Synonym
2-hydroxy Atorvastatin (calcium salt); o-hydroxy Atorvastatin; ortho-hydroxy Atorvastatin; BMS 243887-01; PD 152873; PD-152873; PD152873;
IUPAC/Chemical Name
calcium (3R,5R)-7-(2-(4-fluorophenyl)-4-((2-hydroxyphenyl)carbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
InChi Key
NOCWNJZXNVSDOU-LBSXWHBJSA-L
InChi Code
InChI=1S/2C33H35FN2O6.Ca/c2*1-20(2)31-30(33(42)35-26-10-6-7-11-27(26)39)29(21-8-4-3-5-9-21)32(22-12-14-23(34)15-13-22)36(31)17-16-24(37)18-25(38)19-28(40)41;/h2*3-15,20,24-25,37-39H,16-19H2,1-2H3,(H,35,42)(H,40,41);/q;;+2/p-2/t2*24-,25-;/m11./s1
SMILES Code
O=C(C1=C(C(C)C)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C2=CC=C(F)C=C2)=C1C3=CC=CC=C3)NC4=CC=CC=C4O.O=C(C5=C(C(C)C)N(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C6=CC=C(F)C=C6)=C5C7=CC=CC=C7)NC8=CC=CC=C8O.[Ca+2]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
2-Hydroxy atorvastatin calcium salt is a hydroxy metabolite of Atorvastatin calcium salt. Atorvastatin is a potent HMG-CoA reductase inhibitor with an IC50 value of 8 nM.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,187.36
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
TBD
1: Park, J.-E., Kim, K.-B., Bae, S.K., et al. Contribution of cytochrome P450 3A4 and 3A5 to the metabolism of atorvastatin. Xenobiotica 38(9), 1240-1251 (2008).
2: Mason, R.P., Walter, M.F., Day, C.A., et al. Active metabolite of atorvastatin inhibits membrane cholesterol domain formation by an antioxidant mechanism. J. Biol. Chem. 281(14), 9337-9345 (2006).
3: Guirao, V., Martí-Sistac, O., DeGregorio-Rocasolano, N., et al. Specific rescue by ortho-hydroxy atorvastatin of cortical GABAergic neurons from previous oxygen/glucose deprivation: Role of pCREB. J. Neurochem. 143(3), 359-374 (2017).
Boyd, R. A., Stern, R. H., Stewart, B. H., Wu, X., Reyner, E. L., Zegarac, E. A., ... & Whitfield, L. (2000). Atorvastatin coadministration may increase digoxin concentrations by inhibition of intestinal P‐glycoprotein‐mediated secretion. The Journal of Clinical Pharmacology, 40(1), 91-98.
