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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
Structure of 6-EPI-PRAVASTATIN SODIUM

SMILES

[Na+].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=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

HIDE SMILES / InChI
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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
PRAVASTATIN RELATED COMPOUND B
USP-RS  
Preferred Name English
6-EPI-PRAVASTATIN SODIUM
Common Name English
1-NAPHTHALENEHEPTANOIC ACID, 1,2,6,7,8,8A-HEXAHYDRO-.BETA.,.DELTA.,6-TRIHYDROXY-2-METHYL-8-((2S)-2-METHYL-1-OXOBUTOXY)-, SODIUM SALT (1:1), (.BETA.R,.DELTA.R,1S,2S,6R,8S,8AR)-
Systematic Name English
6-EPI-PRAVASTATIN SODIUM SALT
Common Name English
PRAVASTATIN RELATED COMPOUND B [USP-RS]
Common Name English
SQ-31360
Code English
Code System Code Type Description
PUBCHEM
42630641
Created by admin on Mon Mar 31 22:16:17 GMT 2025 , Edited by admin on Mon Mar 31 22:16:17 GMT 2025
PRIMARY
RS_ITEM_NUM
1554228
Created by admin on Mon Mar 31 22:16:17 GMT 2025 , Edited by admin on Mon Mar 31 22:16:17 GMT 2025
PRIMARY
CAS
81176-41-2
Created by admin on Mon Mar 31 22:16:17 GMT 2025 , Edited by admin on Mon Mar 31 22:16:17 GMT 2025
PRIMARY
FDA UNII
K4A67XJY6V
Created by admin on Mon Mar 31 22:16:17 GMT 2025 , Edited by admin on Mon Mar 31 22:16:17 GMT 2025
PRIMARY