Pitavastatin calciumProduct ingredient for Pitavastatin

Name
Pitavastatin calcium
Drug Entry
Pitavastatin

Pitavastatin, also known as the brand name product Livalo, is a lipid-lowering drug belonging to the statin class of medications. By inhibiting the endogenous production of cholesterol within the liver, statins lower abnormal cholesterol and lipid levels and ultimately reduce the risk of cardiovascular disease. More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase,3 which catalyzes the conversion of HMG-CoA to mevalonic acid. This is the third step in a sequence of metabolic reactions involved in the production of several compounds involved in lipid metabolism and transport including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as "bad cholesterol"), and very low-density lipoprotein (VLDL). Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD, such as those with Type 2 Diabetes. The clear evidence of the benefit of statin use coupled with very minimal side effects or long term effects has resulted in this class becoming one of the most widely prescribed medications in North America.4,5

Pitavastatin and other drugs from the statin class of medications including atorvastatin, pravastatin, rosuvastatin, fluvastatin, and lovastatin are considered first-line options for the treatment of dyslipidemia.4,5 Increasing use of the statin class of drugs is largely due to the fact that cardiovascular disease (CVD), which includes heart attack, atherosclerosis, angina, peripheral artery disease, and stroke, has become a leading cause of death in high-income countries and a major cause of morbidity around the world.6 Elevated cholesterol levels, and in particular, elevated low-density lipoprotein (LDL) levels, are an important risk factor for the development of CVD.4 Use of statins to target and reduce LDL levels has been shown in a number of landmark studies to significantly reduce the risk of development of CVD and all-cause mortality.8,9,10,11,12,13 Statins are considered a cost-effective treatment option for CVD due to their evidence of reducing all-cause mortality including fatal and non-fatal CVD as well as the need for surgical revascularization or angioplasty following a heart attack.4,5 Evidence has shown that even for low-risk individuals (with <10% risk of a major vascular event occurring within 5 years) statins cause a 20%-22% relative reduction in major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks.15,14

While all statin medications are considered equally effective from a clinical standpoint, rosuvastatin is considered the most potent; doses of 10 to 40mg rosuvastatin per day were found in clinical studies to result in a 45.8% to 54.6% decrease in LDL cholesterol levels.16,17,13,18 Study data has confirmed that pitavastatin's potency in lowering LDL-C is comparable to that of other statins but also has increased efficacy in increasing HDL-C (also known as "good cholesterol").21,22,23 Despite these differences in potency, several trials have demonstrated only minimal differences in terms of clinical outcomes between statins.11

Accession Number
DBSALT000140
Structure
Thumb
Synonyms
Not Available
UNII
IYD54XEG3W
CAS Number
147526-32-7
Weight
Average: 880.984
Monoisotopic: 880.284814023
Chemical Formula
C50H46CaF2N2O8
InChI Key
RHGYHLPFVJEAOC-WUVPNHNWSA-L
InChI
InChI=1S/2C25H24FNO4.Ca/c2*26-17-9-7-15(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;/h2*1-4,7-12,16,18-19,28-29H,5-6,13-14H2,(H,30,31);/q;;+2/p-2/b2*12-11+;
IUPAC Name
calcium bis((3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate)
SMILES
[Ca++].[H]\C(=C(\[H])[C@@]([H])(O)C[C@@]([H])(O)CC([O-])=O)C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N=C1C1CC1.[H]\C(=C(\[H])[C@@]([H])(O)C[C@@]([H])(O)CC([O-])=O)C1=C(C2=CC=C(F)C=C2)C2=CC=CC=C2N=C1C1CC1
PubChem Compound
5282451
ChemSpider
19643041
ChEBI
71258
Wikipedia
Pitavastatin
Predicted Properties
PropertyValueSource
Water Solubility0.000657 mg/mLALOGPS
logP6.13ALOGPS
logP2.92ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.13ChemAxon
pKa (Strongest Basic)4.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.48 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity126.58 m3·mol-1ChemAxon
Polarizability43.39 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon