Mevastatin Chemical Properties

Melting point:

151-153 °C

alpha 

D22 +283° (c = 0.48 in acetone)

Boiling point:

555.0±50.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

vapor pressure 

0Pa at 25℃

storage temp. 

2-8°C

solubility 

DMSO: 20 mg/mL

form 

powder

pka

13.49±0.40(Predicted)

color 

white

λmax

246nm(MeOH)(lit.)

Merck 

14,6164

BRN 

1269441

InChIKey

AJLFOPYRIVGYMJ-INTXDZFKSA-N

CAS DataBase Reference

73573-88-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

T+

Risk Statements 

26/27/28

Safety Statements 

22-24/25-45-36/37/39

WGK Germany 

3

RTECS 

EK7907100

F 

1-8-10

HS Code 

29322090

MSDS

• Language:English Provider:Compactin
• Language:English Provider:SigmaAldrich

Mevastatin Usage And Synthesis

Chemical Properties

Off-White Solid

Uses

A fungal metabolite which is a potent inhibitor of HMG-CoA reductase.

Uses

antihyperlipidemic, HMGCoA reductase inhibitor

Uses

anti-hyperlipoproteinemic, 3-hydroxy-3-methyl glutaryl coenzyme A (HMG-CoA) reductase inhibitor

Uses

Mevastatin (compactin) is a diterpene produced by several species of the genera Penicillium and Monascus, first reported in 1976. Mevastatin, the prtotype of the statin class, is a potent competitive inhibitor of HMG-CoA reductase, a regulatory enzyme for cholesterol biosynthesis. Mevastatin has also been shown to induce apoptosis by inhibiting post-translational prenylation of proteins such as Ras, increasing eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho, and inhibiting myoblast fusion. It induces cell cycle arrest in late G1 phase and may induce bone morphogenic protein-2 (BMP-2).

Definition

ChEBI: A carboxylic ester that is pravastatin that is lacking the allylic hydroxy group and in which the lactone moiety has been hydrolysed to the corresponding delta-hydroxy-carboxylic acid. A hydroxymethylglutaryl-CoA reductase inhibitor (stati ) isolated from Penicillium citrinum and from Penicillium brevicompactum, its clinical use as a lipid-regulating drug ceased following reports of toxicity in animals.

General Description

Chemical structure: statin

Biological Activity

Inhibitor of HMG-CoA reductase; decreases cholesterol biosynthesis, in vitro and in vivo . Induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27.

Biochem/physiol Actions

Mevastatin is a selective inhibitor of 3-hydroxy 3-methyl glutaryl coenzyme(A) reductase (HMG-CoA reductase), a major enzyme involved in cholesterol synthesis. It acts as a cholesterol-lowering agent. Mevastatin is obtained from various species of fungi. It acts as an antiresorptive?agent and has therapeutic effects to treat osteoporosis. Mevastatin inhibits bone resorption by triggering osteoclast apoptosis. It is also involved in the inhibition of prenylation of proteins such as Ras. Mevastatin increases endothelial nitric oxide synthase (eNOS) mRNA and protein levels by blocking the geranylgeranylation of transcription factor Rho.

storage

Store at RT

Purification Methods

Purify compactin by recrystallisation from aqueous EtOH. UV (EtOH): max 230, 237 and 246nm (log  4.28, 4.30 and 4.11); IR (KBr): 3520, 1750 (lactone CO) and 1710 (CO ester) cm-1. [Clive et al. J Am Chem Soc 110 6914 1988, Review: Rosen & Heathcock Tetrahedron 42 4909 1986, IR, NMR, MS: Brown et al. J Chem Soc Perkin Trans 1 1165 1976.] It is a potent inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase (HMG-CoA reductase), an enzyme in cholesterol biosynthesis, and lowers cholesterol levels [Brown et al. J Biol Chem 253 1121 1978, Nakamura & Ableles Biochemistry 24 1364 1985, Beilstein 18/3 V 145].

References

[1] endo a. the discovery and development of hmg-coa reductase inhibitors. journal of lipid research, 1992, 33(11): 1569-1582.

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