Pregnenolone
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
Structure for Pregnenolone (DB02789)
- Weight
- Average: 316.4776
Monoisotopic: 316.240230268 - Chemical Formula
- C21H32O2
- Synonyms
- Pregnenolone
Pharmacology
- Indication
Not Available
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism USulfotransferase family cytosolic 2B member 1 Not Available Humans UNuclear receptor subfamily 1 group I member 2 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
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- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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 Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Pregnenolone can be increased when it is combined with Abametapir. Abiraterone The metabolism of Pregnenolone can be decreased when combined with Abiraterone. 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 metabolism of Pregnenolone can be increased when combined with Apalutamide. Aprepitant The metabolism of Pregnenolone can be decreased when combined with Aprepitant. Atazanavir The metabolism of Pregnenolone can be decreased when combined with Atazanavir. Berotralstat The metabolism of Pregnenolone can be decreased when combined with Berotralstat. Boceprevir The metabolism of Pregnenolone can be decreased when combined with Boceprevir. Carbamazepine The metabolism of Pregnenolone can be increased when combined with Carbamazepine. 
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- No interactions found.
Products
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Categories
- Drug Categories
- Adrenal Cortex Hormones
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hydroxycorticosteroids
- Pregnanes
- Pregnenes
- Progesterone Congeners
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- 20-oxosteroids / 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
- Substituents
- 20-oxosteroid / 3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Delta-5-steroid
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3beta-hydroxy steroid, 20-oxo steroid, C21-steroid (CHEBI:16581) / Pregnane and derivatives [Fig], Progestagens (C01953) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030088)
- Affected organisms
- Not Available
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
- 114052
- ChEBI
- 16581
- ChEMBL
- CHEMBL253363
- ZINC
- ZINC000003861150
- Therapeutic Targets Database
- DNC001147
- PDBe Ligand
- PLO
- Wikipedia
- Pregnenolone
- PDB Entries
- 1q20 / 4j6b / 4nkw
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Uterine Fibroids Affecting Pregnancy 1 4 Completed Treatment Bipolar Disorder (BD) / Major Depressive Disorder (MDD) 1 4 Completed Treatment Bipolar Disorder (BD) / Major Depressive Disorder (MDD) / Substance Abuse 1 4 Recruiting Treatment Alcohol Use Disorders (AUD) / Bipolar Disorder (BD) 1 2 Active Not Recruiting Basic Science Perceived Social Isolation 1 2 Completed Treatment Autistic Disorder 1 2 Completed Treatment Back Pain Lower Back 1 2 Completed Treatment Cognitive Decline / Fatigue / Musculoskeletal Pain 1 2 Completed Treatment Marijuana Dependence 1 2 Completed Treatment Schizoaffective Disorders / Schizophrenia 1
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
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 Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Steroid sulfotransferase activity
- Specific Function
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulf...
- Gene Name
- SULT2B1
- Uniprot ID
- O00204
- Uniprot Name
- Sulfotransferase family cytosolic 2B member 1
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific 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 an...
- 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]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-dependent organic anion transmembrane transporter activity
- Specific Function
- Transports sulfoconjugated steroid hormones, as well as taurolithocholic acid-3-sulfate and sulfoconjugated pyrenes in a sodium-dependent manner.
- Gene Name
- SLC10A6
- Uniprot ID
- Q3KNW5
- Uniprot Name
- Solute carrier family 10 member 6
- 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 on June 13, 2005 13:24 / Updated on February 21, 2021 18:51