CHOLESTEROL

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H46O
Molecular Weight	386.6535
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

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)CCCC(C)C

InChI

InChIKey=HVYWMOMLDIMFJA-DPAQBDIFSA-N

InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C27H46O
Molecular Weight	386.6535
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 8
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24616704
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28506805 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=06d72b32-f4cc-4c8f-a449-91146bbc41e1

Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The high level of cholesterol in the blood is a marker of hypercholesterolemia, also called dyslipidemia. As a part of homeopathic product, it helps to support general liver and gallbladder health, and is used for temporary relief of symptoms related to adrenal glands such as fatigue and low energy. Cholesterol binds to and affects the gating of a number of ion channels such as the nicotinic acetylcholine receptor (nAChR) Inwardly-rectifying K+ channels (Kir); Transient receptor potential vanilloid 1 channels (TRPV1) and Large-conductance Ca2+-sensitive voltage-gated K+ channels (BK). It was shown the new mechanistic insights into the role of cholesterol in the regulation of nAChR, showing that cholesterol regulates the channels by two distinct mechanisms: stabilization of the channels in a resting state that depends on specific lipid-protein interactions and facilitation of the transitions between uncoupled and coupled states that depends on the hydrophobic thickness of the membrane

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Inward rectifier potassium channel 2 5 Target ID: P63252 Gene ID: 3759.0 Gene Symbol: KCNJ2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21559361/	Inhibitor 8297
Transient receptor potential cation channel subfamily V member 1 6 Target ID: Q8NER1 Gene ID: 7442.0 Gene Symbol: TRPV1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21555515/	Inhibitor 8297
Nicotinic acetylcholine receptor alpha3/betaX 1 Target ID: CHEMBL2111384 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24013278/	Activator 1430
Calcium-activated potassium channel alpha/beta 1 5 Target ID: CHEMBL3038495 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22474334/	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Fatigue 46 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=06d72b32-f4cc-4c8f-a449-91146bbc41e1	Palliative	Not Provided 504	Unknown Approved Use Unknown
Gallbladder health 1 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0dba0c1b-29e4-3ac3-e054-00144ff88e88	Preventing	Not Provided 504	Unknown Approved Use Unknown
Hypercholesterolemia 47 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28506805	Diagnostic	Natural Metabolite	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP7A1 1 CYP27A1 3 CYP11A1 1 CYP46A1 1 ABCG1 1 ABCA1 1 ABCG5/8 1

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1925	inhibitor 3277 Sources: https://www.jbc.org/content/286/21/18426.short Page: -	yes [Ki 10 uM]

Drug as victim

Target	Modality	Activity
CYP7A1 1	substrate 3367 Sources: https://dmd.aspetjournals.org/content/34/4/513.short Page: -	yes [Km 13.3 uM]
CYP11A1 1	substrate 3367 Sources: https://dmd.aspetjournals.org/content/34/4/513.short Page: -	yes [Km 3.4 uM]
CYP46A1 1	substrate 3367 Sources: https://dmd.aspetjournals.org/content/34/4/513.short Page: -	yes [Km 5.3 uM]
CYP27A1 3	substrate 3367 Sources: https://dmd.aspetjournals.org/content/34/4/513.short Page: -	yes [Km 7 uM]
ABCA1 1	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S0378874119326364 Page: -	yes
ABCG1 1	substrate 3367 Sources: https://www.nature.com/articles/ncomms7354/ Page: -	yes
ABCG5/8 1	substrate 3367 Sources: https://www.jacc.org/doi/full/10.1016/j.jacc.2013.12.055 Page: -	yes
CYP3A4 1737	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S0163725806001161 Page: -	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.tandfonline.com/doi/full/10.4161/chan.25122 Page: -

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16113	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16113
ChemicalBook	CB7383339	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7383339
MolPort	MolPort-002-506-911	https://www.molport.com/shop/molecule-link/MolPort-002-506-911
Selleck Chemicals	cholesterol	http://www.selleckchem.com/products/cholesterol.html
ZINC	ZINC000003875383	http://zinc15.docking.org/substances/ZINC000003875383
eMolecules	29535203	https://www.emolecules.com/cgi-bin/more?vid=29535203
eMolecules	29536225	https://www.emolecules.com/cgi-bin/more?vid=29536225
eMolecules	482145	https://www.emolecules.com/cgi-bin/more?vid=482145

PubMed

Title	Date	PubMed
Oligonucleotides as inhibitors of protein synthesis.	2001	11142014
Eight novel LDL receptor gene mutations among patients under LDL apheresis in Dresden and Leipzig.	2001	11139254
Preoperative lipid control with simvastatin reduces the risk for graft failure already 1 year after myocardial revascularization.	2001 Feb	11137806
Remodeling of the vessel wall after copper-induced injury is highly attenuated in mice with a total deficiency of plasminogen activator inhibitor-1.	2001 Jan	11141484
Screening family members at high risk for coronary disease. Why isn't it done?	2001 Jan	11137774
Frequency of the R3500Q mutation of the apolipoprotein B-100 gene in a sample screened clinically for familial hypercholesterolemia in Hungary.	2001 Jan	11137107
Remnant-like particle (RLP) cholesterol is an independent cardiovascular disease risk factor in women: results from the Framingham Heart Study.	2001 Jan	11137104
Plasma lipids and cardiovascular risk: a POSCH report. Program on the Surgical Control of the Hyperlipidemias.	2001 Jan	11137103
Elevated plasma levels of free-form of TFPI antigen in hypercholesterolemic patients.	2001 Jan	11137101
Impaired renal vascular endothelial function in vitro in experimental hypercholesterolemia.	2001 Jan	11137100
Essential role for the (hepatic) LDL receptor in macrophage apolipoprotein E-induced reduction in serum cholesterol levels and atherosclerosis.	2001 Jan	11137088
Raloxifene and estrogen reduces progression of advanced atherosclerosis--a study in ovariectomized, cholesterol-fed rabbits.	2001 Jan	11137087
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.	2001 Jan	11137086
Gelatin intake increases the atheroma formation in apoE knock out mice.	2001 Jan	11137084
The LDL receptor is the major pathway for beta-VLDL uptake by mouse peritoneal macrophages.	2001 Jan	11137082
17beta-estradiol, gender independently, reduces atheroma development but not neointimal proliferation after balloon injury in the rabbit aorta.	2001 Jan	11137081
Inability of plasma high-density lipoproteins to inhibit cell adhesion molecule expression in human coronary artery endothelial cells.	2001 Jan	11137080
The sialylation of plasma lipoproteins.	2001 Jan	11137077
Alcohol intake, type of beverage, and the risk of cerebral infarction in young women.	2001 Jan	11136918
Ask the doctor. I've been fighting obesity all my life. I'm a 62-year-old woman and every five years or so I lose about 20 pounds, then slowly gain it back. I've heard that this "yo-yo" pattern of weight loss, weight gain, weight loss, may be more dangerous than just staying heavy. Should I give up trying to lose weight?	2001 Jan	11136512
Resolution of alcohols by cholesterol oxidase fromRrhodococcus erythropolis: lack of enantiospecificity for the steroids.	2001 Jan	11135412
Effect of lipid reduction on the progression of renal disease: a meta-analysis.	2001 Jan	11135079
Accumulation of cholesterol with age in human Bruch's membrane.	2001 Jan	11133878
Role of meiosis-activating sterols in rat oocyte maturation: effects of specific inhibitors and changes in the expression of lanosterol 14alpha-demethylase during the preovulatory period.	2001 Jan	11133687
Body mass index and metabolic risk factors for coronary heart disease in women.	2001 Jan	11133209
Maternal hypercholesterolemia during pregnancy influences the later development of atherosclerosis: clinical and pathogenic implications.	2001 Jan	11133201
The effect of isolated soy protein on plasma biomarkers in elderly men with elevated serum prostate specific antigen.	2001 Jan	11125428
Active urea transport and an unusual basolateral membrane composition in the gills of a marine elasmobranch.	2001 Jan	11124129
The role of fibric acids in atherosclerosis.	2001 Jan	11123853
The benefits of niacin in atherosclerosis.	2001 Jan	11123852
Soy proteins and cardiovascular disease.	2001 Jan	11123848
Statins, hormones, and women: benefits and drawbacks for atherosclerosis and osteoporosis.	2001 Jan	11123846
Diabetes: statins, fibrates, or both?	2001 Jan	11123844
New statins and new doses of older statins.	2001 Jan	11123843
Quantification of plasma membrane ergosterol of Saccharomyces cerevisiae by direct-injection atmospheric pressure chemical ionization/tandem mass spectrometry.	2001 Jan 1	11141305
High-density lipoprotein cholesterol and vascular stiffness at baseline in the activity counseling trial.	2001 Jan 1	11137844
Acute increases in plasma oxidized low-density lipoprotein immediately after percutaneous transluminal coronary angioplasty.	2001 Jan 1	11137843
Effects of atorvastatin versus fenofibrate on lipoprotein profiles, low-density lipoprotein subfraction distribution, and hemorheologic parameters in type 2 diabetes mellitus with mixed hyperlipoproteinemia.	2001 Jan 1	11137832
Pharmacological profile of F 12511, (S)-2',3', 5'-trimethyl-4'-hydroxy-alpha-dodecylthioacetanilide a powerful and systemic acylcoenzyme A: cholesterol acyltransferase inhibitor.	2001 Jan 1	11137714
Amyloid-beta is an antioxidant for lipoproteins in cerebrospinal fluid and plasma.	2001 Jan 1	11134902
Targeting and anti-tumor efficacy of liposomal 5'-O-dipalmitoylphosphatidyl 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine in mice lung bearing B16BL6 melanoma.	2001 Jan 10	11121862
Hydroxy-methylglutaryl-coenzyme A reductase inhibition promotes endothelial nitric oxide synthase activation through a decrease in caveolin abundance.	2001 Jan 2	11136695
Effect of type 2 diabetes mellitus on left ventricular geometry and systolic function in hypertensive subjects: Hypertension Genetic Epidemiology Network (HyperGEN) study.	2001 Jan 2	11136693
Women's Healthy Lifestyle Project: A randomized clinical trial: results at 54 months.	2001 Jan 2	11136682
Cracking down on caveolin: role of 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors in modulating edothelial cell nitric oxide production.	2001 Jan 2	11136674
Cardiovascular effects of tamoxifen in women with and without heart disease: breast cancer prevention trial. National Surgical Adjuvant Breast and Bowel Project Breast Cancer Prevention Trial Investigators.	2001 Jan 3	11136837
Estrogen, selective estrogen receptor modulation, and coronary heart disease: something or nothing.	2001 Jan 3	11136828
Glycated haemoglobin, diabetes, and mortality in men in Norfolk cohort of european prospective investigation of cancer and nutrition (EPIC-Norfolk).	2001 Jan 6	11141143
Cholesterol reduction and non-illness mortality: meta-analysis of randomised clinical trials.	2001 Jan 6	11141142
Cholesterol depletion disrupts caveolae and insulin receptor signaling for metabolic control via insulin receptor substrate-1, but not for mitogen-activated protein kinase control.	2001 Mar 30	11121405

Patents

Sample Use Guides

In Vivo Use Guide

fatigue: 1-10 drops under the tongue, 2 times a day or as directed by a health professional. gallbladder health: Adults: Take five granules three times daily or as recommended by your healthcare practitioner. Children: Take three garnules and follow adult directions.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:21:21 GMT 2023` Edited by `admin` on `Fri Dec 15 15:21:21 GMT 2023`
Record UNII	97C5T2UQ7J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHOLESTEROL

Official Name

English

CHOLESTEROL [MI]

Common Name

English

CHOLESTEROL [IARC]

Common Name

English

CHOLESTEROL [USP-RS]

Common Name

English

Cholesterol [WHO-DD]

Common Name

English

NSC-8798

Code

English

CHOLESTEROL [VANDF]

Common Name

English

CHOLESTEROL [JAN]

Common Name

English

CHOLESTEROL [MART.]

Common Name

English

PROVITAMIN-D

Common Name

English

LIDINITE

Common Name

English

DYTHOL

Common Name

English

CHOLESTEROL [II]

Common Name

English

ALF component cholesterol

Common Name

English

Army Liposome Formulation component cholesterol

Common Name

English

CHOLESTEROL [INCI]

Common Name

English

Cholest-5-en-3β-ol

Systematic Name

English

CHOLESTERINUM

Common Name

English

CHOLESTEROL [EP MONOGRAPH]

Common Name

English

CHOLESTERINUM [HPUS]

Common Name

English

LIDINIT

Common Name

English

CHOLEST-5-EN-3-OL (3.BETA.)-

Common Name

English

CHOLESTEROL [HSDB]

Common Name

English

ALFQ component cholesterol

Common Name

English

Classification Tree Code System Code

LOINC

47228-2