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81093-37-0 分子结构
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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编号:60
分子式:C23H36O7
平均质量:424.52774
单一同位素质量:424.24610349
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(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传统名
pravastatin
商标名
Elisor
Lipostat
Mevalotin
Mevinolin
Oliprevin
Pravachol
Pravaselect
Selectin
Selipran
Vasten
别名
Pravastatina [Spanish]
Pravastatin Sodium
Pravastatine [French]
Pravastatinum [Latin]
Pravastatin
(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-3H
CAS号
81093-37-0
PubChem SID
160963523
46504851
PubChem CID
54687

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格
TRC
P702003 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.212299  质子受体
质子供体 LogD (pH = 5.5) 0.34003893 
LogD (pH = 7.4) -1.3779589  Log P 1.6470916 
摩尔折射率 113.5979 cm3 极化性 44.338123 Å3
极化表面积 124.29 Å2 可自由旋转的化学键 11 
里宾斯基五规则 true 
Log P 2.23  LOG S -3.24 
溶解度 2.42e-01 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
2464mg/L expand 查看数据来源
疏水性(logP)
2.2 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
质检报告
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详细说明

详细说明

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.

参考文献

参考文献

供应商提供 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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专利

专利

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