Identification

Name
Estriol
Accession Number
DB04573  (EXPT01361, DB05375)
Type
Small Molecule
Groups
Approved, Investigational, Vet Approved
Description

A hydroxylated metabolite of estradiol or estrone that has a hydroxyl group at C3-beta, 16-alpha, and 17-beta position. Estriol is a major urinary estrogen. During pregnancy, large amount of estriol is produced by the placenta. Isomers with inversion of the hydroxyl group or groups are called epiestriol. Though estriol is used as part of the primarily North American phenomenon of bioidentical hormone replacement therapy, it is not approved for use by the FDA or Health Canada. It is however available in the United States by prescription filled only by compounding pharmacies. It has also been approved and marketed throughout Europe and Asia for approximately 40 years for the treatment of post-menopausal hot flashes.

Structure
Thumb
Synonyms
  • (16alpha,17beta)-Estra-1,3,5(10)-triene-3,16,17-triol
  • (16α,17β)-estra-1,3,5(10)-triene-3,16,17-triol
  • 1,3,5(10)-Estratriene-3,16-alpha,17beta-triol
  • 16-alpha-Hydroxyestradiol
  • 16alpha-hydroxyestradiol
  • 16α-hydroxyestradiol
  • 3,16alpha,17beta-Trihydroxy-delta(1,3,5)-estratriene
  • Deuslon-a
  • Estriel
  • Estriol
  • Oestriol
  • Trihydroxyestrin
External IDs
16.ALPHA.-HYDROXYESTRADIOL
Product Ingredients
IngredientUNIICASInChI Key
Estriol tripropionateS2A0P1AFQ92236-31-9ONMZMZJEZHMWQL-REUUDLSRSA-N
International/Other Brands
Aacifemine (Organon) / Colpoestriol (Temis-Lostalo) / Ovestin (Merck Sharp & Dohme) / Synapause E (Organon)
Categories
UNII
FB33469R8E
CAS number
50-27-1
Weight
Average: 288.3814
Monoisotopic: 288.172544634
Chemical Formula
C18H24O3
InChI Key
PROQIPRRNZUXQM-ZXXIGWHRSA-N
InChI
InChI=1S/C18H24O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,17+,18+/m1/s1
IUPAC Name
(1S,10R,11S,13R,14R,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,13,14-triol
SMILES

Pharmacology

Indication

Used as a test to determine the general health of an unborn fetus.

Structured Indications
Not Available
Pharmacodynamics

Estriol (also oestriol) is one of the three main estrogens produced by the human body. It is only produced in significant amounts during pregnancy as it is made by the placenta. In pregnant women with multiple sclerosis (MS), estriol reduces the disease's symptoms noticeably, according to researchers at UCLA's Geffen Medical School.

Mechanism of action

Estriol levels can be measured to give an indication of the general health of the fetus. DHEA-S is produced by the adrenal cortex of the fetus. This is converted to estriol by the placenta. If levels of "unconjugated estriol" are abnormally low in a pregnant woman, this may indicate a problem with the development of the child. The drug interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estriol upon the target cell. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary.

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Human
UEstrogen receptor beta
agonist
Human
USex hormone-binding globulinNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

ORAL (LD50): Acute: >2000 mg/kg [Rat].

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Estrone MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe serum concentration of 16-Bromoepiandrosterone can be increased when it is combined with Estriol.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Estriol.Experimental, Illicit
5-androstenedioneThe serum concentration of 5-androstenedione can be increased when it is combined with Estriol.Experimental, Illicit
AbciximabEstriol may decrease the anticoagulant activities of Abciximab.Approved
AcenocoumarolEstriol may decrease the anticoagulant activities of Acenocoumarol.Approved
AfatinibThe serum concentration of Afatinib can be decreased when it is combined with Estriol.Approved
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Estriol.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Estriol.Experimental, Investigational
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Estriol.Experimental, Investigational
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Estriol.Approved
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Estriol.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Estriol.Approved, Investigational
AncrodEstriol may decrease the anticoagulant activities of Ancrod.Investigational
AndrostenedioneThe serum concentration of Androstenedione can be increased when it is combined with Estriol.Experimental, Illicit
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Estriol.Investigational
anecortave acetateThe serum concentration of anecortave acetate can be increased when it is combined with Estriol.Investigational
Anthrax immune globulin humanEstriol may increase the thrombogenic activities of Anthrax immune globulin human.Approved
Antithrombin III humanEstriol may decrease the anticoagulant activities of Antithrombin III human.Approved
ApixabanEstriol may decrease the anticoagulant activities of Apixaban.Approved
ArdeparinEstriol may decrease the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanEstriol may decrease the anticoagulant activities of Argatroban.Approved, Investigational
AtamestaneThe serum concentration of Atamestane can be increased when it is combined with Estriol.Investigational
BecaplerminEstriol may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Estriol.Approved, Investigational
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Estriol.Approved, Vet Approved
BivalirudinEstriol may decrease the anticoagulant activities of Bivalirudin.Approved, Investigational
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Estriol.Approved
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Estriol.Approved
Capromab pendetideEstriol may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CelecoxibCelecoxib may increase the thrombogenic activities of Estriol.Approved, Investigational
CertoparinEstriol may decrease the anticoagulant activities of Certoparin.Approved, Investigational
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Estriol.Approved
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Estriol.Approved, Investigational
Citric AcidEstriol may decrease the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Estriol.Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Estriol.Approved
ClobetasoneThe serum concentration of Clobetasone can be increased when it is combined with Estriol.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Estriol.Approved
Conestat alfaEstriol may increase the thrombogenic activities of Conestat alfa.Approved
Cortexolone 17α-propionateThe serum concentration of Cortexolone 17α-propionate can be increased when it is combined with Estriol.Investigational
CorticosteroneThe serum concentration of Corticosterone can be increased when it is combined with Estriol.Experimental
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Estriol.Approved
Dabigatran etexilateThe serum concentration of Dabigatran etexilate can be decreased when it is combined with Estriol.Approved
DalteparinEstriol may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidEstriol may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanEstriol may decrease the anticoagulant activities of Darexaban.Investigational
DeflazacortThe serum concentration of Deflazacort can be increased when it is combined with Estriol.Approved
DesirudinEstriol may decrease the anticoagulant activities of Desirudin.Approved
DesonideThe serum concentration of Desonide can be increased when it is combined with Estriol.Approved, Investigational
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Estriol.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Estriol.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Estriol.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Estriol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Estriol.Vet Approved
DextranEstriol may decrease the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Estriol may decrease the anticoagulant activities of Dextran 40.Approved
Dextran 70Estriol may decrease the anticoagulant activities of Dextran 70.Approved
Dextran 75Estriol may decrease the anticoagulant activities of Dextran 75.Approved
DicoumarolEstriol may decrease the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Estriol.Approved
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Estriol.Approved, Investigational
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Estriol.Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Estriol.Approved, Investigational
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Estriol.Approved
Edetic AcidEstriol may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanEstriol may decrease the anticoagulant activities of Edoxaban.Approved
EnoxaparinEstriol may decrease the anticoagulant activities of Enoxaparin.Approved
EquileninThe serum concentration of Equilenin can be increased when it is combined with Estriol.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Estriol.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Estriol.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Estriol.Approved
Ethyl biscoumacetateEstriol may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Estriol.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Estriol.Approved, Investigational
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Estriol.Approved, Investigational
Ferulic acidEstriol may decrease the anticoagulant activities of Ferulic acid.Experimental
fluasteroneThe serum concentration of fluasterone can be increased when it is combined with Estriol.Investigational
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Estriol.Approved
FluindioneEstriol may decrease the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Estriol.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Estriol.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Estriol.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Estriol.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Estriol.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Estriol.Approved
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Estriol.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Estriol.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Estriol.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Estriol.Approved
Fluticasone propionateThe serum concentration of Fluticasone propionate can be increased when it is combined with Estriol.Approved
FondaparinuxEstriol may decrease the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumEstriol may decrease the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Estriol.Approved, Investigational, Withdrawn
GabexateEstriol may decrease the anticoagulant activities of Gabexate.Investigational
HalcinonideThe serum concentration of Halcinonide can be increased when it is combined with Estriol.Approved, Investigational, Withdrawn
HE3286The serum concentration of HE3286 can be increased when it is combined with Estriol.Investigational
HeparinEstriol may decrease the anticoagulant activities of Heparin.Approved, Investigational
Human C1-esterase inhibitorEstriol may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Estriol.Approved, Investigational
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Estriol.Approved, Vet Approved
IdraparinuxEstriol may decrease the anticoagulant activities of Idraparinux.Investigational
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Estriol.Investigational
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Estriol.Approved
LenalidomideEstriol may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinEstriol may decrease the anticoagulant activities of Lepirudin.Approved
LetaxabanEstriol may decrease the anticoagulant activities of Letaxaban.Investigational
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Estriol.Approved
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Estriol.Approved
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Estriol.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Estriol.Approved
LoteprednolThe serum concentration of Loteprednol can be increased when it is combined with Estriol.Approved
LumacaftorThe serum concentration of Estriol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Estriol.Approved, Investigational
ME-609The serum concentration of ME-609 can be increased when it is combined with Estriol.Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Estriol.Approved
MelagatranEstriol may decrease the anticoagulant activities of Melagatran.Experimental
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Estriol.Vet Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Estriol.Approved, Vet Approved
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Estriol.Approved, Vet Approved
NabumetoneNabumetone may increase the thrombogenic activities of Estriol.Approved
NadroparinEstriol may decrease the anticoagulant activities of Nadroparin.Approved
NafamostatEstriol may decrease the anticoagulant activities of Nafamostat.Approved, Investigational
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Estriol.Investigational
Oleoyl-estroneThe serum concentration of Oleoyl-estrone can be increased when it is combined with Estriol.Investigational
OspemifeneThe risk or severity of adverse effects can be increased when Estriol is combined with Ospemifene.Approved
OtamixabanEstriol may decrease the anticoagulant activities of Otamixaban.Investigational
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Estriol.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Estriol.Approved
Pentaerythritol TetranitrateEstriol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
Pentosan PolysulfateEstriol may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PhenindioneEstriol may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonEstriol may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Estriol.Approved, Nutraceutical
Prasterone sulfateThe serum concentration of Prasterone sulfate can be increased when it is combined with Estriol.Investigational
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Estriol.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Estriol.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Estriol.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Estriol.Experimental, Investigational
Protein CEstriol may decrease the anticoagulant activities of Protein C.Approved
Protein S humanEstriol may decrease the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeEstriol may decrease the anticoagulant activities of Protocatechualdehyde.Approved
RanolazineThe serum concentration of Estriol can be increased when it is combined with Ranolazine.Approved, Investigational
ReviparinEstriol may decrease the anticoagulant activities of Reviparin.Approved, Investigational
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Estriol.Approved
RivaroxabanEstriol may decrease the anticoagulant activities of Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Estriol.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Estriol.Approved, Investigational
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Estriol.Approved
SomatotropinThe therapeutic efficacy of Somatotropin can be decreased when used in combination with Estriol.Approved, Investigational
SulodexideEstriol may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
ThalidomideEstriol may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Estriol.Approved
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Estriol.Approved
TipranavirEstriol may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Estriol.Approved
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Estriol.Approved, Vet Approved
TroxerutinEstriol may decrease the anticoagulant activities of Troxerutin.Investigational
UlobetasolThe serum concentration of Ulobetasol can be increased when it is combined with Estriol.Approved
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Estriol.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Estriol.Investigational, Withdrawn
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Estriol.Approved, Investigational
Vitamin CThe serum concentration of Estriol can be increased when it is combined with Vitamin C.Approved, Nutraceutical
WarfarinEstriol may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranEstriol may decrease the anticoagulant activities of Ximelagatran.Approved, Investigational, Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

James V. Freeman, Gary M. Johnson, "Synthesis of 6.alpha.-functionalized estriol haptens and protein conjugates thereof." U.S. Patent US5902888, issued June, 1973.

US5902888
General References
  1. Soldan SS, Alvarez Retuerto AI, Sicotte NL, Voskuhl RR: Immune modulation in multiple sclerosis patients treated with the pregnancy hormone estriol. J Immunol. 2003 Dec 1;171(11):6267-74. [PubMed:14634144]
  2. Trimesta [Link]
External Links
Human Metabolome Database
HMDB00153
KEGG Drug
D00185
KEGG Compound
C05141
PubChem Compound
5756
PubChem Substance
46505881
ChemSpider
5553
BindingDB
50410506
ChEBI
27974
ChEMBL
CHEMBL193482
Therapeutic Targets Database
DAP001019
PharmGKB
PA164769104
HET
ESL
Wikipedia
Estriol
ATC Codes
G03CC06 — EstriolG03CA04 — Estriol
PDB Entries
1x8v / 3q95
MSDS
Download (75.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionVaginal Health1
1Not Yet RecruitingTreatmentMenopause / Painful Intercourse / Sexual Dysfunctions1
1RecruitingPreventionPregnancy1
1RecruitingTreatmentAtrophic Vaginitis1
2CompletedTreatmentHereditary Haemorrhagic Telangiectasia (HHT) / Nasal Bleeding1
2CompletedTreatmentMenopause1
2CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
2CompletedTreatmentVulvovaginal Atrophy1
2RecruitingTreatmentMultiple Sclerosis, Primary Progressive / Relapsing Remitting Multiple Sclerosis (RRMS) / Secondary Progressive Multiple Sclerosis (SPMS)1
2RecruitingTreatmentVulvovaginal Atrophy1
2Unknown StatusDiagnosticPremenstrual Syndrome1
2Unknown StatusTreatmentPremenstrual Syndrome1
3CompletedTreatmentVulvovaginal Atrophy1
3TerminatedTreatmentAtrophic Vaginitis1
4CompletedSupportive CareAtrophic Vaginitis / Endometrial Hyperplasia / Pelvic Organ Prolapse (POP)1
4CompletedTreatmentVulvovaginal Atrophy1
4Not Yet RecruitingTreatmentGenital Prolapse1
Not AvailableNot Yet RecruitingNot AvailableLocalized Provoked Vulvodynia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)82-86Organon Laboratories Limited, England; British Patent 879,014; October 4, 1961.
logP2.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.119 mg/mLALOGPS
logP2.54ALOGPS
logP2.67ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.27 m3·mol-1ChemAxon
Polarizability33.07 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.7057
Caco-2 permeable+0.7591
P-glycoprotein substrateSubstrate0.7862
P-glycoprotein inhibitor INon-inhibitor0.9208
P-glycoprotein inhibitor IINon-inhibitor0.9805
Renal organic cation transporterNon-inhibitor0.8619
CYP450 2C9 substrateNon-substrate0.7536
CYP450 2D6 substrateNon-substrate0.7993
CYP450 3A4 substrateSubstrate0.6892
CYP450 1A2 substrateNon-inhibitor0.6618
CYP450 2C9 inhibitorNon-inhibitor0.9399
CYP450 2D6 inhibitorNon-inhibitor0.9619
CYP450 2C19 inhibitorNon-inhibitor0.7086
CYP450 3A4 inhibitorNon-inhibitor0.8932
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9152
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9147
BiodegradationNot ready biodegradable0.9811
Rat acute toxicity1.9758 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.948
hERG inhibition (predictor II)Inhibitor0.7684
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-005a-1983000000-2f46d0d29b48132f7670
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000i-4970000000-1aa2bbf3f32fd687c37d
GC-MS Spectrum - GC-MSGC-MSsplash10-005a-1983000000-2f46d0d29b48132f7670
Mass Spectrum (Electron Ionization)MSsplash10-000i-3950000000-c2f0781bc5056d66aaf5
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0a4i-5900000000-2102cb581ac98fea87b0
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0a4i-1900000000-1fab12be883127f80c67
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0a4i-5900000000-2102cb581ac98fea87b0
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , PositiveLC-MS/MSsplash10-000i-4970000000-1aa2bbf3f32fd687c37d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-000i-0390000000-891430228022fb330b42
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxysteroids / 17-hydroxysteroids / 16-alpha-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / 1,2-diols / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-hydroxysteroid / 17-hydroxysteroid / 16-hydroxysteroid / 16-alpha-hydroxysteroid / Hydroxysteroid / Phenanthrene / Tetralin / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
17beta-hydroxy steroid, 3-hydroxy steroid, 16alpha-hydroxy steroid (CHEBI:27974) / C18 steroids (estrogens) and derivatives, Estrane and derivatives, Estrogens (C05141) / C18 steroids (estrogens) and derivatives (LMST02010003)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [PubMed:2011412]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
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 m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Mishra RG, Stanczyk FZ, Burry KA, Oparil S, Katzenellenbogen BS, Nealen ML, Katzenellenbogen JA, Hermsmeyer RK: Metabolite ligands of estrogen receptor-beta reduce primate coronary hyperreactivity. Am J Physiol Heart Circ Physiol. 2006 Jan;290(1):H295-303. Epub 2005 Sep 30. [PubMed:16199482]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871]

Drug created on September 07, 2007 15:04 / Updated on December 01, 2017 17:11