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atorvastatin

File:Atorvastatin.svg · Wikimedia Commons · See Wikimedia Commons

EntityQ668093· pop 44· linked from 248 articles

atorvastatin

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Also known as (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid, LCF872

Atorvastatin, sold under the brand name Lipitor among others, is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels. For the prevention of cardiovascular disease, statins are a first-line treatment in reducing cholesterol. It is taken by mouth.

OverviewAI-generated

Atorvastatin is a chemical compound with the formula C₃₃H₃₅FN₂O₅. Its IUPAC name is (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid. The substance has a mass of 558.253 and a weight of 558.6. It carries a defined daily dose of 20.

Physicochemical properties include an xlogp of 5 and a topological polar surface area of 112. The molecule contains four hydrogen bond donors and six hydrogen bond acceptors, with a charge of 0. Atorvastatin is referenced by 248 other encyclopedia articles.

Synthesized by Vinony from 19 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

Key facts

Drug.legal_UK
POM
Drug.Watchedfields
changed
Drug.verifiedrevid
477861573
Drug.image
Atorvastatin.svg
Drug.image_class
skin-invert-image
Drug.width
275
Drug.image2
Atorvastatin-from-xtal-3D-bs-17.png
Drug.image_class2
bg-transparent
Drug.width2
250
Drug.tradename
Lipitor, others
Drug.MedlinePlus
a600045
Drug.DailyMedID
Atorvastatin
Drug.pregnancy_AU
D
Drug.pregnancy_category
Contraindicated
Drug.routes_of_administration
By mouth
Drug.class
Hypolipidemic agent
Drug.ATC_prefix
C10
Drug.ATC_suffix
AA05

via Wikipedia infobox

Chemical data

Formula
C33H35FN2O5
Molecular weight
558.6 g/mol
IUPAC name
(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid
SMILES
CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
InChIKey
XUKUURHRXDUEBC-KAYWLYCHSA-N
XLogP
5
Polar surface area
112 Ų
H-bond donors
4
H-bond acceptors
6
Formal charge
0

via PubChem

~23 min read

Encyclopedic overview

32 sections
Contents
  • Medical uses
  • Dyslipidemia
  • Cardiovascular disease
  • Kidney disease
  • Administration
  • Specific populations
  • Contraindications
  • Side effects
  • Major
  • Common
  • Other
  • Increased fasting blood glucose
  • Cognitive
  • Pancreatitis
  • Erectile dysfunction
  • Interactions
  • Mechanism of action
  • Pharmacodynamics
  • Pharmacokinetics
  • Absorption
  • Distribution
  • Metabolism
  • Excretion
  • Pharmacogenetics
  • Chemical synthesis
  • History
  • Society and culture
  • Economics
  • Brand names
  • Medication recalls
  • References
  • Further reading

Atorvastatin, sold under the brand name Lipitor among others, is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels. For the prevention of cardiovascular disease, statins are a first-line treatment in reducing cholesterol. It is taken by mouth.

Common side effects may include diarrhea, heartburn, nausea, muscle pain (typically mild and dose-dependent) and, less frequently, joint pain. Muscle symptoms often occur during the first year and are commonly influenced by pre-existing health issues and the nocebo effect. Most patients can continue therapy with dose adjustment or statin switching. Rare (3.75 mmol/L), findings are inconsistent and potentially misleading. Evidence suggests that LDL-C levels are not a reliable predictor of mortality in the hemodialysis population given the complex interplay of patient factors in ESRD. Therefore, LDL-C levels cannot be considered a true predictor of composite risk. Additionally, the impact and relevance of hemodialysis on statin levels and efficacy were not addressed in these trials. Liver impairment: Increased drug levels can be seen in people with advanced cirrhosis. Despite these concerns, a 2017 systematic review and analysis of available evidence has shown that statins, such as atorvastatin, are relatively safe to use in stable, asymptomatic cirrhosis and may even reduce the risk of liver disease progression and death.

Excerpted from Wikipedia’s “atorvastatin” article, available under the CC BY-SA 4.0 licence.

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