobarbital.Approved
HirulogThe serum concentration of Chlorotrianisene can be decreased when it is combined with Hirulog.Experimental
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
idraparinuxThe serum concentration of Chlorotrianisene can be decreased when it is combined with idraparinux.Investigational
ImidaprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Imidapril.Investigational
IndinavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Indinavir.Approved
IsoflurophateThe serum concentration of Chlorotrianisene can be decreased when it is combined with Isoflurophate.Approved, Withdrawn
IsotretinoinThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Isotretinoin.Approved
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Chlorotrianisene.Investigational
IxazomibThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ixazomib.Approved
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Chlorotrianisene.Approved, Investigational
LenalidomideChlorotrianisene may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Lepirudin.Approved
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Chlorotrianisene.Approved
LinagliptinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Linagliptin.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
LisinoprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Lisinopril.Approved, Investigational
LopinavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Lopinavir.Approved
LumacaftorThe serum concentration of Chlorotrianisene can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Chlorotrianisene.Approved, Investigational
ME-609The serum concentration of ME-609 can be increased when it is combined with Chlorotrianisene.Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Chlorotrianisene.Approved
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Chlorotrianisene.Vet Approved
MethohexitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Methylphenobarbital.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
MetreleptinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Mifepristone.Approved, Investigational
ModafinilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Moexipril.Approved
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
Mycophenolic acidThe serum concentration of Chlorotrianisene can be decreased when it is combined with Mycophenolic acid.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Chlorotrianisene can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NabumetoneNabumetone may increase the thrombogenic activities of Chlorotrianisene.Approved
NadroparinChlorotrianisene may decrease the anticoagulant activities of Nadroparin.Approved
NafamostatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Nafamostat.Investigational
NafcillinThe metabolism of Chlorotrianisene can be increased when combined with Nafcillin.Approved
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Chlorotrianisene.Investigational
NCX 4016The serum concentration of Chlorotrianisene can be decreased when it is combined with NCX 4016.Investigational
NelfinavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Chlorotrianisene can be decreased when it is combined with Nevirapine.Approved
NitroaspirinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Nitroaspirin.Investigational
Oleoyl estroneThe serum concentration of Oleoyl estrone can be increased when it is combined with Chlorotrianisene.Investigational
OmapatrilatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Omapatrilat.Investigational
OspemifeneThe risk or severity of adverse effects can be increased when Chlorotrianisene is combined with Ospemifene.Approved
OtamixabanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Otamixaban.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Chlorotrianisene.Approved
OxcarbazepineThe serum concentration of Chlorotrianisene can be decreased when it is combined with Oxcarbazepine.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
PentobarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateChlorotrianisene may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PerindoprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Perindopril.Approved
PhenindioneChlorotrianisene may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonChlorotrianisene may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Chlorotrianisene can be decreased when it is combined with Phosphoramidon.Experimental
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Chlorotrianisene.Approved, Nutraceutical
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Chlorotrianisene.Approved
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.Experimental
PrimidoneThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Chlorotrianisene can be decreased when it is combined with Prinomastat.Investigational
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
PrucaloprideThe serum concentration of Chlorotrianisene can be decreased when it is combined with Prucalopride.Approved
QuinaprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Quinapril.Approved, Investigational
RacecadotrilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ramipril.Approved
RemikirenThe serum concentration of Chlorotrianisene can be decreased when it is combined with Remikiren.Approved
ReviparinChlorotrianisene may decrease the anticoagulant activities of Reviparin.Approved
RifabutinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Chlorotrianisene can be decreased when it is combined with Rifapentine.Approved
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Chlorotrianisene.Approved
RitonavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Chlorotrianisene.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Chlorotrianisene.Approved, Investigational
SaquinavirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Chlorotrianisene.Approved, Investigational, Vet Approved
SimeprevirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Sitagliptin.Approved, Investigational
Somatropin recombinantThe therapeutic efficacy of Somatropin recombinant can be decreased when used in combination with Chlorotrianisene.Approved, Investigational
SpiraprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Spirapril.Approved
St. John's WortThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with St. John's Wort.Nutraceutical
SulodexideChlorotrianisene may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of Chlorotrianisene can be decreased when it is combined with Telaprevir.Approved
TemocaprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Temocapril.Experimental, Investigational
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
ThiamylalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Chlorotrianisene can be decreased when it is combined with Thiorphan.Experimental
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with 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
TopiramateThe serum concentration of Chlorotrianisene can be decreased when it is combined with Topiramate.Approved
TrandolaprilThe serum concentration of Chlorotrianisene can be decreased when it is combined with Trandolapril.Approved
Tranexamic AcidChlorotrianisene may increase the thrombogenic activities of Tranexamic Acid.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Chlorotrianisene.Approved, Investigational
TretinoinThe therapeutic efficacy of Chlorotrianisene can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Chlorotrianisene.Approved, Vet Approved
UbenimexThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ulinastatin.Investigational
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.Investigational, Withdrawn
VildagliptinThe serum concentration of Chlorotrianisene can be decreased when it is combined with Vildagliptin.Approved, Investigational
Vitamin CThe serum concentration of Chlorotrianisene can be increased when it is combined with Vitamin C.Approved, Nutraceutical
VoriconazoleThe metabolism of Chlorotrianisene can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinChlorotrianisene may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Chlorotrianisene can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The serum concentration of Chlorotrianisene can be decreased when it is combined with Ym150.Investigational
Food InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesG03CA06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Banner pharmacaps inc
  • Sanofi aventis us llc
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point113-114REM 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Diphenylmethane
  • Phenylpropene
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Chloroalkene
  • Haloalkene
  • Vinyl halide
  • Vinyl chloride
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23