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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H40O3
Molecular Weight 400.594
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRASTERONE ENANTATE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@H](CC[C@]34C)OC(=O)CCCCCC

InChI

InChIKey=HHENOUDBWKNPAB-BNCSLUSBSA-N
InChI=1S/C26H40O3/c1-4-5-6-7-8-24(28)29-19-13-15-25(2)18(17-19)9-10-20-21-11-12-23(27)26(21,3)16-14-22(20)25/h9,19-22H,4-8,10-17H2,1-3H3/t19-,20-,21-,22-,25-,26-/m0/s1

HIDE SMILES / InChI

Molecular Formula C26H40O3
Molecular Weight 400.594
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dehydroepiandrosterone (INTRAROSA™, prasterone) is a major C19 steroid produced from cholesterol by the adrenal cortex. It is also produced in small quantities in the testis and the ovary. Dehydroepiandrosterone (INTRAROSA, prasterone) is structurally similar to, and is a precursor of, androstenedione, testosterone, estradiol, estrone and estrogen. It indicated for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause. The mechanism of action of dehydroepiandrosterone (INTRAROSA, prasterone) in postmenopausal women with vulvar and vaginal atrophy is not fully established.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
514.55 nM [Ki]
1053.17 nM [Ki]
1177.02 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INTRAROSA

Cmax

ValueDoseCo-administeredAnalytePopulation
36.7 nM
50 mg single, oral
PRASTERONE serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
176.1 nM × h
50 mg single, oral
PRASTERONE serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.35 h
50 mg single, oral
PRASTERONE serum
Homo sapiens

Doses

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Administer one INTRAROSA vaginal insert once daily at bedtime, using the provided applicator.
Route of Administration: Vaginal
In Vitro Use Guide
Dehydroepiandrosterone (DHEA) bound to AR with a Ki of 1 microM, which was associated with AR transcriptional antagonism on both the mouse mammary tumor virus and prostate-specific antigen promoters. DHEA bound to ERalpha and ERbeta, with Ki values of 1.1 and 0.5 microM, respectively. Despite the similar binding affinities, DHEA showed preferential agonism of ERbeta with an EC50 of approximately 200 nm and maximal activation at 1 microM. With ERalpha 30-70% agonism at 5 microM was found.
Substance Class Chemical
Record UNII
2W8I1S6T5L
Record Status Validated (UNII)
Record Version