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
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@@H](O)CC[C@]34C
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 Date1.47925434E12 |
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 |
---|---|---|
The steroid hormone dehydroepiandrosterone inhibits CYP1A1 expression in vitro by a post-transcriptional mechanism. | 1999 Dec 3 |
|
Conversion of dehydroepiandrosterone to downstream steroid hormones in macrophages. | 2000 Feb |
|
Differential estrogen receptor binding of estrogenic substances: a species comparison. | 2000 Nov 15 |
|
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 |
|
Dehydroepiandrosterone sulphate prevents oxygen-glucose deprivation-induced injury in cerebellar granule cell culture. | 2001 |
|
Therapeutic strategies in adrenal insufficiency. | 2001 Apr |
|
Up-regulation of cyclooxygenase-1 in neuroblastoma cell lines by retinoic acid and corticosteroids. | 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 |
|
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 |
|
Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis. | 2001 Feb |
|
Dehydroepiandrosterone decreases mortality rate and improves cellular immune function during polymicrobial sepsis. | 2001 Feb |
|
Bacterial expression, purification, and characterization of rat hydroxysteroid sulfotransferase STa. | 2001 Feb |
|
Food-dependent androgen and cortisol secretion by a gastric inhibitory polypeptide-receptor expressive adrenocortical adenoma leading to hirsutism and subclinical Cushing's syndrome: in vivo and in vitro studies. | 2001 Feb |
|
Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men. | 2001 Feb |
|
[Aging without becoming old. 2 anti-aging days per week]. | 2001 Feb 15 |
|
Differentially expressed genes in zona reticularis cells of the human adrenal cortex. | 2001 Feb 28 |
|
Symposium on endocrinology and aging: the 1st meeting of the European Interest Group hormones and aging. | 2001 Jan |
|
[Replacement therapy in adrenopause. Dehydroepiandrosterone and aging]. | 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 |
|
Effects of dehydroepiandrosterone and quinapril on nephropathy in obese Zucker rats. | 2001 Jan |
|
Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats. | 2001 Jan |
|
Low dehydroepiandrosterone and ischemic heart disease in middle-aged men: prospective results from the Massachusetts Male Aging Study. | 2001 Jan 1 |
|
Dehydroepiandrosterone (DHEA) reduces neuronal injury in a rat model of global cerebral ischemia. | 2001 Jan 12 |
|
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 |
|
Hormonal decline in elderly men and male menopause. | 2001 Jan-Feb |
|
Influence of dehydroepiandrosterone on rabbit intraocular pressure. | 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 |
|
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 |
|
Memory-enhancing effects of DHEAS in aged mice on a win-shift water escape task. | 2001 Mar |
|
Ergogenic aids: counseling the athlete. | 2001 Mar 1 |
|
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 |
|
Hormones as antiaging remedies. | 2001 Mar-Apr |
|
Sebocytes are the key regulators of androgen homeostasis in human skin. | 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 |
|
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures. | 2001 May 1 |
|
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 |
|
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
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
Sun Dec 18 18:45:56 UTC 2022
by
admin
on
Sun Dec 18 18:45:56 UTC 2022
|
Record UNII |
459AG36T1B
|
Record Status |
Validated (UNII)
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Record Version |
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-
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LOINC |
35206-2
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LOINC |
55815-5
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WHO-VATC |
QA14AA07
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LOINC |
29879-4
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WHO-ATC |
A14AA07
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FDA ORPHAN DRUG |
172303
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LOINC |
34283-2
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DSLD |
408 (Number of products:367)
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WHO-VATC |
QG03EA03
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LOINC |
15054-0
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LOINC |
25391-4
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EU-Orphan Drug |
EU/3/03/156
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LOINC |
25895-4
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WHO-ATC |
G03EA03
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LOINC |
30029-3
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LOINC |
31020-1
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LOINC |
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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LOINC |
49716-4
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LOINC |
74361-7
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LOINC |
82879-8
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LOINC |
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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LOINC |
34279-0
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WHO-ATC |
G03XX01
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LOINC |
2193-1
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5881
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DE-05
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C2265
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459AG36T1B
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9896
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200-175-5
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795
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53-43-0
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D003687
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3143
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2869
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459AG36T1B
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DEHYDROEPIANDROSTERONE
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DTXSID4020379
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28689
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CHEMBL90593
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M4145
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SUB10002MIG
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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 |