Tetrahydrodeoxycorticosterone

Tetrahydrodeoxycorticosterone
Systematic (IUPAC) name
(3α,5β)-3,21-dihydroxypregnan-20-one
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 567-03-3
ATC code  ?
PubChem CID 91475
Synonyms THDOC
Chemical data
Formula C21H34O3 
Mol. mass 334.493 g/mol
SMILES eMolecules & PubChem
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Tetrahydrodeoxycorticosterone (3α,21-dihydroxy-5α-pregnan-20-one; THDOC), or more preferred allotetrahydroxycorticosterone, is an endogenous neurosteroid.[1] It is synthesized from the adrenal hormone deoxycorticosterone by the action of two enzymes, 5α-reductase type I and 3α-hydroxysteroid dehydrogenase.[2] THDOC has sedative, anxiolytic and anticonvulsant effect.[3] [4] Changes in the normal levels of this steroid particularly during pregnancy and menstruation may be involved in some types of epilepsy (catamenial epilepsy),[5] as well as stress, anxiety and depression.[6][7][8][9][10]

References

  1. ^ 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. 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