Estradiol glucuronide
[1] It is formed from estradiol in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys.[1] When exogenous estradiol is administered orally, it is subject to extensive first-pass metabolism (95%) in the intestines and liver.[2] Formation of estrogen glucuronide conjugates is particularly important with oral estradiol as the percentage of estrogen glucuronide conjugates in circulation is much higher with oral ingestion than with parenteral estradiol.[2] In demonstration of the importance of first-pass metabolism and the estrogen conjugate reservoir in the pharmacokinetics of estradiol,[2] the elimination half-life of oral estradiol is 13 to 20 hours[4] whereas with intravenous injection its elimination half-life is only about 1 to 2 hours.[6] Estradiol glucuronide is transported into prostate gland, testis, and breast cells by OATP1A2, OATP1B1, OATP1B3, OATP1C1, and OATP3A1.
Estradiol 3-glucuronideIUPAC nameCAS NumberChEMBLChemSpiderPubChemCompTox DashboardSMILESChemical formulaMolar massstandard stateconjugatedmetaboliteestradiolUDP-glucuronyltransferaseglucuronic acidexcretedkidneyswater solubilityexogenousorallyfirst-pass metabolismintestinesabsorbedestroneestrone sulfateestrone glucuronideestrogenparenteralelimination half-lifepharmacokineticsintravenous injectionprostate glandtestisbreastOATP1A2OATP1B1OATP1B3OATP1C1OATP3A1ABC transportersagonistG protein-coupled estrogen receptormembrane estrogen receptorcholestasisdeglucuronidatedβ-glucuronidasetissuesenzymemammary glandpotencyestrogen receptorsin vitropositional isomerovulationEstradiol 3-sulfateEstradiol benzoateEstradiol 17β-acetateEstradiol diacetateEstradiol propionateEstradiol valerateEstradiol cypionateEstradiol palmitateEstradiol stearateEthinylestradiolMestranolQuinestrolRelative binding affinitiesin-vitrolabeledrodentuterinecytosolEstrogen estershydrolyzedhalf-maximal effective concentrationsβ‐galactosidasegreen fluorescent proteinproductionassaysmammalianEstradiol acetateEthanoic acidBenzoic acidEstradiol dipropionatePropanoic acidPentanoic acidEstradiol benzoate butyratebutyric acidCyclopentylpropanoic acidEstradiol enanthateHeptanoic acidEstradiol dienanthateEstradiol undecylateUndecanoic acidOctadecanoic acidEstradiol distearateEstradiol sulfateSulfuric acidEstramustine phosphateNormustinephosphoric acidPolyestradiol phosphatecarbonstraight-chain fatty acidsaromaticcyclicestrogenicoctanol/water partition coefficientlipophilicityhydrophobicityDrugBankPolymerestradiol phosphaterepeat unitsCatechol estrogenEstriol glucuronideEstriol sulfateEstrogen conjugateLipoidal estradiolEstradiol (as a hormone)Estradiol (as a medication)Pharmacodynamics of estradiolPharmacokinetics of estradiolEstrogen (as a hormone)Estrogen (as a medication)