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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H34FNO5
Molecular Weight 459.5503
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CERIVASTATIN

SMILES

COCC1=C(C2=CC=C(F)C=C2)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(N=C1C(C)C)C(C)C

InChI

InChIKey=SEERZIQQUAZTOL-ANMDKAQQSA-N
InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H34FNO5
Molecular Weight 459.5503
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Cerivastatin (BAYCOL®) is a competitive inhibitor of HMG-CoA reductase, which is responsible for the conversion of 3-hydroxy-3-methyl-glutaryl-coenzyme A (HMG-CoA) to mevalonate, a precursor of sterols, including cholesterol. The inhibition of cholesterol biosynthesis by cerivastatin reduces the level of cholesterol in hepatic cells, which stimulates the synthesis of low-density lipoprotein (LDL) receptors, thereby increasing the uptake of cellular LDL particles. The end result of these biochemical processes is a reduction of the plasma cholesterol concentration. On August 8, 2001 the U.S. Food and Drug Administration (FDA) announced that Bayer Pharmaceutical Division voluntarily withdrew BAYCOL® from the U.S. market, due to reports of fatal rhabdomyolysis, a severe adverse reaction from this cholesterol-lowering (lipid-lowering) product. It has also been withdrawn from the Canadian market.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.7 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BAYCOL
Primary
BAYCOL
PubMed

PubMed

TitleDatePubMed
Withdrawal of cerivastatin from the world market.
2001
Preclinical and clinical pharmacology of Rosuvastatin, a new 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor.
2001 Mar 8
Three-dimensional quantitative structure (3-D QSAR) activity relationship studies on imidazolyl and N-pyrrolyl heptenoates as 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitors by comparative molecular similarity indices analysis (CoMSIA).
2005 Feb 15
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Binding thermodynamics of statins to HMG-CoA reductase.
2005 Sep 6
Patents

Sample Use Guides

In Vivo Use Guide
The starting-dose of BAYCOL® is 0.4 mg once daily in the evening regardless of previous lipid therapy. Since the maximal effect of cerivastatin is seen within 4 weeks lipid determinations should be performed at this time and the dose adjusted based upon patient response. Only patients requiring further lipid adjustment should be titrated to 0.8 mg. The dosage range is 0.2 mg to 0.8 mg. Cerivastatin may be taken with or without food.
Route of Administration: Oral
In Vitro Use Guide
Cerivastatin inhibited the membrane-bound (non-solubilized) 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) reductase of the native microsomal fraction isolated from rat liver with a Ki value of 1.3 nM. Cerivastatin inhibited the cholesterol synthesis in the human hepatoma cell line HepG2 cells with a IC50 value of 1.0 nM.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:11:44 UTC 2019
Edited
by admin
on Tue Oct 22 00:11:44 UTC 2019
Record UNII
AM91H2KS67
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CERIVASTATIN
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CERIVASTATIN [HSDB]
Common Name English
CERIVASTATIN [INN]
Common Name English
CERIVASTATIN [MI]
Common Name English
CERIVASTATIN [WHO-DD]
Common Name English
CERIVASTATIN [VANDF]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1655
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
WHO-ATC C10AA06
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
WHO-VATC QC10AA06
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
Code System Code Type Description
WIKIPEDIA
CERIVASTATIN
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
EPA CompTox
145599-86-6
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
PUBCHEM
446156
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
MERCK INDEX
M3262
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY Merck Index
IUPHAR
2950
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
INN
7083
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
MESH
C086276
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
ChEMBL
CHEMBL1477
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
NCI_THESAURUS
C65308
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
CAS
145599-86-6
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
HSDB
145599-86-6
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
EVMPD
SUB07440MIG
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
RXCUI
596723
Created by admin on Tue Oct 22 00:11:44 UTC 2019 , Edited by admin on Tue Oct 22 00:11:44 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE -> PARENT
CYP2C8 accounts for up to 60% of cerivastatin?s oxidation
METABOLITE -> PARENT
CYP3A4 contributes to approximately 40% of mostly M-1 formation
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC