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Tetrahydrodeoxycorticosterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tetrahydrodeoxycorticosterone
Clinical data
Other namesTHDOC
Identifiers
  • (3α,5β)-3,21-dihydroxypregnan-20-one
CAS Number
PubChemCID
UNII
ECHA InfoCard100.008.457Edit this at Wikidata
Chemical and physical data
FormulaC21H34O3
Molar mass334.500 g·mol−1
3D model (JSmol)
  • 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
  (verify)

Tetrahydrodeoxycorticosterone (abbreviated asTHDOC; 3α,21-dihydroxy-5α-pregnan-20-one), also referred to asallotetrahydrocorticosterone, is anendogenousneurosteroid.[1] It is synthesized from the adrenal hormonedeoxycorticosterone by the action of two enzymes,5α-reductase type I and3α-hydroxysteroid dehydrogenase.[2] THDOC is a potentpositive allosteric modulator of theGABAA receptor, and hassedative,anxiolytic andanticonvulsant effects.[3][4][5] Changes in the normal levels of this steroid particularly duringpregnancy andmenstruation may be involved in some types ofepilepsy (catamenial epilepsy) andpremenstrual syndrome,[6] as well asstress,anxiety anddepression.[7][8][9][10][11]

Chemistry

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See also:List of neurosteroids

See also

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References

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  1. ^Hosie AM, Wilkins ME, da Silva HM, Smart TG (November 2006). "Endogenous neurosteroids regulate GABAA receptors through two discrete transmembrane sites".Nature.444 (7118):486–9.Bibcode:2006Natur.444..486H.doi:10.1038/nature05324.PMID 17108970.S2CID 4382394.
  2. ^Agís-Balboa RC, Pinna G, Zhubi A, Maloku E, Veldic M, Costa E, Guidotti A (September 2006)."Characterization of brain neurons that express enzymes mediating neurosteroid biosynthesis".Proceedings of the National Academy of Sciences of the United States of America.103 (39):14602–7.Bibcode:2006PNAS..10314602A.doi:10.1073/pnas.0606544103.PMC 1600006.PMID 16984997.
  3. ^Kokate TG, Svensson BE, Rogawski MA (September 1994). "Anticonvulsant activity of neurosteroids: correlation with gamma-aminobutyric acid-evoked chloride current potentiation".The Journal of Pharmacology and Experimental Therapeutics.270 (3):1223–9.PMID 7932175.
  4. ^Reddy DS, Rogawski MA (May 2002)."Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility".The Journal of Neuroscience.22 (9):3795–805.doi:10.1523/JNEUROSCI.22-09-03795.2002.PMC 6758375.PMID 11978855.
  5. ^Reddy DS (2003). "Pharmacology of endogenous neuroactive steroids".Critical Reviews in Neurobiology.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, et al. (July 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.S2CID 23596739.
  7. ^Reddy DS (March 2003). "Is there a physiological role for the neurosteroid THDOC in stress-sensitive conditions?".Trends in Pharmacological Sciences.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.S2CID 23576732.
  9. ^Eser D, Romeo E, Baghai TC, di Michele F, Schüle C, Pasini A, et al. (2006). "Neuroactive steroids as modulators of depression and anxiety".Neuroscience.138 (3):1041–8.doi:10.1016/j.neuroscience.2005.07.007.PMID 16310959.S2CID 12033307.
  10. ^Eser D, Schüle C, Baghai TC, Romeo E, Rupprecht R (2006)."Neuroactive steroids in depression and anxiety disorders: clinical studies"(PDF).Neuroendocrinology.84 (4):244–54.doi:10.1159/000097879.PMID 17159334.S2CID 15711990.
  11. ^Maguire J, Mody I (February 2007)."Neurosteroid synthesis-mediated regulation of GABA(A) receptors: relevance to the ovarian cycle and stress".The Journal of Neuroscience.27 (9):2155–62.doi:10.1523/JNEUROSCI.4945-06.2007.PMC 6673487.PMID 17329412.
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