Tetrahydrodeoxycorticosterone

From DrugPedia: A Wikipedia for Drug discovery

[edit] Description

Show 3-D Structure

Tetrahydrodeoxycorticosterone (THDOC) is an endogenous neuroactive steroid.<ref>Hosie AM, Wilkins ME, da Silva HM, Smart TG. Endogenous neurosteroids regulate GABAA receptors through two discrete transmembrane sites. Nature. 2006 Nov 23;444(7118):486-9. PMID 17108970 </ref> It is synthesised in the brain from deoxycorticosterone by the action of two enzymes, 5α-reductase type I and 3α-hydroxysteroid dehydrogenase.<ref>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. PMID 16984997</ref> THDOC has sedative, anxiolytic and anticonvulsant effects,<ref>Reddy DS. Pharmacology of endogenous neuroactive steroids. Critical Reviews in Neurobiology. 2003;15(3-4):197-234. PMID 15248811</ref> and changes in the normal levels of this steroid particularly during pregnancy and menstruation may be involved in some types of epilepsy,<ref>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</ref> as well as stress, anxiety and depression.<ref>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</ref><ref>Reddy DS. Physiological role of adrenal deoxycorticosterone-derived neuroactive steroids in stress-sensitive conditions. Neuroscience. 2006;138(3):911-20. PMID 16325348</ref><ref>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</ref><ref>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</ref><ref>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</ref>

[edit] General Properties

*Molecular Weight

334.49

*Molecular Formula

C₂₁H₃₄O₃

*IUPAC NAME

2-hydroxy-1-[(5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

*Canonical Smiles

CC12CCC(CC1CCC3C2CCC4(C3CCC4C(=O)CO)C)O

*Isomeric 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

[edit] PhysioChemical Properties

*Melting Point

*LogP

*Water Solubility

[edit] External Links

• [1]Pubchem
• [2]KEGG Compound
• [3]Human Metabolome DataBase

[Category:Neurosteroids]][[Category:H[Cypnotics]]