Page last updated: 2024-12-08

stigmastanol

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

Description

stigmastanol: saturated analog of beta-sitosterol; RN given refers to (3beta,5alpha)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

stigmastanol : A 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. [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 CID241572
CHEMBL ID252364
CHEBI ID89400
SCHEMBL ID133725
MeSH IDM0075888

Synonyms (62)

Synonym
stigmastan-3-ol,5.alpha.)-
dihydro-.beta.-sitosterol
dihydrositosterol
.beta.-sitosterol, dihydro-
spinastanol
stigmastanol
83-45-4
dihydrositosterin
nsc49081
5.alpha.-stigmastan-3.beta.-ol
nsc-49081
.beta.-sitostanol
stigmastan-3-ol, (3beta,5alpha)-
(3s,5s,8r,9s,10s,13r,14s,17r)-17-[(1r,4r)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol
(3s,10s,13r,17r)-17-((1r,4r)-4-ethyl-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-ol
beta-sitosterol, dihydro-
stigmastanol, >=95%
(3beta,5alpha)-stigmastan-3-ol
sitostanol
beta-sitostanol
nsc 49081
5,6-dihydro-beta-sitosterol
einecs 201-479-0
5alpha-stigmastan-3beta-ol
24alpha-ethylcholestanol
CHEMBL252364
(3s,5s,8r,9s,10s,13r,14s,17r)-17-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-ol
C19644
stigmastane-3-beta-ol
stigmastan-3-ol, (3b)-
138126-65-5
AKOS016036225
stigmastan-3-ol, (3b,5a)-
unii-c2nj9wo6o7
c2nj9wo6o7 ,
stigmastanol [mi]
stigmastanol [who-dd]
24.alpha.-ethylcholestanol
(3.beta.,5.alpha.)-stigmastan-3-ol
sitostanol [mart.]
stigmastanol (constituent of saw palmetto) [dsc]
SCHEMBL133725
(3beta,5alpha,20s)-stigmastan-3-ol
CHEBI:89400 ,
(5alpha)-stigmastan-3beta-ol
stigmastan-3-ol,(3b)-
dihydro-sitosterol
dihydro-beta-sitosterol
LMST01040266
Q3973521
stigmastan-3-ol, (3|a,5|a)-
LGJMUZUPVCAVPU-HRJGVYIJSA-N
DTXSID201016169
CS-0062392
HY-113494
F82244
MS-27267
DTXSID50860237 ,
(3 beta,5 alpha)-stigmastan-3-ol
stigmastanol (constituent of saw palmetto)
sitostanol (mart.)
24 alpha-ethyl-5alpha-choestan-3beta-ol

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Plant stanol ester spread consumption appeared safe in the clinical setting, except for potential lowering of infants' serum beta-carotene concentration, and was reflected in the markers of cholesterol synthesis and absorption in mothers' serum, encouraging further studies in larger settings."( Plant stanol ester spreads as components of a balanced diet for pregnant and breast-feeding women: evaluation of clinical safety.
Gylling, H; Isolauri, E; Kaipiainen, L; Laitinen, K; Miettinen, TA, 2009
)
0.35

Bioavailability

ExcerptReferenceRelevance
" The results show that the absolute difference in absorption rate of different sterols between the patients and healthy volunteers was about the same."( Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment.
Beil, UF; Björkhem, I; Lütjohann, D; von Bergmann, K, 1995
)
0.29
"The hypothesis tested was that the low intestinal bioavailability of purified phytosterols can be increased by formulation with lecithin."( Sitostanol administered in lecithin micelles potently reduces cholesterol absorption in humans.
Ostlund, RE; Spilburg, CA; Stenson, WF, 1999
)
0.3
" However, coadministration of FCP-3P4 at 25, 50, and 100 mg/kg resulted in a significant increase in apparent total body clearance (CL/F, where F is the bioavailability constant), apparent volume of distribution (V(d)/F), and oral absorption rate constant (k(a)) of [(3)H]cholesterol compared with controls."( Assessing plasma pharmacokinetics of cholesterol following oral coadministration with a novel vegetable stanol mixture to fasting rats.
Cassidy, SM; Holtorf, L; Moghadasian, MH; Novak, E; Pritchard, PH; Stewart, DJ; Subramanian, R; Wasan, KM, 2001
)
0.31

Dosage Studied

ExcerptRelevanceReference
" Therefore, we determined the dose-response relationship for serum cholesterol with different doses of plant stanol ester in hypercholesterolemic subjects."( Plant stanol esters affect serum cholesterol concentrations of hypercholesterolemic men and women in a dose-dependent manner.
Hallikainen, MA; Sarkkinen, ES; Uusitupa, MI, 2000
)
0.31
" Rats were dosed by oral gavage with 14C-labelled samples of cholesterol, beta-sitosterol or beta-sitostanol or (3)H-labelled samples of beta-sitostanol, campesterol, campestanol or stigmasterol dissolved in sunflower seed oil."( The safety evaluation of phytosterol esters. Part 6. The comparative absorption and tissue distribution of phytosterols in the rat.
Hepburn, PA; Howes, D; Minter, HJ; Sanders, DJ, 2000
)
0.31
" This method was used to assay commercially available products formulated as oral dosage forms purported to contain African Potato and associated sterols and stanol and proved to be suitable for the routine analysis and quality control of such products."( Determination of stigmasterol, beta-sitosterol and stigmastanol in oral dosage forms using high performance liquid chromatography with evaporative light scattering detection.
Hoogmartens, J; Kanfer, I; Nair, VD, 2006
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
anticholesteremic drugA substance used to lower plasma cholesterol levels.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (2)

ClassDescription
3-hydroxy steroidAny hydroxy steroid carrying a hydroxy group at position 3.
phytosterolsSterols similar to cholesterol which occur in plants and vary only in carbon side chains and/or presence or absence of a double bond.
[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]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID311139Cytotoxicity against mouse J774 cells by alamar blue assay2007Journal of natural products, Aug, Volume: 70, Issue:8
Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds.
AID311138Antitrypanosomal activity against Trypanosoma brucei brucei bloodstream trypomastigotes by alamar blue assay2007Journal of natural products, Aug, Volume: 70, Issue:8
Antitrypanosomal activity of triterpenoids and sterols from the leaves of Strychnos spinosa and related compounds.
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (137)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (6.57)18.7374
1990's43 (31.39)18.2507
2000's53 (38.69)29.6817
2010's29 (21.17)24.3611
2020's3 (2.19)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.67

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 Index25.67 (24.57)
Research Supply Index5.14 (2.92)
Research Growth Index5.02 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.67)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials31 (22.30%)5.53%
Reviews6 (4.32%)6.00%
Case Studies3 (2.16%)4.05%
Observational0 (0.00%)0.25%
Other99 (71.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]