Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H26O4 |
Molecular Weight | 342.4287 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(C)C1=CC=C(CCC(O)COC2=CC=C(C=C2)C(O)=O)C=C1
InChI
InChIKey=LNXBEIZREVRNTF-UHFFFAOYSA-N
InChI=1S/C21H26O4/c1-21(2,3)17-9-4-15(5-10-17)6-11-18(22)14-25-19-12-7-16(8-13-19)20(23)24/h4-5,7-10,12-13,18,22H,6,11,14H2,1-3H3,(H,23,24)
Molecular Formula | C21H26O4 |
Molecular Weight | 342.4287 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Lifibrol is a hypocholesterolemic compound. The effect of lifibrol on serum cholesterol levels has been examined in several animal models and clinical trials. The efficacy of lifibrol in lowering total cholesterol, LDL cholesterol, and apo B is comparable to the 3-Hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitors, the most potent lipid-lowering drugs known so far. In addition, lifibrol reduces serum triglycerides, lipoprotein (a), and fibrinogen. lifibrol acts synergistically upon key regulatory processes of cholesterol homeostasis: it reduces cholesterol absorption from the intestine, moderately decreases hepatic cholesterol biosynthesis and stimulates the expression of low density lipoprotein receptors, presumably by a sterol-independent mechanism. Lifibrol had been in phase II clinical trials for the treatment of hypercholesterolaemia. However, this study was discontinued. It has the potential to accumulate in the liver and induce hepatic peroxisome proliferation.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Clinical pharmacology of the hypocholesterolemic agent K 12.148 (lifibrol) in healthy volunteers. | 1991 |
|
Action of the new hypolipidemic agent lifibrol (K12.148) on lipid homeostasis in normal rats: plasma lipids, hepatic sterologenesis, and the fate of injected [14C]acetate. | 1993 Dec |
|
Effect of the lipid-lowering drug lifibrol on lipid metabolism in rat macrophages and in atherosclerotic arteries from swine and WHHL rabbits, in vitro. Implications in atherogenesis. | 1993 Oct 19 |
|
Chiral assay methods for lifibrol and metabolites in plasma and the observation of unidirectional chiral inversion following administration of the enantiomers to dogs. | 1994 |
|
Safety and efficacy of lifibrol upon four-week administration to patients with primary hypercholesterolaemia. | 1994 |
|
Comparison of lifibrol to other lipid-regulating agents in experimental animals. | 1994 May-Jun |
|
Lifibrol: a novel lipid-lowering drug for the therapy of hypercholesterolemia. Lifibrol Study Group. | 1995 Jan |
|
A novel assay for cytosolic 3-hydroxy-3-methylglutaryl-coenzyme A synthase activity using reversed-phase ion-pair chromatography: demonstration that Lifibrol (K12.148) modulates the enzyme activity. | 1995 Mar |
|
Biotransformation of lifibrol (U-83860) to mixed glyceride metabolites by rat and human hepatocytes in primary culture. | 1996 Feb |
|
Lifibrol: first member of a new class of lipid-lowering drugs? | 1997 May |
|
Polymorphism and preformulation studies of lifibrol. | 2000 Jan |
|
The effects of lifibrol (K12.148) on the cholesterol metabolism of cultured cells: evidence for sterol independent stimulation of the LDL receptor pathway. | 2000 Nov |
|
Lifibrol as a model compound for a novel lipid-lowering mechanism of action. | 2010 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7828385
150, 300, 450, 600, or 900 mg as a single daily dose for 4 weeks
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:42:40 GMT 2023
by
admin
on
Sat Dec 16 16:42:40 GMT 2023
|
Record UNII |
6KWX9X0Q5K
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C29703
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
6470
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
100000082313
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
CHEMBL2105019
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
6KWX9X0Q5K
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
57112
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
SUB08512MIG
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
GG-40
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
C82244
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
DB12448
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY | |||
|
96609-16-4
Created by
admin on Sat Dec 16 16:42:40 GMT 2023 , Edited by admin on Sat Dec 16 16:42:40 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |