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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O2
Molecular Weight 288.4251
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRASTERONE

SMILES

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

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

HIDE SMILES / InChI

Molecular Formula C19H28O2
Molecular Weight 288.4251
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
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
Increased serum cortisol levels are associated with high tumour grade in patients with renal cell carcinoma.
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
Therapeutic strategies in adrenal insufficiency.
2001 Apr
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
Unsulfated and sulfated neurosteroids differentially modulate the binding characteristics of various radioligands of GABA(A) receptors following chronic ethanol administration.
2001 Apr
High-grade prostate cancer is associated with low serum testosterone levels.
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
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
The adrenal and the metabolic syndrome.
2001 Apr
Leuprolide acetate treatment of adrenocortical disease in ferrets.
2001 Apr 15
cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate.
2001 Apr 15
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
Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis.
2001 Feb
Non-aqueous emulsions: hydrocarbon-formamide systems.
2001 Feb 19
Characteristics of cystic breast disease with special regard to breast cancer development.
2001 Jan-Feb
Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates.
2001 Jul
Neurosteroid hydroxylase CYP7B: vivid reporter activity in dentate gyrus of gene-targeted mice and abolition of a widespread pathway of steroid and oxysterol hydroxylation.
2001 Jun 29
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
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
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
Dehydroepiandrosterone replacement in women with adrenal insufficiency: effects on body composition, serum leptin, bone turnover, and exercise capacity.
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
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
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 13:24:59 UTC 2021
Edited
by admin
on Sat Jun 26 13:24:59 UTC 2021
Record UNII
459AG36T1B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRASTERONE
DASH   INCI   INN   MART.   USAN   WHO-DD  
INCI   INN   USAN  
Official Name English
DEHYDROEPIANDROSTERONE [MI]
Common Name English
PRASTERONE [WHO-DD]
Common Name English
EM-760
Code English
BIOLAIF
Brand Name English
PRASTERONE [MART.]
Common Name English
DEHYDROEPIANDROSTERONE
MI   VANDF  
Common Name English
PRASTERONE [INCI]
Common Name English
3.BETA.-HYDROXYANDROST-5-EN-17-ONE
Systematic Name English
DHEA
Common Name English
PRASTERONE [ORANGE BOOK]
Common Name English
INTRAROSA
Brand Name English
ANDROST-5-EN-17-ONE, 3-HYDROXY-, (3.BETA.)-
Systematic Name English
NSC-9896
Code English
DEHYDROANDROSTERONE
Common Name English
DEHYDROISOANDROSTERONE
Common Name English
DEHYDROEPIANDROSTERONE [VANDF]
Common Name English
PRASTERONE [USAN]
Common Name English
PRASTERONE [INN]
Common Name English
VAGINORM
Brand Name English
Classification Tree Code System Code
LOINC 35206-2
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 55815-5
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
WHO-VATC QA14AA07
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 29879-4
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
WHO-ATC A14AA07
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
FDA ORPHAN DRUG 172303
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 34283-2
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
DSLD 408 (Number of products:367)
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
WHO-VATC QG03EA03
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 15054-0
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 25391-4
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
EU-Orphan Drug EU/3/03/156
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 25895-4
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
WHO-ATC G03EA03
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 30029-3
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 31020-1
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 2194-9
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
CFR 21 CFR 862.1430
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
FDA ORPHAN DRUG 83794
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 82878-0
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 49716-4
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 74361-7
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 82879-8
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 2195-6
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
CFR 21 CFR 862.1245
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LIVERTOX 276
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
NCI_THESAURUS C243
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 13612-7
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 34279-0
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
WHO-ATC G03XX01
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
LOINC 2193-1
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
Code System Code Type Description
PUBCHEM
5881
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
NCI_THESAURUS
C2265
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
FDA UNII
459AG36T1B
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-175-5
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
DRUG CENTRAL
795
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
CAS
53-43-0
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
MESH
D003687
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
RXCUI
3143
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY RxNorm
INN
2869
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
WIKIPEDIA
DEHYDROEPIANDROSTERONE
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
EPA CompTox
53-43-0
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL90593
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
MERCK INDEX
M4145
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY Merck Index
EVMPD
SUB10002MIG
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
DRUG BANK
DB01708
Created by admin on Sat Jun 26 13:25:01 UTC 2021 , Edited by admin on Sat Jun 26 13:25:01 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
BINDING
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET -> ACTIVATOR
DERIVATIVE -> PARENT
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METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
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ACTIVE MOIETY