Page last updated: 2024-12-06

cholesteryl sulfate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Cholesteryl sulfate (CS) is a sterol sulfate that is found in various tissues, including the brain, adrenal glands, and liver. It is synthesized from cholesterol by the enzyme cholesterol sulfotransferase (CHST). CS plays a role in cholesterol metabolism and has been implicated in a variety of physiological and pathological processes. CS can inhibit the activity of certain enzymes, including cholesterol esterase and phospholipase A2. It has also been shown to have anti-inflammatory effects. CS is studied for its potential role in neurodegenerative diseases, such as Alzheimer's disease, and in cancer. Research has shown that CS levels are elevated in the brains of patients with Alzheimer's disease. CS may also play a role in the development of atherosclerosis. Research suggests that CS may promote the formation of atherosclerotic plaques. Studies on CS are ongoing to better understand its role in various biological processes and to investigate its potential as a therapeutic target for diseases such as Alzheimer's disease and cancer.'

cholesteryl sulfate: component of human seminal plasma & spermatozoa; RN given refers to (3beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cholesterol sulfate : A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID65076
CHEMBL ID1231592
CHEBI ID41321
SCHEMBL ID161397
MeSH IDM0049977

Synonyms (52)

Synonym
CHEMBL1231592
gtpl2738
nsc628320
cholesteryl sulfate
1256-86-6
[(3s,8s,9s,10r,13r,14s,17r)-17-[(1r)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
cholesterol sulfate
cholest-5-en-3-ol (3.beta.)-, hydrogen sulfate
cholest-5-en-3-yl hydrogen sulfate
ccris 7559
cholest-5-en-3-ol (3beta)-, hydrogen sulfate (9ci)
c3s ,
cholesterol, hydrogen sulfate (7ci,8ci)
y5-cholesten-3beta-yl sulfate
cholesterol 3-sulfate
cmc_13400
chol-sulf
cholest-5-en-3-ol, hydrogen sulfate, (3beta)-
cholest-5-en-3beta-ol sulfate
C9523_SIGMA ,
CHEBI:41321 ,
cholest-5-en-3beta-yl hydrogen sulfate
cholesterol sulphate
DB01990
cholesterol hydrogen sulfate
cholesteryl sulphate
cholesterol 3-sulphate
cholesterol hydrogen sulphate
cholesterol-sulfate
cholest-5-en-3-ol (3beta)-, hydrogen sulfate
[(3s,8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl] hydrogen sulfate
C18043
LMST05020016
5-cholesten-3b-yl sulfate
cholest-5-en-3b-ol sulfate
cholesterol sulfic acid
5-cholesten-3beta-ol sulfate sodium salt
cholesteryl sulfate sodium salt
hmdb00653
BMSE000961
ku576nt9o9 ,
unii-ku576nt9o9
cholest-5-en-3.beta.-ol sulfate
5-cholesten-3.beta.-yl sulfate
cholesterol, hydrogen sulfate
SCHEMBL161397
BHYOQNUELFTYRT-DPAQBDIFSA-N
5-cholesten-3b-yl sulphate
cholest-5-en-3b-ol sulphate
(3alpha,8alpha,17alpha)-cholest-5-en-3-yl hydrogen sulfate
Q27075985
DTXSID401016822

Research Excerpts

Overview

Cholesteryl sulfate (CS) is a minor component of cell membranes, also present in lipoproteins, and its exact function is unknown. It is a crucial metabolite for encystation.

ExcerptReferenceRelevance
"Cholesteryl sulfate (CS) is a crucial metabolite for encystation."( Pleiotropic Roles of Cholesteryl Sulfate during
Arita, M; Mi-Ichi, F; Tsugawa, H; Yoshida, H, 2022
)
1.76
"Cholesteryl sulfate is a normal constituent of human spermatozoa. "( Localization of cholesteryl sulfate in human spermatozoa in support of a hypothesis for the mechanism of capacitation.
Bleau, G; Chapdelaine, A; Langlais, J; Plante, L; Roberts, KD; Zollinger, M, 1981
)
2.05
"Cholesteryl sulfate (CS) is a minor component of cell membranes, also present in lipoproteins, and its exact function is unknown. "( Enhanced susceptibility of cholesteryl sulfate-enriched low density lipoproteins to copper-mediated oxidation.
Blache, D; Davignon, J; Rodriguez, C, 1995
)
2.03
"Cholesteryl sulfate is a component of human seminal plasma (avg. "( Cholesteryl sulfate and sterol sulfatase in the human reproductive tract.
Bleau, G; Chapdelaine, A; Lalumière, G; Roberts, KD, 1976
)
3.14

Toxicity

ExcerptReferenceRelevance
" AB and hypoxia/reoxygenation caused additive, not synergistic, LDH release whereas CS-AB had no adverse effect."( Direct amphotericin B-mediated tubular toxicity: assessments of selected cytoprotective agents.
Bredl, CR; Schimpf, BA; Zager, RA, 1992
)
0.28
" ABCD produced a spectrum of toxic effects in the kidneys, gut, and liver similar to those of m-AmB, but ABCD was eightfold safer than m-AmB."( Relationship of pharmacokinetics and drug distribution in tissue to increased safety of amphotericin B colloidal dispersion in dogs.
Babbar, S; Fielding, RM; Guo, LS; Singer, AW; Wang, LH, 1992
)
0.28

Pharmacokinetics

ExcerptReferenceRelevance
"This study investigated the preparation, characterization of physicochemical properties, ex vivo permeation using human skin, pharmacokinetic parameters and antihypertensive potential in rats, of nitrendipine-loaded nanovesicles of ceramide 2, stearic acid, behenic acid and cholesteryl sulfate containing oleic acid gel (NOVG)."( Nanovesicles of nitrendipine with lipid complex for transdermal delivery: pharmacokinetic and pharmacodynamic studies.
Kumar Gaur, P; Mishra, S; Purohit, S, 2016
)
0.61
"The nanovesicles were made using film hydration method and characterized for physicochemical properties, ex vivo permeation using human skin, pharmacokinetic parameters and antihypertensive potential."( Nanovesicles of nitrendipine with lipid complex for transdermal delivery: pharmacokinetic and pharmacodynamic studies.
Kumar Gaur, P; Mishra, S; Purohit, S, 2016
)
0.43

Compound-Compound Interactions

ExcerptReferenceRelevance
"A systematic method for the sensitive, precise and accurate determination of hair lipids, including trace amounts of intrinsic endogenous cholesterol (CH), ceramide/N-palmitoyl-DL-dihydrosphingosine (CER/PDS), cholesterol sulfate (CS) and chemically bound 18-methyl eicosanoic acid (18-MEA), has been developed in combination with TLC/FID (flame ionization detection), LC/MS and GC/MS."( A systematic method for the sensitive and specific determination of hair lipids in combination with chromatography.
Imokawa, G; Masukawa, Y; Tsujimura, H, 2005
)
0.33

Bioavailability

ExcerptReferenceRelevance
"The purpose of this study was to employ a nanoscale liposomal carrier to resolve the delivery problem, and increase the bioavailability and efficiency of pTT."( Topical delivery of DNA oligonucleotide to induce p53 generation in the skin via thymidine dinucleotide (pTT)-encapsulated liposomal carrier.
Fang, YP, 2011
)
0.37
" The results of digestion and absorption in vitro and in vivo showed that liposomes could significantly improve the bioavailability of fucoxanthin and prolong its residence time in serum."( Preparation and properties of fucoxanthin-loaded liposomes stabilized by sea cucumber derived cholesterol sulfate instead of cholesterol.
Chang, Y; Wang, Y; Xue, C; Yang, J; Zhang, T, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
" Concentrations in plasma reached steady state after ABCD administration, but they increased after repeated dosing with m-AmB."( Relationship of pharmacokinetics and drug distribution in tissue to increased safety of amphotericin B colloidal dispersion in dogs.
Babbar, S; Fielding, RM; Guo, LS; Singer, AW; Wang, LH, 1992
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
steroid sulfateA sulfuric ester obtained by the formal condensation of a hydroxy group of any steroid with sulfuric acid.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cholesterol 24-hydroxylaseHomo sapiens (human)Kd0.05000.05002.00005.0000AID1618238
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
protein localization to membrane raftCholesterol 24-hydroxylaseHomo sapiens (human)
bile acid biosynthetic processCholesterol 24-hydroxylaseHomo sapiens (human)
cholesterol catabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
xenobiotic metabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
nervous system developmentCholesterol 24-hydroxylaseHomo sapiens (human)
sterol metabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
progesterone metabolic processCholesterol 24-hydroxylaseHomo sapiens (human)
regulation of long-term synaptic potentiationCholesterol 24-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
iron ion bindingCholesterol 24-hydroxylaseHomo sapiens (human)
steroid hydroxylase activityCholesterol 24-hydroxylaseHomo sapiens (human)
heme bindingCholesterol 24-hydroxylaseHomo sapiens (human)
cholesterol 24-hydroxylase activityCholesterol 24-hydroxylaseHomo sapiens (human)
testosterone 16-beta-hydroxylase activityCholesterol 24-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
endoplasmic reticulumCholesterol 24-hydroxylaseHomo sapiens (human)
endoplasmic reticulum membraneCholesterol 24-hydroxylaseHomo sapiens (human)
dendriteCholesterol 24-hydroxylaseHomo sapiens (human)
presynapseCholesterol 24-hydroxylaseHomo sapiens (human)
postsynapseCholesterol 24-hydroxylaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID766996Antiviral activity against Influenza A/PR8/34 (H1N1) virus infected in MDCK2 cells assessed as inhibition of virus reproduction by ELISA2013Bioorganic & medicinal chemistry letters, Sep-15, Volume: 23, Issue:18
Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents.
AID1346770Human RAR-related orphan receptor-alpha (1F. Retinoic acid-related orphans)2003Analytical biochemistry, Dec-01, Volume: 323, Issue:1
Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.
AID1346770Human RAR-related orphan receptor-alpha (1F. Retinoic acid-related orphans)2002Structure (London, England : 1993), Dec, Volume: 10, Issue:12
X-ray structure of the hRORalpha LBD at 1.63 A: structural and functional data that cholesterol or a cholesterol derivative is the natural ligand of RORalpha.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (295)

TimeframeStudies, This Drug (%)All Drugs %
pre-199075 (25.42)18.7374
1990's83 (28.14)18.2507
2000's49 (16.61)29.6817
2010's71 (24.07)24.3611
2020's17 (5.76)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.45

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.45 (24.57)
Research Supply Index5.72 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index28.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.45)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.66%)5.53%
Reviews14 (4.65%)6.00%
Case Studies6 (1.99%)4.05%
Observational1 (0.33%)0.25%
Other278 (92.36%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (3)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
An Open Clinical Trial to Evaluate the Safety, Efficacy and Population Pharmacokinetics of Amphotericin B Cholesteryl Sulfate Complex for Injection in Subjects With Invasive Candidiasis and Invasive Aspergillus [NCT05707832]Phase 360 participants (Anticipated)Interventional2023-03-30Not yet recruiting
An Open, Multicenter Clinical Study to Evaluate the Safety, Efficacy, and Population Pharmacokinetics of ABCD for Invasive Candidiasis and Invasive Aspergillosis [NCT04225195]Phase 260 participants (Anticipated)Interventional2020-01-31Not yet recruiting
Clinical Study of Amphotericin B Colloidal Dispersion (ABCD) in the Treatment of Cryptococcal Meningitis [NCT05471063]30 participants (Anticipated)Interventional2022-08-22Not yet recruiting
[information is prepared from clinicaltrials.gov, extracted Sep-2024]