ChemFOnt: Showing chemical card for Fluvastatin (CFc000009515)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:40 UTC

Chemfont ID

CFc000009515

Molecule Identification

Common Name

Fluvastatin

Definition

Fluvastatin is an antilipemic agent that competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase. HMG-CoA reducuase catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Fluvastatin belongs to a class of medications called statins and is used to reduce plasma cholesterol levels and prevent cardiovascular disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(3S,5R)-Fluvastatin	ChEBI
(3S,5R)-(-)-Fluvastatin	ChEBI
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid	ChEBI
Fluvas	Kegg
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate	Generator
Fluindostatin	HMDB
Fluvastatin sodium salt	HMDB
Fluvastatin sodium	HMDB
7-(3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl)-3,5-dihydroxy-6-heptenoate	HMDB
Lescol	HMDB

Chemical Formula

C₂₄H₂₆FNO₄

Average Molecular Weight

411.4659

Monoisotopic Molecular Weight

411.18458653

IUPAC Name

(3S,5R,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid

Traditional Name

fluvastatin

CAS Registry Number

93957-54-1

SMILES

CC(C)N1C(\C=C\[C@H](O)C[C@H](O)CC(O)=O)=C(C2=CC=C(F)C=C2)C2=CC=CC=C12

InChI Identifier

InChI=1S/C24H26FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,18-19,27-28H,13-14H2,1-2H3,(H,29,30)/b12-11+/t18-,19-/m0/s1

InChI Key

FJLGEFLZQAZZCD-JUFISIKESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrroles. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrole ring through a CC or CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroles

Sub Class

Substituted pyrroles

Direct Parent

Phenylpyrroles

Alternative Parents

Substituents

3-phenylpyrrole
N-alkylindole
Indole
Indole or derivatives
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Fluorobenzene
Halobenzene
Halogenated fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Aryl fluoride
Aryl halide
Monocyclic benzene moiety
Hydroxy acid
Fatty acyl
Fatty acid
Benzenoid
Unsaturated fatty acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organohalogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

statin (synthetic) (CHEBI:5136 )
(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid (CHEBI:5136 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015227)

Source

Exogenous

Exogenous (HMDB: HMDB0015227)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Fluvastatin Action Pathway (PathBank: SMP0000119)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	3.69	ALOGPS
logP	3.83	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.56	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.69 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.86 m³·mol⁻¹	ChemAxon
Polarizability	44.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon