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Identification
NameEstramustine
Accession NumberDB01196  (APRD00625)
TypeSmall Molecule
GroupsApproved
DescriptionA nitrogen mustard linked to estradiol, usually as phosphate; used to treat prostatic neoplasms; also has radiation protective properties. [PubChem]
Structure
Thumb
Synonyms
17beta-Estradiol 3-(bis(2-chloroethyl)carbamate)
17β-Estradiol 3-(bis(2-chloroethyl)carbamate)
Estradiol 3-(N,N-bis(2-chloroethyl)carbamate)
Estramustina
Estramustine
Estramustinum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EmcytCapsule140 mg/1OralPharmacia and Upjohn Company1992-01-01Not applicableUs
EmcytCapsule140 mgOralPfizer Canada Inc1995-12-31Not applicableCanada
Emcyt Cap 140mgCapsule140 mgOralKabi Pharmacia Canada Inc.1993-12-311996-09-10Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EstracitNot Available
EstracytPfizer
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Estramustin sodium phosphate
Thumb
  • InChI Key: FRPJXPJMRWBBIH-UHFFFAOYNA-N
  • Monoisotopic Mass: 439.168099277
  • Average Mass: 440.403
DBSALT000845
Categories
UNII35LT29625A
CAS number2998-57-4
WeightAverage: 440.403
Monoisotopic: 439.168099277
Chemical FormulaC23H31Cl2NO3
InChI KeyFRPJXPJMRWBBIH-RBRWEJTLSA-N
InChI
InChI=1S/C23H31Cl2NO3/c1-23-9-8-18-17-5-3-16(29-22(28)26(12-10-24)13-11-25)14-15(17)2-4-19(18)20(23)6-7-21(23)27/h3,5,14,18-21,27H,2,4,6-13H2,1H3/t18-,19-,20+,21+,23+/m1/s1
IUPAC Name
(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl N,N-bis(2-chloroethyl)carbamate
SMILES
[H][C@@]12CC[[email protected]](O)[C@@]1(C)CC[C@]1([H])C3=CC=C(OC(=O)N(CCCl)CCCl)C=C3CC[C@@]21[H]
Pharmacology
IndicationFor the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate
Structured Indications
PharmacodynamicsEstramustine is an antineoplastic agent indicated in the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate. Estramustine is a combination of estradiol with nitrogen mustard. In vivo, the nitrogen-mustard moiety becomes active and participates in alkylation of DNA or other cellular components.. This causes DNA damage in rapidly dividing cancerous cells leading to cell death and ideally, tumor shrinkage.
Mechanism of actionEstramustine is a derivative of estradiol with a nitrogen mustard moiety. This gives it alkylating properties. In vivo, the nitrogen mustard component is active and can alklyate DNA and other cellular components (such as tubulin components) of rapidly dividing cells. This causes DNA strandbreaks or misscoding events. This leads to apoptosis and cell death. Also, due to the drugs estrogen component, it can bind more selectively to active estrogen receptors.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptor betaProteinyes
other/unknown
HumanQ92731 details
Estrogen receptorProteinyes
agonist
HumanP03372 details
Microtubule-associated protein 2Proteinyes
antagonist
HumanP11137 details
Microtubule-associated protein 1AProteinyes
antagonist
HumanP78559 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationThe metabolic urinary patterns of the estradiol moiety of estramustine phosphate and estradiol itself are very similar, although the metabolites derived from estramustine phosphate are excreted at a slower rate.
Half life20 hours
ClearanceNot Available
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
1,10-PhenanthrolineThe serum concentration of Estramustine can be decreased when it is combined with 1,10-Phenanthroline.Experimental
3,4-DichloroisocoumarinThe serum concentration of Estramustine can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDEThe serum concentration of Estramustine can be decreased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Estramustine.Approved
AcenocoumarolEstramustine may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Estramustine.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Estramustine.Approved
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Estramustine.Approved, Vet Approved
AcitretinThe therapeutic efficacy of Estramustine can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Estramustine can be decreased when used in combination with Adapalene.Approved
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Estramustine.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Estramustine.Experimental
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Estramustine.Approved, Investigational
AlogliptinThe serum concentration of Estramustine can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Estramustine can be decreased when it is combined with Alpha-1-proteinase inhibitor.Approved
ALT-110The risk or severity of adverse effects can be increased when Estramustine is combined with ALT-110.Investigational
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Estramustine.Approved, Investigational
AmiodaroneThe metabolism of Estramustine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Estramustine.Approved
AmobarbitalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Amobarbital.Approved, Illicit
AmprenavirThe serum concentration of Estramustine can be decreased when it is combined with Amprenavir.Approved
Antithrombin III humanThe serum concentration of Estramustine can be decreased when it is combined with Antithrombin III human.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Estramustine.Investigational
ApixabanThe serum concentration of Estramustine can be decreased when it is combined with Apixaban.Approved
AprepitantThe serum concentration of Estramustine can be decreased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Estramustine can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArgatrobanThe serum concentration of Estramustine can be decreased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe serum concentration of Estramustine can be decreased when it is combined with Armodafinil.Approved, Investigational
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Estramustine.Approved, Investigational
ArtemetherThe serum concentration of Estramustine can be decreased when it is combined with Artemether.Approved
AsunaprevirThe serum concentration of Estramustine can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe metabolism of Estramustine can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Atenolol can be increased when it is combined with Estramustine.Approved
AtomoxetineThe metabolism of Estramustine can be decreased when combined with Atomoxetine.Approved
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Estramustine.Approved, Investigational
BarbexacloneThe therapeutic efficacy of Estramustine can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Barbital.Illicit
BatimastatThe serum concentration of Estramustine can be decreased when it is combined with Batimastat.Experimental
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Estramustine.Investigational
BenazeprilThe serum concentration of Estramustine can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Estramustine can be decreased when it is combined with Benzamidine.Experimental
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Estramustine.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Estramustine.Approved, Investigational
BexaroteneThe serum concentration of Estramustine can be decreased when it is combined with Bexarotene.Approved, Investigational
Bi201335The serum concentration of Estramustine can be decreased when it is combined with Bi201335.Investigational
BivalirudinThe serum concentration of Estramustine can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Estramustine can be decreased when it is combined with Boceprevir.Approved
BortezomibThe metabolism of Estramustine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Estramustine can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Estramustine.Approved
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Estramustine.Approved
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Estramustine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Estramustine.Approved
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Estramustine.Approved
CalciumCalcium can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Nutraceutical
Calcium AcetateCalcium Acetate can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium carbonateCalcium carbonate can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium ChlorideCalcium Chloride can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium citrateCalcium citrate can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium glubionateCalcium glubionate can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium GluceptateCalcium Gluceptate can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium gluconateCalcium gluconate can cause a decrease in the absorption of Estramustine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Estramustine.Experimental
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Estramustine.Approved
CandoxatrilThe serum concentration of Estramustine can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Estramustine can be decreased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Estramustine can be decreased when it is combined with Captopril.Approved
CarbamazepineThe therapeutic efficacy of Estramustine can be decreased when used in combination with Carbamazepine.Approved, Investigational
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Estramustine.Approved
CDX-110The risk or severity of adverse effects can be increased when Estramustine is combined with CDX-110.Investigational
CeritinibThe serum concentration of Estramustine can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Estramustine.Withdrawn
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Estramustine.Approved, Vet Approved
CholestyramineThe serum concentration of Estramustine can be decreased when it is combined with Cholestyramine.Approved
ChymostatinThe serum concentration of Estramustine can be decreased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Estramustine can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Estramustine can be decreased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Estramustine.Approved
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Estramustine.Approved, Investigational
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Estramustine.Approved
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Estramustine.Approved
ClarithromycinThe metabolism of Estramustine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Estramustine can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Estramustine can be decreased when it is combined with Clobazam.Approved, Illicit
ClodronateThe serum concentration of Estramustine can be increased when it is combined with Clodronate.Approved, Investigational, Vet Approved
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Estramustine.Approved, Investigational
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Estramustine.Approved
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Estramustine.Approved, Nutraceutical
ClotrimazoleThe metabolism of Estramustine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Estramustine.Approved
CobicistatThe serum concentration of Estramustine can be decreased when it is combined with Cobicistat.Approved
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Estramustine.Approved
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Estramustine.Approved
ColesevelamThe serum concentration of Estramustine can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Estramustine can be decreased when it is combined with Colestipol.Approved
ConivaptanThe serum concentration of Estramustine can be increased when it is combined with Conivaptan.Approved, Investigational
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Estramustine.Approved
CrizotinibThe metabolism of Estramustine can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Estramustine.Approved, Investigational
CyclosporineThe metabolism of Estramustine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be increased when Dabigatran etexilate is used in combination with Estramustine.Approved
DabrafenibThe serum concentration of Estramustine can be decreased when it is combined with Dabrafenib.Approved
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Estramustine.Approved
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Estramustine.Approved
DarunavirThe metabolism of Estramustine can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Estramustine can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Estramustine.Approved
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Estramustine.Approved
DeferasiroxThe serum concentration of Estramustine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Estramustine can be decreased when combined with Delavirdine.Approved
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Estramustine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Estramustine.Approved
DexamethasoneThe serum concentration of Estramustine can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Estramustine.Approved, Illicit, Vet Approved
DicoumarolEstramustine may decrease the anticoagulant activities of Dicoumarol.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Estramustine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Estramustine.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Estramustine.Approved
DihydroergotamineThe metabolism of Estramustine can be decreased when combined with Dihydroergotamine.Approved
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Estramustine.Illicit
DiltiazemThe metabolism of Estramustine can be decreased when combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Estramustine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Estramustine.Approved, Investigational
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Estramustine.Approved, Investigational, Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Estramustine.Approved, Investigational
DoxycyclineThe metabolism of Estramustine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Estramustine can be decreased when combined with Dronedarone.Approved
EcabetThe serum concentration of Estramustine can be decreased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Estramustine.Approved
EfavirenzThe serum concentration of Estramustine can be decreased when it is combined with Efavirenz.Approved, Investigational
ElafinThe serum concentration of Estramustine can be decreased when it is combined with Elafin.Investigational
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Estramustine.Approved, Investigational
ElvitegravirThe serum concentration of Estramustine can be decreased when it is combined with Elvitegravir.Approved
EnalaprilThe serum concentration of Estramustine can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Estramustine can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Estramustine can be decreased when it is combined with Enalkiren.Experimental
EnzalutamideThe serum concentration of Estramustine can be decreased when it is combined with Enzalutamide.Approved
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Estramustine.Approved, Investigational
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Estramustine.Approved, Investigational
ErythromycinThe metabolism of Estramustine can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Estramustine can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Estramustine.Approved, Investigational, Vet Approved
EstriolThe serum concentration of Estriol can be increased when it is combined with Estramustine.Approved, Vet Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Estramustine.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Estramustine.Approved
Ethyl biscoumacetateEstramustine may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Estramustine.Approved
EtravirineThe serum concentration of Estramustine can be decreased when it is combined with Etravirine.Approved
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Estramustine.Approved
ExenatideThe serum concentration of Estramustine can be decreased when it is combined with Exenatide.Approved, Investigational
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Estramustine.Approved
FelbamateThe serum concentration of Estramustine can be decreased when it is combined with Felbamate.Approved
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Estramustine.Approved
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Estramustine.Approved
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Estramustine.Approved
FingolimodEstramustine may increase the immunosuppressive activities of Fingolimod.Approved, Investigational
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Estramustine.Approved
FluconazoleThe metabolism of Estramustine can be decreased when combined with Fluconazole.Approved
FluindioneEstramustine may decrease the anticoagulant activities of Fluindione.Investigational
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Estramustine.Approved
FluvoxamineThe metabolism of Estramustine can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Estramustine can be decreased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Estramustine can be decreased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Estramustine can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe therapeutic efficacy of Estramustine can be decreased when used in combination with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Estramustine can be increased when it is combined with Fusidic Acid.Approved
G17DTThe risk or severity of adverse effects can be increased when Estramustine is combined with G17DT.Investigational
GabexateThe serum concentration of Estramustine can be decreased when it is combined with Gabexate.Investigational
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Estramustine.Approved, Investigational
GeldanamycinThe serum concentration of Estramustine can be decreased when it is combined with Geldanamycin.Experimental
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Estramustine.Approved
GI-5005The risk or severity of adverse effects can be increased when Estramustine is combined with GI-5005.Investigational
GM6001The serum concentration of Estramustine can be decreased when it is combined with GM6001.Experimental
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Estramustine.Approved
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Estramustine.Withdrawn
GriseofulvinThe metabolism of Estramustine can be increased when combined with Griseofulvin.Approved, Vet Approved
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Estramustine.Approved
HexobarbitalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Hexobarbital.Approved
HirulogThe serum concentration of Estramustine can be decreased when it is combined with Hirulog.Experimental
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Estramustine.Approved, Vet Approved
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Estramustine.Approved
IdelalisibThe serum concentration of Estramustine can be increased when it is combined with Idelalisib.Approved
idraparinuxThe serum concentration of Estramustine can be decreased when it is combined with idraparinux.Investigational
ImatinibThe metabolism of Estramustine can be decreased when combined with Imatinib.Approved
ImidaprilThe serum concentration of Estramustine can be decreased when it is combined with Imidapril.Investigational
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Estramustine.Approved
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Estramustine.Approved
IndinavirThe metabolism of Estramustine can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Estramustine.Approved, Investigational
INGN 201The risk or severity of adverse effects can be increased when Estramustine is combined with INGN 201.Investigational
INGN 225The risk or severity of adverse effects can be increased when Estramustine is combined with INGN 225.Investigational
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Estramustine.Approved, Investigational
IsavuconazoniumThe metabolism of Estramustine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoflurophateThe serum concentration of Estramustine can be decreased when it is combined with Isoflurophate.Approved, Withdrawn
IsotretinoinThe therapeutic efficacy of Estramustine can be decreased when used in combination with Isotretinoin.Approved
IsradipineThe metabolism of Estramustine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Estramustine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Estramustine can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Estramustine.Approved, Vet Approved
IxazomibThe serum concentration of Estramustine can be decreased when it is combined with Ixazomib.Approved
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Estramustine.Approved
KetoconazoleThe metabolism of Estramustine can be decreased when combined with Ketoconazole.Approved, Investigational
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Estramustine.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Estramustine.Approved, Investigational
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Estramustine.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Estramustine.Approved
LeflunomideThe risk or severity of adverse effects can be increased when Estramustine is combined with Leflunomide.Approved, Investigational
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Estramustine.Approved
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Estramustine.Approved
LepirudinThe serum concentration of Estramustine can be decreased when it is combined with Lepirudin.Approved
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Estramustine.Approved, Investigational
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Estramustine.Approved, Investigational
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Estramustine.Approved
LinagliptinThe serum concentration of Estramustine can be decreased when it is combined with Linagliptin.Approved
LisinoprilThe serum concentration of Estramustine can be decreased when it is combined with Lisinopril.Approved, Investigational
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Estramustine.Approved
LopinavirThe metabolism of Estramustine can be decreased when combined with Lopinavir.Approved
LosartanThe serum concentration of Losartan can be increased when it is combined with Estramustine.Approved
LovastatinThe metabolism of Estramustine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Estramustine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Estramustine can be decreased when it is combined with Lumacaftor.Approved
MannitolThe serum concentration of Mannitol can be increased when it is combined with Estramustine.Approved, Investigational
MethohexitalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Methohexital.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Estramustine.Approved
MethylphenobarbitalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Methylphenobarbital.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Estramustine.Approved, Vet Approved
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Estramustine.Approved, Investigational
MetreleptinThe serum concentration of Estramustine can be decreased when it is combined with Metreleptin.Approved
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Estramustine.Approved, Illicit
MifepristoneThe serum concentration of Estramustine can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Estramustine.Approved
MitotaneThe serum concentration of Estramustine can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Estramustine.Approved, Investigational
ModafinilThe serum concentration of Estramustine can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Estramustine can be decreased when it is combined with Moexipril.Approved
MorphineThe serum concentration of Morphine can be increased when it is combined with Estramustine.Approved, Investigational
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Estramustine.Approved, Investigational
Mycophenolic acidThe serum concentration of Estramustine can be decreased when it is combined with Mycophenolic acid.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Estramustine can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NadololThe serum concentration of Nadolol can be increased when it is combined with Estramustine.Approved
NafamostatThe serum concentration of Estramustine can be decreased when it is combined with Nafamostat.Investigational
NafcillinThe metabolism of Estramustine can be increased when combined with Nafcillin.Approved
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Estramustine.Approved
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Estramustine.Approved, Vet Approved
NatalizumabThe risk or severity of adverse effects can be increased when Estramustine is combined with Natalizumab.Approved, Investigational
NCX 4016The serum concentration of Estramustine can be decreased when it is combined with NCX 4016.Investigational
NefazodoneThe metabolism of Estramustine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Estramustine can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Estramustine can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Estramustine can be decreased when it is combined with Nevirapine.Approved
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Estramustine.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Estramustine.Approved
NilotinibThe metabolism of Estramustine can be decreased when combined with Nilotinib.Approved, Investigational
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Estramustine.Approved
NitroaspirinThe serum concentration of Estramustine can be decreased when it is combined with Nitroaspirin.Investigational
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Estramustine.Approved
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Estramustine.Approved, Investigational
OlaparibThe metabolism of Estramustine can be decreased when combined with Olaparib.Approved
OmapatrilatThe serum concentration of Estramustine can be decreased when it is combined with Omapatrilat.Investigational
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Estramustine.Approved
OsimertinibThe serum concentration of Estramustine can be increased when it is combined with Osimertinib.Approved
OtamixabanThe serum concentration of Estramustine can be decreased when it is combined with Otamixaban.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Estramustine.Approved
OxcarbazepineThe serum concentration of Estramustine 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 Estramustine.Approved, Vet Approved
PalbociclibThe serum concentration of Estramustine can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Estramustine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Estramustine.Approved
PentobarbitalThe metabolism of Estramustine can be increased when combined with Pentobarbital.Approved, Vet Approved
PerindoprilThe serum concentration of Estramustine can be decreased when it is combined with Perindopril.Approved
PhenindioneEstramustine may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Estramustine can be increased when combined with Phenobarbital.Approved
PhenprocoumonEstramustine may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Estramustine can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Estramustine can be decreased when it is combined with Phosphoramidon.Experimental
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Estramustine.Approved, Investigational
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Estramustine.Approved
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Estramustine.Approved
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Estramustine.Approved
PosaconazoleThe metabolism of Estramustine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Estramustine.Approved
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Estramustine.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Estramustine.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Estramustine.Approved, Vet Approved
PrimidoneThe metabolism of Estramustine can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Estramustine can be decreased when it is combined with Prinomastat.Investigational
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Estramustine.Approved, Vet Approved
PropranololThe serum concentration of Propranolol can be increased when it is combined with Estramustine.Approved, Investigational
PrucaloprideThe serum concentration of Estramustine can be decreased when it is combined with Prucalopride.Approved
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Estramustine.Approved
QuinaprilThe serum concentration of Estramustine can be decreased when it is combined with Quinapril.Approved, Investigational
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Estramustine.Approved
QuinineThe serum concentration of Quinine can be increased when it is combined with Estramustine.Approved
Rabies vaccineThe risk or severity of adverse effects can be increased when Estramustine is combined with Rabies vaccine.Approved
Rabies vaccineThe therapeutic efficacy of Rabies vaccine can be decreased when used in combination with Estramustine.Approved
RacecadotrilThe serum concentration of Estramustine can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Estramustine can be decreased when it is combined with Ramipril.Approved
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Estramustine.Approved
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Estramustine.Approved, Investigational
RemikirenThe serum concentration of Estramustine can be decreased when it is combined with Remikiren.Approved
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Estramustine.Approved
RifabutinThe metabolism of Estramustine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Estramustine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Estramustine can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Estramustine.Approved, Investigational
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Estramustine.Approved, Investigational
RitonavirThe metabolism of Estramustine can be decreased when combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Estramustine can be decreased when it is combined with Rivaroxaban.Approved
RoflumilastRoflumilast may increase the immunosuppressive activities of Estramustine.Approved
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Estramustine.Approved, Investigational
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Estramustine.Approved, Vet Approved
SaquinavirThe metabolism of Estramustine can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Estramustine can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe therapeutic efficacy of Estramustine 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 Estramustine.Approved, Investigational, Vet Approved
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Estramustine.Approved
SildenafilThe metabolism of Estramustine can be decreased when combined with Sildenafil.Approved, Investigational
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Estramustine.Approved
SiltuximabThe serum concentration of Estramustine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Estramustine can be increased when it is combined with Simeprevir.Approved
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Estramustine.Approved
SitagliptinThe serum concentration of Estramustine can be decreased when it is combined with Sitagliptin.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Estramustine.Approved
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Estramustine.Approved, Investigational
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Estramustine.Approved
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Estramustine.Experimental
SpiraprilThe serum concentration of Estramustine can be decreased when it is combined with Spirapril.Approved
SRP 299The risk or severity of adverse effects can be increased when Estramustine is combined with SRP 299.Investigational
St. John's WortThe serum concentration of Estramustine can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Estramustine can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Estramustine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Estramustine.Approved, Investigational
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Estramustine.Approved, Investigational
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Estramustine.Approved
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Estramustine.Experimental
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Estramustine.Approved
TelaprevirThe serum concentration of Estramustine can be decreased when it is combined with Telaprevir.Approved
TelithromycinThe metabolism of Estramustine can be decreased when combined with Telithromycin.Approved
TemocaprilThe serum concentration of Estramustine can be decreased when it is combined with Temocapril.Experimental, Investigational
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Estramustine.Approved
TG4010The risk or severity of adverse effects can be increased when Estramustine is combined with TG4010.Investigational
ThalidomideEstramustine may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Estramustine can be decreased when used in combination with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Estramustine can be decreased when it is combined with Thiorphan.Experimental
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Estramustine.Approved
TiclopidineThe metabolism of Estramustine can be decreased when combined with Ticlopidine.Approved
TimololThe serum concentration of Timolol can be increased when it is combined with Estramustine.Approved
TipranavirThe serum concentration of Estramustine can be decreased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Estramustine can be decreased when it is combined with Tocilizumab.Approved
TofacitinibEstramustine may increase the immunosuppressive activities of Tofacitinib.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Estramustine.Approved
TopiramateThe serum concentration of Estramustine can be decreased when it is combined with Topiramate.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Estramustine.Approved, Investigational
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Estramustine.Approved, Investigational
TrandolaprilThe serum concentration of Estramustine can be decreased when it is combined with Trandolapril.Approved
Tranexamic AcidEstramustine may increase the thrombogenic activities of Tranexamic Acid.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Estramustine.Approved, Investigational
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Estramustine.Approved
TretinoinThe therapeutic efficacy of Estramustine can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
UbenimexThe serum concentration of Estramustine can be decreased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Estramustine can be decreased when it is combined with Ulinastatin.Investigational
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Estramustine.Approved
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Estramustine.Approved
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Estramustine.Approved
VenetoclaxThe serum concentration of Venetoclax can be increased when it is combined with Estramustine.Approved
VenlafaxineThe metabolism of Estramustine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Estramustine can be decreased when combined with Verapamil.Approved
VildagliptinThe serum concentration of Estramustine can be decreased when it is combined with Vildagliptin.Approved, Investigational
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Estramustine.Approved
VincristineThe serum concentration of Vincristine can be increased when it is combined with Estramustine.Approved, Investigational
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Estramustine.Approved
VoriconazoleThe metabolism of Estramustine can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinEstramustine may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Estramustine can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The serum concentration of Estramustine can be decreased when it is combined with Ym150.Investigational
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Estramustine.Approved
ZiprasidoneThe metabolism of Estramustine can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Do not take with milk or milk products.
  • Take on an empty stomach.
References
Synthesis Reference

Fex, H.J., Hogtierg, K.B., Konyves, I. and Kneip, P.H.0.L; U.S. Patent 3,299,104; Jan. 17,
1967; assigned to Leo AB, Sweden.

US3299104
General ReferencesNot Available
External Links
ATC CodesL01XX11
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9675
Caco-2 permeable+0.6013
P-glycoprotein substrateSubstrate0.7382
P-glycoprotein inhibitor IInhibitor0.5927
P-glycoprotein inhibitor IINon-inhibitor0.6317
Renal organic cation transporterNon-inhibitor0.5918
CYP450 2C9 substrateNon-substrate0.6261
CYP450 2D6 substrateNon-substrate0.6491
CYP450 3A4 substrateSubstrate0.8003
CYP450 1A2 substrateNon-inhibitor0.6214
CYP450 2C9 inhibitorNon-inhibitor0.6944
CYP450 2D6 inhibitorNon-inhibitor0.6079
CYP450 2C19 inhibitorInhibitor0.5464
CYP450 3A4 inhibitorInhibitor0.8479
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.62
Ames testNon AMES toxic0.6062
CarcinogenicityNon-carcinogens0.8508
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7844 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8235
hERG inhibition (predictor II)Non-inhibitor0.6818
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
CapsuleOral140 mg/1
CapsuleOral140 mg
Prices
Unit descriptionCostUnit
Emcyt 140 mg capsule6.55USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point155Fex, H.J., Hogtierg, K.B., Konyves, I. and Kneip, P.H.0.L; U.S. Patent 3,299,104; Jan. 17, 1967; assigned to Leo AB, Sweden.
logP5.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000385 mg/mLALOGPS
logP4.97ALOGPS
logP5.1ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity116.21 m3·mol-1ChemAxon
Polarizability48.06 Å3ChemAxon
Number of Rings4ChemAxon
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 estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • 17-hydroxysteroid
  • Hydroxysteroid
  • Estrane-skeleton
  • Phenanthrene
  • Tetralin
  • Nitrogen mustard
  • Benzenoid
  • Cyclic alcohol
  • Tertiary amine
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
other/unknown
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by...
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Ho SM: Estrogens and anti-estrogens: key mediators of prostate carcinogenesis and new therapeutic candidates. J Cell Biochem. 2004 Feb 15;91(3):491-503. [PubMed:14755680 ]
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. Ferno M, Borg A, Ingvar C, Jonsson PE: Estrogen receptor and binding site for estramustine in metastatic malignant melanoma. Anticancer Res. 1987 Jul-Aug;7(4B):741-3. [PubMed:3314674 ]
  2. Yoshizumi N: [The effects of site-directed chemotherapy due to E2 as a drug carrier to the human endometrial adenocarcinoma cells in vitro]. Nihon Sanka Fujinka Gakkai Zasshi. 1985 Apr;37(4):637-45. [PubMed:3989343 ]
  3. von Schoultz E, Carlstrom K, Henriksson R, Lagerlof B, Hansson J: Estramustine binding protein in primary tumours and metastases of malignant melanoma. Melanoma Res. 1994 Dec;4(6):401-5. [PubMed:7703721 ]
  4. Tew KD: The mechanism of action of estramustine. Semin Oncol. 1983 Sep;10(3 Suppl 3):21-6. [PubMed:6364362 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Structural molecule activity
Specific Function:
The exact function of MAP2 is unknown but MAPs may stabilize the microtubules against depolymerization. They also seem to have a stiffening effect on microtubules.
Gene Name:
MAP2
Uniprot ID:
P11137
Molecular Weight:
199524.51 Da
References
  1. Moraga D, Rivas-Berrios A, Farias G, Wallin M, Maccioni RB: Estramustine-phosphate binds to a tubulin binding domain on microtubule-associated proteins MAP-2 and tau. Biochim Biophys Acta. 1992 May 22;1121(1-2):97-103. [PubMed:1599956 ]
  2. Stearns ME, Wang M, Sousa O: Evidence that estramustine binds MAP-1A to inhibit type IV collagenase secretion. J Cell Sci. 1991 Jan;98 ( Pt 1):55-63. [PubMed:1647395 ]
  3. Friden B, Rutberg M, Deinum J, Wallin M: The effect of estramustine derivatives on microtubule assembly in vitro depends on the charge of the substituent. Biochem Pharmacol. 1991 Aug 8;42(5):997-1006. [PubMed:1908244 ]
  4. Burns RG: Stoichiometry of estramustine phosphate binding to MAP2 measured by the disassembly of chick brain MAP2:tubulin microtubules. Cell Motil Cytoskeleton. 1990;17(3):167-73. [PubMed:2125244 ]
  5. Falconer MM, Vielkind U, Brown DL: Association of acetylated microtubules, vimentin intermediate filaments, and MAP 2 during early neural differentiation in EC cell culture. Biochem Cell Biol. 1989 Sep;67(9):537-44. [PubMed:2679799 ]
  6. Tew KD: The mechanism of action of estramustine. Semin Oncol. 1983 Sep;10(3 Suppl 3):21-6. [PubMed:6364362 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Structural molecule activity
Specific Function:
Structural protein involved in the filamentous cross-bridging between microtubules and other skeletal elements.
Gene Name:
MAP1A
Uniprot ID:
P78559
Molecular Weight:
305482.26 Da
References
  1. Stearns ME, Wang M, Sousa O: Evidence that estramustine binds MAP-1A to inhibit type IV collagenase secretion. J Cell Sci. 1991 Jan;98 ( Pt 1):55-63. [PubMed:1647395 ]

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. 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
inhibitor
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
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  2. Tiersten AD, Nelsen C, Talbot S, Vahdat L, Fine R, Troxel A, Brafman L, Shriberg L, Antman K, Petrylak DP: A phase II trial of docetaxel and estramustine in patients with refractory metastatic breast carcinoma. Cancer. 2003 Feb 1;97(3):537-44. [PubMed:12548594 ]
  3. Smith CD, Zilfou JT, Zhang X, Hudes GR, Tew KD: Modulation of P-glycoprotein activity by estramustine is limited by binding to plasma proteins. Cancer. 1995 May 15;75(10):2597-604. [PubMed:7736407 ]
  4. Speicher LA, Barone LR, Chapman AE, Hudes GR, Laing N, Smith CD, Tew KD: P-glycoprotein binding and modulation of the multidrug-resistant phenotype by estramustine. J Natl Cancer Inst. 1994 May 4;86(9):688-94. [PubMed:7908988 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23