CAS 73573-88-3|Mevastatin
| 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 | ChineseUSA | Flash Point | 186.5±23.6 °C |
Names
| Name | mevastatin |
|---|---|
| Synonym | More Synonyms |
Mevastatin BiologicalActivity
| 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 | Signaling Pathways >>Autophagy >>AutophagySignaling Pathways >>Metabolic Enzyme/Protease >>HMG-CoA Reductase (HMGCR)Research Areas >>Cancer |
| 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 |
| InChIKey | AJLFOPYRIVGYMJ-INTXDZFKSA-N |
| SMILES | CCC(C)C(=O)OC1CCC=C2C=CC(C)C(CCC3CC(O)CC(=O)O3)C21 |
| Storage condition | 2-8°C |
| Water Solubility | DMSO: 20 mg/mL |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
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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 |
