| 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
[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@]4([H])C[C@H](O)CC[C@]34C
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 |
MOL RATIO
1 MOL RATIO (average) |
| 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.
CNS Activity
Approval Year
PubMed
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).
