Atorvastatin calcium trihydrateProduct ingredient for Atorvastatin

Name
Atorvastatin calcium trihydrate
Drug Entry
Atorvastatin

Atorvastatin (Lipitor®), is a lipid-lowering drug included in the statin class of medications. By inhibiting the endogenous production of cholesterol in 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,8 which catalyzes the conversion of HMG-CoA to mevalonic acid. This conversion is a critical metabolic reaction 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 statins is considered standard practice for patients following any cardiovascular event, and for people who are at moderate to high risk of developing cardiovascular disease. The evidence supporting statin use, coupled with minimal side effects and long term benefits, has resulted in wide use of this medication in North America.9,10

Atorvastatin and other statins including lovastatin, pravastatin, rosuvastatin, fluvastatin, and simvastatin are considered first-line treatment options for dyslipidemia.9,10 The increasing use of this class of drugs is largely attributed to the rise in cardiovascular diseases (CVD) (such as heart attack, atherosclerosis, angina, peripheral artery disease, and stroke) in many countries.11 An elevated cholesterol level (elevated low-density lipoprotein (LDL) levels in particular) is a significant risk factor for the development of CVD.9,12 Several landmark studies demonstrate that the use of statins is associated with both a reduction in LDL levels and CVD risk.13,14,15,16,17,18 Statins were shown to reduce the incidences of all-cause mortality, including fatal and non-fatal CVD, as well as the need for surgical revascularization or angioplasty following a heart attack.9,10 Some evidence has shown that even for low-risk individuals (with <10% risk of a major vascular event occurring within five years) statin use leads to a 20%-22% relative reduction in the number of 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.19,20

Atorvastatin was first synthesized in 1985 by Dr. Bruce Roth and approved by the FDA in 1996.33 It is a pentasubstituted pyrrole 3 formed by two contrasting moieties with an achiral heterocyclic core unit and a 3,5-dihydroxypentanoyl side chain identical to its parent compound.34 Unlike other members of the statin group, atorvastatin is an active compound and therefore does not require activation.4

Accession Number
DBSALT001499
Structure
Thumb
Synonyms
Not Available
UNII
48A5M73Z4Q
CAS Number
344423-98-9
Weight
Average: 1209.408
Monoisotopic: 1208.4846357
Chemical Formula
C66H74CaF2N4O13
InChI Key
SHZPNDRIDUBNMH-NIJVSVLQSA-L
InChI
InChI=1S/2C33H35FN2O5.Ca.3H2O/c2*1-21(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;;;;/h2*3-16,21,26-27,37-38H,17-20H2,1-2H3,(H,35,41)(H,39,40);;3*1H2/q;;+2;;;/p-2/t2*26-,27-;;;;/m11..../s1
IUPAC Name
calcium (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenyl-C-hydroxycarbonimidoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarboximidato)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate trihydrate
SMILES
O.O.O.[Ca++].[H][C@@](O)(CCN1C(C(C)C)=C(C(O)=NC2=CC=CC=C2)C(=C1C1=CC=C(F)C=C1)C1=CC=CC=C1)C[C@@]([H])(O)CC(O)=O.[H][C@@](O)(CCN1C(C(C)C)=C(C([O-])=NC2=CC=CC=C2)C(=C1C1=CC=C(F)C=C1)C1=CC=CC=C1)C[C@@]([H])(O)CC([O-])=O
ChemSpider
571124
ChEBI
2911
Wikipedia
Atorvastatin
Predicted Properties
PropertyValueSource
Water Solubility0.000597 mg/mLALOGPS
logP6.1ALOGPS
logP6.11ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)0.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.94 Å2ChemAxon
Rotatable Bond Count24ChemAxon
Refractivity180.34 m3·mol-1ChemAxon
Polarizability59.95 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon