Estriol (medication)

Estriol (E3), sold under the brand name Ovestin among others, is an estrogen medication and naturally occurring steroid hormone which is used in menopausal hormone therapy. It is also used in veterinary medicine as Incurin to treat urinary incontinence due to estrogen deficiency in dogs. The medication is taken by mouth in the form of tablets, as a cream that is applied to the skin, as a cream or pessary that is applied in the vagina, and by injection into muscle.

Estriol (medication)
Clinical data
Pronunciation/ˈɛstriɒl, -trɒl/
ESS-TREE-ohl
Trade namesOvestin, others
Other namesOestriol; E3; 16α-Hydroxyestradiol; Estra-1,3,5(10)-triene-3,16α,17β-triol
Routes of
administration
By mouth, vaginal, intramuscular injection
Drug classEstrogen
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityOral: ~1–2%
Vaginal: ~10–20%
Protein binding92%:
Albumin: 91%
SHBGTooltip Sex hormone-binding globulin: 1%
• Free: 8%
MetabolismLiver, intestines (conjugation (glucuronidation, sulfation), oxidation, hydroxylation)
MetabolitesEstriol 16α-glucuronide
Estriol 3-glucuronide
Estriol 3-sulfate
Estriol 3-sulfate 16α-gluc.
16α-Hydroxyestrone
• Others (minor)
Elimination half-lifeOral: 5–10 hours
IMTooltip Intramuscular injection: 1.5–5.3 hours (as E3)
IVTooltip Intravenous injection: 20 minutes (as E3)
ExcretionUrine: >95% (as conjugates)
Identifiers
  • (8R,9S,13S,14S,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
CAS Number
  • 50-27-1 Y
    1306-04-3
    514-68-1 (succinate)
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC18H24O3
Molar mass288.387 g·mol−1
3D model (JSmol)
Melting point82 to 86 °C (180 to 187 °F) (experimental)
Solubility in water0.119 mg/mL (20 °C)
SMILES
  • Oc1cc3c(cc1)[C@H]2CC[C@@]4([C@@H](O)[C@H](O)C[C@H]4[C@@H]2CC3)C
  • 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 Y
  • Key:PROQIPRRNZUXQM-ZXXIGWHRSA-N Y
  (verify)

Estriol is well-tolerated and produces relatively few adverse effects. Side effects may include breast tenderness, vaginal discomfort and discharge, and endometrial hyperplasia. Estriol is a naturally occurring and bioidentical estrogen, or an agonist of the estrogen receptor, the biological target of estrogens like endogenous estradiol. It is an atypical and relatively weak estrogen, with much lower potency than estradiol. When present continuously at adequate concentrations however, estriol produces full estrogenic effects similarly to estradiol.

Estriol was first discovered in 1930, and was introduced for medical use shortly thereafter. Estriol esters such as estriol succinate are also used. Although it is less commonly employed than other estrogens like estradiol and conjugated estrogens, estriol is widely available for medical use in Europe and elsewhere throughout the world.

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