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

• ChemBase编号: 322
• 分子式: C26H34FNO5
• 平均质量: 459.5502632
• 单一同位素质量: 459.24210141
• SMILES: Fc1ccc(c2c(c(nc(c2/C=C/[C@@H](O)C[C@@H](O)CC(=O)O)C(C)C)C(C)C)COC)cc1
• Canonical SMILES: COCc1c(c2ccc(cc2)F)c(/C=C/[C@H](C[C@H](CC(=O)O)O)O)c(nc1C(C)C)C(C)C
• 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
• InChIKey: SEERZIQQUAZTOL-ANMDKAQQSA-N

名称和登记号

名称

• IUPAC标准名: (3R,5S,6E)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid; (3R,5S)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
• IUPAC传统名: cerivastatin acid; (3R,5S)-7-[4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
• 商标名: Baycol; Lipobay; Rivastatin
• 别名: Cerivastatin sodium; Cerivastatin, sodium salt; Cerivastatin

登记号

• CAS号: 145599-86-6
• PubChem SID: 46505877; 160963785
• PubChem CID: 446156
• CHEBI ID: 3558
• ATC码: C10AA06
• CHEMBL: 1477
• Chemspider ID: 393588
• DrugBank ID: DB00439
• KEGG ID: D07661
• 美国药典/FDA物质标识码: AM91H2KS67
• 维基百科标题: Cerivastatin

理论计算性质

JChem

• Acid pKa: 4.0493016
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 2.5265858
• LogD (pH = 7.4): 1.146073
• Log P: 2.6681542
• 摩尔折射率: 126.8232 cm^3
• 极化性: 49.7628 Å^3
• 极化表面积: 99.88 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.15
• LOG S: -5.04
• 溶解度: 4.19e-03 g/l

分子性质

理化性质

• 溶解度: Highly solubility
• 疏水性(logP): 3.4

药理学性质

• 半衰期: 2–3 hours
• 法定药品分级: Withdrawn from market

详细说明

DrugBank - DB00439

• Drug Groups: withdrawn
• Description: 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 It has also been withdrawn from the Canadian market.
• Indication: 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.
• Pharmacology: 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).
• Toxicity: Rhabdomyolysis, liver concerns
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: The mean absolute oral bioavailability 60% (range 39 - 101%).
• Half Life: 2-3 hours
• Protein Binding: More than 99% of the circulating drug is bound to plasma proteins (80% to albumin).
• References: Furberg CD, Pitt B: Withdrawal of cerivastatin from the world market. Curr Control Trials Cardiovasc Med. 2001;2(5):205-207. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Furberg CD, Pitt B: Withdrawal of cerivastatin from the world market. Curr Control Trials Cardiovasc Med. 2001;2(5):205-207. Pubmed