Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H36O7 |
| Molecular Weight | 424.5277 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H](C)C(=O)O[C@H]1C[C@@H](O)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@@H]12
InChI
InChIKey=TUZYXOIXSAXUGO-PZSHMICQSA-N
InChI=1S/C23H36O7/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)/t13-,14-,16+,17-,18+,19-,20-,22-/m0/s1
| Molecular Formula | C23H36O7 |
| Molecular Weight | 424.5277 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 8 / 8 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Single-step fermentative production of the cholesterol-lowering drug pravastatin via reprogramming of Penicillium chrysogenum. | 2015-03-03 |
|
| Liquid chromatography-tandem mass spectrometric assay for pravastatin and two isomeric metabolites in mouse plasma and tissue homogenates. | 2010-10-15 |
|
| Clinical pharmacokinetics of pravastatin: mechanisms of pharmacokinetic events. | 2000-12 |
|
| Accumulation of lovastatin, but not pravastatin, in the blood of cyclosporine-treated kidney graft patients after multiple doses. | 1997-09 |
|
| Biotransformation of pravastatin sodium in humans. | 1991-07-01 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:38:05 GMT 2025
by
admin
on
Mon Mar 31 21:38:05 GMT 2025
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| Record UNII |
R76ZW7E32P
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| Record Status |
Validated (UNII)
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| Record Version |
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R76ZW7E32P
Created by
admin on Mon Mar 31 21:38:05 GMT 2025 , Edited by admin on Mon Mar 31 21:38:05 GMT 2025
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250737-12-3
Created by
admin on Mon Mar 31 21:38:05 GMT 2025 , Edited by admin on Mon Mar 31 21:38:05 GMT 2025
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10071008
Created by
admin on Mon Mar 31 21:38:05 GMT 2025 , Edited by admin on Mon Mar 31 21:38:05 GMT 2025
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METABOLITE INACTIVE -> PARENT |
MAJOR
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PARENT -> IMPURITY |