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Identification
NamePregnenolone
Accession NumberDB02789  (EXPT02608)
TypeSmall Molecule
GroupsExperimental
DescriptionA 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. [PubChem]
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII73R90F7MQ8
CAS numberNot Available
WeightAverage: 316.4776
Monoisotopic: 316.240230268
Chemical FormulaC21H32O2
InChI KeyInChIKey=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,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]ethan-1-one
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)C(C)=O
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
Substituents
  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Pregnenolone
Not Available
17-Hydroxypregnenolone sulfateDetails
Pregnenolone
Not Available
Pregnenolone sulfateDetails
Pregnenolone
Not Available
3beta-Hydroxypregn-5-en-20-one sulfateDetails
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9671
Caco-2 permeable+0.8568
P-glycoprotein substrateSubstrate0.6106
P-glycoprotein inhibitor IInhibitor0.6721
P-glycoprotein inhibitor IINon-inhibitor0.7531
Renal organic cation transporterNon-inhibitor0.7825
CYP450 2C9 substrateNon-substrate0.8333
CYP450 2D6 substrateNon-substrate0.8417
CYP450 3A4 substrateSubstrate0.7594
CYP450 1A2 substrateNon-inhibitor0.9179
CYP450 2C9 inhibitorNon-inhibitor0.9333
CYP450 2D6 inhibitorNon-inhibitor0.9558
CYP450 2C19 inhibitorNon-inhibitor0.9023
CYP450 3A4 inhibitorNon-inhibitor0.8332
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9076
Ames testNon AMES toxic0.9439
CarcinogenicityNon-carcinogens0.9346
BiodegradationNot ready biodegradable0.9379
Rat acute toxicity1.9852 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8779
hERG inhibition (predictor II)Non-inhibitor0.7239
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0136 mg/mLALOGPS
logP4.06ALOGPS
logP3.58ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.76 m3·mol-1ChemAxon
Polarizability38.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-0fic-5910000000-4b4de0891180a420522aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-6920000000-2b11c86505b10fe4485fView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
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
  1. 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. [PubMed:17491011 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with 1,10-Phenanthroline.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Pregnenolone.
AldesleukinPregnenolone may decrease the antineoplastic activities of Aldesleukin.
Aluminum hydroxideThe bioavailability of Pregnenolone can be decreased when combined with Aluminum hydroxide.
Aluminum phosphateThe bioavailability of Pregnenolone can be decreased when combined with Aluminum phosphate.
AmbenoniumThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Ambenonium.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Pregnenolone.
AmiodaroneThe serum concentration of Pregnenolone can be increased when it is combined with Amiodarone.
Amphotericin BPregnenolone may increase the hypokalemic activities of Amphotericin B.
AprepitantThe serum concentration of Pregnenolone can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Pregnenolone can be increased when it is combined with Atazanavir.
Atracurium besylateAtracurium besylate may increase the adverse neuromuscular activities of Pregnenolone.
BazedoxifeneThe serum concentration of Pregnenolone can be increased when it is combined with Bazedoxifene.
BendroflumethiazidePregnenolone may increase the hypokalemic activities of Bendroflumethiazide.
Benzoic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Pregnenolone.
Bismuth SubcitrateThe bioavailability of Pregnenolone can be decreased when combined with Bismuth Subcitrate.
BoceprevirThe serum concentration of Pregnenolone can be increased when it is combined with Boceprevir.
BumetanidePregnenolone may increase the hypokalemic activities of Bumetanide.
CalcitriolThe therapeutic efficacy of Calcitriol can be decreased when used in combination with Pregnenolone.
Calcium carbonateThe bioavailability of Pregnenolone can be decreased when combined with Calcium carbonate.
CarbamazepineThe serum concentration of Pregnenolone can be decreased when it is combined with Carbamazepine.
CeritinibPregnenolone may increase the hyperglycemic activities of Ceritinib.
CeritinibThe serum concentration of Pregnenolone can be increased when it is combined with Ceritinib.
ChlorothiazidePregnenolone may increase the hypokalemic activities of Chlorothiazide.
ChlorotrianiseneThe serum concentration of Pregnenolone can be increased when it is combined with Chlorotrianisene.
ChlorthalidonePregnenolone may increase the hypokalemic activities of Chlorthalidone.
CholestyramineCholestyramine can cause a decrease in the absorption of Pregnenolone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ClarithromycinThe serum concentration of Pregnenolone can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Pregnenolone can be increased when it is combined with Cobicistat.
ColesevelamColesevelam can cause a decrease in the absorption of Pregnenolone resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Pregnenolone resulting in a reduced serum concentration and potentially a decrease in efficacy.
Conjugated Equine EstrogensThe serum concentration of Pregnenolone can be increased when it is combined with Conjugated Equine Estrogens.
Corticorelin ovine triflutateThe therapeutic efficacy of Corticorelin ovine triflutate can be decreased when used in combination with Pregnenolone.
CoumaphosThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Coumaphos.
DarunavirThe serum concentration of Pregnenolone can be increased when it is combined with Darunavir.
DecamethoniumThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Decamethonium.
DeferasiroxThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Deferasirox.
DemecariumThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Demecarium.
DichlorvosThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Dichlorvos.
DienestrolThe serum concentration of Pregnenolone can be increased when it is combined with Dienestrol.
DiethylstilbestrolThe serum concentration of Pregnenolone can be increased when it is combined with Diethylstilbestrol.
DiflunisalThe risk or severity of adverse effects can be increased when Diflunisal is combined with Pregnenolone.
DihydrotestosteronePregnenolone may increase the fluid retaining activities of Dihydrotestosterone.
DonepezilThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Donepezil.
EchothiophateThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Echothiophate.
EdrophoniumThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Edrophonium.
EnzalutamideThe serum concentration of Pregnenolone can be decreased when it is combined with Enzalutamide.
EstradiolThe serum concentration of Pregnenolone can be increased when it is combined with Estradiol.
EstriolThe serum concentration of Pregnenolone can be increased when it is combined with Estriol.
EstroneThe serum concentration of Pregnenolone can be increased when it is combined with Estrone.
Etacrynic acidPregnenolone may increase the hypokalemic activities of Etacrynic acid.
Ethinyl EstradiolThe serum concentration of Pregnenolone can be increased when it is combined with Ethinyl Estradiol.
FenthionThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Fenthion.
FluoxymesteronePregnenolone may increase the fluid retaining activities of Fluoxymesterone.
FosaprepitantThe serum concentration of Pregnenolone can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Pregnenolone can be decreased when it is combined with Fosphenytoin.
FurosemidePregnenolone may increase the hypokalemic activities of Furosemide.
GalantamineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Galantamine.
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Gallamine Triethiodide.
GenisteinThe serum concentration of Pregnenolone can be increased when it is combined with Genistein.
Ginkgo bilobaThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Ginkgo biloba.
Glycerol PhenylbutyrateThe therapeutic efficacy of Glycerol Phenylbutyrate can be decreased when used in combination with Pregnenolone.
HexestrolThe serum concentration of Pregnenolone can be increased when it is combined with Hexestrol.
Huperzine AThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Huperzine A.
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Pregnenolone.
HydrochlorothiazidePregnenolone may increase the hypokalemic activities of Hydrochlorothiazide.
HydroflumethiazidePregnenolone may increase the hypokalemic activities of Hydroflumethiazide.
IdelalisibThe serum concentration of Pregnenolone can be increased when it is combined with Idelalisib.
IndacaterolIndacaterol may increase the hypokalemic activities of Pregnenolone.
IndapamidePregnenolone may increase the hypokalemic activities of Indapamide.
IndinavirThe serum concentration of Pregnenolone can be increased when it is combined with Indinavir.
IsoflurophateThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Isoflurophate.
IsoniazidThe serum concentration of Isoniazid can be decreased when it is combined with Pregnenolone.
ItraconazoleThe serum concentration of Pregnenolone can be increased when it is combined with Itraconazole.
KetoconazoleThe serum concentration of Pregnenolone can be increased when it is combined with Ketoconazole.
LopinavirThe serum concentration of Pregnenolone can be increased when it is combined with Lopinavir.
MagaldrateThe bioavailability of Pregnenolone can be decreased when combined with Magaldrate.
Magnesium carbonateThe bioavailability of Pregnenolone can be decreased when combined with Magnesium carbonate.
Magnesium hydroxideThe bioavailability of Pregnenolone can be decreased when combined with Magnesium hydroxide.
Magnesium oxideThe bioavailability of Pregnenolone can be decreased when combined with Magnesium oxide.
Magnesium TrisilicateThe bioavailability of Pregnenolone can be decreased when combined with Magnesium Trisilicate.
MalathionThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Malathion.
MefloquineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Mefloquine.
MemantineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Memantine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Pregnenolone.
MestranolThe serum concentration of Pregnenolone can be increased when it is combined with Mestranol.
MethyclothiazidePregnenolone may increase the hypokalemic activities of Methyclothiazide.
MethyltestosteronePregnenolone may increase the fluid retaining activities of Methyltestosterone.
MetolazonePregnenolone may increase the hypokalemic activities of Metolazone.
MifepristoneThe therapeutic efficacy of Pregnenolone can be decreased when used in combination with Mifepristone.
MinaprineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Minaprine.
MitotaneThe serum concentration of Pregnenolone can be decreased when it is combined with Mitotane.
MivacuriumMivacurium may increase the adverse neuromuscular activities of Pregnenolone.
NefazodoneThe serum concentration of Pregnenolone can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Pregnenolone can be increased when it is combined with Nelfinavir.
NeostigmineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Neostigmine.
NevirapineThe serum concentration of Pregnenolone can be decreased when it is combined with Nevirapine.
NicorandilThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Nicorandil.
OxandrolonePregnenolone may increase the fluid retaining activities of Oxandrolone.
OxymetholonePregnenolone may increase the fluid retaining activities of Oxymetholone.
PentobarbitalThe serum concentration of Pregnenolone can be decreased when it is combined with Pentobarbital.
PhenobarbitalThe serum concentration of Pregnenolone can be decreased when it is combined with Phenobarbital.
Phenylacetic acidThe therapeutic efficacy of Phenylacetic acid can be decreased when used in combination with Pregnenolone.
PhenytoinThe serum concentration of Pregnenolone can be decreased when it is combined with Phenytoin.
PhysostigmineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Physostigmine.
PiretanidePregnenolone may increase the hypokalemic activities of Piretanide.
Polyestradiol phosphateThe serum concentration of Pregnenolone can be increased when it is combined with Polyestradiol phosphate.
PolythiazidePregnenolone may increase the hypokalemic activities of Polythiazide.
PosaconazoleThe serum concentration of Pregnenolone can be increased when it is combined with Posaconazole.
PrimidoneThe serum concentration of Pregnenolone can be decreased when it is combined with Primidone.
PyridostigmineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Pyridostigmine.
QuinestrolThe serum concentration of Pregnenolone can be increased when it is combined with Quinestrol.
QuinethazonePregnenolone may increase the hypokalemic activities of Quinethazone.
Rabies vaccineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Rabies vaccine.
RapacuroniumRapacuronium may increase the adverse neuromuscular activities of Pregnenolone.
RifabutinThe serum concentration of Pregnenolone can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Pregnenolone can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Pregnenolone can be decreased when it is combined with Rifapentine.
RitonavirThe serum concentration of Pregnenolone can be increased when it is combined with Ritonavir.
RivastigmineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Rivastigmine.
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Pregnenolone.
SaquinavirThe serum concentration of Pregnenolone can be increased when it is combined with Saquinavir.
Sodium phenylbutyrateThe therapeutic efficacy of Sodium phenylbutyrate can be decreased when used in combination with Pregnenolone.
StanozololPregnenolone may increase the fluid retaining activities of Stanozolol.
Synthetic Conjugated Estrogens, AThe serum concentration of Pregnenolone can be increased when it is combined with Synthetic Conjugated Estrogens, A.
Synthetic Conjugated Estrogens, BThe serum concentration of Pregnenolone can be increased when it is combined with Synthetic Conjugated Estrogens, B.
TacrineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Tacrine.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Pregnenolone.
TelaprevirThe serum concentration of Pregnenolone can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Pregnenolone can be increased when it is combined with Telithromycin.
TestosteronePregnenolone may increase the fluid retaining activities of Testosterone.
TiboloneThe serum concentration of Pregnenolone can be increased when it is combined with Tibolone.
TorasemidePregnenolone may increase the hypokalemic activities of Torasemide.
TrichlorfonThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Trichlorfon.
TrichlormethiazidePregnenolone may increase the hypokalemic activities of Trichlormethiazide.
TubocurarineThe risk or severity of adverse effects can be increased when Pregnenolone is combined with Tubocurarine.
VoriconazoleThe serum concentration of Pregnenolone can be increased when it is combined with Voriconazole.
WarfarinPregnenolone may increase the anticoagulant activities of Warfarin.
ZeranolThe serum concentration of Pregnenolone can be increased when it is combined with Zeranol.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. I...
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular Weight:
41307.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]

Transporters

Kind
Protein
Organism
Human
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
Molecular Weight:
41258.24 Da
References
  1. 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. [PubMed:17491011 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23