Cerivastatin

hypolipidemic agents

Thuốc Gốc

Small Molecule

CAS: 145599-86-6

ATC: C10AA06

ĐG : Bayer Healthcare , http://www.bayerhealthcare.com

CTHH: C₂₆H₃₄FNO₅

PTK: 459.5503

On August 8, 2001 the U.S. Food and Drug Administration (FDA) announced that Bayer Pharmaceutical Division voluntarily withdrew Baycol from the U.S. market, due to reports of fatal Rhabdomyolysis, a severe adverse reaction from this cholesterol-lowering (lipid-lowering) product. It has also been withdrawn from the Canadian market.

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₂₆H₃₄FNO₅

Phân tử khối

459.5503

Monoisotopic mass

459.242101408

InChI

InChI=1S/C26H34FNO5/c1-15(2)25-21(11-10-19(29)12-20(30)13-23(31)32)24(17-6-8-18(27)9-7-17)22(14-33-5)26(28-25)16(3)4/h6-11,15-16,19-20,29-30H,12-14H2,1-5H3,(H,31,32)/b11-10+/t19-,20-/m1/s1

InChI Key

InChIKey=SEERZIQQUAZTOL-ANMDKAQQSA-N

IUPAC Name

(3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid

Traditional IUPAC Name

cerivastatin

SMILES

COCC1=C(C2=CC=C(F)C=C2)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C(C(C)C)N=C1C(C)C

Độ hòa tan

Highly solubility

logP

3.4

logS

-5

pKa (strongest acidic)

4.05

pKa (Strongest Basic)

5.58

PSA

99.88 Å²

Refractivity

126.82 m³·mol^-1

Polarizability

50.23 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

-1

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : Cerivastatin, a competitive HMG-CoA reductase inhibitor effective in lowering LDL cholesterol and triglycerides, is used to treat primary hypercholesterolemia and mixed dyslipidemia (Fredrickson types IIa and IIb).

Cơ Chế Tác Dụng : On August 8, 2001 the U.S. Food and Drug Administration (FDA) announced that Bayer Pharmaceutical Division voluntarily withdrew Baycol from the U.S. market, due to reports of fatal Rhabdomyolysis, a severe adverse reaction from this cholesterol-lowering (lipid-lowering) product. It has also been withdrawn from the Canadian market. Cerivastatin competitively inhibits hydroxymethylglutaryl-coenzyme A (HMG-CoA) reductase, the hepatic enzyme responsible for converting HMG-CoA to mevalonate. As mevalonate is a precursor of sterols such as cholesterol, this results in a decrease in cholesterol in hepatic cells, upregulation of LDL-receptors, and an increase in hepatic uptake of LDL-cholesterol from the circulation.

Dược Động Học :

▧ Absorption :
The mean absolute oral bioavailability 60% (range 39 - 101%).
▧ Protein binding :
More than 99% of the circulating drug is bound to plasma proteins (80% to albumin).
▧ Metabolism :
Hepatic. Biotransformation pathways for cerivastatin in humans include the following: demethylation of the benzylic methyl ether to form Ml and hydroxylation of the methyl group in the 6'-isopropyl moiety to form M23.
▧ Half Life :
2-3 hours

Độc Tính : Rhabdomyolysis, liver concerns

Chỉ Định : Used as an adjunct to diet for the reduction of elevated total and LDL cholesterol levels in patients with primary hypercholesterolemia and mixed dyslipidemia (Fredrickson Types IIa and IIb) when the response to dietary restriction of saturated fat and cholesterol and other non-pharmacological measures alone has been inadequate.

Tương Tác Thuốc :

Bezafibrate Increased risk of myopathy/rhabdomyolysis
Bosentan Bosentan may decrease the serum concentration of cerivastatin by increasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cerivastatin if bosentan is initiated, discontinued or dose changed.
Clarithromycin The macrolide, clarithromycin, may increase the toxicity of the statin, cerivastatin.
Colchicine Increased risk of rhabdomyolysis with this combination
Cyclosporine Possible myopathy and rhabdomyolysis
Diltiazem Diltiazem may increase the serum concentration of cerivastatin. Cerivastatin may increase the serum concentration of diltiazem. Monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or if doses are changed.
Erythromycin The macrolide, erythromycin, may increase the toxicity of the statin, cerivastatin.
Fenofibrate Increased risk of myopathy/rhabdomyolysis
Gemfibrozil Increased risk of myopathy/rhabdomyolysis
Imatinib Imatinib, a strong CYP3A4 inhibitor, may increase the serum concentration of cerivastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cerivastatin if imatinib is initiated, discontinued or dose changed.
Itraconazole Increased risk of myopathy/rhabdomyolysis
Josamycin The macrolide, josamycin, may increase the toxicity of the statin, cerivastatin.
Ketoconazole Increased risk of myopathy/rhabdomyolysis
Nefazodone Nefazodone, a strong CYP3A4 inhibitor, may increase the serum concentration of cerivastatin by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cerivastatin if nefazodone is initiated, discontinued or dose changed.
Quinupristin This combination presents an increased risk of toxicity
Rifabutin Rifabutin may decrease the effect of cerivastatin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of cerivastatin if rifabutin is initiated, discontinued or dose changed.
Rifampicin Rifampin may decrease the effect of cerivastatin by increasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of cerivastatin if rifampin is initiated, discontinued or dose changed.

Liều Lượng & Cách Dùng : Tablet - Oral

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty :

Sản phẩm biệt dược : Baycol
Công ty :

Sản phẩm biệt dược : Lipobay
Công ty :

Sản phẩm biệt dược : Rivastatin

Đóng gói

Công ty : Bayer Healthcare

Website : http://www.bayerhealthcare.com

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB00439

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=446156

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505877

KEGG Compound

http://www.genome.jp/dbget-bin/www_bget?cpd:C07966

ChemSpider

http://www.chemspider.com/Chemical-Structure.393588.html

BindingDB

http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=18376

PharmGKB

http://www.pharmgkb.org/drug/PA448897

Wikipedia

http://en.wikipedia.org/wiki/Cerivastatin

RxList

http://www.rxlist.com/cgi/generic/cerivastat.htm

Drugs.com

http://www.drugs.com/mtm/cerivastatin.html

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