Atorvastatin

Base Information

• Chemical Name: Atorvastatin
• CAS No.: 134523-00-5
• Molecular Formula: C33H35FN2O5
• Molecular Weight: 558.65
• Hs Code.: 35040000
• UNII: A0JWA85V8F
• DSSTox Substance ID: DTXSID8029868,DTXSID60274003
• Nikkaji Number: J596.930A
• Wikipedia: Atorvastatin
• Wikidata: Q668093
• NCI Thesaurus Code: C61527
• RXCUI: 83366,83367,1297766
• Pharos Ligand ID: W7FPBNURD24G
• Metabolomics Workbench ID: 38695
• ChEMBL ID: CHEMBL1487
• Mol file: 134523-00-5.mol

Synonyms:(3R,5R)-7-(2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid;atorvastatin;atorvastatin calcium;atorvastatin calcium anhydrous;atorvastatin calcium hydrate;atorvastatin calcium trihydrate;atorvastatin, calcium salt;CI 981;CI-981;CI981;Lipitor;liptonorm

Chemical Property of Atorvastatin

Chemical Property:

• Melting Point: 176-178°C
• Boiling Point: 722.2 °C at 760 mmHg
• PKA: pKa 4.46(H2O t=30 Iuncontrolled) (Uncertain)
• Flash Point: 390.6 °C
• PSA: 229.24000
• Density: 1.23 g/cm³
• LogP: 10.10380
• Storage Temp.: 2-8°C
• XLogP3: 5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 558.25300038
• Heavy Atom Count: 41
• Complexity: 822

Purity/Quality:

99% ^*data from raw suppliers

Atorvastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antilipemic Agents
• Canonical SMILES: CC(C)C1=C(C(=C(N1CCC(CC(CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
• Isomeric 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
• Recent ClinicalTrials: Atorvastatin to Reduce Cisplatin-Induced Hearing Loss Among Individuals With Head and Neck Cancer
• Recent EU Clinical Trials: Atorvastatin for patients with Philadelphia-negative chronic myeloproliferative neoplasms - Essential thrombocythemia, polycythemia vera and prefibrotic myelofibrosis
• Recent NIPH Clinical Trials: Effectiveness Of Atorvastatin On Dyslipidemic Erectile Dysfunction Patients
• Uses: antihyperlipoproteimic;HMG-CoA reductase inhibition
• Therapeutic Function: Anticholesteremic

Technology Process of Atorvastatin

There total 47 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)-7-[3-phenyl-4-[(phenylamino)carbonyl]-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid DL-lysine salt

(3R,5R)-7-[3-phenyl-4-[(phenylamino)carbonyl]-2-(4-fluorophenyl)-5-(1-methyl-ethyl)-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid D-lysine salt

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

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.