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MedKoo Cat#: 326938 | Name: Lifibrol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lifibrol, also known as K-12.148; U-83860, is a cholesterol synthesis inhibitor potentially for the treatment of hypercholesterolaemia. Lifibrol enhances the low density lipoprotein apolipoprotein B-100 turnover in patients with hypercholesterolemia and mixed hyperlipidemia. Lifibrol's lipid-lowering profile and putative mode of action clearly distinguish it from other classes of hypolipidaemic drugs, such as HMG-CoA reductase inhibitors or fibric acid derivatives. Thus, lifibrol may represent a new class of agents affecting lipid metabolism.

Chemical Structure

Lifibrol
Lifibrol
CAS#96609-16-4

Theoretical Analysis

MedKoo Cat#: 326938

Name: Lifibrol

CAS#: 96609-16-4

Chemical Formula: C21H26O4

Exact Mass: 342.1831

Molecular Weight: 342.44

Elemental Analysis: C, 73.66; H, 7.65; O, 18.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Lifibrol; K-12.148; K-12148; K12148; U-83860; U 83860; U83860.
IUPAC/Chemical Name
4-(4-(4-(tert-butyl)phenyl)-2-hydroxybutoxy)benzoic acid
InChi Key
LNXBEIZREVRNTF-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(O)C1=CC=C(OCC(O)CCC2=CC=C(C(C)(C)C)C=C2)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 342.44 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Berthold HK, Sudhop T, von Bergmann K, Gouni-Berthold I. Lifibrol as a model compound for a novel lipid-lowering mechanism of action. J Cardiovasc Pharmacol Ther. 2010 Dec;15(4):364-72. doi: 10.1177/1074248410371100. Epub 2010 Aug 6. PubMed PMID: 20693157. 2: Bays H, Stein EA. Pharmacotherapy for dyslipidaemia--current therapies and future agents. Expert Opin Pharmacother. 2003 Nov;4(11):1901-38. Review. PubMed PMID: 14596646. 3: Scharnagl H, Schliack M, Löser R, Nauck M, Gierens H, Jeck N, Wieland H, Gross W, März W. The effects of lifibrol (K12.148) on the cholesterol metabolism of cultured cells: evidence for sterol independent stimulation of the LDL receptor pathway. Atherosclerosis. 2000 Nov;153(1):69-80. PubMed PMID: 11058701. 4: Winkler K, Schaefer JR, Klima B, Nuber C, Friedrich I, Köster W, Gierens H, Scharnagl H, Soufi M, Wieland H, März W. HDL steady state levels are not affected, but HDL apoA-I turnover is enhanced by Lifibrol in patients with hypercholesterolemia and mixed hyperlipidemia. Atherosclerosis. 2000 May;150(1):113-20. PubMed PMID: 10781641. 5: Burger A, Lettenbichler A. Polymorphism and preformulation studies of lifibrol. Eur J Pharm Biopharm. 2000 Jan;49(1):65-72. PubMed PMID: 10613929. 6: Vega GL, von Bergmann K, Grundy SM, Blumenschein S, Carter NB, Laeis P, Lindenthal B, von Bergmann J, Simatupang A, Lutjohann D, Adams-Huet B. Effect of lifibrol on the metabolism of low density lipoproteins and cholesterol. J Intern Med. 1999 Jul;246(1):1-9. PubMed PMID: 10447220. 7: Winkler K, Schäfer JR, Klima B, Nuber C, Sattler A, Friedrich I, Köster W, Steinmetz A, Wieland H, März W. Lifibrol enhances the low density lipoprotein apolipoprotein B-100 turnover in patients with hypercholesterolemia and mixed hyperlipidemia. Atherosclerosis. 1999 May;144(1):167-75. PubMed PMID: 10381290. 8: Scharnagl H, März W, Wieland H. Lifibrol: first member of a new class of lipid-lowering drugs? Expert Opin Investig Drugs. 1997 May;6(5):583-91. PubMed PMID: 15989622. 9: Sun EL, Feenstra KL, Bell FP, Sanders PE, Slatter JG, Ulrich RG. Biotransformation of lifibrol (U-83860) to mixed glyceride metabolites by rat and human hepatocytes in primary culture. Drug Metab Dispos. 1996 Feb;24(2):221-31. PubMed PMID: 8742235. 10: Scharnagl H, März W, Schliack M, Löser R, Gross W. 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. J Lipid Res. 1995 Mar;36(3):622-7. PubMed PMID: 7775873. 11: Locker PK, Jungbluth GL, Francom SF, Hughes GS Jr. Lifibrol: a novel lipid-lowering drug for the therapy of hypercholesterolemia. Lifibrol Study Group. Clin Pharmacol Ther. 1995 Jan;57(1):73-88. PubMed PMID: 7828385. 12: Krause BR, Bousley R, Kieft K, Robertson D, Stanfield R, Urda E, Newton RS. Comparison of lifibrol to other lipid-regulating agents in experimental animals. Pharmacol Res. 1994 May-Jun;29(4):345-57. PubMed PMID: 7971686. 13: Walters RR, Hsu CY. Chiral assay methods for lifibrol and metabolites in plasma and the observation of unidirectional chiral inversion following administration of the enantiomers to dogs. Chirality. 1994;6(2):105-15. PubMed PMID: 8204414. 14: Schwandt P, Elsässer R, Schmidt C, Gertz B, Heil M, Augustin J, Seibel K. Safety and efficacy of lifibrol upon four-week administration to patients with primary hypercholesterolaemia. Eur J Clin Pharmacol. 1994;47(2):133-8. PubMed PMID: 7859799. 15: Bell FP, St John LC. 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. Lipids. 1993 Dec;28(12):1079-85. PubMed PMID: 8121250. 16: Bell FP. 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. Biochem Pharmacol. 1993 Oct 19;46(8):1475-80. PubMed PMID: 8240398. 17: Hasibeder H, Staab HJ, Seibel K, Heibel B, Schmidle G, März W. Clinical pharmacology of the hypocholesterolemic agent K 12.148 (lifibrol) in healthy volunteers. Eur J Clin Pharmacol. 1991;40 Suppl 1:S91-4. PubMed PMID: 2044652. 18: Schliack M, Löser R, Seibel K, Rattel B, Lang G. The hypolipidemic effect of lifibrol during a long term treatment of pigs. Artery. 1990;18(1):1-15. PubMed PMID: 2085283. 19: Schliack M, Löser R, Seibel K, Blay KH. Hypolipemic activity of K12.148 in rats, marmosets and pigs. Artery. 1989;16(2):90-104. PubMed PMID: 2712711.

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