Mevastatin

Modify Date: 2025-08-23 22:33:09

Mevastatin Structure
Mevastatin structure
Common Name Mevastatin
CAS Number 73573-88-3 Molecular Weight 390.513
Density 1.1±0.1 g/cm3 Boiling Point 555.0±50.0 °C at 760 mmHg
Molecular Formula C23H34O5 Melting Point 151-153 °C
MSDS Chinese USA Flash Point 186.5±23.6 °C

 Use of Mevastatin


Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer.

 Names

Name mevastatin
Synonym More Synonyms

 Mevastatin Biological Activity

Description Mevastatin (Compactin; ML236B) inhibits HMGCR (HMG-CoA reductase) (Ki for acid form is 1 nM) which in turn inhibits isoprenoid biosynthesis and therefore blocks protein isoprenylation and reduces plasma cholesterol levels in humans. IC50 value: 1 nM (Ki)Target: HMGCRMevastatin induces apoptosis, arrests cancer cells in G1 phase and downregulates cdk 2, 4, and 6, cyclin D1 and E1, p21 and p27. Mevastatin suppresses TNF-induced NF-κB activation (IC50 = ~17 uM), which potentiates apoptosis in human myeloid leukemia cells and thus, may be useful in treating cancer.
Related Catalog
References

[1]. Sugazaki M, Hirotani H, Echigo S, et al. Effects of mevastatin on grafted bone in MRL/MpJ mice. Connect Tissue Res. 2010 Apr;51(2):105-12. doi: 10.3109/03008200903105098.

[2]. Evangelopoulos ME, Weis J, Krüttgen A. Mevastatin-induced neurite outgrowth of neuroblastoma cells via activation of EGFR. J Neurosci Res. 2009 Jul;87(9):2138-44. doi: 10.1002/jnr.22025.

[3]. W?chtersh?user A, Akoglu B, Stein J. HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2. Carcinogenesis. 2001 Jul;22(7):1061-7.

[4]. Amin-Hanjani S, Stagliano NE, Yamada M, et al. Mevastatin, an HMG-CoA reductase inhibitor, reduces stroke damage and upregulates endothelial nitric oxide synthase in mice. Stroke. 2001 Apr;32(4):980-6.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 555.0±50.0 °C at 760 mmHg
Melting Point 151-153 °C
Molecular Formula C23H34O5
Molecular Weight 390.513
Flash Point 186.5±23.6 °C
Exact Mass 390.240631
PSA 72.83000
LogP 3.57
Vapour Pressure 0.0±3.4 mmHg at 25°C
Index of Refraction 1.535
Storage condition 2-8°C
Water Solubility DMSO: 20 mg/mL

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EK7907100
CHEMICAL NAME :
Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hy droxy-6-oxo-2H-pyran- 2-yl)ethyl)-1-naphthalenyl ester, (1S-(1-alpha(R*),7-beta,8-beta(2S*,4S*),8a-beta))-
CAS REGISTRY NUMBER :
73573-88-3
LAST UPDATED :
199212
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C23-H34-O5
MOLECULAR WEIGHT :
390.57

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 29,1346,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 29,1346,1976

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes T+
Risk Phrases R26/27/28
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS EK7907100

 Synthetic Route

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 Synonyms

ML 236B
Mevastatinum [INN-Latin]
mevastatin
Compactin (penicillium)
Antibiotic ML 236B
L66 AU IUTJ EOVY2&1 H1 G2- FT6OVTJ DQ &&stereoisomer
Mevastatin (Compactin)
MFCD05662341
Statin I
[(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
(+)-Compactin
ML 236 B
(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-1-naphthalenyl (2S)-2-methylbutanoate
Butanoic acid, 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 ester, (2S)-
2b-Methyl-8a-(2-methyl-1-oxobutoxy)mevinic acid lactone
ML-236B
(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
7-[1,2,6,7,8,8a-Hexahydro-2-methyl-8-(methylbutyryloxy)naphthyl]-3-hydroxyheptan-5-olide
[1S-[1a(R*),7b,8b(2S*,4S*),8ab]]-2-Methylbutanoic acid 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
Lovastatin Impurity 1
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