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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

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@H](CC[C@]34C)OS(O)(=O)=O)[C@@H]1CCC2=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
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
INTRAROSA
PubMed

PubMed

TitleDatePubMed
Inhibition of human immunodeficiency virus type-1 (HIV-1) replication by immunor (IM28), a new analog of dehydroepiandrosterone.
2000 Oct-Dec
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
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis.
2001
Therapeutic strategies in adrenal insufficiency.
2001 Apr
[Correlations between acne and polycystic ovary. A study of 60 cases].
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
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
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
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
Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis.
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
Non-aqueous emulsions: hydrocarbon-formamide systems.
2001 Feb 19
Differentially expressed genes in zona reticularis cells of the human adrenal cortex.
2001 Feb 28
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.
2001 Feb 28
[Replacement therapy in adrenopause. Dehydroepiandrosterone and aging].
2001 Jan
Effects of long-term alpha-tocopherol supplementation on serum hormones in older men.
2001 Jan 1
Receptor selectivity, enzymes and tissue specificity.
2001 Jan 31
Characteristics of cystic breast disease with special regard to breast cancer development.
2001 Jan-Feb
Plasma levels of neuroactive steroids are increased in untreated women with anorexia nervosa or bulimia nervosa.
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
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
Ontogeny of the neurosteroid enzyme Cyp7b in the mouse.
2001 Mar 28
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone.
2001 Mar 30
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
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

In Vivo Use Guide
Administer one INTRAROSA vaginal insert once daily at bedtime, using the provided applicator.
Route of Administration: Vaginal
In Vitro Use Guide
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 Tue Oct 22 00:25:29 UTC 2019
Edited
by admin
on Tue Oct 22 00:25:29 UTC 2019
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 Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
Code System Code Type Description
PUBCHEM
12594
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY
CAS
651-48-9
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY
MERCK INDEX
M4145
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY Merck Index
EPA CompTox
651-48-9
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY
EVMPD
SUB34548
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY
WIKIPEDIA
DEHYDROEPIANDROSTERONE SULFATE
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY
MESH
D019314
Created by admin on Tue Oct 22 00:25:29 UTC 2019 , Edited by admin on Tue Oct 22 00:25:29 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
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