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Details

Stereochemistry RACEMIC
Molecular Formula C24H33FO4
Molecular Weight 404.5148
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of rel-(3R,5S,6E)-7-[2-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-cyclohexen-1-yl]-3,5-dihydroxy-6-heptenoic acid

SMILES

CC1=C(F)C=CC(=C1)C2=C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)C(C)(C)CC(C)(C)C2

InChI

InChIKey=ZZIWKZGLXPJEJV-VUOWKATKSA-N
InChI=1S/C24H33FO4/c1-15-10-16(6-9-21(15)25)19-13-23(2,3)14-24(4,5)20(19)8-7-17(26)11-18(27)12-22(28)29/h6-10,17-18,26-27H,11-14H2,1-5H3,(H,28,29)/b8-7+/t17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H33FO4
Molecular Weight 404.5148
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Dalvastatin is a synthetic HMG-CoA reductase inhibitor developed by Rhône-Poulenc Rorer. Dalvastatin is a prodrug and is itself an inactive lactone. After oral ingestion, the drug is hydrolyzed in vivo to the corresponding beta-hydroxy acid, which is the pharmacologically active form. HMG-CoA reductase is the rate-limiting enzyme in the cholesterol biosynthetic pathway. An active form of dalvastatin inhibits HMG-CoA reductase with IC50 of 3.4 nM. In ex vivo assay, orally administered dalvastatin inhibited cholesterol biosynthesis in rat liver slices with an ED50 value of 0.9. The efficacy of dalvastatin to lower cholesterol was investigated in the clinical trials in the 1990s, but no results were reported.

Approval Year

PubMed

PubMed

TitleDatePubMed
Method for separation and determination of lactone and hydroxy acid forms of a new HMG CoA reductase inhibitor (RG 12561) in plasma.
1991 Jul 5
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:23:21 UTC 2023
Edited
by admin
on Sat Dec 16 20:23:21 UTC 2023
Record UNII
XW8UFD4YLA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
rel-(3R,5S,6E)-7-[2-(4-Fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-cyclohexen-1-yl]-3,5-dihydroxy-6-heptenoic acid
Systematic Name English
6-Heptenoic acid, 7-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-cyclohexen-1-yl]-3,5-dihydroxy-, [R*,S*-(E)]-(±)-
Systematic Name English
6-Heptenoic acid, 7-[2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-1-cyclohexen-1-yl]-3,5-dihydroxy-, (3R,5S,6E)-rel-
Systematic Name English
Dalvastatin active metabolite
Common Name English
Code System Code Type Description
CAS
153042-95-6
Created by admin on Sat Dec 16 20:23:21 UTC 2023 , Edited by admin on Sat Dec 16 20:23:21 UTC 2023
PRIMARY
FDA UNII
XW8UFD4YLA
Created by admin on Sat Dec 16 20:23:21 UTC 2023 , Edited by admin on Sat Dec 16 20:23:21 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
IC50
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE