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Dehydroepiandrosterone sulfate information


Dehydroepiandrosterone sulfate
Names
IUPAC name
17-Oxoandrost-5-en-3β-yl hydrogen sulfate
Systematic IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-9a,11a-Dimethyl-1-oxo-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl hydrogen sulfate
Other names
Androstenolone sulfate; Prasterone sulfate; Androst-5-en-3β-ol-17-one 3β-sulfate
Identifiers
CAS Number
  • 651-48-9 checkY
3D model (JSmol)
  • Interactive image
Abbreviations DHEA sulfate; DHEA-S; DHEAS
ChemSpider
  • 12074 ☒N
PubChem CID
  • 12594
UNII
  • 57B09Q7FJR checkY
CompTox Dashboard (EPA)
  • DTXSID8040228 Edit this at Wikidata
InChI
  • 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 ☒N
    Key: CZWCKYRVOZZJNM-USOAJAOKSA-N ☒N
  • InChI=1/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
    Key: CZWCKYRVOZZJNM-USOAJAOKBK
SMILES
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC=C4[C@@]3(CC[C@@H](C4)OS(=O)(=O)O)C
Properties
Chemical formula
C19H28O5S
Molar mass 368.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex.[1] It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) and circulates in far greater relative concentrations than DHEA.[2] The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.[2]

  1. ^ Cite error: The named reference Erkkola2006 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference pmid26908835 was invoked but never defined (see the help page).

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Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that...

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Dehydroepiandrosterone

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Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids...

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Prasterone sulfate

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Prasterone sulfate (brand names Astenile, Mylis, Teloin, others), also known as dehydroepiandrosterone sulfate (DHEA-S), is a naturally occurring androstane...

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Prasterone

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Prasterone, also known as dehydroepiandrosterone (DHEA) and sold under the brand name Intrarosa among others, is a medication as well as over-the-counter...

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Neurosteroid

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dehydroepiandrosterone (DHEA; prasterone), and dehydroepiandrosterone sulfate (DHEA-S; prasterone sulfate), and the cholestane 24(S)-hydroxycholesterol...

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Pregnenolone sulfate

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is the C3β sulfate ester of pregnenolone. A closely related steroid is dehydroepiandrosterone sulfate (DHEA-S), which is the C3β sulfate ester of...

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Hirsutism

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conventionally tested androgens (testosterone, androstenedione, and dehydroepiandrosterone sulfate) are normal. Around 10 to 15% of women with hirsutism have idiopathic...

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Precocious puberty

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with "premature pubarche, clitoromegaly, and increased serum dehydroepiandrosterone sulfate and testosterone" which are some of the presentations associated...

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Adrenal crisis

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adrenal crisis, serum cortisol, aldosterone, ACTH, renin, and dehydroepiandrosterone sulfate should be measured. A low cortisol level of less than 5 mg/dL...

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Adrenarche

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levels of weak adrenal androgens, including dehydroepiandrosterone (DHEA), dehydroepiandrosterone sulfate (DHEA-S), and androstenedione (A4), but without...

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Puberty

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adrenal androgens are dehydroepiandrosterone, androstenedione (which are precursors of testosterone), and dehydroepiandrosterone sulfate which is present in...

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Berberine

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Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan...

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Steroid sulfatase

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sulfatase, dehydroepiandrosterone sulfate sulfatase, arylsulfatase C, steroid 3-sulfatase, steroid sulfate sulfohydrolase, dehydroepiandrosterone sulfatase...

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Adrenopause

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secretion and levels of adrenal androgens such as dehydroepiandrosterone (DHEA) and dehydroepiandrosterone sulfate (DHEA-S) from the zona reticularis of the adrenal...

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ACTH stimulation test

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stimulates the adrenal glands to release cortisol, dehydroepiandrosterone (DHEA), dehydroepiandrosterone sulfate (DHEA-S), and aldosterone. During the test,...

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Endocrine gland

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including adrenaline and the steroids aldosterone cortisol and Dehydroepiandrosterone sulfate (DHEA). Adrenaline increases blood pressure, heart rate, and...

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Estrone sulfate

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glucuronide, while related steroid conjugates include dehydroepiandrosterone sulfate and pregnenolone sulfate. The logP of E1S is 1.4. E1S is produced via estrogen...

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Androstanediol glucuronide

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activity. In women the adrenal steroids, dehydroepiandrosterone sulfate, androstenedione and dehydroepiandrosterone are the major precursors of plasma 3α-ADG...

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Sigma receptor

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for σ1 subtype Berberine Citalopram Cocaine Dehydroepiandrosterone (DHEA) Dehydroepiandrosterone sulfate (DHEA-S) Dextromethorphan (DXM): relatively selective...

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Pubarche

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Premature pubarche is linked to adrenarcheal androgen levels with dehydroepiandrosterone sulfate (DHEAS) of 40–130 ųg/dL. However, premature pubarche may also...

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Cinnarizine

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Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan...

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Saffron

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Pregnenolone

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Mayo W, Le Moal M (November 2001). "Role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging". Brain...

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Theca of follicle

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vessels. ovary theca thecoma polycystic ovarian syndrome (PCOS) dehydroepiandrosterone sulfate (DHEAS) luteinizing hormone (LH) follicle-stimulating hormone...

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Ketamine

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Androgen conjugate

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the sulfates testosterone sulfate, dehydroepiandrosterone sulfate, androstenediol sulfate, dihydrotestosterone sulfate, and androsterone sulfate, and...

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salt of cocaine is by far the most commonly encountered, although the sulfate (SO42−) and the nitrate (NO3−) salts are occasionally seen. Different salts...

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