Atorvastatin

Base Information

• Chemical Name: Atorvastatin
• CAS No.: 110862-48-1
• Molecular Formula: C₃₃H₃₅FN₂O₅
• Molecular Weight: 558.65
• Hs Code.: 2942000000
• Mol file: 110862-48-1.mol

Synonyms:1H-Pyrrole-1-heptanoicacid, 2-(4-fluorophenyl)-b,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-,(R*,R*)-;

Chemical Property of Atorvastatin

Chemical Property:

• Melting Point: 176-178℃
• Boiling Point: 722.198 °C at 760 mmHg
• PKA: 4.29±0.10(Predicted)
• Flash Point: 390.572 °C
• PSA: 111.79000
• Density: 1.236 g/cm³
• LogP: 6.38660

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Clinical Use: Hyperlipidaemia and hypercholesterolaemia
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: concentration possibly increased by dronedarone. Antibacterials: azithromycin, erythromycin, clarithromycin or fusidic acid possibly increased risk of myopathy - avoid atorvastatin for at least 7 days after fusidic acid stopped; concentration increased by clarithromycin - do not exceed 20 mg of atorvastatin1 ; avoid with telithromycin; increased risk of myopathy with daptomycin; concentration possibly reduced by rifampicin. Anticoagulants: may transiently reduce anticoagulant effect of warfarin. Antifungals: increased risk of myopathy with itraconazole - do not exceed 40 mg of atorvastatin1 ; increased risk of myopathy with fluconazole, ketoconazole, posaconazole, voriconazole and possibly other imidazoles and triazoles - avoid. Antivirals: increased risk of myopathy with atazanavir, boceprevir (reduce atorvastatin dose), and possibly darunavir, fosamprenavir, indinavir, lopinavir, ritonavir, saquinavir or tipranavir (max dose of atorvastatin 10 mg); concentration reduced by efavirenz and possibly etravirine; avoid with dasabuvir, ombitasvir, paritaprevir and telaprevir; possible increased risk of myopathy with ledipasvir - reduce atorvastatin dose; concentration increased by simeprevir - consider reducing atorvastatin dose. Calcium channel blockers: concentration increased by diltiazem - increased risk of myopathy; concentration of verapamil increased also possible increased risk of myopathy - consider reducing atorvastatin dose. Ciclosporin: increased risk of myopathy - do not exceed 10 mg of atorvastatin.1 Cobicistat: reduce atorvastatin dose. Colchicine: possible increased risk of myopathy. Grapefruit juice: concentration possibly increased. Lipid lowering agents: increased risk of myopathy with fibrates, gemfibrozil (avoid) and nicotinic acid.

Technology Process of Atorvastatin

There total 55 articles about Atorvastatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

lipitor (134523-03-8) → atorvastatin (134523-00-5,110862-48-1)

Guidance literature:

With hydrogenchloride; In tert-butyl methyl ether; water;

Reference yield:

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester (134395-00-9) → atorvastatin (134523-00-5,110862-48-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/(SICI)1099-1344(20000315)43:3<261::AID-JLCR312>3.0.CO;2-T

Reference yield:

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → atorvastatin (134523-00-5,110862-48-1)

Guidance literature:

Multi-step reaction with 5 steps

1: β-alanine; glacial acetic acid / hexane / Heating

2: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating

3: pivalic acid / tetrahydrofuran; toluene; heptane / Heating

4: HCl / tetrahydrofuran; H₂O / 20 °C

5: sodium hydroxide / H₂O; tetrahydrofuran / 20 °C

With hydrogenchloride; sodium hydroxide; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; acetic acid; triethylamine; 3-amino propanoic acid; Trimethylacetic acid; In tetrahydrofuran; ethanol; hexane; n-heptane; water; toluene; 1: Condensation / 2: Addition / 3: Cycloaddition / 4: Hydrolysis / 5: Hydrolysis;

DOI:10.1002/(SICI)1099-1344(20000315)43:3<261::AID-JLCR312>3.0.CO;2-T

upstream raw materials:

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester

4-methyl-3-oxo-N-phenylpentanamide

benzaldehyde

4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

Downstream raw materials:

(3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

1-((19R,21R)-1-(3',6'-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-5-ylamino)-19,21-dihydroxy-17-oxo-1-thioxo-6,9,12-trioxa-2,16-diazatricosan-23-yl)-5-(4-fluorophenyl)-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide

Refernces

• 1、 -. "Synthesis method of atorvastatin calcium". Paragraph 0051-0053. . Retrieved 2018/12/02.
• 2、 -. "A decongestant atorvastatin". Paragraph 0094-0099. . Retrieved 2017/01/17.