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an androgenic hormone that is less active than testosterone

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/07/17 14:08:53」(JST)

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Not to be confused with androstenone.

Androsterone, or 3α-hydroxy-5α-androstan-17-one, is an endogenous steroid hormone and weak androgen with a potency that is approximately 1/7th that of testosterone.^[1] In addition, it can be converted to dihydrotestosterone (DHT) from 17-hydroxyprogesterone, bypassing conventional intermediates such as androstenedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right.^[2]^[3]

Androsterone's 3β-isomer is epiandrosterone.

History[edit]

It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres (3,700 imp gal; 4,500 US gal) of male urine, from which they got 50 milligrams (0.77 gr) of crystalline androsterone, which was sufficient to find that the chemical formula was very similar to estrone.

Sources[edit]

Androsterone has been shown to naturally occur in pine pollen and is well known in many animal species.^[4]

Effects[edit]

Androsterone is often advertised as influencing human behavior, but there is little data to substantiate its use as a pheromone.^{[citation needed]}

Synthesis[edit]

Androsterone, its 3β-isomer, epiandrosterone, and its 5β-isomer, etiocholanolone, are produced in the body from 5α-reduced metabolites of dehydroepiandrosterone (DHEA), androstenediol, and androstenedione such as, in the case of androsterone, 5α-androstanediol via 17β-hydroxysteroid dehydrogenase and 5α-androstanedione via 3α-hydroxysteroid dehydrogenase.^{[citation needed]}

References[edit]

^ Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Retrieved 25 May 2012.
^ Brian E. Henderson; Bruce A. J. Ponder; Ronald Keith Ross (13 March 2003). Hormones, Genes, and Cancer. Oxford University Press. p. 23. ISBN 978-0-19-513576-3. Retrieved 25 May 2012.
^ Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA (March 2012). "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism 97 (3): E367–75. doi:10.1210/jc.2011-1997. PMID 22170725.
^ FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland

External links[edit]

Androsterone entry in the HMDB

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1. 内因性および外因性ステロイドの尿中排泄の測定 measurement of urinary excretion of endogenous and exogenous glucocorticoids
2. クッシング症候群の原因および病態生理 causes and pathophysiology of cushings syndrome
3. 副腎ステロイドの代謝 metabolism of adrenal steroids
4. 副腎皮質腫瘍の臨床症状および評価 clinical presentation and evaluation of adrenocortical tumors

English Journal

β-cyclodextrin in personal care formulations: role on the complexation of malodours causing molecules.

Lopedota A1, Cutrignelli A1, Laquintana V1, Franco M1, Donelli D2, Ragni L2, Tongiani S2, Denora N1.
International journal of cosmetic science.Int J Cosmet Sci.2015 Aug;37(4):438-45. doi: 10.1111/ics.12215. Epub 2015 Mar 18.
OBJECTIVE: The aim of this study was to prove the capability of β-cyclodextrin (β-CD) to interact with some representative molecules responsible to cause body malodour, such as carboxylic acids, thiols and steroids, present in sweat and body secretions.METHODS: The association constants in guest-C
PMID 25728864

Regulation of Human UDP-Glucuronosyltransferase 2B15 and 2B17 by miR-376c in prostate cancer cell lines.

Wijayakumara DD1, Hu DG1, Meech R1, McKinnon RA1, Mackenzie PI2.
The Journal of pharmacology and experimental therapeutics.J Pharmacol Exp Ther.2015 Jul 10. pii: jpet.115.226118. [Epub ahead of print]
Given the prime importance of UGT2B15 and UGT2B17 in inactivating testosterone and dihydrotestosterone, control of their expression and activity in the prostate is essential for androgen signalling homeostasis in that organ. Although several studies provide evidence of transcriptional control of UGT
PMID 26163549

DHEA metabolism to the neurosteroid androsterone: a possible mechanism of DHEA's antidepressant action.

Dor RB1, Marx CE, Shampine LJ, Rubinow DR, Schmidt PJ.
Psychopharmacology.Psychopharmacology (Berl).2015 Jun 25. [Epub ahead of print]
BACKGROUND: Alterations in neurosteroid secretion have been implicated in the efficacy of antidepressants. In a previous study, the adrenal androgen DHEA, a precursor of the neurosteroid androsterone, produced antidepressant and libido-enhancing effects in patients with midlife depression. To invest
PMID 26105109

Japanese Journal

Ultrasensitive enzyme-linked immunosorbent assay (ELISA) of proteins by combination with the thio-NAD cycling method

Watabe Satoshi,Kodama Hiromi,Kaneda Mugiho,Morikawa Mika,Nakaishi Kazunari,Yoshimura Teruki,Iwai Atsushi,Miura Toshiaki,Ito Etsuro
BIOPHYSICS 10(0), 49-54, 2014
… An androsterone derivative, 3α-hydroxysteroid, is produced by the hydrolysis of 3α-hydroxysteroid 3-phosphate with alkaline phosphatase linked to the secondary antibody. …
NAID 130004687665

ガスクロマトグラフィー‐質量分析によるヒト尿中　１７－ケトステロイドの分析：抱合体の酸加水分解条件の検討と抽出‐誘導体化法の利用

宮田崇,竹川健一,大森毅
日本法科学技術学会誌 17(1), 35-43, 2012
… We have attempted to establish the analytical condition of 17-ketosteroids (17-KS), i.e., androsterone (An), etiocholanolone (Eti) and dehydroepiandrosterone (DHEA) for identification of human urine with gas chromatography-mass spectrometry. …
NAID 130004942640

超長時間持久的負荷(24時間走)における炎症およびストレス反応の推移

清水智美,今西昭雄,杉本健一 [他],武田信彬,平田龍三,安藤隆,森川征一,鈴木良雄,渡辺雅之,奥田美穂,川名孝幸,涛川唯,鈴木政登,渡邉マキノ,岡田隆夫,太田眞
臨床病理 59(10), 930-935, 2011-10-25
NAID 10030462708

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拡張検索	「dehydroepiandrosterone」「dehydroisoandrosterone」

「dehydroepiandrosterone」

Androsterone
Systematic (IUPAC) name
	(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	53-41-8
ATC code	None
PubChem	CID 5879
ChemSpider	5668
UNII	C24W7J5D5R
ChEBI	CHEBI:16032
ChEMBL	CHEMBL87285
Chemical data
Formula	C19H30O2
Mol. mass	290.440 g/mol
	SMILES O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@H](O)CC[C@]34C)C;
	InChI InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1 ; Key:QGXBDMJGAMFCBF-HLUDHZFRSA-N ;
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　　[★] デヒドロエピアンドロステロン DHEA

「dehydroisoandrosterone」

　　[★] デヒドロイソアンドロステロン

[Scott1996-1] Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. p. 49. ISBN 978-3-11-010661-9. Retrieved 25 May 2012.

[HendersonPonder2003-2] Brian E. Henderson; Bruce A. J. Ponder; Ronald Keith Ross (13 March 2003). Hormones, Genes, and Cancer. Oxford University Press. p. 23. ISBN 978-0-19-513576-3. Retrieved 25 May 2012.

[pmid22170725-3] Kamrath C, Hochberg Z, Hartmann MF, Remer T, Wudy SA (March 2012). "Increased activation of the alternative "backdoor" pathway in patients with 21-hydroxylase deficiency: evidence from urinary steroid hormone analysis". The Journal of Clinical Endocrinology and Metabolism 97 (3): E367–75. doi:10.1210/jc.2011-1997. PMID 22170725.

[4] FOLIA HISTOCHEMICA ET CYTOBIOLOGICA Vol. 43, No. 2, 2005 pp. 71-79 Mammalian sex hormones in plants Anna Janeczko and Andrzej Skoczowski Institute of Plant Physiology, Polish Academy of Sciences, Kraków, Poland

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androsterone