Calcium atorvastatin

Base Information

• Chemical Name: Calcium atorvastatin
• CAS No.: 134523-03-8
• Molecular Formula: C66H68CaF2N4O10
• Molecular Weight: 1155.36
• Hs Code.: 2933990090
• European Community (EC) Number: 627-026-0,658-046-8
• Mol file: 134523-03-8.mol

Synonyms:Atorvastatin Hemicalcium;134523-03-8;Calcium atorvastatin;SCHEMBL28457;BWFCZHDTTAYGNN-CNZCJKERSA-N;1H-Pyrrole-1-heptanoicacid,2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-,calciumsalt(2:1),(betaR,deltaR)-

Chemical Property of Calcium atorvastatin

Chemical Property:

• Appearance/Colour: White Crystalline Powder
• Melting Point: 176-178 °C
• Boiling Point: 722.2 °C at 760 mmHg
• Flash Point: 390.6 °C
• PSA: 229.24000
• LogP: 10.10380
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: ≥10mg/mL
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 598.2155912
• Heavy Atom Count: 42
• Complexity: 822

Purity/Quality:

98% ^*data from raw suppliers

Atorvastatin Calcium Salt Trihydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 20/21/22-36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• 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.[Ca]
• 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.[Ca]
• Recent EU Clinical Trials: POESIA Study: Pleiotropic effects of PCSK 9 inhibition and bempedoic acid - Changes in Platelet Function and Inflammation Markers
• Chemical Composition and Structure: Atorvastatin calcium is an organic calcium salt composed of calcium cations and atorvastatin anions in a 1:2 ratio. It is a member of the lipid-lowering agents and a significant inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG-CoA) reductase, which catalyzes the conversion of HMG-CoA to mevalonate, an early step in cholesterol synthesis.
• Formulation and Bioavailability Enhancement: Atorvastatin calcium has limited bioavailability when taken orally due to its low solubility in low pH and extensive first-pass effect. Different formulation strategies have been utilized to overcome these obstacles, such as solid dispersion, co-crystallization, and incorporation of self-emulsifying vehicles.
• Co-crystallization for Solubility Enhancement: Co-crystallization is a method used to enhance the solubility of hydrophobic drugs like atorvastatin calcium. Co-crystals of atorvastatin calcium have been prepared using various co-formers such as citric acid and nicotinamide to enhance solubility. Coamorphous solid forms of atorvastatin calcium with conformers like isonicotinamide (INA) and maleic acid (MA) have also been prepared using spray drying techniques, resulting in improved solubility properties compared to the crystalline form.
• Pleiotropic Effects: Atorvastatin calcium exhibits pleiotropic effects as an anti-inflammatory drug in addition to its main antihyperlipidemic action. These pleiotropic effects contribute to the therapeutic benefits of atorvastatin calcium beyond its cholesterol-lowering properties.
• Pharmacological Action and Clinical Use: Atorvastatin calcium is a statin drug used to lower cholesterol levels effectively. It is prescribed to reduce mortality risks in patients with cardiovascular disease by effectively lowering blood cholesterol levels. Atorvastatin calcium has been shown to effectively reduce both cholesterol and triglycerides in patients.

Technology Process of Calcium atorvastatin

There total 52 articles about Calcium 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: 98.0%

atorvastatin lysine → lipitor (134523-03-8)

Guidance literature:

With calcium acetate; In ethanol; water; at 0 - 40 ℃;

Reference yield: 96.0%

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (125971-95-1) → lipitor (134523-03-8)

Guidance literature:

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate; With hydrogenchloride; methanol; water; at 35 ℃; for 3h;

With calcium hydroxide; In methanol; water; toluene; at 70 ℃; for 2h;

In methanol; water; at 20 - 78 ℃; for 24.25h;

Reference yield: 95.1%

atorvastatin lactone (125995-03-1) → lipitor (134523-03-8)

Guidance literature:

atorvastatin lactone; With calcium hydroxide; In tetrahydrofuran; water; at 45 - 50 ℃; for 2h;

In dichloromethane; di-isopropyl ether; at 10 - 15 ℃; for 0.25h; Product distribution / selectivity;

upstream raw materials:

calcium acetate

atorvastatin

tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate

atorvastatin sodium

Downstream raw materials:

3-<(4-fluorophenyl)carbonyl>-2-(2-methyl-1-oxopropyl)-N,3-diphenyl-2-oxiranecarboxamide

atorvastatin sodium

atorvastatin

4-(4-fluoro-phenyl)-2,4-dihydroxy-2-isopropyl-5-phenyl-3,6-dioxa-bicyclo[3.1.0]hexane-1-carboxylic acid phenylamide

Refernces

• 1、 -. "Method for purifying atorvastatin calcium intermediate". . . Retrieved 2021/09/01.
• 2、 -. "AN IMPROVED AND COMMERCIALLY VIABLE PROCESS FOR PREPARATION OF PYRROLE DERIVATIVES WITH IMPROVED IMPURITY PROFILE & MINIMISATION OF UNIT OPERATIONS.". . . Retrieved 2020/02/14.