beta-Sitosterol

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for beta-Sitosterol (DB14038)

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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

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Pharmacology

Indication

Not Available

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Burned		••• •••			••••••••
Treatment of	Periodontal diseases		••• •••	•••••		••••••
Treatment of	Wounds		••• •••			••••••••

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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

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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

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International/Other Brands

Harzol

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Insadol	Tablet	35 mg/1	Oral	LYDIA Co., Ltd	2019-10-08	Not applicable
Insadol	Tablet	35 mg/1	Oral	OASIS TRADING	2018-11-20	Not applicable
Insadol	Tablet	35 mg/1	Oral	I World Pharmaceutical Co., Ltd.	2019-10-08	Not applicable
มีโบ	Ointment	0.25 %w/w	Topical	บริษัท มีโบ จำกัด	1999-04-08	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
BP Vit 3	beta-Sitosterol (200 mg/1) + Cyanocobalamin (500 ug/1) + Doconexent (350 mg/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1)	Capsule, coated	Oral	Acella Pharmaceuticals, LLC	2009-04-17	Not applicable
Insadol	beta-Sitosterol (35 mg/1)	Tablet	Oral	OASIS TRADING	2018-11-20	Not applicable
Insadol	beta-Sitosterol (35 mg/1)	Tablet	Oral	I World Pharmaceutical Co., Ltd.	2019-10-08	Not applicable
Insadol	beta-Sitosterol (35 mg/1)	Tablet	Oral	LYDIA Co., Ltd	2019-10-08	Not applicable
Mi-Omega NF	beta-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)	Capsule	Oral	Mayne Pharma	2009-01-01	2016-05-31

Categories

Drug Categories

• Biological Factors
• Cholestanes
• Cholestenes
• Fused-Ring Compounds
• Hypolipidemic Agents
• Lipid Regulating Agents
• Lipids
• Membrane Lipids
• Phytochemicals
• Phytosterols
• Steroids
• Sterols

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

External Links

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

Phase	Status	Purpose	Conditions	Count
2	Completed	Treatment	Chronic Periodontitis (Disorder)	1
1, 2	Unknown Status	Treatment	Graft Pain / Recession, Gingival	1
Not Available	Completed	Basic Science	High Cholesterol / Indication for Carotid Endarterectomy / Symptomatic Carotid Stenosis	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Tablet	Oral	35 mg/1
Capsule	Oral
Capsule, coated	Oral
Capsule, gelatin coated	Oral
Ointment	Topical	0.25 %w/w

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.84e-05 mg/mL	ALOGPS
logP	7.27	ALOGPS
logP	7.84	Chemaxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	18.2	Chemaxon
pKa (Strongest Basic)	-1.4	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	1	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	20.23 Å2	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	129.77 m3·mol-1	Chemaxon
Polarizability	54.21 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS (1 TMS)	GC-MS	splash10-054k-3912000000-22f633cd1bdd2ecca960
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-052v-1109000000-2eef6dd56a6c52421610
GC-MS Spectrum - EI-B	GC-MS	splash10-0aor-9810000000-ab4d6cb3490b23c5cb70
GC-MS Spectrum - EI-B	GC-MS	splash10-03di-5947700000-fe0573c7669e97c469f5
GC-MS Spectrum - EI-B	GC-MS	splash10-0002-2931000000-0d63e91b728deb1446a4
GC-MS Spectrum - EI-B	GC-MS	splash10-0a4l-9822000000-2be95863c114e7cd2597
GC-MS Spectrum - EI-B	GC-MS	splash10-0a4l-9601000000-edade780f6cfb8ddc7d1
GC-MS Spectrum - GC-MS	GC-MS	splash10-054k-3912000000-22f633cd1bdd2ecca960
Mass Spectrum (Electron Ionization)	MS	splash10-052f-9821000000-0f43ba6def9281d5c86d
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-014i-0002900000-f2b81675160568c483c5
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-05nb-3930100000-897e65b10be8a412585c
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-0a59-6900000000-b62b8d1bd807fc41256b
MS/MS Spectrum - EI-B (VARIAN MAT-44) , Positive	LC-MS/MS	splash10-0aor-9810000000-fcbfd841778e213b3d3e
MS/MS Spectrum - EI-B (HITACHI M-52) , Positive	LC-MS/MS	splash10-03di-5947700000-4234b723ccdb0e25d290
MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positive	LC-MS/MS	splash10-0002-2931000000-b2156fbd63c29312b076
MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	LC-MS/MS	splash10-0a4l-9822000000-2be95863c114e7cd2597
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-4336900000-433512c4a675f955f497
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0001900000-9ce0428833aef00347fc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0001900000-251eee068026cfe0d420
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01c1-9224100000-b6d7be15df3fabbddf4e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0019500000-ca157475d3b2d0348942
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9631000000-c1c200b83c2fe8ffa326
1H NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	219.1820579	predicted	DarkChem Lite v0.1.0
[M-H]-	224.8486579	predicted	DarkChem Lite v0.1.0
[M-H]-	213.2335579	predicted	DarkChem Lite v0.1.0
[M-H]-	222.7302579	predicted	DarkChem Lite v0.1.0
[M-H]-	194.16098	predicted	DeepCCS 1.0 (2019)
[M+H]+	219.9549579	predicted	DarkChem Lite v0.1.0
[M+H]+	225.2509579	predicted	DarkChem Lite v0.1.0
[M+H]+	213.5245579	predicted	DarkChem Lite v0.1.0
[M+H]+	224.3025579	predicted	DarkChem Lite v0.1.0
[M+H]+	196.33229	predicted	DeepCCS 1.0 (2019)
[M+Na]+	218.9363579	predicted	DarkChem Lite v0.1.0
[M+Na]+	224.6677579	predicted	DarkChem Lite v0.1.0
[M+Na]+	213.3205579	predicted	DarkChem Lite v0.1.0
[M+Na]+	222.7031579	predicted	DarkChem Lite v0.1.0
[M+Na]+	202.60577	predicted	DeepCCS 1.0 (2019)

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