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
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
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 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
| 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 |
|---|---|---|
| Effects of dehydroepiandrosterone vs androstenedione supplementation in men. | 1999 Dec |
|
| Structure and functions of human oxysterol 7alpha-hydroxylase cDNAs and gene CYP7B1. | 1999 Dec |
|
| Conversion of dehydroepiandrosterone to downstream steroid hormones in macrophages. | 2000 Feb |
|
| 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 |
|
| Increased serum cortisol levels are associated with high tumour grade in patients with renal cell carcinoma. | 2001 |
|
| Therapeutic strategies in adrenal insufficiency. | 2001 Apr |
|
| [Correlations between acne and polycystic ovary. A study of 60 cases]. | 2001 Apr |
|
| High-grade prostate cancer is associated with low serum testosterone levels. | 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 |
|
| The adrenal and the metabolic syndrome. | 2001 Apr |
|
| Dehydroepiandrosterone decreases mortality rate and improves cellular immune function during polymicrobial sepsis. | 2001 Feb |
|
| Long-term dehydroepiandrosterone and 16alpha-fluoro-5-androsten-17-one administration enhances DNA synthesis and induces expression of c-fos and c-Ha-ras in a selected population of preneoplastic lesions in liver of diethylnitrosamine-initiated rats. | 2001 Feb |
|
| Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
|
| Enhanced induction of the IgA response in pigs by calcitriol after intramuscular immunization. | 2001 Feb 28 |
|
| Differentially expressed genes in zona reticularis cells of the human adrenal cortex. | 2001 Feb 28 |
|
| Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol. | 2001 Feb 28 |
|
| The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors. | 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 |
|
| Oxidative stress regulates collagen synthesis and matrix metalloproteinase activity in cardiac fibroblasts. | 2001 Jan |
|
| Effects of long-term alpha-tocopherol supplementation on serum hormones in older men. | 2001 Jan 1 |
|
| Crucial role of cytokines in sex steroid formation in normal and tumoral tissues. | 2001 Jan 22 |
|
| [Precocious puberty caused by a testicular Leydig cell tumor]. | 2001 Jan 28 |
|
| Receptor selectivity, enzymes and tissue specificity. | 2001 Jan 31 |
|
| Influence of dehydroepiandrosterone on rabbit intraocular pressure. | 2001 Jan-Feb |
|
| Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates. | 2001 Jul |
|
| Association of vitamin D receptor and 17 hydroxylase gene polymorphisms with benign prostatic hyperplasia and benign prostatic enlargement. | 2001 Mar |
|
| Enhanced dehydroepiandrosterone synthesis by amnion compared to chorion: a comparative study using the reverse-isotope dilution technique. | 2001 Mar |
|
| Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone. | 2001 Mar 30 |
|
| 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 |
|
| Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions. | 2001 May 15 |
|
| Serum hormones and the alcohol-breast cancer association in postmenopausal women. | 2001 May 2 |
|
| Anorectic effect of dehydroepiandrosterone combined with dexfenfluramine or thionisoxetine. | 2001 May 4 |
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.
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SUB04009MIG
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23983-43-9
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C033624
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163331
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245-970-8
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2W8I1S6T5L
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DTXSID00946833
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100000085481
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Dehydroepiandrosterone enanthate
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ACTIVE MOIETY
SUBSTANCE RECORD
