U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H26O3
Molecular Weight 314.4186
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL ACETATE

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC(C)=O)C=C4

InChI

InChIKey=FHXBMXJMKMWVRG-SLHNCBLASA-N
InChI=1S/C20H26O3/c1-12(21)23-14-4-6-15-13(11-14)3-5-17-16(15)9-10-20(2)18(17)7-8-19(20)22/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H26O3
Molecular Weight 314.4186
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Estradiol an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Estradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and 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 estradiol upon the target cell. Estradiol is used for the treatment of urogenital symptoms associated with post-menopausal atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria). Estradiol is marketed under the brand name Climara (among others), indicated for: the treatment of moderate to severe vasomotor symptoms due to menopause, treatment of symptoms of vulvar and vaginal atrophy due to menopause, treatment of hypoestrogenism due to hypogonadism, castration or primary ovarian failure and prevention of postmenopausal osteoporosis.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.0084 nM [EC50]
1.4 nM [EC50]
19.1 nM [IC50]
0.13 nM [Ki]
0.09 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLIMARA
Preventing
CLIMARA
Primary
CLIMARA

Cmax

ValueDoseCo-administeredAnalytePopulation
14.7 pg/mL
0.25 mg 1 times / day steady-state, topical
ESTRADIOL plasma
Homo sapiens
92 pg/mL
0.05 mg 1 times / day multiple, topical
ESTRADIOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
236 pg × h/mL
0.25 mg 1 times / day steady-state, topical
ESTRADIOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
0.25 mg 1 times / day steady-state, topical
ESTRADIOL plasma
Homo sapiens
1.75 h
0.05 mg 1 times / day multiple, topical
ESTRADIOL plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Estradiol-3-sulfate (E2SO4) infused intracerebroventricularly (icv) significantly increased plasma adrenocorticotropic hormone (ACTH) and cortisol concentrations. All minipumps in the treated fetuses were filled with E2SO4 in the vehicle (water) and minipumps in the control fetuses were filled with vehicle only. These minipumps deliver a constant infusion of 5 μL/h; the concentration of E2SO4 in infusates was therefore 8.33 μg/μL. It was concluded, that E2SO4 had complex actions on the fetal brain, which might involve deconjugation by steroid sulfatase. But that the net result of direct E2SO4 icv infusion was more complex than could be accounted for by infusion of E2 alone.
Substance Class Chemical
Record UNII
5R97F5H93P
Record Status Validated (UNII)
Record Version