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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
Structure of STIGMASTANOL

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

HIDE SMILES / InChI

Molecular Formula C29H52O
Molecular Weight 416.7226
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
136.0 nM [EC50]
110.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
C2NJ9WO6O7
Record Status Validated (UNII)
Record Version