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Your Location：Home>Product Center >> Pharmaceutical API >> Rosuvastatin Calcium
  • Rosuvastatin Calcium
Name:Rosuvastatin Calcium
CAS No:147098-20-2

PRODUCT DESCRIPTION

【Name】
Rosuvastatin calcium
【Iupac name】
calcium
(E,3R,
5S)-7-[4-(4-fluorophenyl)-2-[methyl(methylsulfonyl)amino]-6-propan-2-
ylpyrimidin-5-yl]-3,5-dihydroxyhept-6-enoate
【CAS Registry number】
147098-20-2
【Synonyms】
7-{4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid
【Molecular Formula】
2(C22H27FN3O6S).Ca (Products with the same molecular formula)
【Molecular Weight】
1001.14
【Inchi】
InChI=1/2C22H28FN3O6S.Ca/c2*1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32;/h2*5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30);/q;;+2/p-2/b2*10-9+;/t2*16-,17+;/m00./s1
【Canonical SMILES】
CC(C)C1=NC(=NC(=C1C=CC(CC(CC(=O)[O-])O)O)C2=CC=C(C=C2)F)N(C)S(=O)(=O)C.CC(C)C1=NC(=NC(=C1C=CC(CC(CC(=O)[O-])O)O)C2=CC=C(C=C2)F)N(C)S(=O)(=O)C.[Ca+2]
【Isomers smiles】
CC(C1=NC(=NC(=C1/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])C2=CC=C(C=C2)F)N(S(=
O)(=O)C)C)C.CC(C1=NC(=NC(=C1/C=C/[C@@H](O)C[C@@H](O)CC(=O)[O-])C2=CC=C
(C=C2)F)N(S(=O)(=O)C)C)C.[Ca+2]
【MOL File】
147098-20-2.mol

Chemical and Physical Properties

【Appearance】
white to off-white crystalline solid
【Density】
==
【Melting Point】
122℃
【Boiling Point】
745.6 °C at 760 mmHg
【Flash Point】
404.7 °C
【Solubilities】
In water, 41 mg/L at 25 deg C /Estimated/
【Computed Properties】
Molecular Weight:1001.137366 [g/mol]
Molecular Formula:C44H54CaF2N6O12S2
H-Bond Donor:4
H-Bond Acceptor:14
Rotatable Bond Count:18
Tautomer Count:10
Exact Mass:1000.28351
MonoIsotopic Mass:1000.28351
Topological Polar Surface Area:304
Heavy Atom Count:67
Formal Charge:0
Complexity:761
Isotope Atom Count:0
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:2
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:3

Safety and Handling

【Formulations/Preparations】
Oral: Tablets: 5 mg (of rosuvastatin), (Crestor), (AstraZeneca); 10 mg (of rosuvastatin), (Crestor), (AstraZeneca); 20 mg (of rosuvastatin), (Crestor), (AstraZeneca); 40 mg (of rosuvastatin), (Crestor), (AstraZeneca).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl rosuvastatin calcium, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Rosuvastatin Calcium/
【Specification】

?Rosuvastatin Calcium , its cas register number is 147098-20-2. It also can be called?7-{4-(4-Fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl}-3,5-dihydroxyhept-6-enoic acid .It is a?white to off-white crystalline solid.

【Octanol/Water Partition Coefficient】
log Kow = 2.05 /Estimated/
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Use and Manufacturing

【Usage】

A selective, competitive HMG-CoA reductase inhibitor

Biomedical Effects and Toxicity

【Pharmacological Action】
- Compounds that inhibit HMG-CoA reductases. They have been shown to directly lower cholesterol synthesis.
【Therapeutic Uses】
Hyperlipidemia (treatment)-Rosuvastatin is indicated as an adjunct to diet to reduce elevated total cholesterol (total-C), low-density lipoprotein cholesterol (LDL-C), apolipoprotein B (Apo B), non-high-density lipoprotein cholesterol (HDL-C), and triglyceride (TG) concentrations and to increase high-density lipoprotein cholesterol (HDL-C) in patients with primary hypercholesterolemia (heterozygous familial and nonfamilial) and mixed dyslipidemia (Fredrickson Types IIa and IIb)
Rosuvastatin is indicated as an adjunct to diet for the treatment of patients with elevated serum triglyceride levels (Fredrickson Type IV).
Rosuvastatin is ... indicated to reduce LDL-C, total-C, and Apo B in patients with homozygous familial hypercholesterolemia as an adjunct to other lipid-lowering treatments, such as low-density lipoprotein apheresis, or if such treatments are unavailable.
【Biomedical Effects and Toxicity】
In clinical pharmacology studies in man, peak plasma concentrations of rosuvastatin were reached 3 to 5 hours following oral dosing. Both peak concentration (Cmax) and area under the plasma concentration-time curve (AUC) increased in approximate proportion to rosuvastatin dose. The absolute bioavailability of rosuvastatin is approximately 20%. Administration of rosuvastatin with food decreased the rate of drug absorption by 20% as assessed by Cmax , but there was no effect on the extent of absorption as assessed by AUC.
Mean volume of distribution at steady-state of rosuvastatin is approximately 134 liters. Rosuvastatin is 88% bound to plasma proteins, mostly albumin. This binding is reversible and independent of plasma concentrations.
Following oral administration, rosuvastatin and its metabolites are primarily excreted in the feces (90%). ... After an intravenous dose, approximately 28% of total body clearance was via the renal route, and 72% by the hepatic route.
In hemodialysis, rosuvastatin clearance is not significantly enhanced.
Pharmacokinetic studies show an approximate 2-fold elevation in median exposure (AUC) in Japanese subjects residing in Japan and in Chinese subjects residing in Singapore when compared with Caucasians residing in North America and Europe.
Mild to moderate renal impairment (creatinine clearance >/=30 mL/min/1.73 sq m) had no influence on plasma concentrations of rosuvastatin when oral doses of 20 mg rosuvastatin were administered for 14 days. However, plasma concentrations of rosuvastatin increased to a clinically significant extent (about 3-fold) in patients with severe renal impairment (CLcr 80 mL/min/1.73sq m).
In patients with chronic alcohol liver disease, plasma concentrations of rosuvastatin were modestly increased. In patients with Child-Pugh A /scoring for liver/ disease, Cmax and AUC were increased by 60% and 5%, respectively, as compared with patients with normal liver function. In patients with Child-Pugh B disease, Cmax and AUC were increased 100% and 21%, respectively, compared with patients with normal liver function.
Rosuvastatin crosses the placenta and is found in fetal tissue and amniotic fluid at 3% and 20%, respectively, of the maternal plasma concentration following a single 25 mg/kg oral gavage dose on gestation day 16 in rats. A higher fetal tissue distribution (25% maternal plasma concentration) was observed in rabbits after a single oral gavage dose of 1 mg/kg on gestation day 18.
It is not known whether rosuvastatin is excreted in human milk. Studies in lactating rats have demonstrated that rosuvastatin is secreted into breast milk at levels 3 times higher than that obtained in the plasma following oral gavage dosing.
... Healthy male adult volunteers were given a single oral dose of rosuvastatin 40 mg on one trial day and an intravenous infusion of rosuvastatin 8 mg over 4 hours on the other. Pharmacokinetic and tolerability assessments were conducted up to 96 hours after dosing. A 3-compartment pharmacokinetic model was fitted to the plasma concentration-time profiles obtained for each volunteer after intravenous dosing. Ten white male volunteers entered and completed the trial. Their mean age was 35.7 years (range, 21-51 years), their mean height was 177 cm (range, 169-182 cm), and their mean body weight was 77.6 kg (range, 68-85 kg). The absolute oral bioavailability of rosuvastatin was estimated to be 20.1%,and the hepatic extraction ratio was estimated to be 0.63. The mean volume of distribution at steady state was 134 L. Renal clearance accounted for approximately 28% of total plasma clearance (48.9 L/h). Single oral and intravenous doses of rosuvastatin were well tolerated in this small number of healthy male volunteers. The absolute oral bioavailability of rosuvastatin in these 10 healthy volunteers was approximately 20%, and absorption was estimated to be 50%. The volume of distribution at steady state was consistent with extensive distribution of rosuvastatin to the tissues. The modest absolute oral bioavailability and high hepatic extraction of rosuvastatin are consistent with first-pass uptake into the liver after oral dosing. Rosuvastatin was cleared by both renal and nonrenal routes; tubular secretion was the predominant renal process. [Martin PD et al; Clin Ther 25 (10): 2553-63 (2003)] PubMed Abstract
The effects of age and gender on the pharmacokinetics of rosuvastatin (Crestor) were assessed in healthy young (18-35 years) and elderly (> 65 years) males and females in this open, nonrandomized, noncontrolled, parallel-group trial. Sixteen males and 16 females (8 young and elderly volunteers per gender group) were enrolled. Mean (range) ages were 24 (18-33) and 68 (65-73) years for young and elderly volunteers, respectively. Volunteers were given a single oral 40 mg dose of rosuvastatin. Blood samples for measurement of rosuvastatin plasma concentration were collected up to 96 hours following dosing. Age and gender effects were assessed by constructing 90% confidence intervals (CIs) around the ratios of young/elderly and male/female geometric least square means (glsmeans) for AUC(0-t) and Cmax (derived from ANOVA of log-transformed parameters). Small differences in rosuvastatin pharmacokinetics were noted between age and gender groups. Glsmean AUC(0-t) was 6% higher (90% CI = 0.86-1.30) and glsmean Cmax, 12% higher (90% CI = 0.83-1.51) in the young compared with the elderly group. Glsmean AUC(0-t) was 9% lower (90% CI = 0.74-1.12) and glsmean Cmax 18% lower (90% CI = 0.61-1.11) in the male compared with the female group. These small differences are not considered clinically relevant, and dose adjustments based on age or gender are not anticipated. Rosuvastatin was well tolerated in all volunteers. [Martin PD et al; J Clin Pharmacol 42 (10): 1116-21 (2002)] PubMed Abstract

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 21(SRC), determined from a structure estimation method(2), indicates that rosuvastatin is expected to have very high mobility in soil(SRC). The estimated pKas of rosuvastatin are 3.8 (carboxylic acid group), 4.9 and 5.5 (amine groups)(3) indicating that this compound will primarily exist in anion form in the environment and anions do not volatilize from moist soil surfaces nor do they adsorb more strongly to organic carbon and clay than their neutral counterparts(4). Rosuvastatin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.7X10-19 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 21(SRC), determined from a structure estimation method(2), indicates that rosuvastatin is not expected to adsorb to suspended solids and sediment(SRC). The estimated pKas of rosuvastatin are 3.8 (carboxylic acid group), 4.9 and 5.5 (amine groups)(3) indicating that this compound will primarily exist in anion form in the environment and anions do not volatilize from water surfaces. According to a classification scheme(4), an estimated BCF of 3.2(SRC), from an estimated log Kow of 2.05(5) and a regression derived equation(6) suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), rosuvastatin, which has an estimated vapor pressure of 3.7 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase rosuvastatin may be removed from the air by wet and dry deposition(SRC). Rosuvastatin may absorb light with wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight; however, the rate of this reaction is not known(SRC).

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