M2147

Mevinolin

≥98% (HPLC), HMG-CoA reductase inhibitor, crystalline powder

• Synonyme(s) : 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
• Formule empirique (notation de Hill) : C₂₄H₃₆O₅
• Numéro CAS: 75330-75-5
• Poids moléculaire : 404.54
• UNSPSC Code: 12161501
• PubChem Substance ID: 24896706
• NACRES: NA.77
• MDL number: MFCD00072164

Propriétés

• Nom du produit: Mevinolin from Aspergillus sp., ≥98% (HPLC)
• Quality Segment: 300
• assay: ≥98% (HPLC)
• form: crystalline powder
• mp: 175.4 °C
• solubility: ethanol: 9.80-10.20 mg/mL, clear, colorless to faintly yellow
• originator: Abbott
• storage temp.: 2-8°C
• 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
• 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
• Gene Information: human ... HMGCR(3156) ; rat ... Hmgcr(25675)

Description

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.

This compound was developed by Abbott. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Informations sur la sécurité

• pictograms: GHS08
• signalword: Warning
• hcodes: H351,H361f
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 2 - Repr. 2
• Classe de stockage: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)