Pregnenolone

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Identification

Generic Name

Pregnenolone

DrugBank Accession Number

DB02789

Background

A 21-carbon steroid, derived from cholesterol and found in steroid hormone-producing tissues. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids.

Type

Small Molecule

Groups

Approved, Experimental

Structure

Similar Structures

Weight: Average: 316.4776
Monoisotopic: 316.240230268
Chemical Formula: C₂₁H₃₂O₂

Synonyms

Pregnenolone

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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
ASteroid hormone receptor ERR1	agonist	Humans
UNuclear receptor subfamily 1 group I member 2	Not Available	Humans
USulfotransferase 2B1	Not Available	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hover over products below to view reaction partners

Pregnenolone
- 17-Hydroxypregnenolone sulfate
- Pregnenolone sulfate

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abametapir	The serum concentration of Pregnenolone can be increased when it is combined with Abametapir.
Amiodarone	The metabolism of Pregnenolone can be decreased when combined with Amiodarone.
Amprenavir	The metabolism of Pregnenolone can be decreased when combined with Amprenavir.
Apalutamide	The serum concentration of Pregnenolone can be decreased when it is combined with Apalutamide.
Aprepitant	The metabolism of Pregnenolone can be decreased when combined with Aprepitant.

Food Interactions

No interactions found.

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Chemical Identifiers

UNII: 73R90F7MQ8
CAS number: 145-13-1
InChI Key: ORNBQBCIOKFOEO-QGVNFLHTSA-N
InChI: 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
IUPAC Name: 1-[(1S,3aS,3bS,7S,9aR,9bS,11aS)-7-hydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethan-1-one
SMILES: [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C

References

Synthesis Reference

Alexander James Bridges, "Efficient Process for Preparing Steroids and Vitamin D Derivatives With the Unnatural Configuration at C20 (20 Alpha-Methyl) from Pregnenolone." U.S. Patent US20080171728, issued July 17, 2008.

US20080171728

General References

Geyer J, Doring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E: Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. [Article]

External Links

Human Metabolome Database: HMDB0000253
KEGG Drug: D00143
KEGG Compound: C01953
PubChem Compound: 8955
PubChem Substance: 46506718
ChemSpider: 8611
BindingDB: 50375319
RxNav: 114052
ChEBI: 16581
ChEMBL: CHEMBL253363
ZINC: ZINC000003861150
Therapeutic Targets Database: DNC001147
PDBe Ligand: PLO
Wikipedia: Pregnenolone

PDB Entries

1q20 / 4j6b / 4nkw

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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4	Completed	Treatment	Alcohol Use Disorders (AUD) / Bipolar Disorder (BD) / Schizo Affective Disorder-Bipolar Type	1	somestatus	stop reason	just information to hide
4	Completed	Treatment	Bipolar Disorder (BD) / Major Depressive Disorder (MDD)	1	somestatus	stop reason	just information to hide
4	Completed	Treatment	Bipolar Disorder (BD) / Major Depressive Disorder (MDD) / Substance Abuse	1	somestatus	stop reason	just information to hide
2	Completed	Treatment	Autism Disorder	1	somestatus	stop reason	just information to hide
2	Completed	Treatment	Back Pain Lower Back	1	somestatus	stop reason	just information to hide

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Powder		1 kg/1kg

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0136 mg/mL	ALOGPS
logP	4.06	ALOGPS
logP	3.58	Chemaxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.2	Chemaxon
pKa (Strongest Basic)	-1.4	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	37.3 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	93.76 m³·mol^-1	Chemaxon
Polarizability	38.09 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9671
Caco-2 permeable	+	0.8568
P-glycoprotein substrate	Substrate	0.6106
P-glycoprotein inhibitor I	Inhibitor	0.6721
P-glycoprotein inhibitor II	Non-inhibitor	0.7531
Renal organic cation transporter	Non-inhibitor	0.7825
CYP450 2C9 substrate	Non-substrate	0.8333
CYP450 2D6 substrate	Non-substrate	0.8417
CYP450 3A4 substrate	Substrate	0.7594
CYP450 1A2 substrate	Non-inhibitor	0.9179
CYP450 2C9 inhibitor	Non-inhibitor	0.9333
CYP450 2D6 inhibitor	Non-inhibitor	0.9558
CYP450 2C19 inhibitor	Non-inhibitor	0.9023
CYP450 3A4 inhibitor	Non-inhibitor	0.8332
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9076
Ames test	Non AMES toxic	0.9439
Carcinogenicity	Non-carcinogens	0.9346
Biodegradation	Not ready biodegradable	0.9379
Rat acute toxicity	1.9852 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8779
hERG inhibition (predictor II)	Non-inhibitor	0.7239

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	GC-MS	splash10-0fic-5910000000-4b4de0891180a420522a
GC-MS Spectrum - EI-B	GC-MS	splash10-05o0-2982000000-90eb349ceb4f7cdf4bf0
Mass Spectrum (Electron Ionization)	MS	splash10-052f-6920000000-2b11c86505b10fe4485f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kb-0094000000-265640fa48df66ba033f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0019000000-f92e795bb2b5b2fb173e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004j-0791000000-f9b38a0a651740eca72b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014j-0097000000-3aa95a4cdca8ab3b35b1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0093000000-0c6cfb669fd35c7a1220
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0ar3-2920000000-c51f84e215364f0335ec
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	187.9638644	predicted	DarkChem Lite v0.1.0
[M-H]-	187.6042644	predicted	DarkChem Lite v0.1.0
[M-H]-	188.3896644	predicted	DarkChem Lite v0.1.0
[M-H]-	188.5268644	predicted	DarkChem Lite v0.1.0
[M-H]-	178.21066	predicted	DeepCCS 1.0 (2019)
[M+H]+	183.1224208	predicted	DarkChem Standard v0.1.0
[M+H]+	187.7905644	predicted	DarkChem Lite v0.1.0
[M+H]+	189.6726644	predicted	DarkChem Lite v0.1.0
[M+H]+	189.3772644	predicted	DarkChem Lite v0.1.0
[M+H]+	180.10608	predicted	DeepCCS 1.0 (2019)
[M+Na]+	196.7378172	predicted	DarkChem Standard v0.1.0
[M+Na]+	187.5620644	predicted	DarkChem Lite v0.1.0
[M+Na]+	188.9466644	predicted	DarkChem Lite v0.1.0
[M+Na]+	188.9717644	predicted	DarkChem Lite v0.1.0
[M+Na]+	186.19315	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Steroid hormone receptor ERR1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alpha complex is a regulator of energy metabolism. Induces the expression of PERM1 in the skeletal muscle
Specific Function: Dna-binding transcription factor activity
Gene Name: ESRRA
Uniprot ID: P11474
Uniprot Name: Steroid hormone receptor ERR1
Molecular Weight: 45509.11 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. Nuclear receptor subfamily 1 group I member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
Specific Function: Dna-binding transcription activator activity, rna polymerase ii-specific
Gene Name: NR1I2
Uniprot ID: O75469
Uniprot Name: Nuclear receptor subfamily 1 group I member 2
Molecular Weight: 49761.245 Da

References

Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [Article]

Details3. Sulfotransferase 2B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation. Responsible for the sulfation of cholesterol (PubMed:12145317, PubMed:19589875). Catalyzes sulfation of the 3beta-hydroxyl groups of steroids, such as, pregnenolone and dehydroepiandrosterone (DHEA) (PubMed:12145317, PubMed:16855051, PubMed:21855633, PubMed:9799594). Preferentially sulfonates cholesterol, while it has also significant activity with pregnenolone and DHEA (PubMed:12145317, PubMed:21855633). Plays a role in epidermal cholesterol metabolism and in the regulation of epidermal proliferation and differentiation (PubMed:28575648)
Specific Function: Cholesterol binding
Gene Name: SULT2B1
Uniprot ID: O00204
Uniprot Name: Sulfotransferase 2B1
Molecular Weight: 41307.32 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Enzymes

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
Specific Function: 1,8-cineole 2-exo-monooxygenase activity
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Felmlee MA, Lon HK, Gonzalez FJ, Yu AM: Cytochrome P450 expression and regulation in CYP3A4/CYP2D6 double transgenic humanized mice. Drug Metab Dispos. 2008 Feb;36(2):435-41. doi: 10.1124/dmd.107.018838. Epub 2007 Nov 29. [Article]
Wang H, Huang H, Li H, Teotico DG, Sinz M, Baker SD, Staudinger J, Kalpana G, Redinbo MR, Mani S: Activated pregnenolone X-receptor is a target for ketoconazole and its analogs. Clin Cancer Res. 2007 Apr 15;13(8):2488-95. [Article]

Transporters

Details1. Sodium-dependent organic anion transporter

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Transports sulfoconjugated steroid hormones from the extracellular compartment into the cytosol in a sodium-dependent manner without hydrolysis (PubMed:17491011, PubMed:23667501, PubMed:24717977, PubMed:28951227). Steroid sulfate hormones are commonly considered to be biologically inactive metabolites, that may be activated by steroid sulfatases into free steroids (PubMed:23667501, PubMed:24717977). May play an important role by delivering sulfoconjugated steroids to specific target cells in reproductive organs (By similarity). May play a role transporting the estriol precursor 16alpha-hydroxydehydroepiandrosterone 3-sulfate (16a-OH-DHEAS) at the fetal blood vessel endothelium (PubMed:24717977). Can also transport other sulfoconjugated molecules such as taurolithocholic acid-3-sulfate and sulfoconjugated pyrenes (PubMed:17491011)
Specific Function: Bile acid
Gene Name: SLC10A6
Uniprot ID: Q3KNW5
Uniprot Name: Sodium-dependent organic anion transporter
Molecular Weight: 41258.24 Da

References

Geyer J, Doring B, Meerkamp K, Ugele B, Bakhiya N, Fernandes CF, Godoy JR, Glatt H, Petzinger E: Cloning and functional characterization of human sodium-dependent organic anion transporter (SLC10A6). J Biol Chem. 2007 Jul 6;282(27):19728-41. Epub 2007 May 9. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:23

Pregnenolone

Identification

Structure for Pregnenolone (DB02789)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

Enzymes

References

Transporters

References