Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=O
InChI
InChIKey=FMGSKLZLMKYGDP-USOAJAOKSA-N
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,13-16,20H,4-11H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68003687 |
http://www.hmdb.ca/metabolites/HMDB00077
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68003687 |
http://www.hmdb.ca/metabolites/HMDB00077
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8597450
Curator's Comment: Primary source: Butenandt A, Dannenbaum H. Isolierung eines neuen, physiologisch unwirksamen Sterinderivates aus Mannerharn, seine Verknupfung mit Dehydro-androsteron und Androsteron. Z Physiol Chem. 1934; 229:192–195.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348 |
514.55 nM [Ki] | ||
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348 |
1053.17 nM [Ki] | ||
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348 |
1177.02 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | INTRAROSA Approved UseINTRAROSA™ is a steroid indicated for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause. Launch Date2016 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
36.7 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10372727 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRASTERONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
176.1 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10372727 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRASTERONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.35 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10372727 |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRASTERONE serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
healthy, 22-25 years |
|
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: |
unhealthy, 44.9 years Health Status: unhealthy Age Group: 44.9 years Sex: M Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no |
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Structure and functions of human oxysterol 7alpha-hydroxylase cDNAs and gene CYP7B1. | 1999 Dec |
|
The steroid hormone dehydroepiandrosterone inhibits CYP1A1 expression in vitro by a post-transcriptional mechanism. | 1999 Dec 3 |
|
Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases. | 2000 Jan 7 |
|
Sulphonation of N-hydroxy-2-acetylaminofluorene by human dehydroepiandrosterone sulphotransferase. | 2000 Mar |
|
Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
Inhibition of human immunodeficiency virus type-1 (HIV-1) replication by immunor (IM28), a new analog of dehydroepiandrosterone. | 2000 Oct-Dec |
|
The effect of ultraviolet radiation and pretreatment of dehydroepiandrosterone on RMK cells in culture. | 2001 |
|
The use of estrogen, DHEA, and diosgenin in a sustained delivery setting as a novel treatment approach for osteoporosis in the ovariectomized adult rat model. | 2001 |
|
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis. | 2001 |
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Sex hormones and their impact on dementia and depression: a clinical perspective. | 2001 Apr |
|
[Correlations between acne and polycystic ovary. A study of 60 cases]. | 2001 Apr |
|
Biochemical screening for subclinical cortisol-secreting adenomas amongst adrenal incidentalomas. | 2001 Apr |
|
Age-related changes of the hypothalamic-pituitary-adrenal axis: pathophysiological correlates. | 2001 Apr |
|
Leuprolide acetate treatment of adrenocortical disease in ferrets. | 2001 Apr 15 |
|
cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate. | 2001 Apr 15 |
|
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine. | 2001 Apr 25 |
|
DHEA: a novel adjunct for the treatment of male trauma patients. | 2001 Feb |
|
Hormone replacement therapy and fractures in older adults. | 2001 Feb |
|
Corticotrophin-releasing hormone and ACTH levels in maternal and fetal blood during spontaneous and oxytocin-induced labour. | 2001 Feb |
|
Bacterial expression, purification, and characterization of rat hydroxysteroid sulfotransferase STa. | 2001 Feb |
|
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
|
[Aging without becoming old. 2 anti-aging days per week]. | 2001 Feb 15 |
|
Composite effects of group drumming music therapy on modulation of neuroendocrine-immune parameters in normal subjects. | 2001 Jan |
|
Preliminary studies on the effect of dehydroepiandrosterone (DHEA) on both constitutive and phytohaemagglutinin (PHA)-inducible IL-6 and IL-2 mRNA expression and cytokine production in human spleen mononuclear cell suspensions in vitro. | 2001 Jan |
|
Establishment and characterization of a steroidogenic human granulosa-like tumor cell line, KGN, that expresses functional follicle-stimulating hormone receptor. | 2001 Jan |
|
Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats. | 2001 Jan |
|
Crucial role of cytokines in sex steroid formation in normal and tumoral tissues. | 2001 Jan 22 |
|
Characteristics of cystic breast disease with special regard to breast cancer development. | 2001 Jan-Feb |
|
Hormonal decline in elderly men and male menopause. | 2001 Jan-Feb |
|
Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates. | 2001 Jul |
|
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001 Mar |
|
Assessment of endocrine status in patients undergoing in-vitro fertilization treatment. Is it necessary? | 2001 Mar |
|
Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome. | 2001 Mar |
|
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy. | 2001 Mar |
|
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary. | 2001 Mar |
|
Ontogeny of the neurosteroid enzyme Cyp7b in the mouse. | 2001 Mar 28 |
|
Temporal and spatial distribution of corticosteroidogenic enzymes immunoreactivity in developing human adrenal. | 2001 Mar 28 |
|
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone. | 2001 Mar 30 |
|
Sebocytes are the key regulators of androgen homeostasis in human skin. | 2001 May |
|
Regulation of glucocorticoid receptor alpha and beta isoforms and type I 11beta-hydroxysteroid dehydrogenase expression in human skeletal muscle cells: a key role in the pathogenesis of insulin resistance? | 2001 May |
|
Identification of extracellular matrix components and their integrin receptors in the human fetal adrenal gland. | 2001 May |
|
Dehydroepiandrosterone inhibits lipopolysaccharide-induced nitric oxide production in BV-2 microglia. | 2001 May |
|
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions. | 2001 May 15 |
|
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction. | 2001 May 15 |
|
Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001 May 2 |
Sample Use Guides
Administer one INTRAROSA vaginal insert once daily at bedtime, using the provided applicator.
Route of Administration:
Vaginal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348
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
Created
by
admin
on
Edited
Wed Apr 02 07:58:57 GMT 2025
by
admin
on
Wed Apr 02 07:58:57 GMT 2025
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Record UNII |
459AG36T1B
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Record Status |
Validated (UNII)
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Record Version |
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35206-2
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55815-5
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29879-4
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A14AA07
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FDA ORPHAN DRUG |
172303
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34283-2
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DSLD |
408 (Number of products:367)
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WHO-VATC |
QG03EA03
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15054-0
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25391-4
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EU-Orphan Drug |
EU/3/03/156
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25895-4
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G03EA03
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30029-3
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2194-9
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CFR |
21 CFR 862.1430
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FDA ORPHAN DRUG |
83794
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LOINC |
82878-0
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2195-6
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CFR |
21 CFR 862.1245
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LIVERTOX |
276
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NCI_THESAURUS |
C243
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LOINC |
13612-7
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34279-0
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WHO-ATC |
G03XX01
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2193-1
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m4145
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DB01708
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> AGONIST |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> ACTIVATOR |
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DERIVATIVE -> PARENT |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
Oral prasterone is sulfated to 5-DHEAS ester in the intestine and liver by sulfotransferases
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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