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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H27O5S.Na
Molecular Weight 390.4713
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRASTERONE SODIUM SULFATE ANHYDROUS

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-].[Na+]

InChI

InChIKey=GFJWACFSUSFUOG-ZJTJBYBXSA-M
InChI=1S/C19H28O5S.Na/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);/q;+1/p-1/t13-,14-,15-,16-,18-,19-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C19H27O5S
Molecular Weight 367.4815
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: 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
514.549999999999955 nM [Ki]
1053.17000000000007 nM [Ki]
1177.01999999999998 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

1479254400000
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
Health Status: healthy
Age Group: 22-25 years
Sex: M
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
Health Status: unhealthy
Age Group: 44.9 years
Sex: M
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
PubMed

PubMed

TitleDatePubMed
Structure and functions of human oxysterol 7alpha-hydroxylase cDNAs and gene CYP7B1.
1999 Dec
Sulphonation of N-hydroxy-2-acetylaminofluorene by human dehydroepiandrosterone sulphotransferase.
2000 Mar
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
GG-genotype in the promotor region of uncoupling-protein-1 gene is associated with lower level of dehydroepiandrosterone in type 2 diabetes.
2001
Dehydroepiandrosterone sulphate prevents oxygen-glucose deprivation-induced injury in cerebellar granule cell culture.
2001
Therapeutic strategies in adrenal insufficiency.
2001 Apr
Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration.
2001 Apr
Up-regulation of cyclooxygenase-1 in neuroblastoma cell lines by retinoic acid and corticosteroids.
2001 Apr
Novel assay for determination of androgen bioactivity in human serum.
2001 Apr
Sarcopenia.
2001 Apr
Biochemical screening for subclinical cortisol-secreting adenomas amongst adrenal incidentalomas.
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
cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate.
2001 Apr 15
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
[Aging without becoming old. 2 anti-aging days per week].
2001 Feb 15
Composite effects of group drumming music therapy on modulation of neuroendocrine-immune parameters in normal subjects.
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
Dehydroepiandrosterone (DHEA) reduces neuronal injury in a rat model of global cerebral ischemia.
2001 Jan 12
Steroidogenic response of adrenal tissues after administration of ACTH to dogs with hypercortisolemia.
2001 Jan 15
[Precocious puberty caused by a testicular Leydig cell tumor].
2001 Jan 28
Receptor selectivity, enzymes and tissue specificity.
2001 Jan 31
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
Memory-enhancing effects of DHEAS in aged mice on a win-shift water escape task.
2001 Mar
Association of vitamin D receptor and 17 hydroxylase gene polymorphisms with benign prostatic hyperplasia and benign prostatic enlargement.
2001 Mar
Ergogenic aids: counseling the athlete.
2001 Mar 1
Hormones as antiaging remedies.
2001 Mar-Apr
Sebocytes are the key regulators of androgen homeostasis in human skin.
2001 May
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 May
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
Influence of culture system and medium enrichment on sulfotransferase and sulfatase expression in male rat hepatocyte cultures.
2001 May 1
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 12:50:35 UTC 2021
Edited
by admin
on Sat Jun 26 12:50:35 UTC 2021
Record UNII
B9840IHU4T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRASTERONE SODIUM SULFATE ANHYDROUS
Common Name English
ANDROST-5-EN-17-ONE, 3-(SULFOOXY)-, SODIUM SALT (1:1), (3.BETA.)-
Common Name English
DEHYDROEPIANDROSTERONE SULFATE SODIUM SALT
Common Name English
SODIUM PRASTERONE SULFATE ANHYDROUS
Common Name English
PRASTERONE SODIUM SULFATE [MART.]
Common Name English
SODIUM PRASTERONE SULFATE
Common Name English
DEHYDROEPIANDROSTERONE SULFATE SODIUM
Common Name English
DEHYDROEPIANDROSTERONE SODIUM SULFATE [MI]
Common Name English
DEHYDROEPIANDROSTERONE SODIUM SULFATE
MI  
Common Name English
SODIUM DEHYDROEPIANDROSTERONE SULFATE
Common Name English
DEHYDROEPIANDROSTERONE-3-SULFATE SODIUM
Common Name English
PRASTERONE SODIUM SULFATE [WHO-DD]
Common Name English
3.BETA.-HYDROXY-5-ANDROSTEN-17-ONE SODIUM SULFATE
Systematic Name English
ANDROST-5-EN-17-ONE, 3-(SULFOOXY)-, SODIUM SALT, (3.BETA.)-
Common Name English
ANDROST-5-EN-17-ONE, 3.BETA.-HYDROXY-, HYDROGEN SULFATE, SODIUM SALT
Common Name English
NSC-72822
Code English
PRASTERONE SODIUM SULFATE
MART.   WHO-DD  
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 102196
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
FDA ORPHAN DRUG 101996
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
Code System Code Type Description
EPA CompTox
1099-87-2
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
FDA UNII
B9840IHU4T
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
ChEMBL
CHEMBL259898
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
PUBCHEM
23668320
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
WIKIPEDIA
Sodium prasterone sulfate
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
CAS
1099-87-2
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
ECHA (EC/EINECS)
214-152-2
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
RXCUI
1366962
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY RxNorm
EVMPD
SUB04010MIG
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY
MERCK INDEX
M4145
Created by admin on Sat Jun 26 12:50:35 UTC 2021 , Edited by admin on Sat Jun 26 12:50:35 UTC 2021
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY