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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 KeyInChIKey=FRPJXPJMRWBBIH-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]
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
Pharmacology
IndicationFor the palliative treatment of patients with metastatic and/or progressive carcinoma of the prostate
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.
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
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
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
Interactions
Drug Interactions
Drug
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Estramustine.
AcetaminophenThe serum concentration of Acetaminophen can be increased when it is combined with Estramustine.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Estramustine.
Acetylsalicylic acidThe serum concentration of Acetylsalicylic acid can be increased when it is combined with Estramustine.
AfatinibThe serum concentration of Afatinib can be increased when it is combined with Estramustine.
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Estramustine.
AlitretinoinThe serum concentration of Alitretinoin can be increased when it is combined with Estramustine.
AmbrisentanThe serum concentration of Ambrisentan can be increased when it is combined with Estramustine.
AmiodaroneThe metabolism of Estramustine can be decreased when combined with Amiodarone.
AmitriptylineThe serum concentration of Amitriptyline can be increased when it is combined with Estramustine.
ApixabanThe serum concentration of Apixaban can be increased when it is combined with Estramustine.
AprepitantThe serum concentration of Estramustine can be increased when it is combined with Aprepitant.
Arsenic trioxideThe serum concentration of Arsenic trioxide can be increased when it is combined with Estramustine.
AtazanavirThe metabolism of Estramustine can be decreased when combined with Atazanavir.
AtazanavirThe serum concentration of Atazanavir can be increased when it is combined with Estramustine.
AtenololThe serum concentration of Atenolol can be increased when it is combined with Estramustine.
AtomoxetineThe metabolism of Estramustine can be decreased when combined with Atomoxetine.
AxitinibThe serum concentration of Axitinib can be increased when it is combined with Estramustine.
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Estramustine.
BevacizumabBevacizumab may increase the cardiotoxic activities of Estramustine.
BexaroteneThe serum concentration of Estramustine can be decreased when it is combined with Bexarotene.
BoceprevirThe metabolism of Estramustine can be decreased when combined with Boceprevir.
BoceprevirThe serum concentration of Boceprevir can be increased when it is combined with Estramustine.
BortezomibThe metabolism of Estramustine can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Estramustine can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Estramustine.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be increased when it is combined with Estramustine.
BromocriptineThe serum concentration of Bromocriptine can be increased when it is combined with Estramustine.
CabazitaxelThe serum concentration of Cabazitaxel can be increased when it is combined with Estramustine.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Estramustine.
CaffeineThe serum concentration of Caffeine can be increased when it is combined with Estramustine.
CamptothecinThe serum concentration of Camptothecin can be increased when it is combined with Estramustine.
CanagliflozinThe serum concentration of Canagliflozin can be increased when it is combined with Estramustine.
CarbamazepineThe metabolism of Estramustine can be increased when combined with Carbamazepine.
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Estramustine.
CarfilzomibThe serum concentration of Carfilzomib can be increased when it is combined with Estramustine.
CeritinibThe serum concentration of Estramustine can be increased when it is combined with Ceritinib.
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Estramustine.
ChlorpromazineThe serum concentration of Chlorpromazine can be increased when it is combined with Estramustine.
CimetidineThe serum concentration of Cimetidine can be increased when it is combined with Estramustine.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Estramustine.
CisplatinThe serum concentration of Cisplatin can be increased when it is combined with Estramustine.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Estramustine.
ClarithromycinThe metabolism of Estramustine can be decreased when combined with Clarithromycin.
ClarithromycinThe serum concentration of Clarithromycin can be increased when it is combined with Estramustine.
ClemastineThe metabolism of Estramustine can be decreased when combined with Clemastine.
ClobazamThe serum concentration of Clobazam can be increased when it is combined with Estramustine.
ClodronateThe serum concentration of Estramustine can be increased when it is combined with Clodronate.
ClomifeneThe serum concentration of Clomifene can be increased when it is combined with Estramustine.
ClonidineThe serum concentration of Clonidine can be increased when it is combined with Estramustine.
ClopidogrelThe serum concentration of Clopidogrel can be increased when it is combined with Estramustine.
ClotrimazoleThe metabolism of Estramustine can be decreased when combined with Clotrimazole.
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Estramustine.
CobicistatThe metabolism of Estramustine can be decreased when combined with Cobicistat.
CobimetinibThe serum concentration of Cobimetinib can be increased when it is combined with Estramustine.
ColchicineThe serum concentration of Colchicine can be increased when it is combined with Estramustine.
ConivaptanThe serum concentration of Estramustine can be increased when it is combined with Conivaptan.
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be increased when it is combined with Estramustine.
CrizotinibThe metabolism of Estramustine can be decreased when combined with Crizotinib.
CrizotinibThe serum concentration of Crizotinib can be increased when it is combined with Estramustine.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Estramustine.
CyclosporineThe metabolism of Estramustine can be decreased when combined with Cyclosporine.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Estramustine.
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be increased when it is combined with Estramustine.
DabrafenibThe serum concentration of Estramustine can be decreased when it is combined with Dabrafenib.
DabrafenibThe serum concentration of Dabrafenib can be increased when it is combined with Estramustine.
DactinomycinThe serum concentration of Dactinomycin can be increased when it is combined with Estramustine.
DapagliflozinThe serum concentration of Dapagliflozin can be increased when it is combined with Estramustine.
DarunavirThe metabolism of Estramustine can be decreased when combined with Darunavir.
DasatinibThe serum concentration of Estramustine can be increased when it is combined with Dasatinib.
DaunorubicinThe serum concentration of Daunorubicin can be increased when it is combined with Estramustine.
DebrisoquinThe serum concentration of Debrisoquin can be increased when it is combined with Estramustine.
DeferasiroxThe serum concentration of Estramustine can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Estramustine can be decreased when combined with Delavirdine.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Estramustine.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Estramustine.
DexamethasoneThe serum concentration of Estramustine can be decreased when it is combined with Dexamethasone.
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Estramustine.
DiazepamThe serum concentration of Diazepam can be increased when it is combined with Estramustine.
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be increased when it is combined with Estramustine.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Estramustine.
DigitoxinThe serum concentration of Digitoxin can be increased when it is combined with Estramustine.
DigoxinDigoxin may decrease the cardiotoxic activities of Estramustine.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Estramustine.
DihydroergotamineThe metabolism of Estramustine can be decreased when combined with Dihydroergotamine.
DihydrotestosteroneThe serum concentration of Dihydrotestosterone can be increased when it is combined with Estramustine.
DiltiazemThe metabolism of Estramustine can be decreased when combined with Diltiazem.
DiltiazemThe serum concentration of Diltiazem can be increased when it is combined with Estramustine.
DipyridamoleThe serum concentration of Dipyridamole can be increased when it is combined with Estramustine.
DocetaxelThe serum concentration of Docetaxel can be increased when it is combined with Estramustine.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Estramustine.
DomperidoneThe serum concentration of Domperidone can be increased when it is combined with Estramustine.
DoxorubicinThe serum concentration of Doxorubicin can be increased when it is combined with Estramustine.
DoxycyclineThe metabolism of Estramustine can be decreased when combined with Doxycycline.
DronedaroneThe metabolism of Estramustine can be decreased when combined with Dronedarone.
EdoxabanThe serum concentration of Edoxaban can be increased when it is combined with Estramustine.
EfavirenzThe serum concentration of Estramustine can be decreased when it is combined with Efavirenz.
EletriptanThe serum concentration of Eletriptan can be increased when it is combined with Estramustine.
EnzalutamideThe serum concentration of Estramustine can be decreased when it is combined with Enzalutamide.
EpinastineThe serum concentration of Epinastine can be increased when it is combined with Estramustine.
ErlotinibThe serum concentration of Erlotinib can be increased when it is combined with Estramustine.
ErythromycinThe metabolism of Estramustine can be decreased when combined with Erythromycin.
ErythromycinThe serum concentration of Erythromycin can be increased when it is combined with Estramustine.
Eslicarbazepine acetateThe serum concentration of Estramustine can be decreased when it is combined with Eslicarbazepine acetate.
EstradiolThe serum concentration of Estradiol can be increased when it is combined with Estramustine.
EstriolThe serum concentration of Estriol can be increased when it is combined with Estramustine.
EstroneThe serum concentration of Estrone can be increased when it is combined with Estramustine.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Estramustine.
EtoposideThe serum concentration of Etoposide can be increased when it is combined with Estramustine.
EtravirineThe serum concentration of Estramustine can be decreased when it is combined with Etravirine.
EverolimusThe serum concentration of Everolimus can be increased when it is combined with Estramustine.
EzetimibeThe serum concentration of Ezetimibe can be increased when it is combined with Estramustine.
FesoterodineThe serum concentration of Fesoterodine can be increased when it is combined with Estramustine.
FexofenadineThe serum concentration of Fexofenadine can be increased when it is combined with Estramustine.
FidaxomicinThe serum concentration of Fidaxomicin can be increased when it is combined with Estramustine.
FingolimodEstramustine may increase the immunosuppressive activities of Fingolimod.
FluconazoleThe metabolism of Estramustine can be decreased when combined with Fluconazole.
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Estramustine.
FluvoxamineThe metabolism of Estramustine can be decreased when combined with Fluvoxamine.
FosamprenavirThe metabolism of Estramustine can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Estramustine can be increased when it is combined with Fosaprepitant.
FosphenytoinThe metabolism of Estramustine can be increased when combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Estramustine can be increased when it is combined with Fusidic Acid.
GefitinibThe serum concentration of Gefitinib can be increased when it is combined with Estramustine.
GemcitabineThe serum concentration of Gemcitabine can be increased when it is combined with Estramustine.
GrazoprevirThe serum concentration of Grazoprevir can be increased when it is combined with Estramustine.
GrepafloxacinThe serum concentration of Grepafloxacin can be increased when it is combined with Estramustine.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Estramustine.
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Estramustine.
IbuprofenThe serum concentration of Ibuprofen can be increased when it is combined with Estramustine.
IdelalisibThe serum concentration of Estramustine can be increased when it is combined with Idelalisib.
ImatinibThe metabolism of Estramustine can be decreased when combined with Imatinib.
ImatinibThe serum concentration of Imatinib can be increased when it is combined with Estramustine.
ImipramineThe serum concentration of Imipramine can be increased when it is combined with Estramustine.
IndacaterolThe serum concentration of Indacaterol can be increased when it is combined with Estramustine.
IndinavirThe metabolism of Estramustine can be decreased when combined with Indinavir.
IndinavirThe serum concentration of Indinavir can be increased when it is combined with Estramustine.
IndomethacinThe serum concentration of Indomethacin can be increased when it is combined with Estramustine.
IrinotecanThe serum concentration of Irinotecan can be increased when it is combined with Estramustine.
IsavuconazoniumThe metabolism of Estramustine can be decreased when combined with Isavuconazonium.
IsradipineThe metabolism of Estramustine can be decreased when combined with Isradipine.
ItraconazoleThe metabolism of Estramustine can be decreased when combined with Itraconazole.
IvacaftorThe serum concentration of Estramustine can be increased when it is combined with Ivacaftor.
IvermectinThe serum concentration of Ivermectin can be increased when it is combined with Estramustine.
KetazolamThe serum concentration of Ketazolam can be increased when it is combined with Estramustine.
KetoconazoleThe metabolism of Estramustine can be decreased when combined with Ketoconazole.
KetoconazoleThe serum concentration of Ketoconazole can be increased when it is combined with Estramustine.
LamivudineThe serum concentration of Lamivudine can be increased when it is combined with Estramustine.
LamotrigineThe serum concentration of Lamotrigine can be increased when it is combined with Estramustine.
LansoprazoleThe serum concentration of Lansoprazole can be increased when it is combined with Estramustine.
LedipasvirThe serum concentration of Ledipasvir can be increased when it is combined with Estramustine.
LeflunomideThe risk or severity of adverse effects can be increased when Estramustine is combined with Leflunomide.
LenalidomideThe serum concentration of Lenalidomide can be increased when it is combined with Estramustine.
LenvatinibThe serum concentration of Lenvatinib can be increased when it is combined with Estramustine.
LevetiracetamThe serum concentration of Levetiracetam can be increased when it is combined with Estramustine.
LevofloxacinThe serum concentration of Levofloxacin can be increased when it is combined with Estramustine.
LevomilnacipranThe serum concentration of Levomilnacipran can be increased when it is combined with Estramustine.
LinagliptinThe serum concentration of Linagliptin can be increased when it is combined with Estramustine.
LoperamideThe serum concentration of Loperamide can be increased when it is combined with Estramustine.
LopinavirThe metabolism of Estramustine can be decreased when combined with Lopinavir.
LosartanThe serum concentration of Losartan can be increased when it is combined with Estramustine.
LovastatinThe metabolism of Estramustine can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Estramustine can be increased when it is combined with Luliconazole.
MannitolThe serum concentration of Mannitol can be increased when it is combined with Estramustine.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Estramustine.
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Estramustine.
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Estramustine.
MidazolamThe serum concentration of Midazolam can be increased when it is combined with Estramustine.
MifepristoneThe metabolism of Estramustine can be decreased when combined with Mifepristone.
MirabegronThe serum concentration of Mirabegron can be increased when it is combined with Estramustine.
MitotaneThe serum concentration of Estramustine can be decreased when it is combined with Mitotane.
MitoxantroneThe serum concentration of Mitoxantrone can be increased when it is combined with Estramustine.
ModafinilThe serum concentration of Estramustine can be decreased when it is combined with Modafinil.
MorphineThe serum concentration of Morphine can be increased when it is combined with Estramustine.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be increased when it is combined with Estramustine.
NadololThe serum concentration of Nadolol can be increased when it is combined with Estramustine.
NafcillinThe serum concentration of Estramustine can be decreased when it is combined with Nafcillin.
NaloxegolThe serum concentration of Naloxegol can be increased when it is combined with Estramustine.
NaloxoneThe serum concentration of Naloxone can be increased when it is combined with Estramustine.
NatalizumabThe risk or severity of adverse effects can be increased when Estramustine is combined with Natalizumab.
NefazodoneThe metabolism of Estramustine can be decreased when combined with Nefazodone.
NelfinavirThe metabolism of Estramustine can be decreased when combined with Nelfinavir.
NelfinavirThe serum concentration of Nelfinavir can be increased when it is combined with Estramustine.
NetupitantThe serum concentration of Estramustine can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Estramustine can be decreased when combined with Nevirapine.
NicardipineThe serum concentration of Nicardipine can be increased when it is combined with Estramustine.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Estramustine.
NilotinibThe metabolism of Estramustine can be decreased when combined with Nilotinib.
NilotinibThe serum concentration of Nilotinib can be increased when it is combined with Estramustine.
NintedanibThe serum concentration of Nintedanib can be increased when it is combined with Estramustine.
NizatidineThe serum concentration of Nizatidine can be increased when it is combined with Estramustine.
OlanzapineThe serum concentration of Olanzapine can be increased when it is combined with Estramustine.
OlaparibThe metabolism of Estramustine can be decreased when combined with Olaparib.
OmbitasvirThe serum concentration of Ombitasvir can be increased when it is combined with Estramustine.
OsimertinibThe serum concentration of Estramustine can be increased when it is combined with Osimertinib.
OuabainOuabain may decrease the cardiotoxic activities of Estramustine.
PaclitaxelThe serum concentration of Paclitaxel can be increased when it is combined with Estramustine.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Estramustine.
PalbociclibThe serum concentration of Estramustine can be increased when it is combined with Palbociclib.
PanobinostatThe serum concentration of Panobinostat can be increased when it is combined with Estramustine.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Estramustine.
PentobarbitalThe metabolism of Estramustine can be increased when combined with Pentobarbital.
PhenobarbitalThe metabolism of Estramustine can be increased when combined with Phenobarbital.
PhenobarbitalThe serum concentration of Phenobarbital can be increased when it is combined with Estramustine.
PhenytoinThe metabolism of Estramustine can be increased when combined with Phenytoin.
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Estramustine.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Estramustine.
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Estramustine.
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Estramustine.
PonatinibThe serum concentration of Ponatinib can be increased when it is combined with Estramustine.
PosaconazoleThe metabolism of Estramustine can be decreased when combined with Posaconazole.
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Estramustine.
PrazosinThe serum concentration of Prazosin can be increased when it is combined with Estramustine.
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Estramustine.
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Estramustine.
PrimidoneThe metabolism of Estramustine can be increased when combined with Primidone.
ProgesteroneThe serum concentration of Progesterone can be increased when it is combined with Estramustine.
PropranololThe serum concentration of Propranolol can be increased when it is combined with Estramustine.
PrucaloprideThe serum concentration of Prucalopride can be increased when it is combined with Estramustine.
QuetiapineThe serum concentration of Quetiapine can be increased when it is combined with Estramustine.
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Estramustine.
QuinineThe serum concentration of Quinine can be increased when it is combined with Estramustine.
Rabies vaccineThe risk or severity of adverse effects can be increased when Estramustine is combined with Rabies vaccine.
RanitidineThe serum concentration of Ranitidine can be increased when it is combined with Estramustine.
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Estramustine.
RanolazineThe metabolism of Estramustine can be decreased when combined with Ranolazine.
ReserpineThe serum concentration of Reserpine can be increased when it is combined with Estramustine.
RifabutinThe metabolism of Estramustine can be increased when combined with Rifabutin.
RifampicinThe metabolism of Estramustine can be increased when combined with Rifampicin.
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Estramustine.
RifapentineThe metabolism of Estramustine can be increased when combined with Rifapentine.
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Estramustine.
RisperidoneThe serum concentration of Risperidone can be increased when it is combined with Estramustine.
RitonavirThe metabolism of Estramustine can be decreased when combined with Ritonavir.
RitonavirThe serum concentration of Ritonavir can be increased when it is combined with Estramustine.
RivaroxabanThe serum concentration of Rivaroxaban can be increased when it is combined with Estramustine.
RoflumilastRoflumilast may increase the immunosuppressive activities of Estramustine.
RomidepsinThe serum concentration of Romidepsin can be increased when it is combined with Estramustine.
Salicylic acidThe serum concentration of Salicylic acid can be increased when it is combined with Estramustine.
SaquinavirThe metabolism of Estramustine can be decreased when combined with Saquinavir.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Estramustine.
SelexipagThe serum concentration of Selexipag can be increased when it is combined with Estramustine.
SildenafilThe metabolism of Estramustine can be decreased when combined with Sildenafil.
SilodosinThe serum concentration of Silodosin can be increased when it is combined with Estramustine.
SiltuximabThe serum concentration of Estramustine can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Estramustine can be increased when it is combined with Simeprevir.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Estramustine.
SitagliptinThe serum concentration of Sitagliptin can be increased when it is combined with Estramustine.
SofosbuvirThe serum concentration of Sofosbuvir can be increased when it is combined with Estramustine.
SorafenibThe serum concentration of Sorafenib can be increased when it is combined with Estramustine.
SparfloxacinThe serum concentration of Sparfloxacin can be increased when it is combined with Estramustine.
SphingosineThe serum concentration of Sphingosine can be increased when it is combined with Estramustine.
St. John's WortThe serum concentration of Estramustine can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Estramustine can be increased when it is combined with Stiripentol.
SulfisoxazoleThe metabolism of Estramustine can be decreased when combined with Sulfisoxazole.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Estramustine.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Estramustine.
TamoxifenThe serum concentration of Tamoxifen can be increased when it is combined with Estramustine.
Taurocholic AcidThe serum concentration of Taurocholic Acid can be increased when it is combined with Estramustine.
Technetium Tc-99m sestamibiThe serum concentration of Technetium Tc-99m sestamibi can be increased when it is combined with Estramustine.
TelaprevirThe metabolism of Estramustine can be decreased when combined with Telaprevir.
TelaprevirThe serum concentration of Telaprevir can be increased when it is combined with Estramustine.
TelithromycinThe metabolism of Estramustine can be decreased when combined with Telithromycin.
TemsirolimusThe serum concentration of Temsirolimus can be increased when it is combined with Estramustine.
TicagrelorThe serum concentration of Ticagrelor can be increased when it is combined with Estramustine.
TiclopidineThe metabolism of Estramustine can be decreased when combined with Ticlopidine.
TimololThe serum concentration of Timolol can be increased when it is combined with Estramustine.
TocilizumabThe serum concentration of Estramustine can be decreased when it is combined with Tocilizumab.
TofacitinibEstramustine may increase the immunosuppressive activities of Tofacitinib.
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Estramustine.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Estramustine.
ToremifeneThe serum concentration of Toremifene can be increased when it is combined with Estramustine.
TrastuzumabTrastuzumab may increase the neutropenic activities of Estramustine.
Trastuzumab emtansineThe serum concentration of Trastuzumab emtansine can be increased when it is combined with Estramustine.
UlipristalThe serum concentration of Ulipristal can be increased when it is combined with Estramustine.
UmeclidiniumThe serum concentration of Umeclidinium can be increased when it is combined with Estramustine.
VecuroniumThe serum concentration of Vecuronium can be increased when it is combined with Estramustine.
VenlafaxineThe metabolism of Estramustine can be decreased when combined with Venlafaxine.
VenlafaxineThe serum concentration of Venlafaxine can be increased when it is combined with Estramustine.
VerapamilThe metabolism of Estramustine can be decreased when combined with Verapamil.
VerapamilThe serum concentration of Verapamil can be increased when it is combined with Estramustine.
VinblastineThe serum concentration of Vinblastine can be increased when it is combined with Estramustine.
VincristineThe serum concentration of Vincristine can be increased when it is combined with Estramustine.
VismodegibThe serum concentration of Vismodegib can be increased when it is combined with Estramustine.
VoriconazoleThe metabolism of Estramustine can be decreased when combined with Voriconazole.
ZidovudineThe serum concentration of Zidovudine can be increased when it is combined with Estramustine.
ZiprasidoneThe metabolism of Estramustine can be decreased when combined with Ziprasidone.
Food Interactions
  • Do not take with milk or milk products.
  • Take on an empty stomach.

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
  1. Yang CP, Shen HJ, Horwitz SB: Modulation of the function of P-glycoprotein by estramustine. J Natl Cancer Inst. 1994 May 4;86(9):723-5. [PubMed:7908991 ]
  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