| Identification | More | [Name]
Mevastatin | [CAS]
73573-88-3 | [Synonyms]
2-methyl-butanoic acid [1s-[1-alpha(r*),7-beta,8-beta(2s*,4s*),8a-beta]]-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2h-pyran-2-yl)ethyl]-1-naphthalenyl ester
(2S)-2-METHYL-(1S,7S,8S,8AR)-1,2,3,7,8,8A-HEXAHYDRO-7-METHYL-8-[2-[(2R,4R)-TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL]ETHYL]-1-NAPHTHALENYL BUTANOATE
6-DEMETHYLVEVINOLIN
COMPACTIN
CS-500
MEVASTATIN
MEVASTIN
ML-236B
,8-beta(2s*,4s*),8a-beta))-
antibioticml236b
butanoicacid,2-methyl-,1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hy
compactin(penicillium)
droxy-6-oxo-2h-pyran-2-yl)ethyl)-1-naphthalenylester,(1s-(1-alpha(r*),7-beta
ml236blactone
Merastatin
MEVASTATIN 95+%
Compactin, 6-Demethylvevinolin, CS-500, ML-236 B
MEVASTATIN(RG)
2-Methyl-butanoic acid [1S-[1-alpha(R*),7-beta,8-beta(2S*,4S*),8a-beta]]-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester
COMPACTIN (MEVASTATIN) | [EINECS(EC#)]
700-442-0 | [Molecular Formula]
C23H34O5 | [MDL Number]
MFCD05662341 | [Molecular Weight]
390.51 | [MOL File]
73573-88-3.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [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
| [Usage]
A fungal metabolite which is a potent inhibitor of HMG-CoA reductase. | [λmax]
246nm(MeOH)(lit.) | [Merck ]
13,6186 | [BRN ]
1269441 | [InChIKey]
AJLFOPYRIVGYMJ-INTXDZFKSA-N | [CAS DataBase Reference]
73573-88-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
EK7907100
| [F ]
1-8-10 | [HS Code ]
29322090 |
| Hazard Information | Back Directory | [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]
4°C, protect from light | [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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