Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H34O3 |
Molecular Weight | 358.5143 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC=C4C[C@H](CC[C@]34C)OC(C)=O
InChI
InChIKey=CRRKVZVYZQXICQ-RJJCNJEVSA-N
InChI=1S/C23H34O3/c1-14(24)19-7-8-20-18-6-5-16-13-17(26-15(2)25)9-11-22(16,3)21(18)10-12-23(19,20)4/h5,17-21H,6-13H2,1-4H3/t17-,18-,19+,20-,21-,22-,23+/m0/s1
Molecular Formula | C23H34O3 |
Molecular Weight | 358.5143 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24084011https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C82315Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24084011https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C82315
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24084011https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C82315
Curator's Comment: As a precursor of neurosteroid, pregnenolone is endogenously produced in the brain.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24084011 |
7.2 µM [IC50] | ||
Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1654510 |
33.0 µM [EC50] | ||
Target ID: Q7Z4N2|||Q7Z4N3 Gene ID: 4308.0 Gene Symbol: TRPM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/24084011 |
|||
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/24084011 |
|||
Target ID: CHEMBL218 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24385629 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
|||
Primary | PREGNENOLONE Approved UsePregnenolone 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 UsePregnenolone 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 UsePregnenolone 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 UsePregnenolone 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 UsePregnenolone 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 UsePregnenolone 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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
Doses
Dose | Population | Adverse 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
Title | Date | PubMed |
---|---|---|
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: beginning of the story. | 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 |
|
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 |
|
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 Dec |
|
Identification, localization, and function in steroidogenesis of PAP7: a peripheral-type benzodiazepine receptor- and PKA (RIalpha)-associated protein. | 2001 Dec |
|
Adrenodoxin-cytochrome P450scc interaction as revealed by EPR spectroscopy: comparison with the putidaredoxin-cytochrome P450cam system. | 2001 Dec |
|
Implications of progesterone metabolism in MA-10 cells for accurate measurement of the rate of steroidogenesis. | 2001 Dec |
|
Diminished allopregnanolone enhancement of GABA(A) receptor currents in a rat model of chronic temporal lobe epilepsy. | 2001 Dec 1 |
|
Adenosine A2A, 5-HT1A and 5-HT7 receptor in neonatally pregnenolone-treated rats. | 2001 Dec 4 |
|
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 |
|
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 |
|
Neurosteroids: recent findings. | 2001 Nov |
|
The interaction between neuroactive steroids and the sigma1 receptor function: behavioral consequences and therapeutic opportunities. | 2001 Nov |
|
Anatomical and biochemical evidence for the synthesis of unconjugated and sulfated neurosteroids in amphibians. | 2001 Nov |
|
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 |
|
Influence of neurosteroids on the development of rapid tolerance to ethanol in mice. | 2001 Nov 16 |
|
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 |
|
Identification of ST2A1 as a rat brain neurosteroid sulfotransferase mRNA. | 2001 Nov 30 |
|
Automated chromatographic system for the simultaneous measurement of plasma pregnenolone and 17-hydroxypregnenolone by radioimmunoassay. | 2001 Nov 5 |
|
Increased testicular steroid concentrations in patients with idiopathic infertility and normal FSH levels. | 2001 Nov-Dec |
|
Acute effects of ethanol on steroidogenic acute regulatory protein (StAR) in the prepubertal rat ovary. | 2001 Oct |
|
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 |
|
Opposite effects of short- versus long-term administration of fluoxetine on the concentrations of neuroactive steroids in rat plasma and brain. | 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 |
|
Membrane cholesterol modulates serotonin transporter activity. | 2001 Sep 4 |
|
Neuroactive steroid levels in patients with generalized anxiety disorder. | 2001 Summer |
|
Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. | 2002 Jan 25 |
|
Pregnenolone sulfate: from steroid metabolite to TRP channel ligand. | 2013 Sep 27 |
|
Pregnenolone sulfate normalizes schizophrenia-like behaviors in dopamine transporter knockout mice through the AKT/GSK3β pathway. | 2015 Mar 17 |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1654510
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
Edited
Sat Dec 16 20:06:46 UTC 2023
by
admin
on
Sat Dec 16 20:06:46 UTC 2023
|
Record UNII |
0G0WWV404B
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
CFR |
21 CFR 310.530
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
||
|
NCI_THESAURUS |
C776
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
217-212-6
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
1778-02-5
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
C82316
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
DB14626
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
100000085095
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
0G0WWV404B
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
SUB04027MIG
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
Pregnenolone acetate
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
64827
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
2723722
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | |||
|
m9121
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY | Merck Index | ||
|
DTXSID3048942
Created by
admin on Sat Dec 16 20:06:46 UTC 2023 , Edited by admin on Sat Dec 16 20:06:46 UTC 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |