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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+].[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

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C23H35O7
Molecular Weight 423.5198
Charge -1
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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Liquid chromatography-tandem mass spectrometric assay for pravastatin and two isomeric metabolites in mouse plasma and tissue homogenates.
2010 Oct 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:43:09 GMT 2023
Edited
by admin
on Sat Dec 16 08:43:09 GMT 2023
Record UNII
K4A67XJY6V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
PRAVASTATIN RELATED COMPOUND B [USP-RS]
Common Name English
SQ-31360
Code English
Code System Code Type Description
PUBCHEM
42630641
Created by admin on Sat Dec 16 08:43:09 GMT 2023 , Edited by admin on Sat Dec 16 08:43:09 GMT 2023
PRIMARY
RS_ITEM_NUM
1554228
Created by admin on Sat Dec 16 08:43:09 GMT 2023 , Edited by admin on Sat Dec 16 08:43:09 GMT 2023
PRIMARY
CAS
81176-41-2
Created by admin on Sat Dec 16 08:43:09 GMT 2023 , Edited by admin on Sat Dec 16 08:43:09 GMT 2023
PRIMARY
FDA UNII
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
PRIMARY