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Basic Information
CAS No.: 134523-00-5
Name: Atorvastatin
Article Data: 35
Molecular Structure:
Molecular Structure of 134523-00-5 (Atorvastatin)
Formula: C33H35FN2O5
Molecular Weight: 558.65
Synonyms: 1H-Pyrrole-1-heptanoicacid, 2-(4-fluorophenyl)-b,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-,[R-(R*,R*)]-;(3R,5R)-7-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoicacid;(bR,dR)-2-(p-Fluorophenyl)-b,d-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoicacid;Atorvastatin acid;Cardyl;Atorvastatin(base);
EINECS: 806-698-0
Density: 1.23 g/cm3
Melting Point: 176-178°C
Boiling Point: 722.2 °C at 760 mmHg
Flash Point: 390.6 °C
Hazard Symbols: Xn
Risk Codes: 20/21/22-36/37/38
Safety: 26-36
PSA: 229.24000
LogP: 10.10380
Synthetic route
134523-01-6

atorvastatin sodium

134523-00-5

atorvastatin

Conditions
ConditionsYield
With sodium hydroxide at 60 - 70℃; pH=12-13;95%
With hydrogenchloride In dichloromethane; water for 0.5h; Cooling with ice;94%
134523-00-5

atorvastatin

Conditions
ConditionsYield
With hydrogenchloride In tert-butyl methyl ether; water92%
With hydrogenchloride In water; acetonitrile at 20℃; for 0.25h; pH=2.35 - 7;
With sodium hydrogen sulfate In water; ethyl acetate

C7H15NO4

125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

134523-00-5

atorvastatin

Conditions
ConditionsYield
With Trimethylacetic acid In toluene at 90℃; for 22h; Solvent; Temperature;91%
134395-00-9

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

134523-00-5

atorvastatin

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran; water at 20℃; Hydrolysis;
With methanol; potassium hydroxide; water
Stage #1: (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester With methanol; sodium hydroxide; water In tert-butyl methyl ether for 2.08333 - 7.08333h; Heating / reflux;
Stage #2: With hydrogenchloride pH=8.0 - 8.2;
124401-38-3

4-methyl-3-oxo-N-phenylpentanamide

134523-00-5

atorvastatin

Conditions
ConditionsYield
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
View Scheme
100-52-7

benzaldehyde

HI, I2

HI, I2

134523-00-5

atorvastatin

Conditions
ConditionsYield
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
View Scheme
125971-57-5

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

134523-00-5

atorvastatin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
2: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
3: HCl / tetrahydrofuran; H2O / 20 °C
4: sodium hydroxide / H2O; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine / Reflux
2.1: Trimethylacetic acid / toluene; hexane; tetrahydrofuran / Reflux
3.1: hydrogenchloride / methanol / 0.08 h / 60 °C
3.2: 0.08 h / 60 °C
View Scheme
125971-96-2

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

134523-00-5

atorvastatin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
2: HCl / tetrahydrofuran; H2O / 20 °C
3: sodium hydroxide / H2O; tetrahydrofuran / 20 °C
View Scheme
125971-95-1

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

134523-00-5

atorvastatin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / tetrahydrofuran; H2O / 20 °C
2: sodium hydroxide / H2O; tetrahydrofuran / 20 °C
View Scheme
Stage #1: 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; water In tetrahydrofuran; methanol at 20℃;
Stage #2: With sodium hydroxide; water In tetrahydrofuran; methanol at 0 - 20℃;
Stage #1: 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; water In tetrahydrofuran at 25℃; for 8h;
Stage #2: With sodium hydroxide; water In tetrahydrofuran for 8h;
Stage #3: With phosphoric acid In water; ethyl acetate pH=4.0; Product distribution / selectivity;
62-53-3

aniline

Wang resin-bound styrene 4

Wang resin-bound styrene 4

134523-00-5

atorvastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 96 percent / toluene / Heating
2: β-alanine; glacial acetic acid / hexane / Heating
3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating
4: pivalic acid / tetrahydrofuran; toluene; heptane / Heating
5: HCl / tetrahydrofuran; H2O / 20 °C
6: sodium hydroxide / H2O; tetrahydrofuran / 20 °C
View Scheme
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Chemistry

Molecular Structure of Atorvastatin (CAS NO.134523-00-5):

IUPAC Name: (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid 
Empirical Formula: C33H35FN2O5
Molecular Weight: 558.6398
H bond acceptors: 7
H bond donors: 4
Freely Rotating Bonds: 14
Polar Surface Area: 70Å2
Index of Refraction: 1.602
Molar Refractivity: 155.21 cm3
Molar Volume: 451.9 cm3
Surface Tension: 45.9 dyne/cm
Density: 1.23 g/cm3
Flash Point: 390.6 °C
Enthalpy of Vaporization: 110.74 kJ/mol
Boiling Point: 722.2 °C at 760 mmHg
Vapour Pressure: 6.84E-22 mmHg at 25 °C
Classification Code: Anticholesteremic Agents; Antilipemic Agents; Antimetabolites; Enzyme Inhibitors; Hydroxymethylglutaryl-CoA Reductase Inhibitors
InChI: InChI=1/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
Smiles: c1(c(n(CC[C@H](C[C@H](CC(=O)O)O)O)c(c1C(Nc1ccccc1)=O)C(C)C)c1ccc(F)cc1)c1ccccc1

History

  Atorvastatin (CAS NO.134523-00-5) was first synthesized in 1985 by Bruce Roth while working at Parke-Davis Warner-Lambert Company (now Pfizer). With 2006 sales of US$12.9 billion, Lipitor is the largest-selling drug in the world. Lipitor is not the only statin, there are several other statins on the market.

Uses

  Atorvastatin is a member of the drug class known as statins, used for lowering blood cholesterol. It also stabilizes plaque and prevents strokes through anti-inflammatory and other mechanisms.

Safety Profile

Hazard Codes: HarmfulXn
Risk Statements 20/21/22-36/37/38 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.

Specification

 Atorvastatin , with CAS number of 134523-00-5, can be called 1H-Pyrrole-1-heptanoicacid, 2-(4-fluorophenyl)-b,d-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-,[R-(R*,R*)]- ; (bR,dR)-2-(p-Fluorophenyl)-b,d-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoicacid ; (3R,5R)-7-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoicacid . Atorvastatin (CAS NO.134523-00-5) is used for lowering blood Cholesterol. It also stabilizes plaque and prevents strokes through anti-inflammatory and other mechanisms.