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Basic Information
CAS No.: 147526-32-7
Name: Pitavastatin calcium
Article Data: 38
Molecular Structure:
Molecular Structure of 147526-32-7 (Pitavastatin calcium)
Formula: (C25H23FNO4)2.Ca
Molecular Weight: 880.999
Synonyms: Bis((3R,5S,6E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoate), monocalcium salt;6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, calcium salt (2:1), (S-(R*,S*-(E)))-;Pitavastatin hemicalcium;UNII-IYD54XEG3W;Livalo;CCRIS 8652;
EINECS: 807-641-2
Boiling Point: 692 °C at 760 mmHg
Flash Point: 372.3 °C
Appearance: white to off-white powder
Safety: 24/25
PSA: 186.96000
LogP: 6.36680
Related products
Synthetic route
849811-78-5

methyl (3R,5S,6E)-7-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3,5-dihydroxyhept-6-enoate

147526-32-7

pitavastatin

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 0.5h;100%
With water; sodium hydroxide In methanol at 20℃; for 2h; Product distribution / selectivity;
147526-32-7

pitavastatin calcium salt

147526-32-7

pitavastatin

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetate at 25 - 35℃;95.9%
With hydrogenchloride In dichloromethane; water at 0 - 25℃; for 0.833333h; pH=3;
With hydrogenchloride In water; ethyl acetate pH=4;3.7 g
With hydrogenchloride In dichloromethane; water
147489-06-3

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

147526-32-7

pitavastatin

Conditions
ConditionsYield
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With trifluoroacetic acid In acetonitrile at 30 - 35℃;
Stage #2: With caesium carbonate In acetonitrile at 35 - 40℃;		94%
Multi-step reaction with 3 steps
1.1: water; oxalic acid / methanol / 6 h / 35 °C
1.2: 2.75 h / 10 - 30 °C / pH 7
2.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C
2.2: 0.67 h / 25 °C
3.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 4 steps
1.1: water; oxalic acid / methanol / 6 h / 35 °C
1.2: 2.75 h / 10 - 30 °C / pH 7
2.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C
2.2: 0.25 h / 0 °C / pH 4
2.3: 0.5 h / 0 °C
3.1: sodium hydroxide / water / 0.75 h / 30 °C
3.2: 0.75 h / 35 °C
4.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 2 steps
1: hydrogenchloride / acetonitrile; water / 2 h / 13 °C
2: sodium hydroxide / water / 2 h / 10 °C / Large scale
View Scheme
167073-19-0

(E)-(3R,5S)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester

147526-32-7

pitavastatin

Conditions
ConditionsYield
With ethanol; sodium hydroxide In water at 20℃; for 3h;87.4%
586966-54-3

(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester

147526-32-7

pitavastatin

Conditions
ConditionsYield
With sodium hydroxide In water at 10℃; for 2h; Large scale;83.9%
Stage #1: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester With hydrogenchloride; water In methanol at 25℃; for 2.16667h;
Stage #2: With hydrogenchloride In dichloromethane at 0 - 25℃; for 0.916667h; pH=3;
Multi-step reaction with 2 steps
1.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C
1.2: 0.67 h / 25 °C
2.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C
1.2: 0.25 h / 0 °C / pH 4
1.3: 0.5 h / 0 °C
2.1: sodium hydroxide / water / 0.75 h / 30 °C
2.2: 0.75 h / 35 °C
3.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3R,5S,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoate

147526-32-7

pitavastatin

Conditions
ConditionsYield
With sodium hydroxide In methanol for 12h; Ambient temperature;

(±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester

147526-32-7

pitavastatin

Conditions
ConditionsYield
Stage #1: (±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester With sodium hydroxide Hydrolysis;
Stage #2: With (+)-1-phenylethylamine resolution;

(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-[(1S)-1-phenylethyl]hept-6-enamide

147526-32-7

pitavastatin

Conditions
ConditionsYield
Stage #1: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-[(1S)-1-phenylethyl]hept-6-enamide With sodium hydroxide In ethanol at 50 - 55℃; for 26h;
Stage #2: With hydrogenchloride In ethyl acetate Further stages.;
121660-11-5

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

147526-32-7

pitavastatin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: DMSO; P2O5; Et3N
2.1: NaOH; (n-octyl)3MeNCl / toluene; H2O
3.1: DIBAH
4.1: NaH; n-BuLi
5.1: NaBH4; Et2BOMe / -78 °C
6.1: aq. NaOH
6.2: (+)-α-methylbenzylamine
View Scheme
Multi-step reaction with 4 steps
1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C
1.2: 1 h / 75 °C
2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
3.1: water; oxalic acid / methanol / 6 h / 35 °C
3.2: 2.75 h / 10 - 30 °C / pH 7
4.1: hydrogenchloride; water / methanol / 2.17 h / 25 °C
4.2: 0.92 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 5 steps
1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C
1.2: 1 h / 75 °C
2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
3.1: water; oxalic acid / methanol / 6 h / 35 °C
3.2: 2.75 h / 10 - 30 °C / pH 7
4.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C
4.2: 0.67 h / 25 °C
5.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 6 steps
1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C
1.2: 1 h / 75 °C
2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C
3.1: water; oxalic acid / methanol / 6 h / 35 °C
3.2: 2.75 h / 10 - 30 °C / pH 7
4.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C
4.2: 0.25 h / 0 °C / pH 4
4.3: 0.5 h / 0 °C
5.1: sodium hydroxide / water / 0.75 h / 30 °C
5.2: 0.75 h / 35 °C
6.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3
View Scheme
Multi-step reaction with 5 steps
1: thionyl chloride / toluene; dichloromethane / 15 °C
2: toluene / 12 h / Reflux; Large scale
3: potassium carbonate / dimethyl sulfoxide / 3 h / 30 - 50 °C / Large scale
4: hydrogenchloride / acetonitrile; water / 2 h / 13 °C
5: sodium hydroxide / water / 2 h / 10 °C / Large scale
View Scheme
121660-37-5

2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

147526-32-7

pitavastatin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: NaOH; (n-octyl)3MeNCl / toluene; H2O
2.1: DIBAH
3.1: NaH; n-BuLi
4.1: NaBH4; Et2BOMe / -78 °C
5.1: aq. NaOH
5.2: (+)-α-methylbenzylamine
View Scheme
Multi-step reaction with 3 steps
1.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one; 2-methyltetrahydrofuran; tetrahydrofuran / -60 - 22 °C
2.1: hydrogenchloride / acetonitrile; water / 1.5 h / 45 °C
2.2: 1.5 h
3.1: hydrogenchloride / water; ethyl acetate / pH 4
View Scheme
Multi-step reaction with 4 steps
1.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one; 2-methyltetrahydrofuran; tetrahydrofuran / -60 - 22 °C
2.1: hydrogenchloride / acetonitrile; water / 2.5 h / 45 °C
2.2: 1.5 h / 10 °C
3.1: sodium hydroxide / water / pH 12.3
3.2: 1.25 h / pH 9.7
4.1: hydrogenchloride / water; ethyl acetate / pH 4
View Scheme
Raw Materials
166803-31-2
849811-78-5
147526-32-7
586966-54-3
256431-72-8
147489-06-3
121659-86-7
148901-69-3
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147526-32-7
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    Pitavastatin calcium 147526-32-7

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Chemistry

Molecular structure of Pitavastatin calcium (CAS NO.147526-32-7) is:

Product Name: Pitavastatin calcium
CAS Registry Number: 147526-32-7
IUPAC Name: calcium(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate
Molecular Weight: 880.983646 [g/mol]
Molecular Formula: (C25H23FNO4)2.Ca
H-Bond Donor: 4
H-Bond Acceptor: 12 
Flash Point: 372.3 °C
Enthalpy of Vaporization: 106.48 kJ/mol
Boiling Point: 692 °C at 760 mmHg
Vapour Pressure: 4.21E-20 mmHg at 25°C
Product Categories: Active Pharmaceutical Ingredients;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;chemical

Uses

 Pitavastatin calcium (CAS NO.147526-32-7) can be used as a competitive inhibitor of HMG-CoA reductase.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 100mg/kg (100mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 56, Pg. 67, 1998.
rat LDLo oral 500mg/kg (500mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 Oyo Yakuri. Pharmacometrics. Vol. 56, Pg. 67, 1998.

Specification

 Pitavastatin calcium , its cas register number is 147526-32-7. It also can be called Bis((3R,5S,6E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoate), monocalcium salt ; NK 104 ;  CCRIS 8652 ; Livalo ; Pitavastatin hemicalcium ; UNII-IYD54XEG3W ; 6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, calcium salt (2:1), (S-(R*,S*-(E)))- .It is a white to off-white powder.