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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H32O5S
Molecular Weight 396.541
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PREGNENOLONE SULFATE

SMILES

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

InChI

InChIKey=DIJBBUIOWGGQOP-QGVNFLHTSA-N
InChI=1S/C21H32O5S/c1-13(22)17-6-7-18-16-5-4-14-12-15(26-27(23,24)25)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12H2,1-3H3,(H,23,24,25)/t15-,16-,17+,18-,19-,20-,21+/m0/s1

HIDE SMILES / InChI
Molecular Formula C21H32O5S
Molecular Weight 396.541
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

CNS Active
4,002

Originator

Organ.-chem. Institut d. Techn. Hochschule Danzig-Langfuhr
3

Approval Year

1950
105

Targets

Primary TargetPharmacologyConditionPotency
GABA-A receptor; anion channel
203
Negative Allosteric Modulator
43
 7.2 µM [IC50]
Glutamate [NMDA] receptor
125
Positive Allosteric Modulator
186
 33.0 µM [EC50]
Transient receptor potential cation channel subfamily M member 1
3
Activator
1,447
Transient receptor potential cation channel subfamily M member 3
5
Activator
1,447
Cannabinoid CB1 receptor
85
Negative Allosteric Modulator
43

Conditions

ConditionModalityTargetsHighest PhaseProduct
Schizophrenia
305
 Primary
Preclinical
Unknown
Spatial memory disorder
3
 Primary
Preclinical
Unknown
Autism
20
 Primary
Phase II
1,147
PREGNENOLONE
Schizophrenia
305
 Primary
Phase IV
63
PREGNENOLONE
Bipolar disorder
34
 Primary
Phase IV
63
PREGNENOLONE
Major depressive disorder
179
 Primary
Phase IV
63
PREGNENOLONE
Obsessive-compulsive disorder
33
 Primary
Phase II
1,147
PREGNENOLONE
Marijuana dependence
5
 Primary
Phase II
1,147
PREGNENOLONE

Cmax

ValueDoseCo-administeredAnalytePopulation
38 ng/mL
600 mg single, oral
 CLOPIDOGREL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
125.5 ng × h/mL
600 mg single, oral
 CLOPIDOGREL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
600 mg single, oral
 CLOPIDOGREL plasma
Homo sapiens

PubMed

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
Record UNII
04Y4D91RG0
Record Status Validated (UNII)
Record Version
NIH
NCATS
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