| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H28O2 |
| Molecular Weight | 312.4458 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC(=O)\C(=C\C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C
InChI
InChIKey=WDXRGPWQVHZTQJ-AUKWTSKRSA-N
InChI=1S/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4-/t15-,17+,18+,20+,21-/m1/s1
| Molecular Formula | C21H28O2 |
| Molecular Weight | 312.4458 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Guggulsterone is a naturally occuring bioactive plant sterol isolated from the gum resin of guggul (Commiphora wightii), which potently reverses multi-drug resistance in a number of human cancer cell lines, extending the efficacy of chemotherapy. Guggulsterone is a highly efficacious antagonist of the farnesoid X receptor (FXR), a nuclear hormone receptor that is activated by bile acids. Z-guggulsterone and E-guggulsterone were identified as the key active ingredients responsible for the hypolipidemic activity of guggulipid. Both isomers possess similar hypolipidemic activity and mixture of the Z- and E-isomers (80:20) has been shown to lower cholesterol and triglycerides in normal and high-fat-fed rats.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 12.0 nM [IC50] | |||
| 660.0 nM [EC50] | |||
| 6060.0 nM [IC50] | |||
| 1880.0 nM [IC50] | |||
| 2.4 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Patents
Sample Use Guides
in experimental animals: Serum lipids were found to be lowered by Guggulsterone (an 80:20 mixture of the Z- and E-isomers) (50 mgkg, b.w.) in triton WR-1339 induced hyperlipaemia. Chronic feeding of this drug (5 mg/kg, b.w.) in animals simultaneously fed with cholesterol (25 m%kg, b.w.) for 30 days, caused lowering in the lipid and apoprotein levels of very low density and low density lipoproteins in experimental animals.
Route of Administration:
Oral