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79902-63-9 molecular structure
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(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 and InChIs

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

Cite this record

CBID:523 http://www.chembase.cn/molecule-523.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
79902-63-9
PubChem SID
160963986
PubChem CID
6419910

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

ALOGPS 2.1 JChem
LOG S -4.53  Solubility (Water) 1.22e-02 g/l 
Log P 4.51 
Molar Refractivity 117.6834 cm3 Polarizability 46.25644 Å3
Polar Surface Area 72.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true  Acid pKa 14.914537 
H Acceptors H Donor
LogD (pH = 5.5) 4.4582014  LogD (pH = 7.4) 4.4582014 
Log P 4.4582014 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
0.76 mg/L expand Show data source
Hydrophobicity(logP)
4.7 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00641 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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