Lovastatin

Structural formula
General
Non-proprietary name	Lovastatin
other names	Mevinolin; Monacolin-K; MK-803; [(1 S , 3 R , 7 S , 8 S , 8a R ) -8- [2 - [(2 R , 4 R ) -4-hydroxy-6-oxooxan-2-yl] ethyl] -3.7 -dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2 S ) -2-methylbutanoate;
Molecular formula	C 24 H 36 O 5
Brief description	colorless crystals
External identifiers / databases
EC number	616-212-7
ECHA InfoCard	100.115.931
PubChem	53232
DrugBank	DB00227
Wikidata	Q417740
Drug information
ATC code	C10 AA02
Drug class	Statins
Mechanism of action	HMG-CoA reductase - inhibitor
properties
Molar mass	404.54 g mol −1
Physical state	firmly
Melting point	174.5 ° C
solubility	almost insoluble in water (2.14 mg l −1 at 25 ° C); Slightly soluble in ethanol , soluble in chloroform and acetone ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	> 1000 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lovastatin is the generic name of a drug from the group of statins , which for the treatment of hypercholesterolemia is used. It was the first statin used in lipid lowering and was approved for the US market by the FDA as Mevacor in 1987 , and in 1989 in Germany.

Lovastatin belongs to the naturally occurring monacolins and is produced by the molds Aspergillus terreus and Monascus ruber , as well as by certain higher fungi such as Pleurotus ostreatus (oyster mushroom) and the closely related Pleurotus spp. produced. For example, it is contained in red fermented rice (“red mold rice”), a traditional Chinese food , along with a number of other monacolins .

As with all statins, its effect as a lipid-lowering agent is based on the inhibition of HMG-CoA reductase .

Lovastatin was one of the statins that MSD began its first (animal) studies with in 1980. However, since Sankyo discontinued a study with the almost structurally identical mevastatin due to an increased occurrence of side effects, MSD also terminated the studies for the time being.

Arthur A. Patchett played a key role in the development of MSD .

Manufacturing

For use as a medicinal substance, lovastatin is obtained from Aspergillus terreus and Monascus ruber in a multi-stage fermentation process; the total synthesis is also described.

stability

Lovastatin is susceptible to oxidation and can be stabilized by adding antioxidants .

unwanted effects

As with other statins, possible side effects include upper abdominal discomfort, increased transaminases, and myopathies.

Trade names

Monopreparations

Mevacor (A), Mevinacor (D), numerous generics

Individual evidence

↑ ^a ^b ^c Entry on lovastatin. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
↑ ^a ^b Entry on lovastatin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b data sheet Mevinolin from Aspergillus sp. at Sigma-Aldrich , accessed April 8, 2011 ( PDF ).
↑ Product information Mevinacor 20 mg / 40 mg; As of September 2010.
↑ K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 7.4, Lovastatin. Loose-leaf collection, 40th delivery 2012, Wissenschaftliche Verlagsgesellschaft Stuttgart.
↑ Javernik, S., Kreft, S., Štrukelj, B., Vrečer, F. (2001). Oxidation of lovastatin in the solid state and its stabilization with natural antioxidants. Pharmazie, 56, 9: 738-740, PMID 11593996 .
↑ Richard Daikeler, idols Use, Sylke Waibel: diabetes. Evidence-based diagnosis and therapy. 10th edition. Kitteltaschenbuch, Sinsheim 2015, ISBN 978-3-00-050903-2 , p. 149.

[Römpp-1] Entry on lovastatin. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[ChemIDplus-2] Entry on lovastatin in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-3] ta sheet Mevinolin from Aspergillus sp. at Sigma-Aldrich , accessed April 8, 2011 ( PDF ).

[4] Product information Mevinacor 20 mg / 40 mg; As of September 2010.

[5] K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 7.4, Lovastatin. Loose-leaf collection, 40th delivery 2012, Wissenschaftliche Verlagsgesellschaft Stuttgart.

[6] Javernik, S., Kreft, S., Štrukelj, B., Vrečer, F. (2001). Oxidation of lovastatin in the solid state and its stabilization with natural antioxidants. Pharmazie, 56, 9: 738-740, PMID 11593996 .

[7] Richard Daikeler, idols Use, Sylke Waibel: diabetes. Evidence-based diagnosis and therapy. 10th edition. Kitteltaschenbuch, Sinsheim 2015, ISBN 978-3-00-050903-2 , p. 149.