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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O3
Molecular Weight 328.4452
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL 17-PROPIONATE

SMILES

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

InChI

InChIKey=PQCRZWCSVWBYSC-AGRFSFNASA-N
InChI=1S/C21H28O3/c1-3-20(23)24-19-9-8-18-17-6-4-13-12-14(22)5-7-15(13)16(17)10-11-21(18,19)2/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H28O3
Molecular Weight 328.4452
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 benzoate is the synthetic benzoate ester of estradiol, a steroid sex hormone vital to the maintenance of fertility and secondary sexual characteristics in females. As the primary, most potent estrogen hormone produced by the ovaries, estradiol binds to and activates specific nuclear receptors. This agent exhibits mild anabolic and metabolic properties, and increases blood coagulability. Although estradiol benzoate is not approved by the FDA for use in humans in the United States, it is approved for veterinary use as a subdermal implant both alone (CELERIN®) and in combination with the anabolic steroid trenbolone acetate (SYNOVEX® Plus).

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

AUC

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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.75 h
0.05 mg 1 times / day multiple, topical
ESTRADIOL serum
Homo sapiens
10 h
0.25 mg 1 times / day steady-state, topical
ESTRADIOL serum
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
K31PC34297
Record Status Validated (UNII)
Record Version