Mevastatin

Bezeichnung:Mevastatin

CAS-Nr73573-88-3

Englisch Name:Mevastatin

CBNumberCB1388569

SummenformelC23H34O5

Molgewicht390.51

MOL-Datei73573-88-3.mol

Mevastatin physikalisch-chemischer Eigenschaften

Schmelzpunkt	151-153 °C
alpha	D22 +283° (c = 0.48 in acetone)
Siedepunkt	555.0±50.0 °C(Predicted)
Dichte	1.13±0.1 g/cm3(Predicted)
Dampfdruck	0Pa at 25℃
storage temp.	2-8°C
Löslichkeit	DMSO: 20 mg/mL
pka	13.49±0.40(Predicted)
Aggregatzustand	powder
Farbe	white
maximale Wellenlänge (λmax)	246nm(MeOH)(lit.)
Merck	14,6164
BRN	1269441
InChIKey	AJLFOPYRIVGYMJ-INTXDZFKSA-N
CAS Datenbank	73573-88-3(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	T+
R-Sätze:	26/27/28
S-Sätze:	22-24/25-45-36/37/39
WGK Germany	3
RTECS-Nr.	EK7907100
F	1-8-10
HS Code	29322090

Gefahreninformationscode (GHS)

Mevastatin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R26/27/28:Sehr giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Off-White Solid
Verwenden
anti-hyperlipoproteinemic, 3-hydroxy-3-methyl glutaryl coenzyme A (HMG-CoA) reductase inhibitor
Verwenden
antihyperlipidemic, HMGCoA reductase inhibitor
Verwenden
A fungal metabolite which is a potent inhibitor of HMG-CoA reductase.
Verwenden
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.
Allgemeine Beschreibung
Chemical structure: statin
Biologische Aktivität
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.
Lager
Store at RT
läuterung methode
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].
Einzelnachweise
[1] endo a. the discovery and development of hmg-coa reductase inhibitors. journal of lipid research, 1992, 33(11): 1569-1582.

Mevastatin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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