U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
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 Sat Dec 16 06:45:08 GMT 2023 , Edited by admin on Sat Dec 16 06:45:08 GMT 2023
PRIMARY
CAS
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
PUBCHEM
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