Atorvastatin

Product Name: Atorvastatin
CAS No.: 134523-00-5
Chemical Name: Atorvastatin
Synonyms: ATORVASTATIN CA;Atorvastatin (Subject to Patent free);ATORVASTATIN CALCIUM SALT;Atorvastatin acid;ATORVASTATIN DIPROTECTED;Atorvastatin CalciuM Tablets;(3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid;Cardyl;Atrovastitne;025-83371857
CBNumber: CB4239912
Molecular Formula: C33H35FN2O5
Formula Weight: 558.65
MOL File: 134523-00-5.mol

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Atorvastatin Property

Melting point:: 176-178°C
Boiling point:: 722.2±60.0 °C(Predicted)
Density: 1.23±0.1 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: 100 mg/mL (179.01 mM)
pka: pKa 4.46(H2O t=30 Iuncontrolled) (Uncertain)
form: Solid
color: White to light yellow
CAS DataBase Reference: 134523-00-5(CAS DataBase Reference)
EPA Substance Registry System: 1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-?,?-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-, (?R,?R)- (134523-00-5)

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Safety

Hazard Codes: Xn
Risk Statements: 20/21/22-36/37/38
Safety Statements: 26-36
HS Code: 35040000
Hazardous Substances Data: 134523-00-5(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H272May intensify fire; oxidizer

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P221Take any precaution to avoid mixing with combustibles/…

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P370+P380+P375in case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.

P380Evacuate area.

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N-Bromosuccinimide Price

Oakwood

Product number: 079255
Product name: Atorvastatin
Packaging: 250mg
Price: $40
Updated: 2021/12/16

ChemScene

Product number: CS-2798
Product name: Atorvastatin
Purity: 99.05%
Packaging: 10mg
Price: $50
Updated: 2021/12/16

Matrix Scientific

Product number: 075942
Product name: (3R,5R)-7-(2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid
Purity: 95+%
Packaging: 1g
Price: $69
Updated: 2021/12/16

Oakwood

Product number: 079255
Product name: Atorvastatin
Packaging: 1g
Price: $75
Updated: 2021/12/16

AK Scientific

Product number: H942
Product name: Atorvastatin
Packaging: 1g
Price: $143
Updated: 2021/12/16

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Atorvastatin Chemical Properties,Usage,Production

Chemical Properties

white Crystalline powder

Originator

Cardyl,Pfizer,Spain

Uses

antihyperlipoproteimic;HMG-CoA reductase inhibition

Definition

ChEBI: Atorvastatin is a dihydroxy monocarboxylic acid that is a member of the drug class known as statins, used primarily for lowering blood cholesterol and for preventing cardiovascular diseases. It has a role as an environmental contaminant and a xenobiotic. It is an aromatic amide, a member of monofluorobenzenes, a statin (synthetic), a dihydroxy monocarboxylic acid and a member of pyrroles. It is functionally related to a heptanoic acid. It is a conjugate acid of an atorvastatin(1-).

Manufacturing Process

285 ml 2.2 M n-butyl lithium in hexane was added dropwise to 92 ml diisopropylamine at -50-60°C under nitrogen. The well stirred solutions warmed to about -20°C, then it was cannulated into a suspension of 99 g of S(+)-2-acetoxy-1,1,2-triphenylethanol in 500 ml absolute tetrahydrophuran (THF) at -70°C and the reaction mixture was allowed to warm to -10°C for 2 hours. A suspension of MgBr2 was made from 564 ml (0.63 mol) of bromine and 15.3 g of magnesium (0.63 mol) in 500 ml THF cooled to -78°C. The enolate solution was cannulated into this suspension within 30 min and was stirred for 60 min at -78°C. 150 g 5-(4-fluorophenyl)-2-(1-methylethyl)-1-(3- oxopropyl)-N,4-diphenyl-1H-pyrrole-3-carboxamide in 800 ml absolute THF was added dropwise over 30 min, stirred 90 min at -78°C, then was added 200 ml acetic acid, this is removed to a cool bath, 500 ml of H2O was added and the mixture concentrate in vacuo at 40-50°C. After adding of 500 ml of 1:1 EtOAc/heptane the mixture was filtered. The filtrate was washed extensively with 0.5 N HCl, then several times with H2O and finally EtOAc/heptane (3:1) and cooled with dry ice to -20°C. The light brown crystalline product was dried in vacuum oven at 40°C. The yield was 194 g. 112 g of the same product was produced by evaporation of mother liquor after recrystallization and chromatographic purification on a silicagel.
162 g of this substance was suspended in methanol/THF (5:3) and was stirred with 11.7 g of sodium methoxide until everything was dissolved and kept in the freezer overnight. Later it was quenched with AcOH concentrated in vacuo, was added to 500 ml H2O and extracted twice with EtOAc (300 ml). The combined extracts was washed with saturated NaHCO3 brine and dried over anhydrous MgSO4, purified on silica-gel and gave 86.1 g of white crystals m.p. 125-126°C, αD 20=4.23° (1.17 M, CH3OH).
81 g of the last product in 500 ml absolute THF was added as quickly as possible to the mixture of 77 ml THF at diisopropylamine, 200 ml 2.2 M of nbutyl lithium and 62 ml of t-butylacetate in 200 ml THF -40-42°C under nitrogen. Stirring was continued for 4 hours at -70°C. The reaction mixture was concentrated in vacuo, the residue was taken up in EtOAc, washed with water, then saturated NH4Cl, NaHCO3 (saturated), dried over anhydrous MgSO4, filtred and the solvent evaporated.
The organic phase was dried and concentrated in vacuo to yield 73 g crude product, that was dissolved in 500 ml absolute THF, 120 ml triehtylborane and 0.7 g t-butylcarboxylic acid, 70 ml methanol and 4.5 g sodium borohydride was added. The mixture was stirred at -78°C under a dry atmosphere for 6 hours, poured slowly into 4:1:1 mixture of ice/30%H2O2/H2O and stirred overnight. CHCl3 (400 ml) was added and organic layer washed extensively with H2O until no peroxide could be found, was dried over MgSO4, filtered and was treated by chromatography on silica gel to yield 51 g. The product was dissolved in THF/methanol and saponificated with NaOH and, concentrated to remove organic solvents at room temperature, added 100 ml H2O, and extracted with Et2O twice. Organic layer was thoroughly dried and it was left at room temperature for the next 10 days, then concentrated.
Chromatography on silica gel yielded 13.2 g racemate of lactone - trans-(+/- )-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-di-diphenyl-1-[2-(tetrahydro-4- hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide. This racemate was divided by chiral synthesis which was made analogously the method in US Pat. No. 4,581,893. Then each isomer was saponificated with NaOH and purificated by HPLC. The calcium salt corresponding acid was prepared by reaction with 1 eq. of CaCl2·2H2O in water.

brand name

Lipitor (Pfizer).

Therapeutic Function

Anticholesteremic

General Description

Atorvastatin, [R-(R*,R*)]-2-(4-fluorophenyl)-b,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-lH-pyrrole-1-heptanoic acid(Lipitor), also possesses the heptanoic acid side chain,which is critical for inhibition of HMG-CoA reductase.Although the side chain is less lipophilic than the lactoneform, the high amount of lipophilic substitution causes this agent to have a slightly higher level of CNS penetration thanpravastatin, resulting in a slight increase in CNS side effects.Even so, its CNS profile is much lower than that of lovastatin.Atorvastatin is marketed as a combination therapywith amlodipine under the trade name Norvasc for managementof high cholesterol and high blood pressure.

General Description

Cerivastatin (Baycol) is one of the neweragents in this class of cholesterol-lowering agents. However,it carries a higher incidence of rhabdomyolysis and, as a result,was voluntarily withdrawn from the market by its manufacturerin 2001.

Atorvastatin Preparation Products And Raw materials

Raw materials

Triethylborane Sodium borohydride 2,3-diaminonaphthalene

Preparation Products

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View Lastest Price from Atorvastatin manufacturers

Baoji Guokang Bio-Technology Co., Ltd.

Product: Atorvastatin 134523-00-5
Price: US $484.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100KG
Release date: 2021-06-04

Hangzhou Hyper Chemicals Limited

Product: Atorvastatin 134523-00-5
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%, USP
Supply Ability: 5,000KG
Release date: 2024-08-02

R&D Scientific Inc.

Product: Atorvastatin 134523-00-5
Price: US $80.00/g
Min. Order: 1g
Purity: 98
Supply Ability: 20 Kg
Release date: 2024-02-02

134523-00-5, AtorvastatinRelated Search:

PHENYL VALERATE Simvastatin Pyrrolidine N-Vinyl-2-pyrrolidone Diphenyl ether Polyvinylpyrrolidone Phenyl salicylate Propane N-Methyl-2-pyrrolidone ATORVASTATIN LACTONE,Atorvastatin d-Lactone PHENYL RESIN ATORVASTATIN SODIUM O-HYDROXY ATORVASTATIN LACTONE Phenylacetic acid ATORVASTATIN CA,ATORVASTATIN CALCIUM,ATORVASTATIN CA,ATORVASTATIN CALCIUM SALT,Atorvastatin Calclum,ATORVASTATIN CALCIUM MM(CRM STANDARD) Atorvastatin tert-Butyl Ester Atorvastatin Intermediate Ⅰ,Atorvastatin Intermediate 1 Atorvastatin Intermediate 2 ,Atorvastatin Intermediate Ⅱ

Atorvastatin (Subject to Patent free)

(3r,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid

(3R,5R)-2-(4-Fluorophenyl)-3,5-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid

Atorvastatin free ACID

Atorvastatin&Ats-5Ats-8Ats-9M4L1

Atrovastitne

(bR,dR)-2-(p-Fluorophenyl)-β,δ-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoic acid

1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-, (βR,δR)-

1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-, [R-(R*,R*)]-

Cardyl

[R-(R^<*>^，R^<*>^)]-2-(4-Fluorophenyl)- β，δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylarnino)carbonyl]-1H．Pyrrole-1- heptanoic acid

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxy-enanthic acid

(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbaMoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid

Atorvastatin acid

Atorvastatin CalciuM Tablets

ATORVASTATIN DIPROTECTED

025-83371857

(3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbaMoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid

(3R,5R)-7-(2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydr

(3R,5R)-7-(2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dih

ATORVASTATIN

ATORVASTATIN CA

ATORVASTATIN CALCIUM SALT

Atorvastatin USP/EP/BP

Atorvastatin DISCONTINUED See A791750 or A791730

Atorvastatin calcium salt Calcium (3R,5R)-7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3- phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl]- 3,5dihydroxyheptanoate

(3R，5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3，5-dihydroxyheptanoic acid

Atorvastatin in methanol

134523-00-5

134523-03-0

C33H34FN2O53H2O

C33H35FN2O5

C33H33CaFNO5