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Atorvastatin calcium(CAS No. 134523-03-8)

Atorvastatin calcium C66H68CaF2N4O10 (cas 134523-03-8) Molecular Structure

134523-03-8 Structure

Identification and Related Records

【Name】
Atorvastatin calcium
【CAS Registry number】
134523-03-8
【Synonyms】
1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-, (betaR,deltaR)-rel-
Atorvastatin calcium [USAN]
Lipitor (TN)
Atorvastatin Calcium (amorphous)
calcium (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoate
(3S,5S)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-yl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid
CI-981
(1betaR,deltaR)-2-(p-Fluorophenyl)-beta,delta-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoic acid
Atorvastatin (R*,R*)
Calcium (betaR,deltaR)-2-(p-fluorophenyl)-beta,delta-dihydroxy-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrole-1-heptanoate (1:2)
Atrovastatin
(3R,5R)-7-[2-(4-Fluorophenyl)-5-Isopropyl-3-Phenyl-
【Molecular Formula】
C66H68CaF2N4O10 (Products with the same molecular formula)
【Molecular Weight】
558.639803
【Inchi】
InChI=1S/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
【InChIKey】
XUKUURHRXDUEBC-KAYWLYCHSA-N
【Canonical SMILES】
CC(C)C1=C(C(=C(N1CCC(CC(CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
【Isomers smiles】
CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C
(=O)NC4=CC=CC=C4
【MOL File】
134523-03-8.mol

Chemical and Physical Properties

【Appearance】
White Crystalline Powder
【Melting Point】
176-178°C
【Boiling Point】
722.2 °C at 760 mmHg
【Flash Point】
390.6 °C
【Water】
Slightly soluble
【Computed Properties】
Molecular Weight:558.639803 [g/mol]
Molecular Formula:C33H35FN2O5
XLogP3-AA:5
H-Bond Donor:4
H-Bond Acceptor:6
Rotatable Bond Count:12
Tautomer Count:2
Exact Mass:558.253
MonoIsotopic Mass:558.253
Topological Polar Surface Area:112
Heavy Atom Count:41
Formal Charge:0
Complexity:822
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:5
Feature 3D Donor Count:3
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:4
Effective Rotor Count:13
Conformer Sampling RMSD:1.2
CID Conformer Count:25

Safety and Handling

【Hazard Codes】
Xn
【Risk Statements】
R20/21/22
【Safety Statements 】
26-36
【Safety】

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.

【Formulations/Preparations】
The main ingredient in the drug Lipitor produced by Pfizer (oral tablets). /Calcium salt/
Lipitor; Sortis; Torvast; Totalip; Xarator /Calcium salt/
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Prepn: B.D. Roth, EP 409281; idem, US 5273995 (1991, 1993 both to Warner-Lambert)
【Usage】

A selective, competitive HMG-CoA reductase inhibitor. The only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia

Biomedical Effects and Toxicity

【Biological Activity】
Potent HMG-CoA reductase inhibitor (IC 50 = 8 nM). Reduces circulating LDL-C by inhibiting cholesterol biosynthesis and inducing expression of LDL receptors. Inhibits smooth muscle cell proliferation in vitro and exhibits antinociceptive effects in the inflammatory hypernociception model.
【Pharmacological Action】
- Substances used to lower plasma cholesterol levels.
- Compounds that inhibit HMG-CoA reductases. They have been shown to directly lower cholesterol synthesis.
【Therapeutic Uses】
The statins are the most effective & best-tolerated agents for treating dyslipidemia. /Statins/
A HMG-CoA reductase inhibitors are indicated as adjuncts to diet in the treatment of primary hypercholesterolemia (heterozygous familial and nonfamilial) and mixed dyslipedemia (type IIa and IIb hyperlipoproteinemia) caused by elevated low-density lipoprotein cholesterol (LDL-C) concentrations in patients with a significant risk of coronary artery disease, who have not responded to diet or other measures alone. the HMG-CoA reductase inhibitors may also be useful for the reduction of elevated LDL-C concentrations in patients with combined hypercholesterolemia and hypertriglyceridemia, and for the reduction of total-C, LDL-C, apolipoprotein B (Apo-B), and triglyceride (TG), and to increase HDL-C levels in patients with combined hypercholesterolemia and mixed dyslipidemia. Atorvastatin ... /is/ indicated as adjunctive therapy with other lipid lowering treatments (eg LDL apheresis) in homozygous familial hypercholesterolemia to reduce total cholesterol (total-C) and LDL-C. Atorvastatin ... /is/ indicated for the treatment of dysbetalipoproteinemia (type III hyperlipoproteinemia) in patients who did not respond adequately to diet. Atorvastatin ... /is/ indicated as adjunctive therapy to diet for the treatment of patients with elevated serum triglyceride levels (type IV hyperlipoproteinemia). /Included in US product labeling/
【Biomedical Effects and Toxicity】
All the statins are admin as the active beta-hydroxy acid form ... /and/ are subject to extensive first-pass metab by the liver. 95% of most of these drugs & their active metabolites, the beta-hydroxy acids, are bound to plasma proteins. After an oral dose, plasma concns peak in 1-4 hr. The liver biotransforms all statins, resulting in low systemic availability of the parent compounds. About 70% of statin metabolites are excreted by the liver. /Statins/
Rapidly absorbed; bioavailablity of parent compound 14%.
The absorption, distribution and excretion of radioactivity were investigated after repeated oral administration of (14)C-CI-981 at 1 mg/kg once daily for 21 days to male rats. Also, the transfer to fetuses, milk and suckling pups were investigated after single oral administration of (14)C-CI-981 at 1 mg/kg to pregnant or lactating rats. 1) During the course of repeated administration, plasma levels of radioactivity at 24 hr after daily dosing reached a steady state after the 2nd dosing. The steady state plasma levels of radioactivity varied with a range of 2.1 to 4.1 times higher than that after the 1st dosing. After the 21st dosing, plasma levels of radioactivity reached its maximum of 17.5 ng eq./mL at 2.7 hr and then declined with a terminal half-life of 12.0 hr. 2) During the course of repeated administration, concentrations of radioactivity in most tissues increased with the number of dose. In any cases, however, the increases at 4 and 24 hr after the 21st dosing were less than 2.7 and 4.1 times, respectively. After the 21st dosing, in most tissues, levels of radioactivity attained the maxima at 4 hr, and thereafter decreased with time. At all the sampling points, the highest concentrations of radioactivity were observed in the liver. Whole-body autoradiograms showed similar distribution of radioactivity, and at 168 hr after the 21st dosing low radioactivity was found only in the liver, intestinal contents and gastric wall. 3) During the course of repeated administration, excretion profiles of radioactivity in urine and feces up to 24 hr after daily dosing remained fairly constant from Day 5. Up to 168 hr after the last dosing, 0.3 and 96.4% of the cumulative dose were excreted in urine and feces, respectively. 4) Whole-body autoradiograms of rats on Days 13 and 18 of pregnancy showed trace levels of radioactivity in the fetuses. After administration to rats on Day 18 of pregnancy, radioactivity was found in the fetal tissues. Although fetal liver and digestive tract showed relatively high concentrations, percentage of radioactivity transferred per fetus was 0.00% of the administered dose. 5) After administration to lactating rats, radioactivity in milk reached the maximum of 17.1 ng eq./mL at 6.0 hr and thereafter declined with a half-life of 7.8 hr. When compared with the plasma levels determined simultaneously, Cmax in milk appeared later and then declined more slowly. In suckling pups, radioactivity was detected only in the liver, clotted milk in the stomach and carcass, and the levels in the other tissues were below the detection limit.

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