EPIPREGNANOLONE

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 Search

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-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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1320747
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11978813 | https://www.ncbi.nlm.nih.gov/pubmed/15950269 | https://www.ncbi.nlm.nih.gov/pubmed/24800894 | https://www.ncbi.nlm.nih.gov/pubmed/20735426 | https://www.ncbi.nlm.nih.gov/pubmed/9396781

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 Target	Pharmacology	Potency
Voltage-gated T-type calcium channel alpha-1H subunit 7 Target ID: CHEMBL1859 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24800894	Inhibitor 8504
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8381526 \| https://www.ncbi.nlm.nih.gov/pubmed/1320747 \| https://www.ncbi.nlm.nih.gov/pubmed/11978813	Negative Allosteric Modulator 43	10.5 µM [Ki]
Transient receptor potential cation channel subfamily M member 3 5 Target ID: Q9HCF6\|\|\|Q86SH6\|\|\|Q86Z01 Gene ID: 80036.0 Gene Symbol: TRPM3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/20735426	Activator 1447
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9396781	Negative Allosteric Modulator 43

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24800894	Primary		Basic research	Unknown Approved Use Unknown
Alcohol addiction 24 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15950269	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Neurochemicals for the investigation of GABA(C) receptors.	2010-12	20963487
Allopregnanolone-induced rise in intracellular calcium in embryonic hippocampal neurons parallels their proliferative potential.	2008-12-03	19090984
Effect of an oral contraceptive with chlormadinone acetate on depressive mood : analysis of data from four observational studies.	2008	18991472
Influence of epipregnanolone on the modulation of rapid tolerance to ethanol by neurosteroids.	2007-12	18200398
Relationships of circulating pregnanolone isomers and their polar conjugates to the status of sex, menstrual cycle, and pregnancy.	2007-10	17911398
Serum profiles of free and conjugated neuroactive pregnanolone isomers in nonpregnant women of fertile age.	2006-08	16720657
Syntheses of 19-[O-(carboxymethyl)oxime] haptens of epipregnanolone and pregnanolone.	2006-02	16242742
Epipregnanolone and a novel synthetic neuroactive steroid reduce alcohol self-administration in rats.	2005-07	15950269
Altered profiles of serum neuroactive steroids in premenopausal women treated for alcohol addiction.	2005-07	15894035
Reinstatement of serum pregnanolone isomers and progesterone during alcohol detoxification therapy in premenopausal women.	2005-06	15976527
Neuroactive pregnanolone isomers during pregnancy.	2005-01	15486056
Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.	2004-07	15225127
Estradiol and testosterone modulate the anesthetic action of the GABA-A agonist THIP, but not of the neurosteroid 3alpha,5beta-pregnanolone in the rat.	2004-03	14685643
Discriminative stimulus effects of positive GABAA modulators and other anxiolytics, sedatives, and anticonvulsants in untreated and diazepam-treated monkeys.	2003-01	12490581
Pregnenolone sulfate, dehydroepiandrosterone sulfate and allotetrahydrodeoxycorticosterone affect rapid tolerance to the hypothermic effect of ethanol.	2002-05	12121819
Neuroactive ring A-reduced metabolites of progesterone in human plasma during pregnancy: elevated levels of 5 alpha-dihydroprogesterone in depressed patients during the latter half of pregnancy.	2001-12	11739473
In ovo chronic neurosteroid treatment affects the function and allosteric interactions of GABA(A) receptor modulatory sites.	2001-05-25	11376596
Characterization of discriminative stimulus effects of the neuroactive steroid pregnanolone.	2001-05	11303034

Patents

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 Created by `admin` on `Mon Mar 31 17:46:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:37 GMT 2025`
Record UNII	3KQ00893OL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIPREGNANOLONE

Common Name

English

NSC-21450

Preferred Name

English

PREGNANOLONE I

Common Name

English

PREGNAN-20-ONE, 3-HYDROXY-, (3.BETA.,5.BETA.)-

Systematic Name

English

3.BETA.,5.BETA.-PREGNANOLONE

Common Name

English

Classification Tree Code System Code

LOINC

78376-1