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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H34O6
Molecular Weight 406.5125
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PRAVASTATIN LACTONE

SMILES

[H][C@]12[C@H](C[C@H](O)C=C1C=C[C@H](C)[C@@H]2CC[C@@H]3C[C@@H](O)CC(=O)O3)OC(=O)[C@@H](C)CC

InChI

InChIKey=OQARDMYXSOFTLN-PZAWKZKUSA-N
InChI=1S/C23H34O6/c1-4-13(2)23(27)29-20-11-16(24)9-15-6-5-14(3)19(22(15)20)8-7-18-10-17(25)12-21(26)28-18/h5-6,9,13-14,16-20,22,24-25H,4,7-8,10-12H2,1-3H3/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1

HIDE SMILES / InChI
Pravastatin Lactone is a metabolite of pravastatin. Pravastatin is HMG-CoA reductase inhibitor and it is primarily used for the treatment of dyslipidemia and the prevention of cardiovascular disease. Pravastatin and pravastatin-lactone uptake is liver cell specific. Pravastatin-lactone uptake into isolated rat liver cells is carrier mediated. The mutual competitive transport inhibition of bile acids and pravastatin and pravastatin-lactone in sodium-free medium indicates that these compounds share a common transport system. Pravastatin lactone, based on its lipophilicity, showed a high myotoxic potential.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Hepatoselective carrier-mediated sodium-independent uptake of pravastatin and pravastatin-lactone.
1993 Nov 21
Grapefruit juice increases serum concentrations of atorvastatin and has no effect on pravastatin.
1999 Aug
Quantitative determination of pravastatin and its biotransformation products in human serum by turbo ion spray LC/MS/MS.
2000 Oct
Effects of grapefruit juice on pharmacokinetics of atorvastatin and pravastatin in Japanese.
2004 Apr
Statin induced myotoxicity: the lactone forms are more potent than the acid forms in human skeletal muscle cells in vitro.
2008 Apr 23
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Pravastatin-lactone is not accumulated into AS-30D ascites hepatoma cells, FAO cells or fibroblasts. Pravastatin-lactone uptake rates were 1053 pmol/mg per min for hepatocytes, 2 pmol/mg per min for AS-30D ascites cells and 10 pmol/mg per rain for fibroblasts.
Name Type Language
PRAVASTATIN LACTONE
Common Name English
PRAVASTATIN SODIUM IMPURITY, PRAVASTATIN LACTONE- [USP IMPURITY]
Common Name English
(+)-PRAVASTATIN LACTONE
Systematic Name English
BUTANOIC ACID, 2-METHYL-, (1S,3S,7S,8S,8AR)-1,2,3,7,8,8A-HEXAHYDRO-3-HYDROXY-7-METHYL-8-(2-((2R,4R)-TETRAHYDRO-4-HYDROXY-6-OXO-2H-PYRAN-2-YL)ETHYL)-1-NAPHTHALENYL ESTER, (2S)-
Systematic Name English
PRAVASTATIN SODIUM IMPURITY D [EP IMPURITY]
Common Name English
SQ-31369
Code English
(1S,3S,7S,8S,8AR)-3-HYDROXY-8-(2-((2R,4R)-4-HYDROXY-6-OXOTETRAHYDRO-2H-PYRAN-2-YL)ETHYL)-7-METHYL-1,2,3,7,8,8AHEXAHYDRONAPHTHALEN-1-YL (2S)-2-METHYLBUTANOATE
Systematic Name English
R-414
Code English
Code System Code Type Description
PUBCHEM
9931182
Created by admin on Sat Dec 16 08:43:09 GMT 2023 , Edited by admin on Sat Dec 16 08:43:09 GMT 2023
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CAS
85956-22-5
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
EPA CompTox
DTXSID70235286
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
JBE3Z4192Q
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