Atorvastatin

Atorvastatin
Clinical data
Pronunciation	/əˌtɔːrvəˈstætən/
Trade names	Lipitor, others
AHFS/Drugs.com	Monograph
MedlinePlus	a600045
License data	US DailyMed: Atorvastatin;
Pregnancy; category	AU: D; Contraindicated;
Routes of; administration	By mouth
ATC code	C10AA05 (WHO) C10BX08 (WHO) C10BX03 (WHO) C10BA05 (WHO) C10BA08 (WHO) C10BX15 (WHO) C10BX12 (WHO) C10BX06 (WHO) C10BX11 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only"Lipitor". European Medicines Agency. 17 September 2018. Retrieved 26 February 2023.</ref>;
Pharmacokinetic data
Bioavailability	12%
Metabolism	Liver (CYP3A4)
Elimination half-life	14 hours
Excretion	Bile duct
Identifiers
	IUPAC name (3R,5R)-7-[2-(4-Fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid;
CAS Number	134523-00-5 ;
PubChem CID	60823;
IUPHAR/BPS	2949;
DrugBank	APRD00055 ;
ChemSpider	54810 ;
UNII	A0JWA85V8F;
KEGG	D07474 ;
ChEBI	CHEBI:39548 ;
ChEMBL	ChEMBL1487 ;
PDB ligand	117 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8029868 ;
ECHA InfoCard	100.125.464
Chemical and physical data
Formula	C33H35FN2O5
Molar mass	558.650 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)C[C@H](O)C[C@H](O)CCn2c(c(c(c2c1ccc(F)cc1)c3ccccc3)C(=O)Nc4ccccc4)C(C)C;
	InChI InChI=1S/C33H35FN2O5/c1-21(2)31-30(33(41)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-26(37)19-27(38)20-28(39)40/h3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40)/t26-,27-/m1/s1 ; Key:XUKUURHRXDUEBC-KAYWLYCHSA-N ;
	(verify)

Atorvastatin is a statin medication used to prevent cardiovascular disease in those at high risk and to treat abnormal lipid levels.^[4] For the prevention of cardiovascular disease, statins are a first-line treatment.^[4] It is taken by mouth.^[4]

Common side effects include joint pain, diarrhea, heartburn, nausea, and muscle pains.^[4] Serious side effects may include rhabdomyolysis, liver problems, and diabetes.^[4] Use during pregnancy may harm the fetus.^[4] Like all statins, atorvastatin works by inhibiting HMG-CoA reductase, an enzyme found in the liver that plays a role in producing cholesterol.^[4]

Atorvastatin was patented in 1986, and approved for medical use in the United States in 1996.^[4]^[5] It is on the World Health Organization's List of Essential Medicines.^[6] It is available as a generic medication.^[4]^[7] In 2021, it was the most commonly prescribed medication in the United States, with more than 116 million prescriptions filled for over 28 million patients.^[8]^[9]

^ ^a ^b "Atorvastatin (Lipitor) Use During Pregnancy". Drugs.com. 3 February 2020. Archived from the original on 4 December 2019. Retrieved 26 February 2020.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ Cite error: The named reference Lipitor label was invoked but never defined (see the help page).
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Atorvastatin Calcium Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 25 October 2010. Retrieved 23 December 2018.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 473. ISBN 9783527607495. Archived from the original on 12 January 2023. Retrieved 10 May 2020.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ Cite error: The named reference Hit2014 was invoked but never defined (see the help page).
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Atorvastatin - Drug Usage Statistics". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[Drugs.com_pregnancy-1] "Atorvastatin (Lipitor) Use During Pregnancy". Drugs.com. 3 February 2020. Archived from the original on 4 December 2019. Retrieved 26 February 2020.

[2] "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.

[Lipitor_label-3] Cite error: The named reference Lipitor label was invoked but never defined (see the help page).

[AHFS2018-4] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Atorvastatin Calcium Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 25 October 2010. Retrieved 23 December 2018.

[Fis2006-5] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 473. ISBN 9783527607495. Archived from the original on 12 January 2023. Retrieved 10 May 2020.

[WHO22nd-6] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[Hit2014-7] Cite error: The named reference Hit2014 was invoked but never defined (see the help page).

[8] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[9] "Atorvastatin - Drug Usage Statistics". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

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