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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H28O2
Molecular Weight 288.4244
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRASTERONE

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

HIDE SMILES / InChI

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

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
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
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 Sun Dec 18 18:45:56 UTC 2022
Edited
by admin
on Sun Dec 18 18:45:56 UTC 2022
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
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?-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 [WHO-DD]
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 Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 55815-5
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
WHO-VATC QA14AA07
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 29879-4
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
WHO-ATC A14AA07
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
FDA ORPHAN DRUG 172303
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 34283-2
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
DSLD 408 (Number of products:367)
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
WHO-VATC QG03EA03
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 15054-0
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 25391-4
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
EU-Orphan Drug EU/3/03/156
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 25895-4
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
WHO-ATC G03EA03
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 30029-3
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 31020-1
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LOINC 2194-9
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
CFR 21 CFR 862.1430
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
FDA ORPHAN DRUG 83794
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 82878-0
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 49716-4
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 74361-7
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 82879-8
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 2195-6
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
CFR 21 CFR 862.1245
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LIVERTOX 276
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
NCI_THESAURUS C243
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 13612-7
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 34279-0
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
WHO-ATC G03XX01
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
LOINC 2193-1
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
Code System Code Type Description
PUBCHEM
5881
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
USAN
DE-05
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
NCI_THESAURUS
C2265
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
FDA UNII
459AG36T1B
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
NSC
9896
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-175-5
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
DRUG CENTRAL
795
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
CAS
53-43-0
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
MESH
D003687
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
RXCUI
3143
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY RxNorm
INN
2869
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
DAILYMED
459AG36T1B
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
WIKIPEDIA
DEHYDROEPIANDROSTERONE
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
EPA CompTox
DTXSID4020379
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
CHEBI
28689
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
ChEMBL
CHEMBL90593
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
MERCK INDEX
M4145
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY Merck Index
EVMPD
SUB10002MIG
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
DRUG BANK
DB01708
Created by admin on Sun Dec 18 18:45:59 UTC 2022 , Edited by admin on Sun Dec 18 18:45:59 UTC 2022
PRIMARY
Related Record Type Details
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DERIVATIVE -> PARENT
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