U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PRASTERONE SULFATE

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

HIDE SMILES / InChI

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

Description
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.

Originator

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

Targets

Primary TargetPharmacologyConditionPotency
514.55 nM [Ki]
1053.17 nM [Ki]
1177.02 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INTRAROSA

Approved Use

INTRAROSA™ is a steroid indicated for the treatment of moderate to severe dyspareunia, a symptom of vulvar and vaginal atrophy, due to menopause.

Launch Date

2016
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
36.7 nM
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

AUC

ValueDoseCo-administeredAnalytePopulation
176.1 nM × h
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

T1/2

ValueDoseCo-administeredAnalytePopulation
5.35 h
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

Doses

DosePopulationAdverse 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

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Evidence for the involvement of the fatty acid and peroxisomal beta-oxidation pathways in the inhibition by dehydroepiandrosterone (DHEA) and induction by 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) and benz(a)anthracene (BA) of cytochrome P4501B1 (CYP1B1) in mouse embryo fibroblasts (C3H10T1/2 cells).
1999 Aug
Dehydroepiandrosterone suppresses elevated hepatic glucose-6-phosphatase mRNA level in C57BL/KsJ-db/db mice: comparison with troglitazone.
2000 Dec
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
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
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
Dehydroepiandrosterone sulphate prevents oxygen-glucose deprivation-induced injury in cerebellar granule cell culture.
2001
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
Effect of estrogen on serum DHEA in younger and older women and the relationship of DHEA to adiposity and gender.
2001 Apr
Sarcopenia.
2001 Apr
Regulation of calcitonin receptor by glucocorticoid in human osteoclast-like cells prepared in vitro using receptor activator of nuclear factor-kappaB ligand and macrophage colony-stimulating factor.
2001 Apr
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine.
2001 Apr 25
Expression and localization of cytochrome P450 17 alpha-hydroxylase/c17,20-lyase in the avian brain.
2001 Apr 27
DHEA: a novel adjunct for the treatment of male trauma patients.
2001 Feb
Dehydroepiandrosterone decreases mortality rate and improves cellular immune function during polymicrobial sepsis.
2001 Feb
Hormone replacement therapy and fractures in older adults.
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
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
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
[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
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
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
[Precocious puberty caused by a testicular Leydig cell tumor].
2001 Jan 28
Hormonal decline in elderly men and male menopause.
2001 Jan-Feb
Plasma levels of neuroactive steroids are increased in untreated women with anorexia nervosa or bulimia nervosa.
2001 Jan-Feb
Influence of dehydroepiandrosterone on rabbit intraocular pressure.
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
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary.
2001 Mar
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
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
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Dehydroepiandrosterone restores hepatocellular function and prevents liver damage in estrogen-deficient females following trauma and hemorrhage.
2001 May 15
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
Patents

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 Fri Dec 15 15:24:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:43 GMT 2023
Record UNII
57B09Q7FJR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRASTERONE SULFATE
MART.   WHO-DD  
Common Name English
ANDROST-5-EN-17-ONE, 3-(SULFOOXY)-, (3.BETA.)-
Systematic Name English
Prasterone sulfate [WHO-DD]
Common Name English
PRASTERONE SULPHATE
Common Name English
DEHYDROEPIANDROSTERONE SULFATE
MI  
Common Name English
GENAFLOW
Brand Name English
PRASTERONE SULFATE [MART.]
Common Name English
ANDROST-5-EN-17-ONE, 3.BETA.-HYDROXY-, HYDROGEN SULFATE
Systematic Name English
DEHYDROANDROSTERONE SULFATE
Common Name English
DEHYDROEPIANDROSTERONE SULFATE [MI]
Common Name English
DHEA SULFATE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 862.1245
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LOINC 16721-3
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LOINC 34282-4
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LOINC 76347-4
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LOINC 15053-2
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LOINC 34280-8
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LOINC 2192-3
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LOINC 2191-5
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LOINC 34281-6
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LOINC 14688-6
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LOINC 35205-4
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Code System Code Type Description
DRUG BANK
DB05804
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
PUBCHEM
12594
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
DRUG CENTRAL
4049
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
CAS
651-48-9
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
MERCK INDEX
m4145
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY Merck Index
CHEBI
16814
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PRIMARY
EPA CompTox
DTXSID8040228
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PRIMARY
EVMPD
SUB34548
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
WIKIPEDIA
DEHYDROEPIANDROSTERONE SULFATE
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
FDA UNII
57B09Q7FJR
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
SMS_ID
100000128006
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
MESH
D019314
Created by admin on Fri Dec 15 15:24:43 GMT 2023 , Edited by admin on Fri Dec 15 15:24:43 GMT 2023
PRIMARY
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TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
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ACTIVE MOIETY