Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H28O5S |
Molecular Weight | 368.488 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@H](CC[C@]34C)OS(O)(=O)=O
InChI
InChIKey=CZWCKYRVOZZJNM-USOAJAOKSA-N
InChI=1S/C19H28O5S/c1-18-9-7-13(24-25(21,22)23)11-12(18)3-4-14-15-5-6-17(20)19(15,2)10-8-16(14)18/h3,13-16H,4-11H2,1-2H3,(H,21,22,23)/t13-,14-,15-,16-,18-,19-/m0/s1
Molecular Formula | C19H28O5S |
Molecular Weight | 368.488 |
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 n = 5 Health Status: healthy Age Group: 22-25 years Sex: M Population Size: 5 Sources: |
|
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 n = 29 Health Status: unhealthy Condition: HIV infection Age Group: 44.9 years Sex: M Population Size: 29 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 |
---|---|---|
Effects of dehydroepiandrosterone vs androstenedione supplementation in men. | 1999 Dec |
|
The steroid hormone dehydroepiandrosterone inhibits CYP1A1 expression in vitro by a post-transcriptional mechanism. | 1999 Dec 3 |
|
The effect of ultraviolet radiation and pretreatment of dehydroepiandrosterone on RMK cells in culture. | 2001 |
|
The prevention of osteoporotic progression by means of steroid loaded TCPL drug delivery systems. | 2001 |
|
Therapeutic strategies in adrenal insufficiency. | 2001 Apr |
|
Novel assay for determination of androgen bioactivity in human serum. | 2001 Apr |
|
Effect of estrogen on serum DHEA in younger and older women and the relationship of DHEA to adiposity and gender. | 2001 Apr |
|
Leuprolide acetate treatment of adrenocortical disease in ferrets. | 2001 Apr 15 |
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Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine. | 2001 Apr 25 |
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Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men. | 2001 Feb |
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Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
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Non-aqueous emulsions: hydrocarbon-formamide systems. | 2001 Feb 19 |
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Enhanced induction of the IgA response in pigs by calcitriol after intramuscular immunization. | 2001 Feb 28 |
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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 |
|
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors. | 2001 Jan |
|
Oxidative stress regulates collagen synthesis and matrix metalloproteinase activity in cardiac fibroblasts. | 2001 Jan |
|
Low dehydroepiandrosterone and ischemic heart disease in middle-aged men: prospective results from the Massachusetts Male Aging Study. | 2001 Jan 1 |
|
[Precocious puberty caused by a testicular Leydig cell tumor]. | 2001 Jan 28 |
|
Plasma levels of neuroactive steroids are increased in untreated women with anorexia nervosa or bulimia nervosa. | 2001 Jan-Feb |
|
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001 Mar |
|
Exploratory biochemical data analysis: a comparison of two sample means and diagnostic displays. | 2001 Mar |
|
Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome. | 2001 Mar |
|
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 |
|
Identification of extracellular matrix components and their integrin receptors in the human fetal adrenal gland. | 2001 May |
|
Dehydroepiandrosterone replacement in women with adrenal insufficiency: effects on body composition, serum leptin, bone turnover, and exercise capacity. | 2001 May |
|
Dehydroepiandrosterone inhibits lipopolysaccharide-induced nitric oxide production in BV-2 microglia. | 2001 May |
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
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Record UNII |
57B09Q7FJR
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 862.1245
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DEHYDROEPIANDROSTERONE SULFATE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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PARENT -> METABOLITE |
Oral prasterone is sulfated to 5-DHEAS ester in the intestine and liver by sulfotransferases
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Related Record | Type | Details | ||
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ACTIVE MOIETY |