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
[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=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
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 |
---|---|---|
Biotransformation of pravastatin sodium in humans. | 1991 Jul-Aug |
|
Accumulation of lovastatin, but not pravastatin, in the blood of cyclosporine-treated kidney graft patients after multiple doses. | 1997 Sep |
|
Clinical pharmacokinetics of pravastatin: mechanisms of pharmacokinetic events. | 2000 Dec |
|
Liquid chromatography-tandem mass spectrometric assay for pravastatin and two isomeric metabolites in mouse plasma and tissue homogenates. | 2010 Oct 15 |
|
Single-step fermentative production of the cholesterol-lowering drug pravastatin via reprogramming of Penicillium chrysogenum. | 2015 Mar 3 |
Patents
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
R76ZW7E32P
Created by
admin on Sat Dec 16 06:45:08 GMT 2023 , Edited by admin on Sat Dec 16 06:45:08 GMT 2023
|
PRIMARY | |||
|
250737-12-3
Created by
admin on Sat Dec 16 06:45:08 GMT 2023 , Edited by admin on Sat Dec 16 06:45:08 GMT 2023
|
PRIMARY | |||
|
10071008
Created by
admin on Sat Dec 16 06:45:08 GMT 2023 , Edited by admin on Sat Dec 16 06:45:08 GMT 2023
|
PRIMARY |
METABOLITE INACTIVE (PARENT)
SUBSTANCE RECORD