You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameToremifene
Accession NumberDB00539  (APRD00391)
TypeSmall Molecule
GroupsApproved, Investigational
DescriptionA first generation nonsteroidal selective estrogen receptor modulator (SERM) that is structurally related to tamoxifen. Like tamoxifen, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue. [PubChem]
Structure
Thumb
Synonyms
Toremifeno
Toremifenum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FarestonTablet60 mg/1OralG Tx, Inc.1997-06-30Not applicableUs
FarestonTablet60 mgOralOrion Corporation1996-02-14Not applicableEu
FarestonTablet60 mgOralOrion Corporation1996-02-14Not applicableEu
FarestonTablet60 mg/1OralKyowa Kirin, Inc,1997-06-30Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcapodeneNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Toremifene citrate
ThumbNot applicableDBSALT001447
Categories
UNII7NFE54O27T
CAS number89778-26-7
WeightAverage: 405.96
Monoisotopic: 405.18594223
Chemical FormulaC26H28ClNO
InChI KeyXFCLJVABOIYOMF-QPLCGJKRSA-N
InChI
InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-
IUPAC Name
(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine
SMILES
CN(C)CCOC1=CC=C(C=C1)C(=C(\CCCl)C1=CC=CC=C1)\C1=CC=CC=C1
Pharmacology
IndicationFor the treatment of metastatic breast cancer in postmenopausal women with estrogen receptor-positive or receptor-unknown tumors. Toremifene is currently under investigation as a preventative agent for prostate cancer in men with high-grade prostatic intraepithelial neoplasia and no evidence of prostate cancer.
Structured Indications
PharmacodynamicsToremifene is an antineoplastic hormonal agent primarily used in the treatment of advanced breast cancer. Toremifene is a nonsteroidal agent that has demonstrated potent antiestrogenic properties in animal test systems. The antiestrogenic effects may be related to its ability to compete with estrogen for binding sites in target tissues such as breast. Toremifene inhibits the induction of rat mammary carcinoma induced by dimethylbenzanthracene (DMBA) and causes the regression of already established DMBA-induced tumors. In this rat model, Toremifene appears to exert its antitumor effects by binding the estrogen receptors. In cytosols derived from human breast adenocarcinomas, Toremifene competes with estradiol for estrogen receptor protein.
Mechanism of actionToremifene is a nonsteroidal triphenylethylene derivative. Toremifene binds to estrogen receptors and may exert estrogenic, antiestrogenic, or both activities, depending upon the duration of treatment, animal species, gender, target organ, or endpoint selected. The antitumor effect of toremifene in breast cancer is believed to be mainly due to its antiestrogenic effects, in other words, its ability to compete with estrogen for binding sites in the cancer, blocking the growth-stimulating effects of estrogen in the tumor. Toremifene may also inhibit tumor growth through other mechanisms, such as induction of apoptosis, regulation of oncogene expression, and growth factors.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
modulator
HumanP03372 details
Related Articles
AbsorptionWell absorbed
Volume of distribution
  • 580 L
Protein bindingToremifen is primarily bound to albumin (92%), 2% bound to α1-acid glycoprotein, and 6% bound to β1-globulin in the serum.
Metabolism

Hepatic. Mainly by CYP3A4 to N-demethyltoremifene, which exhibits antiestrogenic effects but has weak antitumor potency in vivo.

SubstrateEnzymesProduct
Toremifene
N-desmethyltoremifeneDetails
Route of eliminationToremifene is extensively metabolized, principally by CYP3A4 to N-demethyltoremifene, which is also antiestrogenic but with weak in vivo antitumor potency.
Half life5 days
Clearance
  • 5 L/h
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Toremifene can be increased when it is combined with Abiraterone.Approved
AcenocoumarolToremifene may increase the anticoagulant activities of Acenocoumarol.Approved
AcetaminophenThe serum concentration of Toremifene can be increased when it is combined with Acetaminophen.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Toremifene.Approved
AfatinibThe serum concentration of Toremifene can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Toremifene can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Toremifene can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Toremifene can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Toremifene can be increased when it is combined with Alfentanil.Approved, Illicit
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
AmantadineAmantadine may increase the QTc-prolonging activities of Toremifene.Approved
Aminohippuric acidThe serum concentration of Toremifene can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe risk or severity of adverse effects can be increased when Amiodarone is combined with Toremifene.Approved, Investigational
AmitriptylineAmitriptyline may increase the QTc-prolonging activities of Toremifene.Approved
AmlodipineThe serum concentration of Toremifene can be increased when it is combined with Amlodipine.Approved
AmoxapineAmoxapine may increase the QTc-prolonging activities of Toremifene.Approved
AmprenavirThe serum concentration of Toremifene can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Toremifene can be increased when it is combined with Amsacrine.Approved
AnagrelideAnagrelide may increase the QTc-prolonging activities of Toremifene.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Toremifene.Investigational
ApomorphineApomorphine may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
AprepitantThe serum concentration of Toremifene can be increased when it is combined with Aprepitant.Approved, Investigational
ArformoterolArformoterol may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
Arsenic trioxideToremifene may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherToremifene may increase the QTc-prolonging activities of Artemether.Approved
AsenapineToremifene may increase the QTc-prolonging activities of Asenapine.Approved
AstemizoleThe serum concentration of Toremifene can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe risk or severity of adverse effects can be increased when Atazanavir is combined with Toremifene.Approved, Investigational
AtenololThe serum concentration of Toremifene can be increased when it is combined with Atenolol.Approved
AtomoxetineAtomoxetine may increase the QTc-prolonging activities of Toremifene.Approved
AtorvastatinThe serum concentration of Toremifene can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Toremifene can be increased when it is combined with Azelastine.Approved
AzithromycinAzithromycin may increase the QTc-prolonging activities of Toremifene.Approved
BedaquilineBedaquiline may increase the QTc-prolonging activities of Toremifene.Approved
BendroflumethiazideBendroflumethiazide may increase the hypercalcemic activities of Toremifene.Approved
BenzocaineThe serum concentration of Toremifene can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Toremifene can be increased when it is combined with Bepridil.Approved, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Toremifene.Approved, Investigational
BexaroteneThe serum concentration of Toremifene can be decreased when it is combined with Bexarotene.Approved, Investigational
BiperidenThe serum concentration of Toremifene can be increased when it is combined with Biperiden.Approved
BoceprevirThe risk or severity of adverse effects can be increased when Boceprevir is combined with Toremifene.Approved
BortezomibBortezomib may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
BosentanThe serum concentration of Toremifene can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Toremifene can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Toremifene can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Toremifene can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuserelinBuserelin may increase the QTc-prolonging activities of Toremifene.Approved
BuspironeThe serum concentration of Toremifene can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Toremifene.Approved
CaffeineThe serum concentration of Toremifene can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Toremifene can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Toremifene can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Toremifene can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Toremifene can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Toremifene can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Toremifene can be increased when it is combined with Caspofungin.Approved
CeritinibThe risk or severity of adverse effects can be increased when Ceritinib is combined with Toremifene.Approved
ChloroquineChloroquine may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
ChlorothiazideChlorothiazide may increase the hypercalcemic activities of Toremifene.Approved, Vet Approved
ChlorpromazineChlorpromazine may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
ChlorpropamideThe serum concentration of Toremifene can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Toremifene can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
ChlorthalidoneChlorthalidone may increase the hypercalcemic activities of Toremifene.Approved
CholesterolThe serum concentration of Toremifene can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Toremifene can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Toremifene can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Toremifene can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinCiprofloxacin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
CisaprideToremifene may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Withdrawn
CitalopramCitalopram may increase the QTc-prolonging activities of Toremifene.Approved
ClarithromycinThe risk or severity of adverse effects can be increased when Clarithromycin is combined with Toremifene.Approved
ClemastineThe metabolism of Toremifene can be decreased when combined with Clemastine.Approved
ClofazimineThe serum concentration of Toremifene can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineClomipramine may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
ClotrimazoleThe metabolism of Toremifene can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineClozapine may increase the QTc-prolonging activities of Toremifene.Approved
CobicistatThe risk or severity of adverse effects can be increased when Cobicistat is combined with Toremifene.Approved
ColchicineThe serum concentration of Toremifene can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Toremifene can be increased when it is combined with Colforsin.Experimental
ConivaptanThe serum concentration of Toremifene can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibCrizotinib may increase the QTc-prolonging activities of Toremifene.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Toremifene.Approved, Investigational
CyclosporineThe metabolism of Toremifene can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Toremifene can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Toremifene can be decreased when it is combined with Dabrafenib.Approved
DaclatasvirThe serum concentration of Toremifene can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Toremifene can be increased when it is combined with Dactinomycin.Approved
DarunavirThe risk or severity of adverse effects can be increased when Darunavir is combined with Toremifene.Approved
DasatinibThe serum concentration of Toremifene can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Toremifene can be decreased when it is combined with Daunorubicin.Approved
DeferasiroxThe serum concentration of Toremifene can be decreased when it is combined with Deferasirox.Approved, Investigational
DegarelixDegarelix may increase the QTc-prolonging activities of Toremifene.Approved
DelavirdineThe metabolism of Toremifene can be decreased when combined with Delavirdine.Approved
DesfluraneDesflurane may increase the QTc-prolonging activities of Toremifene.Approved
DesipramineDesipramine may increase the QTc-prolonging activities of Toremifene.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Toremifene.Approved
DesloratadineThe serum concentration of Toremifene can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Toremifene can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Toremifene can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Toremifene can be increased when it is combined with Diclofenac.Approved, Vet Approved
DicoumarolToremifene may increase the anticoagulant activities of Dicoumarol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Toremifene.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Toremifene.Approved
DihydroergotamineThe metabolism of Toremifene can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Toremifene can be decreased when combined with Diltiazem.Approved
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Toremifene.Approved
DipyridamoleThe serum concentration of Toremifene can be increased when it is combined with Dipyridamole.Approved
DisopyramideDisopyramide may increase the QTc-prolonging activities of Toremifene.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Toremifene.Approved, Investigational
DofetilideDofetilide may increase the QTc-prolonging activities of Toremifene.Approved
DolasetronDolasetron may increase the QTc-prolonging activities of Toremifene.Approved
DomperidoneToremifene may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxazosinThe serum concentration of Toremifene can be increased when it is combined with Doxazosin.Approved
DoxepinDoxepin may increase the QTc-prolonging activities of Toremifene.Approved
DoxorubicinThe serum concentration of Toremifene can be decreased when it is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Toremifene can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Toremifene can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneToremifene may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolDroperidol may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
EfavirenzThe serum concentration of Toremifene can be decreased when it is combined with Efavirenz.Approved, Investigational
ElbasvirThe serum concentration of Toremifene can be increased when it is combined with Elbasvir.Approved
EliglustatToremifene may increase the QTc-prolonging activities of Eliglustat.Approved
EnalaprilThe serum concentration of Toremifene can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Toremifene can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Toremifene can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Toremifene can be increased when it is combined with Ergotamine.Approved
EribulinEribulin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
ErythromycinErythromycin may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
EscitalopramToremifene may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Toremifene can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstramustineThe serum concentration of Toremifene can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Toremifene can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Toremifene can be decreased when it is combined with Estrone.Approved
Ethyl biscoumacetateToremifene may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtoposideThe serum concentration of Toremifene can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Toremifene can be decreased when it is combined with Etravirine.Approved
EzogabineEzogabine may increase the QTc-prolonging activities of Toremifene.Approved
FamotidineFamotidine may increase the QTc-prolonging activities of Toremifene.Approved
FelbamateFelbamate may increase the QTc-prolonging activities of Toremifene.Approved
FelodipineThe serum concentration of Toremifene can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Toremifene can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Toremifene can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Toremifene can be increased when it is combined with Fidaxomicin.Approved
FingolimodFingolimod may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
FlecainideFlecainide may increase the QTc-prolonging activities of Toremifene.Approved, Withdrawn
FluconazoleFluconazole may increase the QTc-prolonging activities of Toremifene.Approved
FluindioneToremifene may increase the anticoagulant activities of Fluindione.Investigational
FluoxetineFluoxetine may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
FlupentixolToremifene may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Toremifene can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Toremifene can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe metabolism of Toremifene can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolFormoterol may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
FosamprenavirThe metabolism of Toremifene can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Toremifene can be increased when it is combined with Fosaprepitant.Approved
FoscarnetFoscarnet may increase the QTc-prolonging activities of Toremifene.Approved
FosphenytoinThe serum concentration of Toremifene can be decreased when it is combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Toremifene can be increased when it is combined with Fusidic Acid.Approved
Gadobenic acidGadobenic acid may increase the QTc-prolonging activities of Toremifene.Approved
GalantamineGalantamine may increase the QTc-prolonging activities of Toremifene.Approved
GefitinibThe serum concentration of Toremifene can be increased when it is combined with Gefitinib.Approved, Investigational
GemifloxacinGemifloxacin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
GenisteinThe serum concentration of Toremifene can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Toremifene can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Toremifene can be increased when it is combined with Glycerol.Experimental
GoserelinGoserelin may increase the QTc-prolonging activities of Toremifene.Approved
Gramicidin DThe serum concentration of Toremifene can be increased when it is combined with Gramicidin D.Approved
GranisetronGranisetron may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
GrepafloxacinThe serum concentration of Toremifene can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolHaloperidol may increase the QTc-prolonging activities of Toremifene.Approved
HistrelinHistrelin may increase the QTc-prolonging activities of Toremifene.Approved
HydrochlorothiazideHydrochlorothiazide may increase the hypercalcemic activities of Toremifene.Approved, Vet Approved
HydrocortisoneThe serum concentration of Toremifene can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
HydroflumethiazideHydroflumethiazide may increase the hypercalcemic activities of Toremifene.Approved
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Toremifene.Approved
IbandronateIbandronate may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
IbutilideIbutilide may increase the QTc-prolonging activities of Toremifene.Approved
IdelalisibThe serum concentration of Toremifene can be increased when it is combined with Idelalisib.Approved
IloperidoneToremifene may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe metabolism of Toremifene can be decreased when combined with Imatinib.Approved
ImipramineImipramine may increase the QTc-prolonging activities of Toremifene.Approved
IndacaterolIndacaterol may increase the QTc-prolonging activities of Toremifene.Approved
IndapamideIndapamide may increase the hypercalcemic activities of Toremifene.Approved
IndinavirThe risk or severity of adverse effects can be increased when Indinavir is combined with Toremifene.Approved
IndomethacinThe serum concentration of Toremifene can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe metabolism of Toremifene can be decreased when combined with Isavuconazonium.Approved, Investigational
IsofluraneIsoflurane may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
IsradipineIsradipine may increase the QTc-prolonging activities of Toremifene.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Itraconazole is combined with Toremifene.Approved, Investigational
IvabradineIvabradine may increase the QTc-prolonging activities of Toremifene.Approved
IvacaftorThe serum concentration of Toremifene can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Toremifene can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Toremifene can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Toremifene.Approved, Investigational
LansoprazoleThe serum concentration of Toremifene can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibLapatinib may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
LenvatinibLenvatinib may increase the QTc-prolonging activities of Toremifene.Approved
LeuprolideLeuprolide may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
LevofloxacinLevofloxacin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
LevothyroxineThe serum concentration of Toremifene can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Toremifene can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Toremifene can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Toremifene can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Toremifene can be increased when it is combined with Lisinopril.Approved, Investigational
LithiumLithium may increase the QTc-prolonging activities of Toremifene.Approved
LomitapideThe serum concentration of Toremifene can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Toremifene can be increased when it is combined with Loperamide.Approved
LopinavirThe risk or severity of adverse effects can be increased when Lopinavir is combined with Toremifene.Approved
LoratadineThe serum concentration of Toremifene can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Toremifene can be increased when it is combined with Losartan.Approved
LovastatinThe metabolism of Toremifene can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Toremifene can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Toremifene can be decreased when it is combined with Lumacaftor.Approved
LumefantrineToremifene may increase the QTc-prolonging activities of Lumefantrine.Approved
MaprotilineMaprotiline may increase the QTc-prolonging activities of Toremifene.Approved
MebendazoleThe serum concentration of Toremifene can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineMefloquine may increase the QTc-prolonging activities of Toremifene.Approved
Megestrol acetateThe serum concentration of Toremifene can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Toremifene can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneMethadone may increase the QTc-prolonging activities of Toremifene.Approved
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Toremifene.Approved
MethyclothiazideMethyclothiazide may increase the hypercalcemic activities of Toremifene.Approved
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
MetolazoneMetolazone may increase the hypercalcemic activities of Toremifene.Approved
MetoprololThe serum concentration of Toremifene can be increased when it is combined with Metoprolol.Approved, Investigational
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Toremifene.Approved
MexiletineThe metabolism of Toremifene can be decreased when combined with Mexiletine.Approved
MibefradilThe serum concentration of Toremifene can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Toremifene can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Toremifene can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneMifepristone may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
MirabegronMirabegron may increase the QTc-prolonging activities of Toremifene.Approved
MirtazapineMirtazapine may increase the QTc-prolonging activities of Toremifene.Approved
MitomycinThe serum concentration of Toremifene can be increased when it is combined with Mitomycin.Approved
MitotaneThe serum concentration of Toremifene can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Toremifene can be decreased when it is combined with Mitoxantrone.Approved, Investigational
ModafinilThe serum concentration of Toremifene can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilMoexipril may increase the QTc-prolonging activities of Toremifene.Approved
MorphineThe serum concentration of Toremifene can be increased when it is combined with Morphine.Approved, Investigational
MoxifloxacinMoxifloxacin may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
NafcillinThe serum concentration of Toremifene can be decreased when it is combined with Nafcillin.Approved
NaltrexoneThe serum concentration of Toremifene can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Toremifene can be increased when it is combined with Naringenin.Experimental
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Toremifene.Approved, Withdrawn
NelfinavirThe risk or severity of adverse effects can be increased when Nelfinavir is combined with Toremifene.Approved
NeostigmineThe serum concentration of Toremifene can be increased when it is combined with Neostigmine.Approved, Vet Approved
NetupitantThe serum concentration of Toremifene can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Toremifene can be decreased when it is combined with Nevirapine.Approved
NicardipineNicardipine may increase the QTc-prolonging activities of Toremifene.Approved
NifedipineThe serum concentration of Toremifene can be decreased when it is combined with Nifedipine.Approved
NilotinibToremifene may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Toremifene can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Toremifene can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Toremifene can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Toremifene can be decreased when it is combined with Norethisterone.Approved
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Toremifene.Approved
NortriptylineNortriptyline may increase the QTc-prolonging activities of Toremifene.Approved
OctreotideOctreotide may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
OfloxacinOfloxacin may increase the QTc-prolonging activities of Toremifene.Approved
OlanzapineOlanzapine may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
OlaparibThe metabolism of Toremifene can be decreased when combined with Olaparib.Approved
OlodaterolOlodaterol may increase the QTc-prolonging activities of Toremifene.Approved
OmeprazoleThe serum concentration of Toremifene can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronOndansetron may increase the QTc-prolonging activities of Toremifene.Approved
OsimertinibThe serum concentration of Toremifene can be increased when it is combined with Osimertinib.Approved
OspemifeneThe risk or severity of adverse effects can be increased when Toremifene is combined with Ospemifene.Approved
OuabainOuabain may decrease the cardiotoxic activities of Toremifene.Approved
OxytocinOxytocin may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
P-NitrophenolThe serum concentration of Toremifene can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Toremifene.Approved, Vet Approved
PalbociclibThe serum concentration of Toremifene can be increased when it is combined with Palbociclib.Approved
PaliperidoneToremifene may increase the QTc-prolonging activities of Paliperidone.Approved
Palmitic AcidThe serum concentration of Toremifene can be increased when it is combined with Palmitic Acid.Experimental
PanobinostatPanobinostat may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
PantoprazoleThe serum concentration of Toremifene can be increased when it is combined with Pantoprazole.Approved
ParoxetineParoxetine may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
PasireotidePasireotide may increase the QTc-prolonging activities of Toremifene.Approved
PazopanibPazopanib may increase the QTc-prolonging activities of Toremifene.Approved
Peginterferon alfa-2bThe serum concentration of Toremifene can be increased when it is combined with Peginterferon alfa-2b.Approved
PentamidinePentamidine may increase the QTc-prolonging activities of Toremifene.Approved
PentobarbitalThe serum concentration of Toremifene can be decreased when it is combined with Pentobarbital.Approved, Vet Approved
PerflutrenPerflutren may increase the QTc-prolonging activities of Toremifene.Approved
PerindoprilThe serum concentration of Toremifene can be increased when it is combined with Perindopril.Approved
PhenindioneToremifene may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe serum concentration of Toremifene can be decreased when it is combined with Phenobarbital.Approved
PhenprocoumonToremifene may increase the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe serum concentration of Toremifene can be decreased when it is combined with Phenytoin.Approved, Vet Approved
PimozideToremifene may increase the QTc-prolonging activities of Pimozide.Approved
Platelet Activating FactorThe serum concentration of Toremifene can be decreased when it is combined with Platelet Activating Factor.Experimental
PolythiazidePolythiazide may increase the hypercalcemic activities of Toremifene.Approved
PonatinibThe serum concentration of Toremifene can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Posaconazole is combined with Toremifene.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Toremifene can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Toremifene can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Toremifene can be increased when it is combined with Prednisone.Approved, Vet Approved
PrimaquinePrimaquine may increase the QTc-prolonging activities of Toremifene.Approved
PrimidoneThe serum concentration of Toremifene can be decreased when it is combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Toremifene can be increased when it is combined with Probenecid.Approved
ProcainamideToremifene may increase the QTc-prolonging activities of Procainamide.Approved
ProgesteroneThe serum concentration of Toremifene can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromazinePromazine may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
PromethazinePromethazine may increase the QTc-prolonging activities of Toremifene.Approved
PropafenonePropafenone may increase the QTc-prolonging activities of Toremifene.Approved
PropofolPropofol may increase the QTc-prolonging activities of Toremifene.Approved, Investigational, Vet Approved
PropranololThe serum concentration of Toremifene can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineProtriptyline may increase the QTc-prolonging activities of Toremifene.Approved
QuercetinThe serum concentration of Toremifene can be increased when it is combined with Quercetin.Experimental
QuetiapineToremifene may increase the QTc-prolonging activities of Quetiapine.Approved
QuinacrineThe serum concentration of Toremifene can be increased when it is combined with Quinacrine.Approved
QuinethazoneQuinethazone may increase the hypercalcemic activities of Toremifene.Approved
QuinidineToremifene may increase the QTc-prolonging activities of Quinidine.Approved
QuinineQuinine may increase the QTc-prolonging activities of Toremifene.Approved
RanitidineThe serum concentration of Toremifene can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Toremifene can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Toremifene can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Toremifene can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Toremifene can be decreased when it is combined with Reserpine.Approved
RifabutinThe serum concentration of Toremifene can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Toremifene can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Toremifene can be decreased when it is combined with Rifapentine.Approved
RilpivirineRilpivirine may increase the QTc-prolonging activities of Toremifene.Approved
RisperidoneRisperidone may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
RitonavirThe risk or severity of adverse effects can be increased when Ritonavir is combined with Toremifene.Approved, Investigational
RolapitantThe serum concentration of Toremifene can be increased when it is combined with Rolapitant.Approved
RopiniroleThe metabolism of Toremifene can be decreased when combined with Ropinirole.Approved, Investigational
SalbutamolSalbutamol may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
SalmeterolSalmeterol may increase the QTc-prolonging activities of Toremifene.Approved
SaquinavirThe risk or severity of adverse effects can be increased when Saquinavir is combined with Toremifene.Approved, Investigational
ScopolamineThe serum concentration of Toremifene can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Toremifene can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineSertraline may increase the QTc-prolonging activities of Toremifene.Approved
SevofluraneSevoflurane may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
SildenafilThe metabolism of Toremifene can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Toremifene can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Toremifene can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Toremifene can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Toremifene can be decreased when it is combined with Sirolimus.Approved, Investigational
SolifenacinSolifenacin may increase the QTc-prolonging activities of Toremifene.Approved
SorafenibSorafenib may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
SotalolSotalol may increase the QTc-prolonging activities of Toremifene.Approved
SpironolactoneThe serum concentration of Toremifene can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Toremifene can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Toremifene can be increased when it is combined with Staurosporine.Experimental
StiripentolThe serum concentration of Toremifene can be increased when it is combined with Stiripentol.Approved
StreptozocinThe serum concentration of Toremifene can be decreased when it is combined with Streptozocin.Approved
SugammadexThe therapeutic efficacy of Sugammadex can be decreased when used in combination with Toremifene.Approved
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Toremifene.Approved
SulfinpyrazoneThe serum concentration of Toremifene can be increased when it is combined with Sulfinpyrazone.Approved
SulfisoxazoleSulfisoxazole may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
SumatriptanThe serum concentration of Toremifene can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibSunitinib may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TacrineThe serum concentration of Toremifene can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Toremifene can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenTamoxifen may increase the QTc-prolonging activities of Toremifene.Approved
Taurocholic AcidThe serum concentration of Toremifene can be increased when it is combined with Taurocholic Acid.Experimental
TelaprevirThe risk or severity of adverse effects can be increased when Telaprevir is combined with Toremifene.Approved
TelavancinTelavancin may increase the QTc-prolonging activities of Toremifene.Approved
TelithromycinThe risk or severity of adverse effects can be increased when Telithromycin is combined with Toremifene.Approved
TelmisartanThe serum concentration of Toremifene can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Toremifene can be increased when it is combined with Temsirolimus.Approved
TenofovirThe metabolism of Toremifene can be decreased when combined with Tenofovir.Approved, Investigational
TerazosinThe serum concentration of Toremifene can be increased when it is combined with Terazosin.Approved
TerbutalineTerbutaline may increase the QTc-prolonging activities of Toremifene.Approved
TerfenadineThe serum concentration of Toremifene can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe serum concentration of Toremifene can be decreased when it is combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Toremifene can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Toremifene can be increased when it is combined with Testosterone.Approved, Investigational
TetrabenazineToremifene may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe metabolism of Toremifene can be decreased when combined with Theophylline.Approved
ThioridazineToremifene may increase the QTc-prolonging activities of Thioridazine.Approved
ThiothixeneThiothixene may increase the QTc-prolonging activities of Toremifene.Approved
TicagrelorThe serum concentration of Toremifene can be increased when it is combined with Ticagrelor.Approved
TiclopidineThe metabolism of Toremifene can be decreased when combined with Ticlopidine.Approved
TizanidineTizanidine may increase the QTc-prolonging activities of Toremifene.Approved
TocilizumabThe serum concentration of Toremifene can be decreased when it is combined with Tocilizumab.Approved
TolterodineTolterodine may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TolvaptanThe serum concentration of Toremifene can be increased when it is combined with Tolvaptan.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Toremifene.Approved, Investigational
TrazodoneTrazodone may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TreprostinilTreprostinil may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
TrichlormethiazideTrichlormethiazide may increase the hypercalcemic activities of Toremifene.Approved, Vet Approved
TrifluoperazineThe serum concentration of Toremifene can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Toremifene can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimTrimethoprim may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
TrimipramineTrimipramine may increase the QTc-prolonging activities of Toremifene.Approved
TriptorelinTriptorelin may increase the QTc-prolonging activities of Toremifene.Approved, Vet Approved
TroleandomycinThe serum concentration of Toremifene can be increased when it is combined with Troleandomycin.Approved
VandetanibToremifene may increase the QTc-prolonging activities of Vandetanib.Approved
VardenafilVardenafil may increase the QTc-prolonging activities of Toremifene.Approved
VemurafenibThe serum concentration of Toremifene can be increased when it is combined with Vemurafenib.Approved
VenlafaxineVenlafaxine may increase the QTc-prolonging activities of Toremifene.Approved
VerapamilThe metabolism of Toremifene can be decreased when combined with Verapamil.Approved
VilanterolVilanterol may increase the QTc-prolonging activities of Toremifene.Approved
VinblastineThe serum concentration of Toremifene can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Toremifene can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Toremifene can be increased when it is combined with Vinorelbine.Approved, Investigational
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Toremifene.Approved, Investigational
VorinostatVorinostat may increase the QTc-prolonging activities of Toremifene.Approved, Investigational
WarfarinToremifene may increase the anticoagulant activities of Warfarin.Approved
ZimelidineThe serum concentration of Toremifene can be increased when it is combined with Zimelidine.Withdrawn
ZiprasidoneZiprasidone may increase the QTc-prolonging activities of Toremifene.Approved
ZuclopenthixolToremifene may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food InteractionsNot Available
References
Synthesis Reference

Reijo Toivola, Tuomas Huuhtanen, “Toremifene crystallization method.” U.S. Patent US20070093556, issued April 26, 2007.

US20070093556
General References
  1. Price N, Sartor O, Hutson T, Mariani S: Role of 5a-reductase inhibitors and selective estrogen receptor modulators as potential chemopreventive agents for prostate cancer. Clin Prostate Cancer. 2005 Mar;3(4):211-4. [PubMed:15882476 ]
  2. Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [PubMed:16503765 ]
  3. Thompson IM: Chemoprevention of prostate cancer: agents and study designs. J Urol. 2007 Sep;178(3 Pt 2):S9-S13. Epub 2007 Jul 20. [PubMed:17644117 ]
  4. Ariazi EA, Ariazi JL, Cordera F, Jordan VC: Estrogen receptors as therapeutic targets in breast cancer. Curr Top Med Chem. 2006;6(3):181-202. [PubMed:16515478 ]
  5. Musa MA, Khan MO, Cooperwood JS: Medicinal chemistry and emerging strategies applied to the development of selective estrogen receptor modulators (SERMs). Curr Med Chem. 2007;14(11):1249-61. [PubMed:17504144 ]
External Links
ATC CodesL02BA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7488
Caco-2 permeable+0.8266
P-glycoprotein substrateSubstrate0.7067
P-glycoprotein inhibitor IInhibitor0.79
P-glycoprotein inhibitor IINon-inhibitor0.5917
Renal organic cation transporterInhibitor0.7552
CYP450 2C9 substrateNon-substrate0.7502
CYP450 2D6 substrateNon-substrate0.759
CYP450 3A4 substrateSubstrate0.7574
CYP450 1A2 substrateInhibitor0.8683
CYP450 2C9 inhibitorNon-inhibitor0.882
CYP450 2D6 inhibitorInhibitor0.7217
CYP450 2C19 inhibitorNon-inhibitor0.7443
CYP450 3A4 inhibitorNon-inhibitor0.8824
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5128
Ames testNon AMES toxic0.7545
CarcinogenicityNon-carcinogens0.616
BiodegradationNot ready biodegradable0.9601
Rat acute toxicity2.3467 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7708
hERG inhibition (predictor II)Inhibitor0.5086
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Gtx inc
Packagers
Dosage forms
FormRouteStrength
TabletOral60 mg/1
TabletOral60 mg
Prices
Unit descriptionCostUnit
Fareston 60 mg tablet11.84USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4696949 No1992-09-292009-09-29Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point108-110 °CNot Available
logP6.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000409 mg/mLALOGPS
logP5.65ALOGPS
logP6.27ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.41 m3·mol-1ChemAxon
Polarizability46.49 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
  • Phenol ether
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
modulator
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. Locci P, Bellocchio S, Lilli C, Marinucci L, Cagini L, Baroni T, Giustozzi G, Balducci C, Becchetti E: Synthesis and secretion of transforming growth factor-beta1 by human desmoid fibroblast cell line and its modulation by toremifene. J Interferon Cytokine Res. 2001 Nov;21(11):961-70. [PubMed:11747628 ]
  2. Liu X, Pisha E, Tonetti DA, Yao D, Li Y, Yao J, Burdette JE, Bolton JL: Antiestrogenic and DNA damaging effects induced by tamoxifen and toremifene metabolites. Chem Res Toxicol. 2003 Jul;16(7):832-7. [PubMed:12870885 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  4. Jones KL, Buzdar AU: A review of adjuvant hormonal therapy in breast cancer. Endocr Relat Cancer. 2004 Sep;11(3):391-406. [PubMed:15369444 ]
  5. Shelly W, Draper MW, Krishnan V, Wong M, Jaffe RB: Selective estrogen receptor modulators: an update on recent clinical findings. Obstet Gynecol Surv. 2008 Mar;63(3):163-81. doi: 10.1097/OGX.0b013e31816400d7. [PubMed:18279543 ]
  6. Gennari L, Merlotti D, Valleggi F, Martini G, Nuti R: Selective estrogen receptor modulators for postmenopausal osteoporosis: current state of development. Drugs Aging. 2007;24(5):361-79. [PubMed:17503894 ]
  7. Lewis-Wambi JS, Jordan VC: Treatment of Postmenopausal Breast Cancer with Selective Estrogen Receptor Modulators (SERMs). Breast Dis. 2005-2006;24:93-105. [PubMed:16917142 ]
  8. Ariazi EA, Ariazi JL, Cordera F, Jordan VC: Estrogen receptors as therapeutic targets in breast cancer. Curr Top Med Chem. 2006;6(3):181-202. [PubMed:16515478 ]
  9. Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [PubMed:16503765 ]
  10. Goldstein LJ: Controversies in adjuvant endocrine treatment of premenopausal women. Clin Breast Cancer. 2006 Feb;6 Suppl 2:S36-40. [PubMed:16595024 ]
  11. Smith MR: Treatment-related osteoporosis in men with prostate cancer. Clin Cancer Res. 2006 Oct 15;12(20 Pt 2):6315s-6319s. [PubMed:17062721 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Taneja SS, Smith MR, Dalton JT, Raghow S, Barnette G, Steiner M, Veverka KA: Toremifene--a promising therapy for the prevention of prostate cancer and complications of androgen deprivation therapy. Expert Opin Investig Drugs. 2006 Mar;15(3):293-305. [PubMed:16503765 ]
  2. Kivisto KT, Villikka K, Nyman L, Anttila M, Neuvonen PJ: Tamoxifen and toremifene concentrations in plasma are greatly decreased by rifampin. Clin Pharmacol Ther. 1998 Dec;64(6):648-54. [PubMed:9871429 ]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23