| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H34O2 |
| Molecular Weight | 318.4935 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)[C@H]1CC[C@H]2[C@@H]3CC[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=AURFZBICLPNKBZ-YZRLXODZSA-N
InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1
| Molecular Formula | C21H34O2 |
| Molecular Weight | 318.4935 |
| 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 |
Eltanolone (pregnanolone) is an endogenous neuro active steroid that is biosynthesized from progesterone. It is a positive allosteric modulator of the GABAA receptor, as well as a negative allosteric modulator of the glycine receptor. There is strong evidence that it is involved in the pathophysiology of premenstrual syndrome, catamenial epilepsy, major depression, and stress-sensitive brain disorders and is known to have sedative, anxiolytic, anesthetic, and anticonvulsant effects. It was investigated for clinical use as a general (intravenous) anesthetic. It produced unwanted side effects such as convulsions on occasion, and for that reason was not marketed. Pregnanolone possesses neuroprotective and neurotrophic properties thus has been through a number of clinical trials including for treatment of traumatic brain injury (TBI), Alzheimer disease, cognitive impairment and fragile X-associated tremor/ataxia syndrome.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Pregnenolone 50 mg BID for 14 days, followed by 150 mg BID for 14 days, followed by 250 mg BID x thereafter for the remainder of the 8-week trial
Route of Administration:
Oral
Cholesterol enrichment of the neurones, isolated from 10 to 16-day-old Wistar rat brains, was achieved by incubation with cholesterol + phosphatidylcholine liposomes. Cholesterol enrichment (25.8+/-3.4%) reduced the potentiation of GABA(A) currents by pregnanolone (0.3 and 1 uM). Acute application of cholesterol (1 uM) did not significantly change the potentiation of GABA(A) currents by pregnanolone (1 uM).
