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81093-37-0 molecular structure
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(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

ChemBase ID: 60
Molecular Formular: C23H36O7
Molecular Mass: 424.52774
Monoisotopic Mass: 424.24610349
SMILES and InChIs

SMILES:
O([C@@H]1[C@@H]2[C@H]([C@H](C=CC2=C[C@@H](O)C1)C)CC[C@@H](O)C[C@@H](O)CC(=O)O)C(=O)[C@H](CC)C
Canonical SMILES:
CC[C@@H](C(=O)O[C@H]1C[C@H](O)C=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)O)O)O)[C@H](C=C2)C)C
InChI:
InChI=1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
InChIKey:
TUZYXOIXSAXUGO-PZAWKZKUSA-N

Cite this record

CBID:60 http://www.chembase.cn/molecule-60.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
IUPAC Traditional name
pravastatin
Brand Name
Elisor
Lipostat
Mevalotin
Mevinolin
Oliprevin
Pravachol
Pravaselect
Selectin
Selipran
Vasten
Synonyms
Pravastatina [Spanish]
Pravastatin Sodium
Pravastatine [French]
Pravastatinum [Latin]
(βR,δR,1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β,δ,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic Acid-3H
Pravastatin
Pravastatin-3H
CAS Number
81093-37-0
PubChem SID
160963523
46504851
PubChem CID
54687

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
P702003 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.212299  H Acceptors
H Donor LogD (pH = 5.5) 0.34003893 
LogD (pH = 7.4) -1.3779589  Log P 1.6470916 
Molar Refractivity 113.5979 cm3 Polarizability 44.338123 Å3
Polar Surface Area 124.29 Å2 Rotatable Bonds 11 
Lipinski's Rule of Five true 
Log P 2.23  LOG S -3.24 
Solubility (Water) 2.42e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
2464mg/L expand Show data source
Hydrophobicity(logP)
2.2 expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00175 external link
Item Information
Drug Groups approved
Description Pravastatin is a cholesterol-lowering agent that belongs to a class of medications known as statins. It was derived from microbial transformation of mevastatin, the first statin discovered. It is a ring-opened dihydroxyacid with a 6’-hydroxyl group that does not require in vivo activation. Pravastatin is one of the lower potency statins; however, its increased hydrophilicity is thought to confer advantages such as minimal penetration through lipophilic membranes of peripheral cells, increased selectivity for hepatic tissues, and a reduction in side effects compared with lovastatin and simvastatin.
Indication For the treatment of hypercholesterolemia and to reduce the risk of cardiovascular disease.
Pharmacology The primary cause of cardiovascular (CV) disease is atherosclerotic plaque formation and sustained elevation of cholesterol in the blood increases the risk of CV disease. Pravastatin lowers hepatic production of cholesterol by competitively inhibiting HMG-CoA reductase, the enzyme that catalyzes the rate-limiting step in the cholesterol biosynthesis pathway via the mevalonic acid pathway. Decreased hepatic cholesterol levels causes increased uptake of low density lipoprotein (LDL) cholesterol and reduces cholesterol levels in the circulation. Pravastatin also inhibits hepatic synthesis if VLDL. At therapeutic doses, pravastatin lowers LDL cholesterol by 20-30%, increase high density lipoprotein (HDL) cholesterol by 3-10%, and decrease plasma triglycerides by 19-34%. HDL cholesterol is thought to confer protective effects against CV disease, whereas high LDL and triglyceride levels are associated with higher risk of disease.
Toxicity Side effects include diarrhea, nausea, constipation, gas abdominal pain, myopathy, myositis, rhabdomyolysis, and hepatotoxicity. LD50=mg/kg (orally in rat)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic, there is a small amount of metabolism by P450 enzymes, but this effect is so minimal that inhibitory pharmacokinetic drug interactions have no real effect on its overall activity and elimination. An in vitro study which found moderate affinity for P450 2C9 (major), 2D6 and 3A4.
Absorption Average oral absorption of pravastatin is 34% and absolute bioavailability is 17%.
Half Life 77 hours
Protein Binding 50%
Elimination Approximately 20% of a radiolabeled oral dose is excreted in urine and 70% in the feces.
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - P702003 external link
Radiolabelled Pravastatin (P702000). A competitive inhibitor of HMG-CoA reductase. Bioactive metabolite of Mevastatin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Watanabe, M., et al.: Bioorg. Med. Chem., 5, 437 (1997)
  • • Lee, E., et al.: Clin. Pharmacol. Ther., 78, 330 (1997)
  • • Ferdinand, K.C., et al.: Am. J. Cardiol., 97, 229 (1997)
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PATENTS

PATENTS

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INTERNET

INTERNET

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