PRASTERONE SULFATE

First approved in 2014

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 Search

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@H](CC[C@]34C)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	368.488
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208470s000lbl.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348	Agonist 2678	514.55 nM [Ki]
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348	Partial Agonist 290	1053.17 nM [Ki]
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348	Antagonist 2778	1177.02 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dyspareunia 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208470s000lbl.pdf	Primary		Approved 8429	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 2016

C_max

Value	Dose	Co-administered	Analyte	Population
36.7 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10372727	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

Value	Dose	Co-administered	Analyte	Population
176.1 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10372727	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.35 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10372727	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/2961787	healthy, 22-25 years n = 5 Health Status: healthy Age Group: 22-25 years Sex: M Population Size: 5 Sources: https://pubmed.ncbi.nlm.nih.gov/2961787	Sources: https://pubmed.ncbi.nlm.nih.gov/2961787
400 mg 1 times / day multiple, oral Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16784956	unhealthy, 44.9 years n = 29 Health Status: unhealthy Condition: HIV infection Age Group: 44.9 years Sex: M Population Size: 29 Sources: https://pubmed.ncbi.nlm.nih.gov/16784956	Sources: https://pubmed.ncbi.nlm.nih.gov/16784956

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882	17-beta-HSD1 6 5-alpha-reductase 1 6 CYP19A1 23 UGT 192 sulfotransferases 38 17-beta-HSD3 6 17-beta-HSD5 6 17-beta-HSD2 10 17-beta-HSD13 6 5-alpha-reductase 2 6 3-beta-HSD1 6 3-alpha-HSD1 6 3-alpha-HSD3 10 UGT2B28 63 UGT2B15 203 UGT2B17 213 UGT1A1 418

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no

Drug as victim

Target	Modality	Activity
17-beta-HSD1 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD13 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD2 10	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD3 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD5 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
3-alpha-HSD1 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
3-alpha-HSD3 10	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
3-beta-HSD1 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
5-alpha-reductase 1 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes
5-alpha-reductase 2 6	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes
CYP19A1 23	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	yes
UGT 192	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
UGT1A1 418	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
UGT2B15 203	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
UGT2B17 213	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
UGT2B28 63	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
sulfotransferases 38	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes

Sourcing

Vendor/Aggregator	ID	URL
AEchem Scientific Corp., USA	AE1-000705	http://www.aechemsc.com/info_products/AE1-000705.php
AHH Chemical co.,ltd	MT-00368	http://www.ahhchemical.com/product/MT-00368.html
AHH Chemical co.,ltd	MT-07566	http://www.ahhchemical.com/product/MT-07566.html
AK Scientific, Inc. (AKSCI)	70793	http://www.aksci.com/item_detail.php?cat=70793
AK Scientific, Inc. (AKSCI)	J10065	http://www.aksci.com/item_detail.php?cat=J10065
Aaron Chemicals	AR0039QK	http://www.aaronchem.com/53-43-0
AbMole Bioscience	M9061	http://www.abmole.com/products/dehydroepiandrosterone.html
Acadechem	ACDS-064086	http://www.acadechemical.com/product/138785
Achemo Scientific Limited	AC-15211	http://www.achemo.com/product_view.asp?ID=5101
Achemtek	0104-014342	http://www.achemtek.com/53-43-0
Acorn PharmaTech	ACN-036240	http://www.acornpharmatech.com/
Acros Organics	AC154980025	https://www.fishersci.com/shop/products/dehydroisoandrosterone-99-acros-organics-1/AC154980025
Acros Organics	AC154980100	https://www.fishersci.com/shop/products/dehydroisoandrosterone-99-acros-organics-1/AC154980100
Acros Organics	AC154980500	https://www.fishersci.com/shop/products/dehydroisoandrosterone-99-acros-organics/AC154980500
Alfa Chemistry	53-43-0	https://www.alfa-chemistry.com/dehydroepiandrosterone-cas-53-43-0-item-79560.htm
Alsachim	3710	http://www.alsachim.com/product-C5001-glo.bal-view.html
Ansion Pharma	53-43-0	http://www.ansionpharma.com/English/Product/0974815742.html
ApexBio Technology	B1375	http://www.apexbt.com/dehydroepiandrosterone-dhea.html
Aurora Fine Chemicals LLC	A17.877.349	http://online.aurorafinechemicals.com/info?ID=A17.877.349
Aurum Pharmatech LLC	M-1336	http://www.Aurumpharmatech.com/Product/ProductDetails/M_1336
AvaChem Scientific	3973	http://www.avachem.com/productSearch.asp?3973
BioChemPartner	BCP02453	http://www.biochempartner.com/53-43-0-BCP02453
BioSynth	D-0340	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/D-0340.html
Chem Scene	CS-1667	http://www.chemscene.com/53-43-0.html
ChemFaces	CFN90043	http://www.chemfaces.com/natural/Dehydroepiandrosterone-CFN90043.html
ChemMol	30100413	http://www.chemmol.com/chemmol/30100413.html
Chemspace	CSSS00000029485	https://chem-space.com/CSSS00000029485
DC Chemicals	DC5201	http://www.dcchemicals.com/product_show-Dehydroepiandrosterone_DHEA_.html
Enamine	Z2213891300	https://www.enaminestore.com/catalog/Z2213891300
Glentham Life Sciences	GP0612	http://www.glentham.com/products/product/GP0612/
LGC Standards	DRE-C16286250	https://www.lgcstandards.com/US/en/p/DRE-C16286250
LGC Standards	LGCAMP0651.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP0651.00-11
LGC Standards	LGCFOR0651.00	https://www.lgcstandards.com/US/en/p/LGCFOR0651.00
LGC Standards	MM0651.00-0250	https://www.lgcstandards.com/US/en/p/MM0651.00-0250
Matrix Scientific	89314	https://www.matrixscientific.com/089314.html
MedChem Express	HY-14650	https://www.medchemexpress.com/DHEA.html
MuseChem	A000700	https://www.musechem.com/product/A000700.html
Octagon Chemicals	API Dehydroepiandrosterone 53-43-0	https://octagonchem.com/
Parchem	18496	http://www.parchem.com/chemical-supplier-distributor/DHEA-008496.aspx
Parchem	10897	http://www.parchem.com/chemical-supplier-distributor/Dehydroepiandrosterone-000897.aspx
Sigma-Aldrich	D-063_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/d063?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D4000_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/d4000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S048429	http://www.sinfoobiotech.com/product/1051827
Smolecule	S525573	http://www.smolecule.com/products/s525573
THE BioTek	bt-266623	https://www.thebiotek.com/product/inhibitors/bt-266623
VladaChem	VL162585	https://www.vladachem.com/product.php?products=53-43-0
VladaChem	VL277861-1G	https://www.vladachem.com/product.php?products=53-43-0
W&J PharmaChem	100968	http://www.wjpharmachem.com/new/100968.html
eNovation Chemicals	K39145	https://www.enovationchem.com/ProductDetails.asp?ProductID=K39145
iChemical	EBD1328208	http://www.ichemical.com/products/53-43-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
The effect of ultraviolet radiation and pretreatment of dehydroepiandrosterone on RMK cells in culture.	2001	11347408
Intraadrenal mechanisms of DHEA regulation: a hypothesis for adrenopause.	2001	11341302
GG-genotype in the promotor region of uncoupling-protein-1 gene is associated with lower level of dehydroepiandrosterone in type 2 diabetes.	2001	11341297
Increased serum cortisol levels are associated with high tumour grade in patients with renal cell carcinoma.	2001	11321667
Effects of transdermal application of 7-oxo-DHEA on the levels of steroid hormones, gonadotropins and lipids in healthy men.	2001	11300231
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis.	2001	11299059
Dehydroepiandrosterone sulphate prevents oxygen-glucose deprivation-induced injury in cerebellar granule cell culture.	2001	11166128
Sex hormones and their impact on dementia and depression: a clinical perspective.	2001 Apr	11336603
Up-regulation of cyclooxygenase-1 in neuroblastoma cell lines by retinoic acid and corticosteroids.	2001 Apr	11299304
Novel assay for determination of androgen bioactivity in human serum.	2001 Apr	11297580
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	11250927
DHEA: a novel adjunct for the treatment of male trauma patients.	2001 Feb	11286760
Corticotrophin-releasing hormone and ACTH levels in maternal and fetal blood during spontaneous and oxytocin-induced labour.	2001 Feb	11182747
Bacterial expression, purification, and characterization of rat hydroxysteroid sulfotransferase STa.	2001 Feb	11162411
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	11158012
Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men.	2001 Feb	11158004
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.	2001 Feb 28	11223173
[Replacement therapy in adrenopause. Dehydroepiandrosterone and aging].	2001 Jan	11260976
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.	2001 Jan	11145985
Low dehydroepiandrosterone and ischemic heart disease in middle-aged men: prospective results from the Massachusetts Male Aging Study.	2001 Jan 1	11159150
Dehydroepiandrosterone (DHEA) reduces neuronal injury in a rat model of global cerebral ischemia.	2001 Jan 12	11150483
Crucial role of cytokines in sex steroid formation in normal and tumoral tissues.	2001 Jan 22	11165008
Characteristics of cystic breast disease with special regard to breast cancer development.	2001 Jan-Feb	11299838
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy.	2001 Mar	11298105
Ergogenic aids: counseling the athlete.	2001 Mar 1	11261867
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	11344242
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Dehydroepiandrosterone restores hepatocellular function and prevents liver damage in estrogen-deficient females following trauma and hemorrhage.	2001 May 15	11341799
Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions.	2001 May 15	11339818

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 `Fri Dec 15 15:24:43 GMT 2023` Edited by `admin` on `Fri Dec 15 15:24:43 GMT 2023`
Record UNII	57B09Q7FJR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PRASTERONE SULFATE

Common Name

English

ANDROST-5-EN-17-ONE, 3-(SULFOOXY)-, (3.BETA.)-

Systematic Name

English

Prasterone sulfate [WHO-DD]

Common Name

English

PRASTERONE SULPHATE

Common Name

English

DEHYDROEPIANDROSTERONE SULFATE

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