PRASTERONE

First approved in 2014

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 Search

SMILES

C[C@]12CC[C@H]3[C@@H](CC=C4C[C@@H](O)CC[C@]34C)[C@@H]1CCC2=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	288.4244
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 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348	Agonist 2752	514.55 nM [Ki]
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348	Partial Agonist 297	1053.17 nM [Ki]
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15994348	Antagonist 2849	1177.02 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dyspareunia 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208470s000lbl.pdf	Primary		Approved 8583	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 Health Status: healthy Age Group: 22-25 years Sex: M 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 Health Status: unhealthy Age Group: 44.9 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/16784956	Sources: https://pubmed.ncbi.nlm.nih.gov/16784956

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060	17-beta-HSD1 7 5-alpha-reductase 1 7 CYP19A1 26 UGT 219 sulfotransferases 39 17-beta-HSD3 7 17-beta-HSD5 7 17-beta-HSD2 11 17-beta-HSD13 7 5-alpha-reductase 2 7 3-beta-HSD1 7 3-alpha-HSD1 7 3-alpha-HSD3 11 UGT2B28 65 UGT2B15 236 UGT2B17 237 UGT1A1 479

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	no
CYP3A4 2633	inhibitor 4027 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 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD13 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD2 11	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD3 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
17-beta-HSD5 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
3-alpha-HSD1 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
3-alpha-HSD3 11	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
3-beta-HSD1 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
5-alpha-reductase 1 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes
5-alpha-reductase 2 7	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes
CYP19A1 26	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=4 Page: 4.0	yes
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes
UGT1A1 479	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
UGT2B15 236	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
UGT2B17 237	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
UGT2B28 65	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000PharmR.pdf#page=8 Page: 8.0	yes
sulfotransferases 39	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208470Orig1s000ClinPharmR.pdf#page=9 Page: 9.0	yes

Sourcing

Vendor/Aggregator	ID	URL
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
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
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
eNovation Chemicals	K39145	https://www.enovationchem.com/ProductDetails.asp?ProductID=K39145
Glentham Life Sciences	GP0612	http://www.glentham.com/products/product/GP0612/
iChemical	EBD1328208	http://www.ichemical.com/products/53-43-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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	10897	http://www.parchem.com/chemical-supplier-distributor/Dehydroepiandrosterone-000897.aspx
Parchem	18496	http://www.parchem.com/chemical-supplier-distributor/DHEA-008496.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

PubMed

Title	Date	PubMed
Structure and functions of human oxysterol 7alpha-hydroxylase cDNAs and gene CYP7B1.	1999 Dec	10588945
The steroid hormone dehydroepiandrosterone inhibits CYP1A1 expression in vitro by a post-transcriptional mechanism.	1999 Dec 3	10575002
Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases.	2000 Jan 7	10623578
Sulphonation of N-hydroxy-2-acetylaminofluorene by human dehydroepiandrosterone sulphotransferase.	2000 Mar	10752640
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Inhibition of human immunodeficiency virus type-1 (HIV-1) replication by immunor (IM28), a new analog of dehydroepiandrosterone.	2000 Oct-Dec	11200288
The effect of ultraviolet radiation and pretreatment of dehydroepiandrosterone on RMK cells in culture.	2001	11347408
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	11347403
Hyposecretion of the adrenal androgen dehydroepiandrosterone sulfate and its relation to clinical variables in inflammatory arthritis.	2001	11299059
Sex hormones and their impact on dementia and depression: a clinical perspective.	2001 Apr	11336603
[Correlations between acne and polycystic ovary. A study of 60 cases].	2001 Apr	11319503
Biochemical screening for subclinical cortisol-secreting adenomas amongst adrenal incidentalomas.	2001 Apr	11275951
Age-related changes of the hypothalamic-pituitary-adrenal axis: pathophysiological correlates.	2001 Apr	11275940
Leuprolide acetate treatment of adrenocortical disease in ferrets.	2001 Apr 15	11330611
cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate.	2001 Apr 15	11284740
Solvent and solid-phase extraction of natural and synthetic anabolic steroids in human urine.	2001 Apr 25	11339285
DHEA: a novel adjunct for the treatment of male trauma patients.	2001 Feb	11286760
Hormone replacement therapy and fractures in older adults.	2001 Feb	11207873
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
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.	2001 Feb	11087962
[Aging without becoming old. 2 anti-aging days per week].	2001 Feb 15	11268750
Composite effects of group drumming music therapy on modulation of neuroendocrine-immune parameters in normal subjects.	2001 Jan	11191041
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	11167994
Establishment and characterization of a steroidogenic human granulosa-like tumor cell line, KGN, that expresses functional follicle-stimulating hormone receptor.	2001 Jan	11145608
Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats.	2001 Jan	11133670
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
Hormonal decline in elderly men and male menopause.	2001 Jan-Feb	11223793
Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates.	2001 Jul	11322966
Circulating plasma leptin and IGF-1 levels in girls with premature adrenarche: potential implications of a preliminary study.	2001 Mar	11355746
Assessment of endocrine status in patients undergoing in-vitro fertilization treatment. Is it necessary?	2001 Mar	11327087
Sex hormone-binding globulin as a marker of the effect of hormonal treatment in Turner's syndrome.	2001 Mar	11308992
Peroxisomal proliferator-activated ligand therapy for HIV lipodystrophy.	2001 Mar	11298105
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary.	2001 Mar	11254372
Ontogeny of the neurosteroid enzyme Cyp7b in the mouse.	2001 Mar 28	11306180
Temporal and spatial distribution of corticosteroidogenic enzymes immunoreactivity in developing human adrenal.	2001 Mar 28	11306177
Effect of beta-estradiol on voltage-gated Ca(2+) channels in rat hippocampal neurons: a comparison with dehydroepiandrosterone.	2001 Mar 30	11290370
Sebocytes are the key regulators of androgen homeostasis in human skin.	2001 May	11348472
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 of extracellular matrix components and their integrin receptors in the human fetal adrenal gland.	2001 May	11344212
Dehydroepiandrosterone inhibits lipopolysaccharide-induced nitric oxide production in BV-2 microglia.	2001 May	11331412
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney.	2001 May	11306713
Metabolism of DHEA by cytochromes P450 in rat and human liver microsomal fractions.	2001 May 15	11339818
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.	2001 May 15	11336660
Serum hormones and the alcohol-breast cancer association in postmenopausal women.	2001 May 2	11333294

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 `Wed Apr 02 07:58:57 GMT 2025` Edited by `admin` on `Wed Apr 02 07:58:57 GMT 2025`
Record UNII	459AG36T1B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEHYDROEPIANDROSTERONE

Preferred Name

English

PRASTERONE

Official Name

English

DEHYDROEPIANDROSTERONE [MI]

Common Name

English

EM-760

Code

English

BIOLAIF

Brand Name

English

PRASTERONE [MART.]

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