(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 ID: 322
• Molecular Formular: C26H34FNO5
• Molecular Mass: 459.5502632
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• 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; (3R,5S)-7-[4-(4-fluorophenyl)-5-(methoxymethyl)-2,6-bis(propan-2-yl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
• IUPAC Traditional name: cerivastatin acid; (3R,5S)-7-[4-(4-fluorophenyl)-2,6-diisopropyl-5-(methoxymethyl)pyridin-3-yl]-3,5-dihydroxyhept-6-enoic acid
• Brand Name: Baycol; Lipobay; Rivastatin
• Synonyms: Cerivastatin sodium; Cerivastatin, sodium salt; Cerivastatin

Database IDs

• CAS Number: 145599-86-6
• PubChem SID: 46505877; 160963785
• PubChem CID: 446156
• CHEBI ID: 3558
• ATC CODE: C10AA06
• CHEMBL: 1477
• Chemspider ID: 393588
• DrugBank ID: DB00439
• KEGG ID: D07661
• Unique Ingredient Identifier: AM91H2KS67
• Wikipedia Title: Cerivastatin

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.0493016
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 2.5265858
• LogD (pH = 7.4): 1.146073
• Log P: 2.6681542
• Molar Refractivity: 126.8232 cm^3
• Polarizability: 49.7628 Å^3
• Polar Surface Area: 99.88 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.15
• LOG S: -5.04
• Solubility (Water): 4.19e-03 g/l

PROPERTIES

Physical Property

• Solubility: Highly solubility
• Hydrophobicity(logP): 3.4

Pharmacology Properties

• Half Life: 2–3 hours
• Legal Status: Withdrawn from market

DETAILS

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• Drug Groups: withdrawn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 It has also been withdrawn from the Canadian market.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

REFERENCES

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