LovastatinA hypocholesterolemic HMGCR inhibitor (statin that lowers cholesterol levels)

Lovastatin (CAS 75330-75-5)

Lovastatin | CAS 75330-75-5 is rated 3.0 out of 5 by 1.
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Synonym: Mevacor;Monacolin K;mevinolin;6-α-Methylcompactin
Application: A hypocholesterolemic HMGCR inhibitor (statin that lowers cholesterol levels)
CAS Number: 75330-75-5
Purity: ≥97%
Molecular Weight: 404.54
Molecular Formula: C24H36O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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Lovastatin is a statin natural product isolated from numerous sources including the Pleurotus ostreatus oyster mushroom, demonstrating hypocholesterolemic and antiproliferative properties. Lovastatin inhibits HMGCR (3-hydroxy-3-methylglutaryl coenzyme A reductase), blocking the enzyme-catalyzed transformation of 3-hydroxy-3-methylglutaryl CoA into mevalonate. The biosynthesis of cholesterol requires mevalonate as a building block and elimination of mevalonate generation subsequently interrupts cholesterol synthesis, leading to a reduction of circulating low-density lipoproteins. Lovastatin demonstrates arrest of the cell cycle at the G1 phase in bladder carcinoma T24 cells expressing activated p21ras oncoprotein - the posttranslational isoprenylation of the p21ras with mevalonate is crucial for translocation and membrane adhesion of the protein, and blockade of this modification by Lovastatin-induced depletion of cellular mevalonate leads to suspension of cell progress. The signaling activity of epidermal growth factor (EGF) and insulin-like growth factor (IGF-I) are similarly affected by impairment of mevalonate-dependent protein prenylation. Induction of apoptosis by Lovastatin in malignant mesothelioma cells is also ascribed to the inhibition of mevalonate synthesis and posttranslational protein modifications. Lovastatin is a substrate of CYP and Mdr-1.


References

1. Alberts, A.W. 1988. Am. J. Cardiol. 62: 10J-15J. PMID: 3055919
2. Hancock, J.F., et al. 1989. Cell. 57: 1167-1177. PMID: 2661017
3. Mendola, C.E. and Backer, J.M. 1990. Cell Growth Differ. 1: 499-502. PMID: 2278880
4. Vincent, T.S., et al. 1991. Biochem. Biophys. Res. Commun. 180: 1284-1289. PMID: 1953779
5. Jakóbisiak, M., et al. 1991. Proc. Natl. Acad. Sci. U.S.A. 88: 3628-3632. PMID: 1673788
6. Rubins, J.B., et al. 1998. Am. J. Respir. Crit. Care Med. 157: 1616-1622. PMID: 9603146
7. Bobek, P., et al. 1998. Nutrition. 14: 282-286. PMID: 9583372
8. Kim, W.S., et al. 2001. Invest New Drugs. 19: 81-83. PMID: 11291836

Physical State :
Solid
Derived From :
Non-native source; synthetic
Solubility :
Soluble in DMSO (10 mg/ml), ethanol (10 mg/ml), methanol, chloroform, acetone, acetonitrile, DMF, and water (0.4 µg/ml).
Storage :
Store at -20° C
Melting Point :
175.4° C
Boiling Point :
~559.2° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.53
Optical Activity :
α20/D 320°±10°, c = 0.5 in CH3CN
IC50 :
HMG-CoA reductase: IC50 = 0.01 µM (rat); Inhibition of the incorporation of sodium [14C]acetate into cholesterol: IC50 = 0.05 µM (HEP G2 cells); inhibition of recombinant ICAM-1 binding to purified immobilized LFA-1: IC50 = 3.78 µM; CYP51: IC50 = 200 µM (human)
Ki Data :
HMG-CoA reductase: Ki= 0.6 nM
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
EK7907000
PubChem CID :
53232
Merck Index :
14: 5586
MDL Number :
MFCD00072164
SMILES :
CC[C@H](C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)O)C

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Certificate of Analysis

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Lovastatin  Product Citations

See how others have used Lovastatin. Click on the entry to view the PubMed entry .

Citations 1 to 7 of 7 total

PMID: # 27159577  Shimada, K. et al. 2016. Nature chemical biology. 12: 497-503.

PMID: # 26243146  Meunier, S. et al. 2015. Nature communications. 6: 7889.

PMID: # 10196184  Reimer, CL. et al. 1999. J. Biol. Chem. 274: 11022-11029.

PMID: # 10196184  Reimer, CL. et al. 1999. J. Biol. Chem. 274: 11022-11029.

PMID: # 9653194  De Petrocellis, L. et al. 1998. Proc. Natl. Acad. Sci. USA. 95: 8375-8380.

PMID: # 9341167  Vogt, A. et al. 1997. J. Biol. Chem. 272: 27224-27229.

PMID: # 9341167  Vogt, A. et al. 1997. J. Biol. Chem. 272: 27224-27229.

Citations 1 to 7 of 7 total
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Rated 3 out of 5 by from I use this product often in my research I use this product often in my research. Satisfied.
Date published: 2015-03-20
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