Tetrahydrodeoxycorticosterone

Tetrahydrodeoxycorticosterone

Identifiers
IUPAC name (3α,5β)-3,21-dihydroxypregnan-20-one
Synonyms	THDOC
CAS Number	567-03-3
PubChem (CID)	91475
Chemical and physical data
Formula	C21H34O3
Molar mass	334.493 g/mol
3D model (Jmol)	Interactive image
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
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Tetrahydrodeoxycorticosterone (abbreviated as THDOC; 3α,21-dihydroxy-5α-pregnan-20-one), also referred to as allotetrahydrocorticosterone, 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 is a potent positive allosteric modulator of the GABA_A receptor, and has sedative, anxiolytic and anticonvulsant effects.^[3][4][5] Changes in the normal levels of this steroid particularly during pregnancy and menstruation may be involved in some types of epilepsy (catamenial epilepsy) and premenstrual syndrome,^[6] as well as stress, anxiety and depression.^{[7][8][9][10][11]}

See also

• Allopregnanolone
• Dihydrodeoxycorticosterone (DHDOC)
• Tetrahydrocorticosterone (THB)

References

1. Hosie, AM; Wilkins, ME; Da Silva, HM; Smart, TG (2006). "Endogenous neurosteroids regulate GABAA receptors through two discrete transmembrane sites". Nature. 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 (2006). "Characterization of brain neurons that express enzymes mediating neurosteroid biosynthesis". Proc. Natl. Acad. Sci. U.S.A. 103 (39): 14602–7. doi:10.1073/pnas.0606544103. PMC 1600006. PMID 16984997.
3. Kokate, TG; Svensson, BE; Rogawski, MA (1994). "Anticonvulsant activity of neurosteroids: Correlation with gamma-aminobutyric acid-evoked chloride current potentiation". J. Pharmacol. Exper. Therapeut. 270 (3): 1223–9. PMID 7932175.
4. Reddy, DS; Rogawski, MA (2002). "Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility". J. Neurosci. 22 (9): 3795–805. PMID 11978855.
5. Reddy, DS (2003). "Pharmacology of endogenous neuroactive steroids". Crit. Rev. Neurobiol. 15 (3–4): 197–234. doi:10.1615/critrevneurobiol.v15.i34.20. PMID 15248811.
6. Tuveri, A; Paoletti, AM; Orrù, M; Melis, GB; Marotto, MF; Zedda, P; Marrosu, F; Sogliano, C; Marra, C; Biggio, G; Concas, A (2008). "Reduced serum level of THDOC, an anticonvulsant steroid, in women with perimenstrual catamenial epilepsy". Epilepsia. 49 (7): 1221–9. doi:10.1111/j.1528-1167.2008.01555.x. PMID 18325018.
7. Reddy, DS (2003). "Is there a physiological role for the neurosteroid THDOC in stress-sensitive conditions?". Trends Pharmacol. Sci. 24 (3): 103–6. doi:10.1016/S0165-6147(03)00023-3. PMID 12628349.
8. Reddy, DS (2006). "Physiological role of adrenal deoxycorticosterone-derived neuroactive steroids in stress-sensitive conditions". Neuroscience. 138 (3): 911–20. doi:10.1016/j.neuroscience.2005.10.016. PMID 16325348.
9. Eser, D; Romeo, E; Baghai, TC; Di Michele, F; Schüle, C; Pasini, A; Zwanzger, P; Padberg, F; Rupprecht, R (2006). "Neuroactive steroids as modulators of depression and anxiety". Neuroscience. 138 (3): 1041–8. doi:10.1016/j.neuroscience.2005.07.007. PMID 16310959.
10. Eser, D; Schüle, C; Baghai, TC; Romeo, E; Rupprecht, R (2006). "Neuroactive steroids in depression and anxiety disorders: Clinical studies". Neuroendocrinology. 84 (4): 244–54. doi:10.1159/000097879. PMID 17159334.
11. Maguire, J; Mody, I (2007). "Neurosteroid synthesis-mediated regulation of GABA(A) receptors: Relevance to the ovarian cycle and stress". J. Neurosci. 27 (9): 2155–62. doi:10.1523/JNEUROSCI.4945-06.2007. PMID 17329412.