3D Mol Similar

Pitavastatin calcium

: Iupac Name：calcium
(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,
5-dihydroxyhept-6-enoate; CAS No.: 147526-32-7; Molecular Weight：463.56; Modify Date.: 2022-12-14 04:53; Introduction:
Pitavastatin calcium, with the chemical formula C50H46CaF2N2O8 and CAS registry number 147526-32-7, is a compound used for the treatment of high cholesterol and triglyceride levels. It belongs to the class of drugs known as statins and works by inhibiting the enzyme HMG-CoA reductase, which is involved in the production of cholesterol in the liver. Pitavastatin calcium is available in tablet form and is typically taken once daily. Common side effects may include muscle pain, headache, and stomach upset. It is important to note that this overview provides a general summary and should not be used as a substitute for professional medical advice. Please consult a healthcare provider for personalized information and guidance regarding the use of Pitavastatin calcium.
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1. Names and Identifiers

: 1.1 Name; Pitavastatin calcium; 1.2 Synonyms; (+)-Monocalcium bis{(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoate} (+)-Monocalciumbis{(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoate} (+)-Monocalciunbis{(3r,5s,6e)-7-[2-cyclopropyl-4-(4-fluorophenyl-3-quinolyl]-3,5-dihydroxy-6-heptenotate} (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoic acid,calcium salt (2:1) (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid [14C]-Pitavastatin [3H]-Pitavastatin 6-Heptenoic acid, 7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-, calcium salt, (3R,5S,6E)- (2:1) Alipza Calcium (3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-quinolin-3-yl)-3,5-dihydroxyhept-6-enoate Calcium bis{(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl]-3,5-dihydroxy-6-heptenoate} calcium,(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate Livalo Livazo MFCD01937979 Nisvastatin NK-104 NK-104 Calcium Pitavastatin (Calcium) Pitavastatin Calcium /NK-104 Pitavastatin CalciuM DISCONTINUED Pitavastatin calciuM(Livalo) Pitavastatin hemicalcium Pitavasttin Calcium UNII-IYD54XEG3W; View all

1.3 CAS No.: 147526-32-7

1.4 CID: 5282451

1.5 EINECS(EC#): 807-641-2

1.6 Molecular Formula: C25H26CaFNO4 (isomer)

1.7 Inchi: InChI=1/C25H24FNO4.Ca/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-18(28)13-19(29)14-23(30)31;/h1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31);/b12-11+;/t18-,19-;/s2

1.8 InChIkey: AMUDYCAFPCQTAZ-ZADPHQEYNA-N

1.9 Canonical Smiles: [Ca].O[C@H](C[C@H](O)\C=C\C1=C(C2=CC=C(F)C=C2)C2=C(C=CC=C2)N=C1C1CC1)CC(O)=O

1.10 Isomers Smiles: C1C(C1)C2=NC3=CC=CC=C3C(=C2/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])C4=CC=C(C=C4)F.C1C(C1)C2=NC3=CC=CC=C3C(=C2/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])C4=CC=C(C=C4)F.[Ca+2]

2. Properties

2.1 Melting point: >138oC (dec.)

2.1 Boiling point: 692 °C at 760 mmHg

2.1 Flash Point: 372.3 °C

2.1 Precise Quality: 880.28500

2.1 PSA: 186.96000

2.1 logP: 6.36680

2.1 Appearance: white to off-white powder

2.2 Chemical Properties: White to Off-White Powder

2.3 Color/Form: Powder

2.4 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The calcium salt of pitavastatin. Used for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lower their cholesterol levels by diet and exercise.

3.2 Usage: A competitive inhibitor of HMG-CoA reductase.

4. Safety and Handling

4.1 Safety Statements: 24/25

4.1 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.

4.2 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

147526-32-7Total: 15 Synthesis Route

765-43-5 248 Suppliers

147526-32-7 280 Suppliers

Literatures:
US2012/16129 A1, ;
Yield: null

32249-35-7 73 Suppliers

147526-32-7 280 Suppliers

Literatures:
US2012/16129 A1, ;
Yield: null

147526-32-7 280 Suppliers

Literatures:
DR. REDDY'S LABORATORIES LTD.; DR. REDDY'S LABORATORIES, INC.; KVS, Rama Rao; KATKAM, Srinivas; SAGYAM, Rajeswar Reddy; PITTA, Jayaprakash; MUNAGALA, Sridhar; PEDDY, Vishweshwar; TUMMALA, Arjun Kumar; RAGINENI, Srinivasulu; DOOSA, Hima Bindu Patent: WO2012/106584 A2, 2012 ; Location in patent: Page/Page column 23 ;
Yield: ~97%

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7. Precursor and Product

precursor:

147526-32-7

1343494-43-8

148901-68-2

849811-78-5

586966-54-3

765-43-5

147489-06-3

256431-72-8

121659-86-7

121660-11-5

1392469-74-7

32249-35-7

148901-69-3

121660-37-5

166803-31-2

View all

product :

147526-32-7

8. Other Information

8.0 Statin lipid-lowering drugs: Pitavastatin calcium is jointly developed by two companies Nissan Chemical and Kowa Co.it is the first total synthesis HMG-CoA reductase inhibitor, it belongs to statin drugs ,it reduces the ability of the liver to manufacture cholesterol mainly through inhibition of some liver enzymes called HMGCo-A reductase , thus it improves the elevated blood cholesterol levels, it is primarily used for the treatment of hypercholesterolemia and familial hypercholesterolemia patients,its lipid-lowering effect is very good, it is the most potent lipid-lowering drug so far.

8.1 Pharmacokinetics: The main parts of its absorption after oral administration are the duodenum and colon,its rate of binding plasma protein in the body is 96%and it is more selectively distributed in the liver after absorption , the drug concentration in body tissues is lower than that in the plasma or the same as that in the plasma . Pitavastatin calcium is mainly metabolized in the liver, kidney, lung, heart, muscle , metabolite concentrations are lower than the concentration of drug prototype, it is excreted through feces,there is also a small amount of drug excretion through urine , total excretion rate is almost 100%.
A healthy male adult oral pitavastatin is 0.5~8mg, t1/2 is about 10h,the cmax and AUC of the prototype drug in plasma increase with increasing dose , repeatedly taking does not result in medication savings.

8.2 Chemical Properties: White to Off-White Powder

8.3 Uses: A competitive inhibitor of HMG-CoA reductase.

8.4 Uses: Pitavastatin calcium (Livalo) is a novel member of the medication class of statins

8.5 Definition: ChEBI: The calcium salt of pitavastatin. Used for treatment of hypercholesterolemia (elevated levels of cholesterol in the blood) on patients unable to sufficiently lower their cholesterol levels by diet and exercise.

8.6 Hazard: A poison by ingestion.

8.7 Description: Pitavastatin, launched for the treatment of hypercholesterolemia, belongs to the family of second-generation statins, also referred to as superstatins due to their improved efficacy as cholesterol lowering agents. Like other statins, pitavastatin reduces plasma cholesterol levels by competitively inhibiting HMG-CoA reductase, the rate-limiting enzyme of cholesterol biosynthesis in the liver. It is a more potent inhibitor of HMG-CoA reductase than the previously marketed statins and has the potential benefit of not undergoing significant metabolism by CYP3A4. Pitavastatin is synthesized in a multi-step sequence, including the key step of introducing the dihydroxyheptenoate side chain by cross-coupling of a 3-iodoquinoline intermediate with an alkenylborane reagent. Unlike rosuvastatin, pitavastatin has a high oral bioavailability (～80%). Plasma protein binding is also high for pitavastatin (＞95%), and regardless of the dosing, the highest tissue levels are found in the liver, its target organ. After oral administration, the peak plasma concentration is reached at ,0.8 h and the mean elimination half-life is ～11 h. Pitavastatin is only minimally metabolized, mainly by CYP2C8 and CYP2C9, and the predominant route of elimination of the parent drug and its metabolites is by means of bile excretion followed by elimination in the feces. In clinical studies, oral doses of 2–4 mg/day of pitavastatin produced dose-dependent reduction in LDL-cholesterol levels by 40–48% from baseline in patients with heterozygous familial hypercholesterolemia. In a 12-week double-blind comparative study, pitavastatin (2 mg/day) was more effective than pravastatin (10 mg/day) in reducing LDL-cholesterol levels (38 and 18%, respectively); however, both agents produced similar increases in HDL-cholesterol (～9%). The drug was well tolerated and the adverse reactions were mild and transient.; View all

8.8 Originator: Nissan (Japan)

8.9 Uses: A competitive inhibitor of HMG-CoA reductase. Antilipemic.

8.10 Safety Profile: A poison by ingestion.Experimental reproductive effects. When heated todecomposition it emits toxic vapors of NOx and Fí.

8.11 Chemical Synthesis: The convergent synthesis was achieved by cross-coupling of aryl halide 149 with (E)- alkenyl borane 155 which was derived from terminal acetylene 154 by via hydroboration. Anthranilic acid (143) was treated with TsCl and sodium carbonate in hot water to give N-tosylated intermediate in 78% yield, which was converted to the corresponding acid chloride 144 with PCl5 in o-dichlorobenzene at 85°C. Intermediate 144, without isolation, was reacted with fluorobenzene in the presence of AlCl3 at 80°C to give the Friedel-Crafts product which was then hydrolyzed in hot water to give fluorobenzophenone free aniline 145 in 64% yield from the N-tosyl anthranilic acid. Acetyl cyclopropane (146) was reacted with diethyl carbonate to give the corresponding ethyl ester 147. The quinoline core structure was obtained by condensing fluorobenzophenone 145 with 147 under acidic conditions with a Dean-Stark trap to give quinoline-3- carboxylic ethyl ester 148 in 90% yield. Ester 148 was hydrolyzed with potassium hydroxide, and the free carboxylic acid thus obtained was subsequently photoiododecarboxylated with iodine and PhI(OAc)2 to give aryl iodide 149 in 74% yield. 3-Trimethylsilylpropynal (150) was used as the starting material to prepare the chiral side chain. Compound 150 was reacted with di-anion 151 in THF at low temperature to give the corresponding diol ester which was first reacted with Et2BOMe and then reduced to acetylene with sodium borohydride. The free diol was protected as ketal with 2,2-dimethoxypropane in the presence of TsOH to give dimethylketal acetylene 152 in 99% yield. The ester functionality was hydrolyzed with sodium hydroxide to give the acid in 92% yield. The racemic free acid was resolved with (R)-(1-naphthyl)ethylamine to give the pure diastereomeric salt 153 which crystallized out in 31% yield and 97% e.e. Esterification of the free carboxylic acid liberated from the crystalline salt with ethyl iodide gave optically pure acetylene 154 in 70% yield. Hydroboration of acetylene 154 with disiamylborane gave (E)-alkenyldisiamylborane 155 and the excess borane reagent was quenched with sodium ethoxide in ethanol. After evaporation of all volatile material, the residue was directly subjected to the cross-coupling reaction. Palladium (II) chloride and aryl iodide 149 were mixed in acetonitrile to give coupling product 156 in 99% yield. After the ketal in 156 was hydrolyzed under acid conditions and the ester was hydrolyzed with sodium hydroxide, the resulting carboxylic sodium salt was reacted with calcium chloride to yield pitavastatin calcium (XIX) with 99% e.e.; View all

9. Computational chemical data

Molecular Weight: 463.56g/mol
Molecular Formula: C₂₅H₂₆CaFNO₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 880.2848136
Monoisotopic Mass: 880.2848136
Complexity: 626
Rotatable Bond Count: 14
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 12
Topological Polar Surface Area: 187
Heavy Atom Count: 63
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 2
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 3
CACTVS Substructure Key Fingerprint: AAADcfB/PYAAAAgAAAAAAAAAGDAAAAAAAAA8eMGCAAAAAACx/gAAHwAACAAADRyhngowyPIIEgCoAyTyTACCgCAhAiAImCEwZJgINPbAkZGEcAhloADI2AeY7MROgAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

10. Question & Answer

How much does Pitavastatin calcium usually cost? Apr 12 2023
Pitavastatin calcium is a chemical raw material that appears as a crystalline powder. The purity of Pitavastatin calcium sold on the market is around 99%. When purchasing Pitavastatin calcium, consume..
What is Pitavastatin calcium and how does it work? Jan 28 2023
Pitavastatin calcium is a statin medication used to regulate blood lipids. It competitively inhibits HMG-CoA reductase, preventing the liver from synthesizing cholesterol. Pitavastatin calcium is main..
What are the side effects of Pitavastatin calcium? Mar 09 2022
When the indices of blood sugar and blood pressure are high, it is necessary to increase exercise and avoid consuming high-calorie, high-energy foods, as they can cause hypercholesterolemia and famili..
What is the significance of sodium iodothyronine? Oct 20 2020
[Background and Overview][1][2] More than eight million Americans have hypothyroidism. Hypothyroidism occurs when the thyroid gland fails to produce sufficient amounts of thyroid hormone. Low levels o..

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Pitavastatin calcium