Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H27O5S.Na.2H2O |
| Molecular Weight | 426.5 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[Na+].C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](CC[C@]34C)OS([O-])(=O)=O)[C@@H]1CCC2=O
InChI
InChIKey=NLNMKDUYGPNWAO-OXNWJOIVSA-M
InChI=1S/C19H28O5S.Na.2H2O/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);;2*1H2/q;+1;;/p-1/t13-,14-,15-,16-,18-,19-;;;/m0.../s1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL242 |
514.55 nM [Ki] | ||
Target ID: CHEMBL206 |
1053.17 nM [Ki] | ||
Target ID: CHEMBL1871 |
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
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates. | 2001-07 |
|
| Neurosteroid hydroxylase CYP7B: vivid reporter activity in dentate gyrus of gene-targeted mice and abolition of a widespread pathway of steroid and oxysterol hydroxylation. | 2001-06-29 |
|
| Dehydroepiandrosterone restores hepatocellular function and prevents liver damage in estrogen-deficient females following trauma and hemorrhage. | 2001-05-15 |
|
| Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions. | 2001-05-15 |
|
| Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction. | 2001-05-15 |
|
| Anorectic effect of dehydroepiandrosterone combined with dexfenfluramine or thionisoxetine. | 2001-05-04 |
|
| Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001-05-02 |
|
| Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures. | 2001-05-01 |
|
| Sebocytes are the key regulators of androgen homeostasis in human skin. | 2001-05 |
|
| 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? | 2001-05 |
|
| Identification of extracellular matrix components and their integrin receptors in the human fetal adrenal gland. | 2001-05 |
|
| Dehydroepiandrosterone replacement in women with adrenal insufficiency: effects on body composition, serum leptin, bone turnover, and exercise capacity. | 2001-05 |
|
| Dehydroepiandrosterone inhibits lipopolysaccharide-induced nitric oxide production in BV-2 microglia. | 2001-05 |
|
| Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001-05 |
|
| Hormones as antiaging remedies. | 2001-04-28 |
|
| Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain. | 2001-04-27 |
|
| Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine. | 2001-04-25 |
|
| Leuprolide acetate treatment of adrenocortical disease in ferrets. | 2001-04-15 |
|
| cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate. | 2001-04-15 |
|
| Characteristics of cystic breast disease with special regard to breast cancer development. | 2001-04-13 |
|
| Adrenal steroids in human prostatic cancer cell lines. | 2001-04-12 |
|
| Therapeutic strategies in adrenal insufficiency. | 2001-04 |
|
| Sex hormones and their impact on dementia and depression: a clinical perspective. | 2001-04 |
|
| [Correlations between acne and polycystic ovary. A study of 60 cases]. | 2001-04 |
|
| Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration. | 2001-04 |
|
| High-grade prostate cancer is associated with low serum testosterone levels. | 2001-04 |
|
| Up-regulation of cyclooxygenase-1 in neuroblastoma cell lines by retinoic acid and corticosteroids. | 2001-04 |
|
| Novel assay for determination of androgen bioactivity in human serum. | 2001-04 |
|
| Effect of estrogen on serum DHEA in younger and older women and the relationship of DHEA to adiposity and gender. | 2001-04 |
|
| Sarcopenia. | 2001-04 |
|
| Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone. | 2001-03-30 |
|
| Ontogeny of the neurosteroid enzyme Cyp7b in the mouse. | 2001-03-28 |
|
| Temporal and spatial distribution of corticosteroidogenic enzymes immunoreactivity in developing human adrenal. | 2001-03-28 |
|
| Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study. | 2001-03 |
|
| Exploratory biochemical data analysis: a comparison of two sample means and diagnostic displays. | 2001-03 |
|
| Assessment of endocrine status in patients undergoing in-vitro fertilization treatment. Is it necessary? | 2001-03 |
|
| Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome. | 2001-03 |
|
| Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy. | 2001-03 |
|
| Memory-enhancing effects of DHEAS in aged mice on a win-shift water escape task. | 2001-03 |
|
| Non-aqueous emulsions: hydrocarbon-formamide systems. | 2001-02-19 |
|
| DHEA: a novel adjunct for the treatment of male trauma patients. | 2001-02 |
|
| Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis. | 2001-02 |
|
| 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 |
|
| The prevention of osteoporotic progression by means of steroid loaded TCPL drug delivery systems. | 2001 |
|
| Intraadrenal mechanisms of DHEA regulation: a hypothesis for adrenopause. | 2001 |
|
| GG-genotype in the promotor region of uncoupling-protein-1 gene is associated with lower level of dehydroepiandrosterone in type 2 diabetes. | 2001 |
|
| Increased serum cortisol levels are associated with high tumour grade in patients with renal cell carcinoma. | 2001 |
|
| Effects of transdermal application of 7-oxo-DHEA on the levels of steroid hormones, gonadotropins and lipids in healthy men. | 2001 |
|
| Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis. | 2001 |
Sample Use Guides
Administer one INTRAROSA vaginal insert once daily at bedtime, using the provided applicator.
Route of Administration:
Vaginal
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
Mon Mar 31 18:25:01 GMT 2025
by
admin
on
Mon Mar 31 18:25:01 GMT 2025
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| Record UNII |
E1CR8487EN
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C243
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C77220
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300000025753
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78590-17-7
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DTXSID9045764
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E1CR8487EN
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23694217
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
