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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

CC(=O)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

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/25781227 https://www.ncbi.nlm.nih.gov/pubmed/10661509

Pregnenolone sulfate is an endogenous neurosteroid with excitatory effects in the brain, acting as a potent negative allosteric modulator of the GABAA receptor, a positive allosteric modulator of the NMDA receptor, and activator of transient receptor potential cation channel TRPM1 and TRPM3. In the model of schizophrenia, treatment with pregnenolone sulfate normalized the hyperlocomotion and stereotypic bouts, and rescued the PPI deficits of dopamine transporter knockout mice. Promnesic properties of pregnenolone sulfate were demonstrated in rat models of spatial memory performance.

CNS Activity

Originator

Approval Year

1950
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Negative Allosteric Modulator
43
 7.2 µM [IC50]
Positive Allosteric Modulator
186
 33.0 µM [EC50]
Transient receptor potential cation channel subfamily M member 1
3
Target ID: Q7Z4N2|||Q7Z4N3
Gene ID: 4308.0
Gene Symbol: TRPM1
Target Organism: Homo sapiens (Human)
Activator
1447
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)
Activator
1447
Negative Allosteric Modulator
43
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Phase II
1147
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
Phase IV
63
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
Phase IV
63
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
Phase IV
63
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
Phase II
1147
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
Phase II
1147
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/15269827
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/15269827
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/15269827
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:16581
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16581
ChemicalBook
CB1684326
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1684326
eMolecules
531097
https://www.emolecules.com/cgi-bin/more?vid=531097
MolPort
MolPort-002-506-906
https://www.molport.com/shop/molecule-link/MolPort-002-506-906
Selleck Chemicals
pregnenolone
http://www.selleckchem.com/products/pregnenolone.html
ZINC
ZINC000003861150
http://zinc15.docking.org/substances/ZINC000003861150
PubMed

PubMed

TitleDatePubMed
Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor.
2002-01-25
Adenosine A2A, 5-HT1A and 5-HT7 receptor in neonatally pregnenolone-treated rats.
2001-12-04
Diminished allopregnanolone enhancement of GABA(A) receptor currents in a rat model of chronic temporal lobe epilepsy.
2001-12-01
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
Differential involvement of the sigma(1) (sigma(1)) receptor in the anti-amnesic effect of neuroactive steroids, as demonstrated using an in vivo antisense strategy in the mouse.
2001-12
Identification, localization, and function in steroidogenesis of PAP7: a peripheral-type benzodiazepine receptor- and PKA (RIalpha)-associated protein.
2001-12
Adrenodoxin-cytochrome P450scc interaction as revealed by EPR spectroscopy: comparison with the putidaredoxin-cytochrome P450cam system.
2001-12
Implications of progesterone metabolism in MA-10 cells for accurate measurement of the rate of steroidogenesis.
2001-12
Identification of ST2A1 as a rat brain neurosteroid sulfotransferase mRNA.
2001-11-30
Influence of neurosteroids on the development of rapid tolerance to ethanol in mice.
2001-11-16
Increased testicular steroid concentrations in patients with idiopathic infertility and normal FSH levels.
2001-11-07
Automated chromatographic system for the simultaneous measurement of plasma pregnenolone and 17-hydroxypregnenolone by radioimmunoassay.
2001-11-05
Hormonal steroidogenesis in liver and small intestine of the green frog, Rana esculenta L.
2001-11-02
Neuroactive steroids modulate crustacean locomotor activity.
2001-11-02
Neurosteroids: recent findings.
2001-11
The interaction between neuroactive steroids and the sigma1 receptor function: behavioral consequences and therapeutic opportunities.
2001-11
Anatomical and biochemical evidence for the synthesis of unconjugated and sulfated neurosteroids in amphibians.
2001-11
Influence of membrane cholesterol on modulation of the GABA(A) receptor by neuroactive steroids and other potentiators.
2001-11
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.
2001-11
Purification of cytochromes P-450(scc) and P-450(17 alpha) by steroid-binding affinity column chromatography.
2001-10-30
Activity and localization of 3beta-hydroxysteroid dehydrogenase/ Delta5-Delta4-isomerase in the zebrafish central nervous system.
2001-10-22
Acute effects of ethanol on steroidogenic acute regulatory protein (StAR) in the prepubertal rat ovary.
2001-10
Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes.
2001-10
Opposite effects of short- versus long-term administration of fluoxetine on the concentrations of neuroactive steroids in rat plasma and brain.
2001-10
Prevention of the stress-induced increase in frontal cortical dopamine efflux of freely moving rats by long-term treatment with antidepressant drugs.
2001-10
Aldosterone increases T-type calcium currents in human adrenocarcinoma (H295R) cells by inducing channel expression.
2001-10
2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands.
2001-10
Pregnenolone sulfate modulates angiotensin II-induced inositol 1,4,5-trisphosphate changes in the anterior pituitary of female rat.
2001-09-28
Membrane cholesterol modulates serotonin transporter activity.
2001-09-04
Immunohistochemical localization of steroidogenic enzymes in the corpus luteum and the placenta of the ribbon seal (Phoca fasciata) and steller sea lion (Eumetopias jubatus).
2001-09
Analysis of neurosteroid levels in attention deficit hyperactivity disorder.
2001-09
Pregnenolone sulfate and aging of cognitive functions: behavioral, neurochemical, and morphological investigations.
2001-09
Subunit-specific modulation of glycine receptors by neurosteroids.
2001-09
Cytochrome P450 in the brain; a review.
2001-09
Regulation of the rat glutathione S-transferase A2 gene by glucocorticoids: involvement of both the glucocorticoid and pregnane X receptors.
2001-09
Stimulatory effect of lactate on testosterone production by rat Leydig cells.
2001-08-14
Effect of treatment of hypothyroidism on the plasma concentrations of neuroactive steroids and homocysteine.
2001-08
Effects of different steroid-biosynthesis inhibitors on the testicular steroidogenesis of the toad Bufo arenarum.
2001-08
Development of an enzyme immunoassay for serum 16-dehydropregnenolone.
2001-08
Heterozygous mutation in the cholesterol side chain cleavage enzyme (p450scc) gene in a patient with 46,XY sex reversal and adrenal insufficiency.
2001-08
Cerebral venous thrombosis in a patient of paroxysmal nocturnal haemoglobinuria following aplastic anaemia.
2001-07
Ontogeny of steroid metabolizing enzymes in rat oligodendrocytes.
2001-07
Serum concentration of androstenediol and androstenediol sulfate in patients with hyperthyroidism and hypothyroidism.
2001-06
Luteinization factor-stimulated steroidogenesis in porcine granulosa cells.
2001-06
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: beginning of the story.
2001
Neuroactive steroid levels in patients with generalized anxiety disorder.
2001
[Neurosteroids, their role in brain physiology: neurotrophicity, memory, aging...].
2001
Patents

Patents

05591733
6
JPH06113883A
4
JPS54138192A
3
WO-1993004687-A1
3
WO-1993005786-A1
3

Sample Use Guides

In Vivo Use Guide
Pregnenolone supplements are administered orally at 100-500 mg a day.
Route of Administration: Oral
In Vitro Use Guide
Pregnenolone (between 10nMand 1 μM, depending on the cellular model) inhibited the increase in P-Erk1/2MAPK and the decrease in cellular and mitochondrial respiration induced by tetrahydrocannabinol in cells transfected with human CB1 receptor.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:50:57 GMT 2025
Edited
by admin
on Wed Apr 02 08:50:57 GMT 2025
Record UNII
73R90F7MQ8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Pregnenolone
INN   JAN   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-1616
Preferred 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
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 Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
CFR 21 CFR 862.1615
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
NCI_THESAURUS C1636
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
LOINC 17480-5
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
DSLD 1868 (Number of products:84)
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
CFR 21 CFR 310.530
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
LOINC 25507-5
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
LOINC 2837-3
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL2105373
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
DAILYMED
73R90F7MQ8
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
NSC
1616
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
MERCK INDEX
m9121
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY Merck Index
CAS
145-13-1
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PRIMARY
FDA UNII
73R90F7MQ8
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
EVMPD
SUB10024MIG
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
EPA CompTox
DTXSID1036541
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
IUPHAR
2376
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PRIMARY
DRUG BANK
DB02789
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-647-4
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
WIKIPEDIA
Pregnenolone (medication)
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
MESH
D011284
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
INN
4178
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PRIMARY
RXCUI
114052
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PRIMARY RxNorm
CHEBI
16581
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
NSC
18158
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
SMS_ID
100000081407
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
PUBCHEM
8955
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
WIKIPEDIA
PREGNENOLONE
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
NCI_THESAURUS
C82315
Created by admin on Wed Apr 02 08:50:57 GMT 2025 , Edited by admin on Wed Apr 02 08:50:57 GMT 2025
PRIMARY
Related Record Type Details
CANNABINOID RECEPTOR 1
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.
NUCLEAR RECEPTOR SUBFAMILY 1 GROUP I MEMBER 2
TARGET -> AGONIST
Related Record Type Details
Structure of CHOLESTEROL
PARENT -> METABOLITE
In steroidogenic tissues
Related Record Type Details
Structure of Pregnenolone
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
BRAIN/PLASMA RATIO PHARMACOKINETIC
NIH
NCATS
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