Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H35O7.Na |
Molecular Weight | 446.5096 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12[C@H](C[C@@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H](O)C[C@@H](O)CC([O-])=O)OC(=O)[C@@H](C)CC
InChI
InChIKey=VWBQYTRBTXKKOG-QUJYXMMOSA-M
InChI=1S/C23H36O7.Na/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28;/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28);/q;+1/p-1/t13-,14-,16+,17-,18+,19-,20-,22-;/m0./s1
6'-Epipravastatin is a secondary isomeric metabolite of pravastatin. Pravastatin, one of the 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase inhibitors (statins) widely used in the management of hypercholesterolaemia, has unique pharmacokinetic characteristics among the members of this class. The major metabolites of Pravastatin found in plasma, urine and feces are 3′α-isopravastatin, 3′α,5′β-dihydroxy-pravastatin, desacyl-dehydropravastatin, 3′′-hydroxy-pravastatin and 6′-epipravastatin. The major pravastatin metabolites are generated by non-CYP-dependent processes: 3alpha-isopravastatin and metabolite 6-epipravastatin are either formed by acidic degradation of pravastatin in the stomach or by sulfation at the 6’beta-hydroxy group by sulfotransferases, followed by a nucleophilic attack of hydroxy anions at the 3alpha- or 6’alpha-position.
Approval Year
PubMed
Title | Date | PubMed |
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Biotransformation of pravastatin sodium in humans. | 1991 Jul-Aug |
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Accumulation of lovastatin, but not pravastatin, in the blood of cyclosporine-treated kidney graft patients after multiple doses. | 1997 Sep |
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Single-step fermentative production of the cholesterol-lowering drug pravastatin via reprogramming of Penicillium chrysogenum. | 2015 Mar 3 |
Patents
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42630641
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1554228
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81176-41-2
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K4A67XJY6V
Created by
admin on Sat Dec 16 08:43:09 GMT 2023 , Edited by admin on Sat Dec 16 08:43:09 GMT 2023
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SUBSTANCE RECORD