Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H34O3 |
| Molecular Weight | 334.4929 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@H](O)CC[C@]34C)[C@@H]1CC[C@@H]2C(=O)CO
InChI
InChIKey=CYKYBWRSLLXBOW-DATPGIFZSA-N
InChI=1S/C21H34O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13-18,22-23H,3-12H2,1-2H3/t13-,14-,15+,16+,17+,18-,20+,21+/m1/s1
| Molecular Formula | C21H34O3 |
| Molecular Weight | 334.4929 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Tetrahydrodeoxycorticosterone (THDOC) is a neuroactive steroid. Neurosteroids represent a class of endogenous steroids that are synthesized in the brain, the adrenals, and the gonads. It potentiates synaptic GABAA-receptor function. THDOC is extremely potent positive allosteric modulators of GABAA receptors with sedative, anxiolytic, and anticonvulsant properties. THDOC can regulate gene expression via the progesterone receptor. The induction of DNA-binding and transcriptional activation of the progesterone receptor requires intracellular oxidation of the neurosteroids into progesterone receptor-active 5 alpha-pregnane steroid. THDOC is involved in the pathophysiology of premenstrual syndrome, catamenial epilepsy, major depression, and stress-sensitive brain disorders.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chronic ethanol exposure produces tolerance to elevations in neuroactive steroids: mechanisms and reversal by exogenous ACTH. | 2010-10 |
|
| Screening and diagnosis of beta-ureidopropionase deficiency by gas chromatographic/mass spectrometric analysis of urine. | 2002-09 |
|
| Membrane-initiated events account for progesterone's ability to regulate intracellular free calcium levels and inhibit rat granulosa cell mitosis. | 2002-08 |
|
| Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level. | 2001-12 |
|
| The relationship between the effects of metyrapone treatment on depressed mood and urinary steroid profiles. | 1996-04 |
|
| Adrenal cortex, tumor, and peripheral production of deoxycorticosterone. | 1992-01 |
|
| Incomplete virilization and subclinical mineralocorticoid excess in a boy with partial 17,20-desmolase/17 alpha-hydroxylase deficiency. | 1990-02 |
|
| Effect of a single oral dose of metyrapone on secretion of growth hormone and urinary tetrahydro-11-deoxycortisol and tetrahydro-11-deoxycorticosterone excretion in children. | 1972-06 |
|
| Determination of urinary tetrahydro-11-deoxycortisol and tetrahydro-11-deoxycorticosterone by gas chromatography. | 1971-04 |
Patents
Sample Use Guides
5 alpha-pregnane-3 alpha, 21-diol-20-one (5 alpha-tetrahydrodeoxycorticosterone; 5 alpha-THDOC) (10 microM) increased and prolonged the inhibitory postsynaptic potential (IPSP) in pyramidal neurons in an in vitro slice preparation of the adult rat frontal neocortex. At a concentration of 1 microM 5 alpha-THDOC increased only the early IPSP. Responses to the iontophoretically applied specific GABAA receptor agonist muscimol but not to the specific GABAB receptor agonist L-baclofen were enhanced by 5 alpha-THDOC (10 microM). In the giga-seal whole-cell configuration when the GABAB receptor-mediated IPSP component was absent due to intracellular perfusion, 5 alpha-THDOC (10 microM) increased IPSPs to a similar extent as in the conventional microelectrode recordings. Excitatory postsynaptic potentials, resting membrane potential, input resistance and action potential amplitude were not affected by 5 alpha-THDOC (10 microM).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:04:39 GMT 2025
by
admin
on
Mon Mar 31 22:04:39 GMT 2025
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| Record UNII |
4AB717DP4A
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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| Code System | Code | Type | Description | ||
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Tetrahydrodeoxycorticosterone
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DTXSID401308374
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209-301-3
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9974162
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567-03-3
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4AB717DP4A
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admin on Mon Mar 31 22:04:39 GMT 2025 , Edited by admin on Mon Mar 31 22:04:39 GMT 2025
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