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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32O2
Molecular Weight 316.4776
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pregnenolone

SMILES

[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@@H](O)CC[C@]34C

InChI

InChIKey=ORNBQBCIOKFOEO-QGVNFLHTSA-N
InChI=1S/C21H32O2/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/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H32O2
Molecular Weight 316.4776
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18068870 | https://www.ncbi.nlm.nih.gov/pubmed/24385629 | https://www.ncbi.nlm.nih.gov/pubmed/21756978

Pregnenolone is an endogenous steroid and precursor the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is a precursor of neurosteroid pregnenolone sulfate, which is positive modulator of NMDA receptors and negative modulator of GABAA. Pregnenolone itself is a negative allosteric modulator of cannabinoid receptors. Pregnenolone is available as a dietary supplement, and is being investigated in clinical trials agains schizophrenia, bipolar disorder, major depressive disorder, marijuana dependency and other conditions.

CNS Activity

Curator's Comment: As a precursor of neurosteroid, pregnenolone is endogenously produced in the brain.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.2 µM [IC50]
33.0 µM [EC50]
Target ID: Q7Z4N2|||Q7Z4N3
Gene ID: 4308.0
Gene Symbol: TRPM1
Target Organism: Homo sapiens (Human)
Target ID: Q9HCF6|||Q86SH6|||Q86Z01
Gene ID: 80036.0
Gene Symbol: TRPM3
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
PREGNENOLONE

Approved Use

Pregnenolone is a dietary supplement designed to promote mood and mental balance between body systems. Pregnenolone is a hormone similar to DHEA (dehydroepiandrosterone) and may be taken in addition to DHEA, or as an alternative. Pregnenolone is manufactured by many body tissues and under certain conditions, may be converted into similar substances, such as DHEA or progesterone.
Primary
PREGNENOLONE

Approved Use

Pregnenolone is a dietary supplement designed to promote mood and mental balance between body systems. Pregnenolone is a hormone similar to DHEA (dehydroepiandrosterone) and may be taken in addition to DHEA, or as an alternative. Pregnenolone is manufactured by many body tissues and under certain conditions, may be converted into similar substances, such as DHEA or progesterone.
Primary
PREGNENOLONE

Approved Use

Pregnenolone is a dietary supplement designed to promote mood and mental balance between body systems. Pregnenolone is a hormone similar to DHEA (dehydroepiandrosterone) and may be taken in addition to DHEA, or as an alternative. Pregnenolone is manufactured by many body tissues and under certain conditions, may be converted into similar substances, such as DHEA or progesterone.
Primary
PREGNENOLONE

Approved Use

Pregnenolone is a dietary supplement designed to promote mood and mental balance between body systems. Pregnenolone is a hormone similar to DHEA (dehydroepiandrosterone) and may be taken in addition to DHEA, or as an alternative. Pregnenolone is manufactured by many body tissues and under certain conditions, may be converted into similar substances, such as DHEA or progesterone.
Primary
PREGNENOLONE

Approved Use

Pregnenolone is a dietary supplement designed to promote mood and mental balance between body systems. Pregnenolone is a hormone similar to DHEA (dehydroepiandrosterone) and may be taken in addition to DHEA, or as an alternative. Pregnenolone is manufactured by many body tissues and under certain conditions, may be converted into similar substances, such as DHEA or progesterone.
Primary
PREGNENOLONE

Approved Use

Pregnenolone is a dietary supplement designed to promote mood and mental balance between body systems. Pregnenolone is a hormone similar to DHEA (dehydroepiandrosterone) and may be taken in addition to DHEA, or as an alternative. Pregnenolone is manufactured by many body tissues and under certain conditions, may be converted into similar substances, such as DHEA or progesterone.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
38 ng/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOPIDOGREL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
125.5 ng × h/mL
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOPIDOGREL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLOPIDOGREL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
250 mg 2 times / day multiple, oral
Highest studied dose
Dose: 250 mg, 2 times / day
Route: oral
Route: multiple
Dose: 250 mg, 2 times / day
Sources:
unhealthy, 22.5 years (range: 18.1–35.5 years)
n = 12
Health Status: unhealthy
Condition: Autism Spectrum Disorder
Age Group: 22.5 years (range: 18.1–35.5 years)
Sex: M+F
Population Size: 12
Sources:
PubMed

PubMed

TitleDatePubMed
Pregnenolone sulfate increases hippocampal acetylcholine release and spatial recognition.
2000 Jan 3
Neurosteroid analysis.
2001
Neurosteroid 7-hydroxylation products in the brain.
2001
Role of the peripheral-type benzodiazepine receptor in adrenal and brain steroidogenesis.
2001
[Neurosteroids, their role in brain physiology: neurotrophicity, memory, aging...].
2001
Mechanism of action of noradrenaline on secretion of progesterone and oxytocin by the bovine corpus luteum in vitro.
2001
Effect of treatment of hypothyroidism on the plasma concentrations of neuroactive steroids and homocysteine.
2001 Aug
Effects of different steroid-biosynthesis inhibitors on the testicular steroidogenesis of the toad Bufo arenarum.
2001 Aug
Development of an enzyme immunoassay for serum 16-dehydropregnenolone.
2001 Aug
Heterozygous mutation in the cholesterol side chain cleavage enzyme (p450scc) gene in a patient with 46,XY sex reversal and adrenal insufficiency.
2001 Aug
Tracking the role of a star in the sky of the new millennium.
2001 Aug
Neurosteroid synthesis by cytochrome p450-containing systems localized in the rat brain hippocampal neurons: N-methyl-D-aspartate and calcium-dependent synthesis.
2001 Aug
Decreased expression of steroidogenic acute regulatory protein: a novel mechanism participating in the leptin-induced inhibition of glucocorticoid biosynthesis.
2001 Aug
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
Identification, localization, and function in steroidogenesis of PAP7: a peripheral-type benzodiazepine receptor- and PKA (RIalpha)-associated protein.
2001 Dec
Diminished allopregnanolone enhancement of GABA(A) receptor currents in a rat model of chronic temporal lobe epilepsy.
2001 Dec 1
Pregnenolone protects mouse hippocampal (HT-22) cells against glutamate and amyloid beta protein toxicity.
2001 Jan
Cerebral venous thrombosis in a patient of paroxysmal nocturnal haemoglobinuria following aplastic anaemia.
2001 Jul
Ontogeny of steroid metabolizing enzymes in rat oligodendrocytes.
2001 Jul
Neuroactive steroid-serotonergic interaction: responses to an intravenous L-tryptophan challenge in women with premenstrual syndrome.
2001 Jul
Serum concentration of androstenediol and androstenediol sulfate in patients with hyperthyroidism and hypothyroidism.
2001 Jun
Luteinization factor-stimulated steroidogenesis in porcine granulosa cells.
2001 Jun
Expression and characterization of the human 3 beta-hydroxysteroid sulfotransferases (SULT2B1a and SULT2B1b).
2001 Jun
Aryl hydrocarbon receptor (AhR)-linked inhibition of luteal cell progesterone secretion in 2,3,7,8-tetrachlorodibenzo-p-dioxin treated cells.
2001 Jun
Molecular modelling of 17 alpha-hydroxylase-17,20-lyase.
2001 Jun
Steroids in the nervous system: a Pandora's box?
2001 Jun
Creation and activity of COS-1 cells stably expressing the F2 fusion of the human cholesterol side-chain cleavage enzyme system.
2001 Jun
Stimulatory effect of lactate on testosterone production by rat Leydig cells.
2001 Jun 26-Jul 25
Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides.
2001 Mar-Apr
[Effect of genotype and social stress on cAMP- and substrate-dependent mechanisms of regulating hormonal function of testis in mice].
2001 May
Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators.
2001 Nov
Immunoelectron microscopic localization of three key steroidogenic enzymes (cytochrome P450(scc), 3 beta-hydroxysteroid dehydrogenase and cytochrome P450(c17)) in rat adrenal cortex and gonads.
2001 Nov
Hormonal steroidogenesis in liver and small intestine of the green frog, Rana esculenta L.
2001 Nov 2
Neuroactive steroids modulate crustacean locomotor activity.
2001 Nov 2
Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes.
2001 Oct
Prevention of the stress-induced increase in frontal cortical dopamine efflux of freely moving rats by long-term treatment with antidepressant drugs.
2001 Oct
Aldosterone increases T-type calcium currents in human adrenocarcinoma (H295R) cells by inducing channel expression.
2001 Oct
2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands.
2001 Oct
Activity and localization of 3beta-hydroxysteroid dehydrogenase/ Delta5-Delta4-isomerase in the zebrafish central nervous system.
2001 Oct 22
Purification of cytochromes P-450(scc) and P-450(17 alpha) by steroid-binding affinity column chromatography.
2001 Oct 30
Immunohistochemical localization of steroidogenic enzymes in the corpus luteum and the placenta of the ribbon seal (Phoca fasciata) and steller sea lion (Eumetopias jubatus).
2001 Sep
Analysis of neurosteroid levels in attention deficit hyperactivity disorder.
2001 Sep
Pregnenolone sulfate and aging of cognitive functions: behavioral, neurochemical, and morphological investigations.
2001 Sep
Subunit-specific modulation of glycine receptors by neurosteroids.
2001 Sep
Cytochrome P450 in the brain; a review.
2001 Sep
Regulation of the rat glutathione S-transferase A2 gene by glucocorticoids: involvement of both the glucocorticoid and pregnane X receptors.
2001 Sep
Pregnenolone sulfate modulates angiotensin II-induced inositol 1,4,5-trisphosphate changes in the anterior pituitary of female rat.
2001 Sep 28
The interaction of bovine adrenodoxin with CYP11A1 (cytochrome P450scc) and CYP11B1 (cytochrome P45011beta ). Acceleration of reduction and substrate conversion by site-directed mutagenesis of adrenodoxin.
2001 Sep 28
Membrane cholesterol modulates serotonin transporter activity.
2001 Sep 4
Neuroactive steroid levels in patients with generalized anxiety disorder.
2001 Summer
Patents

Sample Use Guides

In the model of schizophrenia, pregnenolone sulfate was administered to mice intraperitoneally at 40 or 60 mg/kg. When administered to rats intracerebroventricularly, 12 nmol but not 192 nmol pregnenolone sulfate enhanced spatial memory performance.
Route of Administration: Other
In Vitro Use Guide
Activity with respect to NMDA and GABA uiion channels was measured using whole cell variant of the patch-clamp technique. Patch electrodes were fabricated with a double pull from thin-wall borosilicate glass microcapillary pipets. Electrode resistance was 5.2 ± 0.12 MOhm (n = 65) when filled with intracellular solution. After formation of a tight seal (typically 1-10 GOhm), capacitative transients were minimized. The patch of membrane under the pipet tip was then ruptured by gentle suction, to obtain the whole-cell configuration. Drug solutions were applied to single neurons by pressure ejection (15 psi) from seven-barrel pipets. Under these conditions, the drug solution in the pressure pipet rapidly and effectively replaces the solution surrounding the target neuron, with <10% dilution. In all experiments, neurons received a 10-sec prepulse of either external buffer or drug solution, followed by a 10-sec application of agonist, followed by a 10-20-sec pulse of external buffer solution.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:13:51 UTC 2023
Edited
by admin
on Sat Dec 16 17:13:51 UTC 2023
Record UNII
73R90F7MQ8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Pregnenolone
INN   JAN   MI   VANDF   WHO-DD  
INN  
Official Name English
17.BETA.-(1-KETOETHYL)-.DELTA. SUP(5)-ANDROSTEN-3.BETA.-OL
Common Name English
NSC-18158
Code English
.DELTA. SUP(5)-PREGNEN-3.BETA.-OL-20-ONE
Common Name English
PREGN-5-EN-20-ONE, 3-(3-CARBOXY-, (3.BETA.)-
Common Name English
PREGNENOLONE [JAN]
Common Name English
PREGNENOLONE [VANDF]
Common Name English
NSC-1616
Code English
ARTHENOLONE
Common Name English
ENELONE
Common Name English
PREGNENOLONE [MI]
Common Name English
Pregnenolone [WHO-DD]
Common Name English
pregnenolone [INN]
Common Name English
3.BETA.-HYDROXYPREGN-5-EN-20-ONE
Systematic Name English
Classification Tree Code System Code
LOINC 13894-1
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
CFR 21 CFR 862.1615
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
NCI_THESAURUS C1636
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
LOINC 17480-5
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
DSLD 1868 (Number of products:84)
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
CFR 21 CFR 310.530
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
LOINC 25507-5
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
LOINC 2837-3
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL2105373
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
DAILYMED
73R90F7MQ8
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
NSC
1616
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
MERCK INDEX
m9121
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY Merck Index
CAS
145-13-1
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PRIMARY
FDA UNII
73R90F7MQ8
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
EVMPD
SUB10024MIG
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PRIMARY
EPA CompTox
DTXSID1036541
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
IUPHAR
2376
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PRIMARY
DRUG BANK
DB02789
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PRIMARY
ECHA (EC/EINECS)
205-647-4
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
WIKIPEDIA
Pregnenolone (medication)
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
MESH
D011284
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
INN
4178
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PRIMARY
RXCUI
114052
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY RxNorm
CHEBI
16581
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
NSC
18158
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
SMS_ID
100000081407
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
PUBCHEM
8955
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
WIKIPEDIA
PREGNENOLONE
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
NCI_THESAURUS
C82315
Created by admin on Sat Dec 16 17:13:51 UTC 2023 , Edited by admin on Sat Dec 16 17:13:51 UTC 2023
PRIMARY
Related Record Type Details
TARGET->NEGATIVE ALLOSTERIC MODULATOR (NAM)
∆9-tetrahydrocannabinol (THC), substantially increases the synthesis of pregnenolone in the brain via activation of the type-1 cannabinoid (CB1) receptor. Pregnenolone then, acting as a signaling-specific inhibitor of the CB1 receptor, reduces several effects of THC. This negative feedback mediated by pregnenolone reveals a previously unknown paracrine/autocrine loop protecting the brain from CB1 receptor overactivation.
Related Record Type Details
PARENT -> METABOLITE
In steroidogenic tissues
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
BRAIN/PLASMA RATIO PHARMACOKINETIC