Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C29H52O |
Molecular Weight | 416.7226 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@@H](CC)C(C)C
InChI
InChIKey=LGJMUZUPVCAVPU-HRJGVYIJSA-N
InChI=1S/C29H52O/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/h19-27,30H,7-18H2,1-6H3/t20-,21-,22+,23+,24+,25-,26+,27+,28+,29-/m1/s1
Molecular Formula | C29H52O |
Molecular Weight | 416.7226 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 10 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Stigmastanol is a plant lipid molecule that resembles cholesterol in structure. It inhibits cholesterol absorption. Sitostanol powder (1 g) reduced cholesterol absorption by only 11.3 /- 7.4% (P = 0.2), confirming in vitro data showing poor solubility of sitostanol powder in artificial bile. In contrast, sitostanol in lecithin micelles reduced cholesterol absorption by 36.7 /- 4.2% (P = 0.003) at a dose of 700 mg and by 34.4 /- 5.8% (P = 0.01) at a dose of 300 mg. Stigmasterol, which is used for the synthesis of progesterone and vitamin D3 is a potential anti-inflammatory compound. Its action is mediated by the inhibition of several pro-inflammatory and matrix degradation mediators involved in osteoarthritis-induced cartilage degradation.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4984 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25356831 |
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Target ID: CHEMBL2808 |
136.0 nM [EC50] | ||
Target ID: CHEMBL4093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16150823 |
110.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16035372
Curator's Comment: The administration of a dairy product in the form of liquid yoghurt, marketed in Spain, that contains 2 g per container of plant stanol esters: sitostanol (Stigmastanol) and campestanol (AHA recommended dose - 1.5 to 3 g). The enriched product and the placebo will have the same characteristics (composition and outward appearance), but the placebo will not contain stanol esters. The dose will be one container a day, after the main meal, for 24 months. The participants may continue with their previously prescribed lipid-lowering treatment and new treatment needed for this disease or for other diseases. Composition per container: proteins 1.8 g, carbohydrates 9.8 g, fat (except stanol) 1.4 g, plant stanol 2 g, vitamin B6 0.6 mg, folic acid 60 mg. The control group will receive one unit a day of yoghurt not supplemented with stanol esters that has a similar appearance to the enriched yoghurt. https://clinicaltrials.gov/ct2/show/NCT01406106
From a total number of 137 male subjects with hypercholesterolemia, eight subjects with the lowest and eight subjects with the highest ratios of lathosterol to campesterol in serum were included in the study. They received 1 g sitostanol (Stigmastanol)-supplemented margarine b.i.d. for four weeks.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25356831
Mouse bone marrow derived macrophages incubated with plant stanols produced
less Tnf-a after exposure to sitostanol (Stigmastanol), both after 0.6 and 1.2 um
concentrations as compared to cyclodextrin (carrier control).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:05:46 GMT 2023
by
admin
on
Fri Dec 15 15:05:46 GMT 2023
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Record UNII |
C2NJ9WO6O7
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68422
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LOINC |
74887-1
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DSLD |
2050 (Number of products:4)
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DSLD |
1905 (Number of products:6)
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DSLD |
4138 (Number of products:1)
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241572
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83-45-4
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m10213
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SUB129669
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100000155633
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49081
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DTXSID201016169
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201-479-0
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Stigmastanol
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C2NJ9WO6O7
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C68323
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C021255
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89400
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Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |