Dehidroepiandrosteron

Dehidroepiandrosteron
(IUPAC) ime
	(3S,8R,9S,10R,13S,14S)-3-hidroksi-10,13-dimetil-1,2,3,4,7,8,9,11,12,14,15,16-dodekahidrociklopenta[a]fenantren-17-on
Klinički podaci
Identifikatori
CAS broj	53-43-0
ATC kod	A14AA07 G03EA03 (kombinacija sa estrogenom)
PubChem	5881
DrugBank	DB01708
ChemSpider	5670
UNII	459AG36T1B
ChEBI	CHEBI:28689
ChEMBL	CHEMBL90593
Hemijski podaci
Formula	C19H28O2
Mol. masa	288,424 g/mol
SMILES	eMolekuli & PubHem
InChI
	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 ; Key: FMGSKLZLMKYGDP-USOAJAOKSA-N
Sinonimi	(3β)-3-Hidroksiandrost-5-en-17-on
Fizički podaci
Tačka topljenja	148.5 °C (299 °F)
Farmakokinetički podaci
Metabolizam	Hepatički
Poluvreme eliminacije	12 sata
Izlučivanje	Urinarno:?%
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Komercijalno dostupan
Način primene	Oralno

Dehidroepiandrosteron (DHEA, Fidelin, androstenolon, prasteron, 3β-hidroksiandrost-5-en-17-on, 5-androsten-3β-ol-17-on) je važan endogeni steroidni hormon.^[5] On je najzastupljeniji circulišući steroid kod ljudi,^[6] kod kojih ga proizvode nadbubrežne žlezde,^[7] gonade, i mozak,^[8] gde on predominentno funkcioniše kao metabolički intermedijer u biosintezi androgena i estrogena seksualnih steroida.^[5]^[9] Međutim, DHEA takođe ima raznovrsne samostalne potencijalne biološke efekte. On se vezuje za niz nuklearnih površinskih receptora,^[10] i deluje kao neurosteroid.^[11]

Istraživanja

Kancer

Više in vitro studija je utvrdilo da DHEA ima antiproliferativne i apoptozne efekte na ćelijama kancera.^[12]^[13]^[14] Kliničkih značaj tih nalaza nije poznat. Visoki nivoi DHEA i drughi endogenih seks hormona su u znatnoj meri vezani za povišeni rizik od razvoja raka dojki pre- i postmenopozalno.^[15]^[16]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ ^5,0 ^5,1 Mo Q, Lu SF, Simon NG (April 2006). „Dehydroepiandrosterone and its metabolites: differential effects on androgen receptor trafficking and transcriptional activity”. J. Steroid Biochem. Mol. Biol. 99 (1): 50–8. DOI:10.1016/j.jsbmb.2005.11.011. PMID 16524719.
↑ William F Ganong MD, 'Review of Medical Physiology', 22nd Ed, McGraw Hill, 2005, page 362.
↑ The Merck Index, 13th Edition, 7798
↑ Schulman, Robert A., M.D.; Dean, Carolyn, M.D. (2007). Solve It With Supplements. New York City: Rodale, Inc.. str. 100. ISBN 978-1-57954-942-8. »DHEA (Dehydroepiandrosterone) is a common hormone produced in the adrenal glands, the gonads, and the brain.«
↑ Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. str. 49. ISBN 978-3-11-010661-9. Pristupljeno 25. 5. 2012.
↑ Webb SJ, Geoghegan TE, Prough RA, Michael Miller KK (2006). „The biological actions of dehydroepiandrosterone involves multiple receptors”. Drug Metabolism Reviews 38 (1–2): 89–116. DOI:10.1080/03602530600569877. PMC 2423429. PMID 16684650.
↑ Friess E, Schiffelholz T, Steckler T, Steiger A (December 2000). „Dehydroepiandrosterone--a neurosteroid”. European Journal of Clinical Investigation 30 Suppl 3: 46–50. DOI:10.1046/j.1365-2362.2000.0300s3046.x. PMID 11281367.
↑ Yang, N. C.; Jeng, K. C.; Ho, W. M.; Hu, M. L. (2002). „ATP depletion is an important factor in DHEA-induced growth inhibition and apoptosis in BV-2 cells”. Life Sci. 70 (17): 1979–88. DOI:10.1016/S0024-3205(01)01542-9. PMID 12148690.
↑ Schulz, S.; Klann, R. C.; Schönfeld, S.; Nyce, J. W. (1992). „Mechanisms of cell growth inhibition and cell cycle arrest in human colonic adenocarcinoma cells by dehydroepiandrosterone: role of isoprenoid biosynthesis”. Cancer Res. 52 (5): 1372–6. PMID 1531325.
↑ Loria, R. M. (2002). „Immune up-regulation and tumor apoptosis by androstene steroids”. Steroids 67 (12): 953–66. DOI:10.1016/S0039-128X(02)00043-0. PMID 12398992.
↑ Tworoger, S. S.; Missmer, S. A.; Eliassen, A. H. et al. (2006). „The association of plasma DHEA and DHEA sulfate with breast cancer risk in predominantly premenopausal women”. Cancer Epidemiol. Biomarkers Prev. 15 (5): 967–71. DOI:10.1158/1055-9965.EPI-05-0976. PMID 16702378.
↑ Key, T.; Appleby, P.; Barnes, I.; Reeves, G. (2002). „Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies”. J. Natl. Cancer Inst. 94 (8): 606–16. DOI:10.1093/jnci/94.8.606. PMID 11959894.

Literatura

Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. str. 49. ISBN 978-3-11-010661-9. Pristupljeno 25. 5. 2012.
Schulman, Robert A., M.D.; Dean, Carolyn, M.D. (2007). Solve It With Supplements. New York City: Rodale, Inc.. str. 100. ISBN 978-1-57954-942-8. »DHEA (Dehydroepiandrosterone) is a common hormone produced in the adrenal glands, the gonads, and the brain.«

Vanjske veze

	Portal Medicina
	Portal Hemija

Information on DHEA from the Mayo Clinic
DHEA in elderly women and DHEA or testosterone in elderly men Arhivirano 2010-03-26 na Wayback Machine-u, published in the New England Journal of Medicine in 2006. "Neither DHEA nor low-dose testosterone replacement in elderly people has physiologically relevant beneficial effects on body composition, physical performance, insulin sensitivity, or quality of life."
DHEA, from the Skeptic's Dictionary
ChemSub Online: Dehydroepiandrosterone - DHEA

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[pmid16524719-5] 5,0 ^5,1 Mo Q, Lu SF, Simon NG (April 2006). „Dehydroepiandrosterone and its metabolites: differential effects on androgen receptor trafficking and transcriptional activity”. J. Steroid Biochem. Mol. Biol. 99 (1): 50–8. DOI:10.1016/j.jsbmb.2005.11.011. PMID 16524719.

[6] William F Ganong MD, 'Review of Medical Physiology', 22nd Ed, McGraw Hill, 2005, page 362.

[7] The Merck Index, 13th Edition, 7798

[8] Schulman, Robert A., M.D.; Dean, Carolyn, M.D. (2007). Solve It With Supplements. New York City: Rodale, Inc.. str. 100. ISBN 978-1-57954-942-8. »DHEA (Dehydroepiandrosterone) is a common hormone produced in the adrenal glands, the gonads, and the brain.«

[Scott1996-9] Thomas Scott (1996). Concise Encyclopedia Biology. Walter de Gruyter. str. 49. ISBN 978-3-11-010661-9. Pristupljeno 25. 5. 2012.

[pmid16684650-10] Webb SJ, Geoghegan TE, Prough RA, Michael Miller KK (2006). „The biological actions of dehydroepiandrosterone involves multiple receptors”. Drug Metabolism Reviews 38 (1–2): 89–116. DOI:10.1080/03602530600569877. PMC 2423429. PMID 16684650.

[pmid11281367-11] Friess E, Schiffelholz T, Steckler T, Steiger A (December 2000). „Dehydroepiandrosterone--a neurosteroid”. European Journal of Clinical Investigation 30 Suppl 3: 46–50. DOI:10.1046/j.1365-2362.2000.0300s3046.x. PMID 11281367.

[12] Yang, N. C.; Jeng, K. C.; Ho, W. M.; Hu, M. L. (2002). „ATP depletion is an important factor in DHEA-induced growth inhibition and apoptosis in BV-2 cells”. Life Sci. 70 (17): 1979–88. DOI:10.1016/S0024-3205(01)01542-9. PMID 12148690.

[13] Schulz, S.; Klann, R. C.; Schönfeld, S.; Nyce, J. W. (1992). „Mechanisms of cell growth inhibition and cell cycle arrest in human colonic adenocarcinoma cells by dehydroepiandrosterone: role of isoprenoid biosynthesis”. Cancer Res. 52 (5): 1372–6. PMID 1531325.

[14] Loria, R. M. (2002). „Immune up-regulation and tumor apoptosis by androstene steroids”. Steroids 67 (12): 953–66. DOI:10.1016/S0039-128X(02)00043-0. PMID 12398992.

[15] Tworoger, S. S.; Missmer, S. A.; Eliassen, A. H. et al. (2006). „The association of plasma DHEA and DHEA sulfate with breast cancer risk in predominantly premenopausal women”. Cancer Epidemiol. Biomarkers Prev. 15 (5): 967–71. DOI:10.1158/1055-9965.EPI-05-0976. PMID 16702378.

[16] Key, T.; Appleby, P.; Barnes, I.; Reeves, G. (2002). „Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies”. J. Natl. Cancer Inst. 94 (8): 606–16. DOI:10.1093/jnci/94.8.606. PMID 11959894.

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