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

[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

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 8297
GABA-A receptor; anion channel 202 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 42	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 1430
Glutamate [NMDA] receptor 125 Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9396781	Negative Allosteric Modulator 42

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24800894	Primary		Basic research	Unknown Approved Use Unknown
Alcohol addiction 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15950269	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
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 Dec	11739473
Characterization of discriminative stimulus effects of the neuroactive steroid pregnanolone.	2001 May	11303034
Pregnenolone sulfate, dehydroepiandrosterone sulfate and allotetrahydrodeoxycorticosterone affect rapid tolerance to the hypothermic effect of ethanol.	2002 May	12121819
Discriminative stimulus effects of positive GABAA modulators and other anxiolytics, sedatives, and anticonvulsants in untreated and diazepam-treated monkeys.	2003 Jan	12490581
Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids.	2004 Jul	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 Mar	14685643
Neuroactive pregnanolone isomers during pregnancy.	2005 Jan	15486056
Epipregnanolone and a novel synthetic neuroactive steroid reduce alcohol self-administration in rats.	2005 Jul	15950269
Altered profiles of serum neuroactive steroids in premenopausal women treated for alcohol addiction.	2005 Jul	15894035
Reinstatement of serum pregnanolone isomers and progesterone during alcohol detoxification therapy in premenopausal women.	2005 Jun	15976527
Serum profiles of free and conjugated neuroactive pregnanolone isomers in nonpregnant women of fertile age.	2006 Aug	16720657
Syntheses of 19-[O-(carboxymethyl)oxime] haptens of epipregnanolone and pregnanolone.	2006 Feb	16242742
Influence of epipregnanolone on the modulation of rapid tolerance to ethanol by neurosteroids.	2007 Dec	18200398
Relationships of circulating pregnanolone isomers and their polar conjugates to the status of sex, menstrual cycle, and pregnancy.	2007 Oct	17911398
Effect of an oral contraceptive with chlormadinone acetate on depressive mood : analysis of data from four observational studies.	2008	18991472
Allopregnanolone-induced rise in intracellular calcium in embryonic hippocampal neurons parallels their proliferative potential.	2008 Dec 3	19090984
Neurochemicals for the investigation of GABA(C) receptors.	2010 Dec	20963487

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 `Fri Dec 15 15:06:22 UTC 2023` Edited by `admin` on `Fri Dec 15 15:06:22 UTC 2023`
Record UNII	3KQ00893OL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EPIPREGNANOLONE

Common 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

NSC-21450

Code

English

Classification Tree Code System Code

LOINC

78376-1