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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
Structure of 6'-EPIPRAVASTATIN

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

HIDE SMILES / InChI

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

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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 Thu Jul 06 12:19:20 UTC 2023
Edited
by admin
on Thu Jul 06 12:19:20 UTC 2023
Record UNII
R76ZW7E32P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
6'-EPIPRAVASTATIN
Common Name English
PRAVASTATIN SODIUM IMPURITY, 6'-EPIPRAVASTATIN- [USP IMPURITY]
Common Name English
(3R,5R)-3,5-DIHYDROXY-7-((1S,2S,6R,8S,8AR)-6-HYDROXY-2-METHYL-8-(((2S)-2-METHYLBUTANOYL)OXY)-1,2,6,7,8,8A-HEXAHYDRONAPHTHALEN-1-YL)HEPTANOIC ACID
Systematic Name English
PRAVASTATIN SODIUM IMPURITY A [EP IMPURITY]
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)-, (.BETA.R,.DELTA.R,1S,2S,6R,8S,8AR)-
Systematic Name English
Code System Code Type Description
FDA UNII
R76ZW7E32P
Created by admin on Thu Jul 06 12:19:20 UTC 2023 , Edited by admin on Thu Jul 06 12:19:20 UTC 2023
PRIMARY
CAS
250737-12-3
Created by admin on Thu Jul 06 12:19:20 UTC 2023 , Edited by admin on Thu Jul 06 12:19:20 UTC 2023
PRIMARY
PUBCHEM
10071008
Created by admin on Thu Jul 06 12:19:20 UTC 2023 , Edited by admin on Thu Jul 06 12:19:20 UTC 2023
PRIMARY
Related Record Type Details
METABOLITE INACTIVE -> PARENT
MAJOR
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP