Fluvastatin

Names

[ Name ]:
Fluvastatin

[Synonym ]:
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid
UNII:4L066368AS
fluvastatin
6-Heptenoic acid, 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-, (3R,5S,6E)-
FLUVASTATIN NA
Lipaxan
MFCD00929076
(3R,5S,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid
Lescol
(3R,5S,6E)-rel-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid
(3S,5R,6E)-7-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid
(±)-(3R*,5S*,6E)-7-[3-(p-fluorophenyl)-1-isopropylindol-2-yl]-3,5-dihydroxy-6-heptenoate
6-Heptenoic acid, 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-, (3S,5R,6E)-
FLUVASTATIN SODIUM
Primexin

Biological Activity

[Description]:

Fluvastatin (Leschol) inhibits HMG-CoA reductase activity with IC50 of 8 nM.IC50 value: 8 nMTarget: HMG-CoA reductaseFluvastatin is a competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase (HMGCR), the enzyme that catalyzes the conversion of HMG-CoA to mevalonic acid, the rate-limiting step in cholesterol biosynthesis. Human hepatocellular carcinoma cell (HCC) studies indicate that Fluvastatin induces G2/M phase arrest. In the presence of Fluvastatin, HCC cells show a decrease of Bcl-2 and procaspase-9 expression, and an increase in Bax, cleaved caspase-3, and cytochrome c. Fluvastatin is antilipemic and is used to reduce plasma cholesterol levels and prevent cardiovascular disease.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> HMG-CoA Reductase (HMGCR)

Research Areas >> Cardiovascular Disease

[References]

[1]. Araújo FA, Rocha MA, Capettini LS, et al. 3-Hydroxy-3-methylglutaryl coenzyme A reductase inhibitor (fluvastatin) decreases inflammatory angiogenesis in mice. APMIS. 2012 24. [Epub ahead of print]

[2]. Makabe S, Takahashi Y, Watanabe H, et al. Fluvastatin protects vascular smooth muscle cells against oxidative stress through the Nrf2-dependent antioxidant pathway. Atherosclerosis. 2010 Dec;213(2):377-84.

[3]. Zhang W, Wu J, Zhou L, et al. Fluvastatin, a lipophilic statin, induces apoptosis in human hepatocellular carcinoma cells through mitochondria-operated pathway. Indian J Exp Biol. 2010 Dec;48(12):1167-74.

[4]. Scripture CD, Pieper JA. Clinical pharmacokinetics of fluvastatin. Clin Pharmacokinet. 2001;40(4):263-81.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
681.8±55.0 °C at 760 mmHg

[ Melting Point ]:
194-197ºC

[ Molecular Formula ]:
C₂₄H₂₆FNO₄

[ Molecular Weight ]:
411.466

[ Flash Point ]:
366.1±31.5 °C

[ Exact Mass ]:
411.184601

[ PSA ]:
82.69000

[ LogP ]:
3.62

[ Vapour Pressure ]:
0.0±2.2 mmHg at 25°C

[ Index of Refraction ]:
1.587

[ Storage condition ]:
2-8℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MJ9675050

CHEMICAL NAME :: 6-Heptenoic acid, 7-(3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl )- 3,5-dihydroxy-, (R*,S*-(E))-(+-)-

CAS REGISTRY NUMBER :: 93957-54-1

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C24-H26-F-N-O4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 11648 mg/kg/2Y-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other Enzymes

REFERENCE :: LETRET Lens and Eye Toxicity Research. (Marcel Dekker, Journal Customer Service, POB 5017, Monticello, NY 12701) V.6n.1-2- 1989- Volume(issue)/page/year: 7,563,1990

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38:Irritating to eyes, respiratory system and skin . R42/43:May cause sensitization by inhalation and skin contact .

[ Safety Phrases ]:
S23-S26-S37

[ RIDADR ]:
UN 3272 3/PG 3

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
3

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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