Fluvastatin (CED0003052)

Record Information

Version

1.0

Creation Date

2016-05-22 03:27:12 UTC

Update Date

2026-08-30 22:42:53 UTC

Accession Number

CHEM016315

Identification

Common Name

Fluvastatin

Class

Small Molecule

Description

Fluvastatin is an organic compound with the chemical formula C24H26FNO4 and an average molecular weight of 411.47 g/mol. Fluvastatin belongs to the substituted pyrroles, a subclass of pyrroles within the organic compounds. It is categorized as an organoheterocyclic compound. This substance acts on two recorded protein targets, serving as an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) and histone deacetylase 2 (HDAC2). In terms of application, it is utilized as a lipid modifying agent within healthcare, pharmaceuticals, and veterinary products. Fluvastatin has been identified in eight recorded sources. These include food, food processing, and cookware, specifically in the preparation of vinegar, as well as indoor air, dust, and atmospheric transport. It is also found in electrical and electronic equipment, such as television systems and antennas, and in household cleaning and consumer products, including tobacco product cases, other smoking requisites, and non-electric simulated smoking devices. Recorded routes of exposure for this compound include oral and inhalation.

Contaminant Type

Not Available

Chemical 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 Mass

411.466 g/mol

Monoisotopic Mass

411.185 g/mol

CAS Registry Number

93957-54-1

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

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0006-6229000000-e7e9a4f18c77b8a3f328	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-03g0-9113255000-bbcec21c7d8450380f53	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03xr-0082900000-af0bcdb98404aa7485cd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-0090000000-fbe9d82e356a4c40ed62	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0290000000-4e6800fc8ed4bacd61c7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0190000000-8d3aabcab51b7427b00c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-01b9-0091000000-91a05c153cd55276cb1e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03xr-0064900000-6073674eb901911a6505	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-002f-0009100000-48400cafdfe7b1ae8e91	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fbc-2029000000-d4584fe54d4a4dee073e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0f79-8196000000-fb302f9ef42c788b0d34	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-2009600000-fceb838edec69ac58798	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pi1-6109100000-0037246c25ef1a9001ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-9124000000-574e6db0baf9d8f4ad3b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0007900000-94ec3a6470255ed0e510	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kmj-2009000000-f827f5fc9e84c0d8a8ee	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-01u3-5094000000-5b650479bc088483a8c2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-0019500000-b32ac44df58c44fecd76	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ou-0039000000-533fcd1fe96ff3c27509	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0079-0091000000-fb70ed9366fe79b510e5	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
298.0	Log mg/kg	[170:530]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
19	Indoor air	Air, dust & atmospheric transport	Not Available
298	Lipid modifying agents	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available
567	Tobacco Product Cases	Household cleaning & consumer products	Not Available

Pathways

3 pathways

Fluvastatin Action Pathway

Fluvastatin Action Pathway (New)

Fluvastatin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	3-hydroxy-3-methylglutaryl-coenzyme A reductase	P51639	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	114.361
Click to view 3D structure	Nuclear receptor subfamily 4 group A member 2	P43354	Humans	Predicted (SEA)	0.622794
Click to view 3D structure	Rho-related GTP-binding protein RhoC	P08134	Humans	Predicted (SEA)	0.778492
Click to view 3D structure	Photoreceptor-specific nuclear receptor	Q9Y5X4	Humans	Predicted (SEA)	4.82665
Click to view 3D structure	Tegument protein VP16	P06492	Herpes simplex virus (type 1 / strain 17)	Predicted (SEA)	2.72472
Click to view 3D structure	NAD-dependent protein deacylase sirtuin-6	Q8N6T7	Humans	Predicted (SEA)	1.16774
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	2380.78
Click to view 3D structure	Solute carrier organic anion transporter family member 1B1	Q9Y6L6	Humans	Predicted (SEA)	38.3018
Click to view 3D structure	Broad substrate specificity ATP-binding cassette transporter ABCG2	Q9UNQ0	Humans	Predicted (SEA)	352.579
Click to view 3D structure	Prostaglandin D2 receptor 2	Q9Y5Y4	Humans	Predicted (SEA)	90.6165
Click to view 3D structure	3-hydroxy-3-methylglutaryl-coenzyme A reductase	Q1W675	Sus scrofa	Predicted (SEA)	1.08989
Click to view 3D structure	DNA (cytosine-5)-methyltransferase 1	P13864	Mus musculus	Predicted (SEA)	8.95266
Click to view 3D structure	Cytosolic phospholipase A2	A4IFJ5	Bos taurus	Predicted (SEA)	29.6606
Click to view 3D structure	Macrophage metalloelastase	P39900	Humans	Predicted (SEA)	641.711
Click to view 3D structure	Thromboxane A2 receptor	P21731	Humans	Predicted (SEA)	244.524
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	1230.56
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	475.503
Click to view 3D structure	Caspase-3	P42574	Humans	Predicted (SEA)	641.633
Click to view 3D structure	Prostaglandin G/H synthase 1	P23219	Humans	Predicted (SEA)	606.913
Click to view 3D structure	11-beta-hydroxysteroid dehydrogenase 1	P28845	Humans	Predicted (SEA)	110.234
Click to view 3D structure	Caspase-1	P29452	Mus musculus	Predicted (SEA)	116.54
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	3123.0
Click to view 3D structure	Collagenase 3	P45452	Humans	Predicted (SEA)	1352.55