Synonym: 2-Methyl-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester butanoic acid; 6-α-Methylcompactin; Lovastatin; Monacolin K
CAS Number: 75330-75-5
Empirical Formula (Hill Notation): C24H36O5
Molecular Weight: 404.54
MDL Number: MFCD00072164
Linear Formula: C24H36O5
Product Type: Chemical
| assay |
≥98% (HPLC) |
| form |
crystalline powder |
| InChI |
1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1 |
| InChI key |
PCZOHLXUXFIOCF-BXMDZJJMSA-N |
| mp |
175.4 °C |
| originator |
Abbott |
| Quality Level |
300  |
| SMILES string |
[H][C@]12[C@H](C[C@@H](C)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)[C@@H](C)CC |
| solubility |
ethanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow |
| storage temp. |
2-8°C |
| Biochem/physiol Actions: |
Lovastatin is a cholesterol lowering drug and competitive inhibitor of HMG-CoA reductase, a rate limiting enzyme in cholesterol synthesis. Blocks the production of mevalonate, a critical compound in the production of cholesterol and isoprenoids. This product is a substrate of Pgp and CYP3A. It increases cellular resistance to anticancer agents such as doxorubicin and induces apoptosis in myeloma cells. The roles of Pgp and CYP3A, possible connection between drug resistance, regulation of the mevalonate pathway, and iosprenylation of signaling proteins in these observations remain to be resolved. The product induces apoptosis in numerous cancer cell lines perhaps, in part, by inhibiting the isoprenylation of Rho family GTPases. It causes cell cycle arrest in G1 and G2/M phases. |
| Features and Benefits: |
This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm . |
| Features and Benefits: |
This compound was developed by Abbott . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here . |
| Packaging: |
25 mg in glass bottle |
| Purity |
≥98% (HPLC) |
| mp |
175.4 °C |
| Storage Temp. |
2-8°C |
| UNSPSC |
12161501 |
GHS08