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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O5S
Molecular Weight 368.4894
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRASTERONE SULFATE

SMILES

C[C@@]12CC[C@@]([H])(CC2=CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@@]31[H])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 368.4894
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

1.47925434E12
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
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
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
Therapeutic strategies in adrenal insufficiency.
2001 Apr
Sex hormones and their impact on dementia and depression: a clinical perspective.
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
Sarcopenia.
2001 Apr
The adrenal and the metabolic syndrome.
2001 Apr
Age-related changes of the hypothalamic-pituitary-adrenal axis: pathophysiological correlates.
2001 Apr
Leuprolide acetate treatment of adrenocortical disease in ferrets.
2001 Apr 15
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
Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis.
2001 Feb
Hormone replacement therapy and fractures in older adults.
2001 Feb
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.
2001 Feb 28
Symposium on endocrinology and aging: the 1st meeting of the European Interest Group hormones and aging.
2001 Jan
Effects of long-term alpha-tocopherol supplementation on serum hormones in older men.
2001 Jan 1
Low dehydroepiandrosterone and ischemic heart disease in middle-aged men: prospective results from the Massachusetts Male Aging Study.
2001 Jan 1
Receptor selectivity, enzymes and tissue specificity.
2001 Jan 31
Chalcones are potent inhibitors of aromatase and 17beta-hydroxysteroid dehydrogenase activities.
2001 Jan 5
Hormonal decline in elderly men and male menopause.
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
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
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy.
2001 Mar
Ontogeny of the neurosteroid enzyme Cyp7b in the mouse.
2001 Mar 28
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
Adrenal steroids in human prostatic cancer cell lines.
2001 Mar-Apr
Identification of extracellular matrix components and their integrin receptors in the human fetal adrenal gland.
2001 May
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.
2001 May
Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions.
2001 May 15
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
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 Sat Jun 26 14:31:36 UTC 2021
Edited
by admin
on Sat Jun 26 14:31:36 UTC 2021
Record UNII
57B09Q7FJR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRASTERONE SULFATE
MART.   WHO-DD  
Common Name English
PRASTERONE SULFATE [WHO-DD]
Common Name English
ANDROST-5-EN-17-ONE, 3-(SULFOOXY)-, (3.BETA.)-
Systematic 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
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 16721-3
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 34282-4
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LOINC 76347-4
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LOINC 15053-2
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 34280-8
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 2192-3
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 2191-5
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 34281-6
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 2190-7
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 14688-6
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
LOINC 35205-4
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
Code System Code Type Description
DRUG BANK
DB05804
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
PUBCHEM
12594
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
DRUG CENTRAL
4049
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
CAS
651-48-9
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
MERCK INDEX
M4145
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY Merck Index
EPA CompTox
651-48-9
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
EVMPD
SUB34548
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
WIKIPEDIA
DEHYDROEPIANDROSTERONE SULFATE
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
FDA UNII
57B09Q7FJR
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
MESH
D019314
Created by admin on Sat Jun 26 14:31:36 UTC 2021 , Edited by admin on Sat Jun 26 14:31:36 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
PARENT -> METABOLITE
Oral prasterone is sulfated to 5-DHEAS ester in the intestine and liver by sulfotransferases
Related Record Type Details
ACTIVE MOIETY