beta-Sitosterol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
beta-Sitosterol
DrugBank Accession Number
DB14038
Background

Active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 414.718
Monoisotopic: 414.38616623
Chemical Formula
C29H50O
Synonyms
  • (-)-β-Sitosterol
  • (24R)-Ethylcholest-5-en-3beta-ol
  • (24R)-ethylcholest-5-en-3β-ol
  • (24R)-Stigmast-5-en-3beta-ol
  • (3β)-Stigmast-5-en-3-ol
  • 22,23-Dihydrostigmasterol
  • 24α-Ethylcholesterol
  • Azuprostat
  • Cupreol
  • Nimbosterol
  • Sitosterol
  • Triastonal
  • α-Dihydrofucosterol
  • β-Sitosterin
External IDs
  • SKF 14463

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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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.
Not Available
Food Interactions
Not Available

Products

Products
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International/Other Brands
Harzol
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
InsadolTablet35 mg/1OralOASIS TRADING2018-11-20Not applicableUS flag
InsadolTablet35 mg/1OralI World Pharmaceutical Co., Ltd.2019-10-08Not applicableUS flag
InsadolTablet35 mg/1OralLYDIA Co., Ltd2019-10-08Not applicableUS flag
มีโบOintment0.25 %w/wTopicalบริษัท มีโบ จำกัด1999-04-08Not applicableThailand flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Insadolbeta-Sitosterol (35 mg/1)TabletOralOASIS TRADING2018-11-20Not applicableUS flag
Insadolbeta-Sitosterol (35 mg/1)TabletOralI World Pharmaceutical Co., Ltd.2019-10-08Not applicableUS flag
Insadolbeta-Sitosterol (35 mg/1)TabletOralLYDIA Co., Ltd2019-10-08Not applicableUS flag
Mi-Omega NFbeta-Sitosterol (200 mg/1) + Cyanocobalamin (500 ug/1) + Folic acid (1 mg/1) + Omega-3-acid ethyl esters (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1)CapsuleOralMayne Pharma2009-01-012016-05-31US flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Stigmastanes and derivatives
Direct Parent
Stigmastanes and derivatives
Alternative Parents
Triterpenoids / C24-propyl sterols and derivatives / 3-beta-hydroxysteroids / 3-beta-hydroxy delta-5-steroids / Delta-5-steroids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
3-beta-hydroxy-delta-5-steroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-5-steroid / 3-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / C24-propyl-sterol-skeleton / Cyclic alcohol / Delta-5-steroid / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3beta-sterol, phytosterols (CHEBI:27693) / stigmastane, Stigmasterols and C24-ethyl derivatives (C01753) / Stigmasterols and C24-ethyl derivatives (LMST01040129)
Affected organisms
Not Available

Chemical Identifiers

UNII
S347WMO6M4
CAS number
83-46-5
InChI Key
KZJWDPNRJALLNS-VJSFXXLFSA-N
InChI
InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1
IUPAC Name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol
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@H](C)CC[C@@H](CC)C(C)C

References

General References
Not Available
Human Metabolome Database
HMDB0000852
KEGG Drug
D08518
KEGG Compound
C01753
ChemSpider
192962
BindingDB
50218197
RxNav
47070
ChEBI
27693
ChEMBL
CHEMBL221542
ZINC
ZINC000004095717
Wikipedia
Beta-Sitosterol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentPeriodontitis, Chronic1
1, 2Not Yet RecruitingTreatmentGraft Pain / Recession, Gingival1
Not AvailableCompletedBasic ScienceHigh Cholesterol / Indication for Carotid Endarterectomy / Symptomatic Carotid Stenosis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral35 mg/1
CapsuleOral
Capsule, coatedOral
Capsule, gelatin coatedOral
OintmentTopical0.25 %w/w
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.84e-05 mg/mLALOGPS
logP7.27ALOGPS
logP7.84ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.77 m3·mol-1ChemAxon
Polarizability54.21 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-054k-3912000000-22f633cd1bdd2ecca960
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0aor-9810000000-ab4d6cb3490b23c5cb70
GC-MS Spectrum - EI-BGC-MSsplash10-03di-5947700000-fe0573c7669e97c469f5
GC-MS Spectrum - EI-BGC-MSsplash10-0002-2931000000-0d63e91b728deb1446a4
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9822000000-2be95863c114e7cd2597
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9601000000-edade780f6cfb8ddc7d1
GC-MS Spectrum - GC-MSGC-MSsplash10-054k-3912000000-22f633cd1bdd2ecca960
Mass Spectrum (Electron Ionization)MSsplash10-052f-9821000000-0f43ba6def9281d5c86d
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-014i-0002900000-f2b81675160568c483c5
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05nb-3930100000-897e65b10be8a412585c
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0a59-6900000000-b62b8d1bd807fc41256b
MS/MS Spectrum - EI-B (VARIAN MAT-44) , PositiveLC-MS/MSsplash10-0aor-9810000000-fcbfd841778e213b3d3e
MS/MS Spectrum - EI-B (HITACHI M-52) , PositiveLC-MS/MSsplash10-03di-5947700000-4234b723ccdb0e25d290
MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , PositiveLC-MS/MSsplash10-0002-2931000000-b2156fbd63c29312b076
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0a4l-9822000000-2be95863c114e7cd2597
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Drug created on May 17, 2018 20:50 / Updated on June 12, 2020 16:53