Tetraidrodeossicorticosterone

Tetraidrodeossicorticosterone
	Tetraidrodeossicorticosterone
Nome IUPAC
	(3α,5β)-3,21-diidrossipregnan-20-one
Nomi alternativi
	THDOC
Caratteristiche generali
Formula bruta o molecolare	C21H34O3
Massa molecolare (u)	334.493 g/mol
Numero CAS	567-03-3
Numero EINECS	209-301-3
PubChem	91475
SMILES	C[C@]12CCC(C[C@H]1CC [C@@H]3[C@@H]2CC [C@]4([C@H]3CC[C@@H] 4C(=O)CO)C)O
Indicazioni di sicurezza

Il tetraidrodeossicorticosterone (3α,21-diidrossi-5α-pregnan-20-one; THDOC), o più comunemente allotetraidrossicorticosterone, è un neurosteroide endogeno^[1]. È sintetizzato dall'ormone adrenale deossicorticosterone per azione di due enzimi, la 5α-riduttasi tipo I e la 3α-idrossisteroide deidrogenasi^[2]. Il THDOC ha effetti sedativi, ansiolitici e anticonvulsivi^[3]^[4]. Variazioni nei livelli normali di questo steroide, in particolare durante la gravidanza e la mestruazione, possono essere coinvolte in alcuni tipi di epilessia (epilessia catameniale)^[5], come anche nelle condizioni di stress, ansia e depressione^[6]^[7]^[8]^[9]^[10].

Note

^ Hosie AM, Wilkins ME, da Silva HM, Smart TG. Endogenous neurosteroids regulate GABA_A receptors through two discrete transmembrane sites. Nature. 2006 Nov 23;444(7118):486-9. DOI: 10.1038/nature05324 PMID 17108970
^ Agís-Balboa RC, Pinna G, Zhubi A, Maloku E, Veldic M, Costa E, Guidotti A. Characterization of brain neurons that express enzymes mediating neurosteroid biosynthesis. Proceedings of the National Academy of Sciences USA. 2006 Sep 26;103(39):14602-7. DOI: 10.1073/pnas.0606544103 PMID 16984997
^ Reddy DS, Rogawski MA. Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA-A receptor function and seizure susceptibility. J Neurosci. 2002 May 1;22(9):3795-805. PubMed PMID 11978855
^ Reddy DS. Pharmacology of endogenous neuroactive steroids. Critical Reviews in Neurobiology. 2003;15(3-4):197-234. PMID 15248811
^ Tuveri A, Paoletti AM, Orrù M, Melis GB, Marotto MF, Zedda P, Marrosu F, Sogliano C, Marra C, Biggio G, Concas A. Reduced serum level of THDOC, an anticonvulsant steroid, in women with perimenstrual catamenial epilepsy. Epilepsia. 2008 Jul;49(7):1221-9. PMID 18325018
^ Reddy DS. Is there a physiological role for the neurosteroid THDOC in stress-sensitive conditions? Trends in Pharmacological Sciences. 2003 Mar;24(3):103-6. PMID 12628349
^ Reddy DS. Physiological role of adrenal deoxycorticosterone-derived neuroactive steroids in stress-sensitive conditions. Neuroscience. 2006;138(3):911-20. PMID 16325348
^ Eser D, Romeo E, Baghai TC, di Michele F, Schüle C, Pasini A, Zwanzger P, Padberg F, Rupprecht R. Neuroactive steroids as modulators of depression and anxiety. Neuroscience. 2006;138(3):1041-8. PMID 16310959
^ Eser D, Schüle C, Baghai TC, Romeo E, Rupprecht R. Neuroactive steroids in depression and anxiety disorders: clinical studies. Neuroendocrinology. 2006;84(4):244-54. PMID 17159334
^ Maguire J, Mody I. Neurosteroid synthesis-mediated regulation of GABA(A) receptors: relevance to the ovarian cycle and stress. Journal of Neuroscience. 2007 Feb 28;27(9):2155-62. PMID 17329412

Portale Chimica

Portale Medicina

[1] Hosie AM, Wilkins ME, da Silva HM, Smart TG. Endogenous neurosteroids regulate GABA_A receptors through two discrete transmembrane sites. Nature. 2006 Nov 23;444(7118):486-9. DOI: 10.1038/nature05324 PMID 17108970

[2] Agís-Balboa RC, Pinna G, Zhubi A, Maloku E, Veldic M, Costa E, Guidotti A. Characterization of brain neurons that express enzymes mediating neurosteroid biosynthesis. Proceedings of the National Academy of Sciences USA. 2006 Sep 26;103(39):14602-7. DOI: 10.1073/pnas.0606544103 PMID 16984997

[3] Reddy DS, Rogawski MA. Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA-A receptor function and seizure susceptibility. J Neurosci. 2002 May 1;22(9):3795-805. PubMed PMID 11978855

[4] Reddy DS. Pharmacology of endogenous neuroactive steroids. Critical Reviews in Neurobiology. 2003;15(3-4):197-234. PMID 15248811

[5] Tuveri A, Paoletti AM, Orrù M, Melis GB, Marotto MF, Zedda P, Marrosu F, Sogliano C, Marra C, Biggio G, Concas A. Reduced serum level of THDOC, an anticonvulsant steroid, in women with perimenstrual catamenial epilepsy. Epilepsia. 2008 Jul;49(7):1221-9. PMID 18325018

[6] Reddy DS. Is there a physiological role for the neurosteroid THDOC in stress-sensitive conditions? Trends in Pharmacological Sciences. 2003 Mar;24(3):103-6. PMID 12628349

[7] Reddy DS. Physiological role of adrenal deoxycorticosterone-derived neuroactive steroids in stress-sensitive conditions. Neuroscience. 2006;138(3):911-20. PMID 16325348

[8] Eser D, Romeo E, Baghai TC, di Michele F, Schüle C, Pasini A, Zwanzger P, Padberg F, Rupprecht R. Neuroactive steroids as modulators of depression and anxiety. Neuroscience. 2006;138(3):1041-8. PMID 16310959

[9] Eser D, Schüle C, Baghai TC, Romeo E, Rupprecht R. Neuroactive steroids in depression and anxiety disorders: clinical studies. Neuroendocrinology. 2006;84(4):244-54. PMID 17159334

[10] Maguire J, Mody I. Neurosteroid synthesis-mediated regulation of GABA(A) receptors: relevance to the ovarian cycle and stress. Journal of Neuroscience. 2007 Feb 28;27(9):2155-62. PMID 17329412

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