(1S,3R,7S,8S,8aR)-8-{2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate

• ChemBase ID: 523
• Molecular Formular: C25H38O5
• Molecular Mass: 418.56622
• Monoisotopic Mass: 418.27192432
• SMILES: [C@@H]12[C@H](C[C@H](C=C2C=C[C@@H]([C@@H]1CCC1OC(=O)C[C@H](O)C1)C)C)OC(=O)C(CC)(C)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CCC1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)(C)C
• InChI: InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19?,20-,21-,23-/m0/s1
• InChIKey: RYMZZMVNJRMUDD-IIIOEECLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7S,8S,8aR)-8-{2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• IUPAC Traditional name: (1S,3R,7S,8S,8aR)-8-{2-[(4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• Brand Name: Cholestat; Coledis; Colemin; Corolin; Denan; Labistatin; Lipex; Lodales; Medipo; Nivelipol; Pantok; Rendapid; Simovil; Sinvacor; Sivastin; Synvinolin; Vasotenal; Zocor; Zocord
• Synonyms: Simvastatina [Spanish]; Simvastatin [Usan:Ban:Inn]; Simvastatine [French]; Simvastatinum [Latin]; Simvastatin

Database IDs

• CAS Number: 79902-63-9
• PubChem SID: 160963986
• PubChem CID: 6419910

CALCULATED PROPERTIES

ALOGPS 2.1

• LOG S: -4.53
• Solubility (Water): 1.22e-02 g/l
• Log P: 4.51

JChem

• Molar Refractivity: 117.6834 cm^3
• Polarizability: 46.25644 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.4582014
• LogD (pH = 7.4): 4.4582014
• Log P: 4.4582014

PROPERTIES

Physical Property

• Solubility: 0.76 mg/L
• Hydrophobicity(logP): 4.7

DETAILS

DrugBank - DB00641

• Drug Groups: approved
• Description: A derivative of lovastatin and potent competitive inhibitor of 3-hydroxy-3-methylglutaryl coenzyme A reductase (hydroxymethylglutaryl COA reductases), which is the rate-limiting enzyme in cholesterol biosynthesis. It may also interfere with steroid hormone production. Due to the induction of hepatic LDL receptors, it increases breakdown of LDL cholesterol. [PubChem]
• Indication: For the treatment of hypercholesterolemia.
• Pharmacology: Simvastatin, the methylated form of lovastatin, is an oral antilipemic agent which inhibits HMG-CoA reductase. simvastatin is used in the treatment of primary hypercholesterolemia and is effective in reducing total and LDL-cholesterol as well as plasma triglycerides and apolipoprotein B.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, simvastatin is a substrate for CYP3A4.
• Absorption: Absorption of simvastatin, estimated relative to an intravenous reference dose, in each of two animal species tested, averaged about 85% of an oral dose. In animal studies, after oral dosing, simvastatin achieved substantially higher concentrations in the liver than in non-target tissues.
• Half Life: 3 hours
• Protein Binding: Both simvastatin and its b-hydroxyacid metabolite are highly bound (approximately 95%) to human plasma proteins.
• Elimination: Following an oral dose of 14C-labeled simvastatin in man, 13% of the dose was excreted in urine and 60% in feces.
• References: Wolozin B, Wang SW, Li NC, Lee A, Lee TA, Kazis LE: Simvastatin is associated with a reduced incidence of dementia and Parkinson's disease. BMC Med. 2007 Jul 19;5:20. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Wolozin B, Wang SW, Li NC, Lee A, Lee TA, Kazis LE: Simvastatin is associated with a reduced incidence of dementia and Parkinson's disease. BMC Med. 2007 Jul 19;5:20. Pubmed