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Details

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
Structure of EPIPREGNANOLONE

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@]4([H])C[C@@H](O)CC[C@]34C

InChI

InChIKey=AURFZBICLPNKBZ-GRWISUQFSA-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

HIDE SMILES / InChI

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

Description

Epipregnanolone is an epimer of endogenous neurosteroid pregnanolone, it has been shown to antagonize GABAA and NMDA receptors. In addition epipregnanolone inhibits calcium T-currents and stimulates TRPM3 channel. Epipregnanolone displays anesthetic properties. Epipregnanolone has been shown to reduce alcohol self-administration in rats.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
10.5 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Intraperitoneal epipregnanolone (5, 10, and 20 mg/kg) dose-dependently attenuated ethanol self-administration in rats. Intraplantar injections (0.1, 1 or 10 uM) of epipregnanolone directly into peripheral receptive fields reduced responses to nociceptive stimuli in rodents in a dose-dependent fashion.
Route of Administration: Other
In Vitro Use Guide
Epipregnanolone reversibly blocked T-type calcium channels in rat dorsal root ganglia (DRG) cells in vitro in a dose-dependent fashion (IC50 = 2 μM) and stabilized the channel in the inactive state.
Substance Class Chemical
Record UNII
3KQ00893OL
Record Status Validated (UNII)
Record Version