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(3R,5S) -Fluvastatin

CAT: 0804-HY-14664BSize: 1 EachDry Ice: NoHazardous: No
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Description
(3R,5S) -Fluvastatin is the 3R,5S-isomer Fluvastatin. Fluvastatin (XU 62-320 free acid) is a first fully synthetic, competitive HMG-CoA reductase inhibitor with an IC50 of 8 nM. Fluvastatin protects vascular smooth muscle cells against oxidative stress through the Nrf2-dependent antioxidant pathway[1][2][3].
CAS Number
155229-75-7
Product Name Alternative
(3R,5S) -XU 62-320 (free acid)
UNSPSC
12352005
Hazard Statement
H302-H312-H332
Target
Autophagy; HMG-CoA Reductase (HMGCR)
Type
Reference compound
Related Pathways
Autophagy; Metabolic Enzyme/Protease
Applications
Cancer-programmed cell death
Field of Research
Cancer; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/3r-5s-fluvastatin.html
Solubility
10 mM in DMSO
Smiles
O=C(O)C[C@H](O)C[C@H](O)/C=C/C(N1C(C)C)=C(C2=CC=C(F)C=C2)C3=C1C=CC=C3
Molecular Formula
C24H26FNO4
Molecular Weight
411.47
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501
References & Citations
[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.|[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]Makabe S, et al. Fluvastatin protects vascular smooth muscle cells against oxidative stress through the Nrf2-dependent antioxidant pathway. Atherosclerosis. 2010 Dec;213 (2) :377-84.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Fluvastatin, (3R,5S)-

(3R,5S)-fluvastatin is a (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid diastereoisomer in which the stereocentres beta- and delta- to the carboxy group have R and S configuration, respectively. The drug fluvastatin is an equimolar mixture of this compound and its enantiomer. It is a (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid and a statin (synthetic). It is a conjugate acid of a (3R,5S)-fluvastatin(1-). It is an enantiomer of a (3S,5R)-fluvastatin.

CAS Number155229-75-7
PubChem CID446155
IUPAC Name(E,3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid
Molecular FormulaC24H26FNO4
Molecular Weight411.5
XLogP3.5
Topological Polar Surface Area82.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Heavy Atom Count30
Formal Charge0
Complexity590
SMILES
CC(C)N1C2=CC=CC=C2C(=C1/C=C/[C@H](C[C@H](CC(=O)O)O)O)C3=CC=C(C=C3)F
InChI
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-/m1/s1
InChIKey
FJLGEFLZQAZZCD-MCBHFWOFSA-N
Chemical Structure
2D Structure
2D structure of Fluvastatin, (3R,5S)-
CAS: 155229-75-7
CID: 446155
Formula: C24H26FNO4
MW: 411.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight411.5
XLogP33.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass411.18458647
Monoisotopic Mass411.18458647
Topological Polar Surface Area82.7 Ų
Heavy Atom Count30
Formal Charge0
Complexity590
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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