Fluvastatin, (3R,5S)-
Basic information
- CAS
155229-75-7- Standard SMILES
CC(C)n1c(/C=C/[C@@H](O)C[C@@H](O)CC(=O)O)c(-c2ccc(F)cc2)c2ccccc21- InChIKey
FJLGEFLZQAZZCD-MCBHFWOFSA-N- Molecular formula
- C24H26FNO4
- Average molar mass
- 411.5 g/mol
- Monoisotopic mass
- 411.18458647
Overview
(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.
Names & identifiers
- Preferred name
- Fluvastatin, (3R,5S)-
- IUPAC
- (E,3R,5S)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoic acid
- English name
- (+)-3R,5S-FLUVASTATIN SODIUM SALT
- Molecular formula
- C24H26FNO4
- Molecular weight
- 411.47
Names & synonyms
(3R,5S)-fluvastatin155229-75-7(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acidFluvastatin, (3R,5S)-2PW4S9RUR4CHEBI:38565DTXSID201020962(3R,5S,6E)-7-(3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoic acidRefChem:69316DTXCID00636(+)-3R,5S-Fluvastatin sodium salt(+)-(3R,5S)-fluvastatin
Show more names
5S)-XU 62-320 free acid(+)-3R,5S-Fluvastatin-d6 sodiuM salt(3R,5S,6E)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic acid6-Heptenoic acid, 7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-, (3R,5S,6E)-
(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acid(3R,5S,E)-7-(3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoic acid(3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoic acidCHEMBL1078(E,3R,5S)-7-[3-(4-fluorophenyl)-1-isopropyl-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acidC24H26FNO4Fluvastatin & PrimycinXU 62-320 (free acid)
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 82.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 8
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 590
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Statins
Pharmaceuticals -> Used in Switzerland
Collision Cross Section
202.95 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
200.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 150 °C · >150°C (dec.)
- Boiling point
- 681.8 · 681.8±55.0 °C(Predicted)
- Density
- 1.23 · 1.23
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO, Methanol, Water
- pka
- 4.27 · 4.27±0.10(Predicted)
- form
- Solid
- color
- Pale Yellow
Chemistry & industry
Pharmacology
ATC CodeC10AA04
Applications
UsesA synthetic HMG-CoA reductase inhibitor. Antilipemic.This compound contains residual sodium chloride which is quantified on the certificate of analysis.
Additional notes
DefinitionChEBI: (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.
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