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75330-75-5 分子结构
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(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate

ChemBase编号:112
分子式:C24H36O5
平均质量:404.53964
单一同位素质量:404.25627425
SMILES和InChIs

SMILES:
O([C@@H]1[C@@H]2[C@H]([C@H](C=CC2=C[C@@H](C1)C)C)CC[C@H]1OC(=O)C[C@H](O)C1)C(=O)[C@H](CC)C
Canonical SMILES:
CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
InChI:
InChI=1S/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
InChIKey:
PCZOHLXUXFIOCF-BXMDZJJMSA-N

引用这个纪录

CBID:112 http://www.chembase.cn/molecule-112.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
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
IUPAC传统名
lovastatin
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
商标名
Altocor
Altoprev
Artein
Belvas
Cholestra
Closterol
Colevix
Hipolip
Hipovastin
Lestatin
Lipdip
Lipivas
Lipofren
Lovalip
Lovalord
Lovasterol
Lovastin
Lozutin
Mevacor
Mevinacor
Mevlor
Monacolin K
Nergadan
Paschol
Rodatin
Rovacor
Sivlor
Taucor
Tecnolip
Teroltrat
别名
洛伐司他汀
Lovastatina [Spanish]
Lovastatine [French]
Lovastatinum [Latin]
6 alpha-Methylcompactin
lovastatin
Lovastatin
8-[2-(4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethy l]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-1-naphthale
(S)-(1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate
2-Methyl-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester butanoic acid
6-α-Methylcompactin
Monacolin K
Mevinolin from Aspergillus sp.
(2S)-2-Methylbutanoic Acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester
(+)-Mevinolin
6α-Methylcompactin
Altocor
Antibiotic MB 530B
L 154803
Lostatin
Lovalip
Lovastatin Lactone
MK 803
MSD 803
Mevacor
Mevinacor
Mevinolin
Mevlor
Monacolin K Lactone
Sivlor
Lipofren
Nergadan
Tancor
lovastatin
(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
CAS号
75330-75-5
MDL号
MFCD00072164
PubChem SID
46508223
160963575
24896706
PubChem CID
53232
CHEBI ID
40303
ATC码
C10AA02
CHEMBL
503
Chemspider ID
48085
DrugBank ID
DB00227
IUPHAR配体索引
2739
KEGG ID
D00359
美国药典/FDA物质标识码
9LHU78OQFD
维基百科标题
Lovastatin
Medline Plus
a688006

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.914537  质子受体
质子供体 LogD (pH = 5.5) 3.9021869 
LogD (pH = 7.4) 3.9021869  Log P 3.9021869 
摩尔折射率 113.1824 cm3 极化性 44.4169 Å3
极化表面积 72.83 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 4.11  LOG S -4.22 
溶解度 2.43e-02 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
0.0004 mg/mL expand 查看数据来源
Chloroform expand 查看数据来源
DMSO expand 查看数据来源
Hot Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
熔点
152-154°C expand 查看数据来源
166 - 168°C expand 查看数据来源
175°C expand 查看数据来源
疏水性(logP)
4.082 expand 查看数据来源
4.5 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
EK7907000 expand 查看数据来源
欧盟危险性物质标志
X expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
22-36/37/38 expand 查看数据来源
安全公开号
26-36/37 expand 查看数据来源
TSCA收录
false expand 查看数据来源
expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302 expand 查看数据来源
H302-H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305+P351+P338-P302+P352-P321-P405-P501A expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
给药途径
oral expand 查看数据来源
生物利用度
<5% expand 查看数据来源
排泄
negligible expand 查看数据来源
半衰期
1.1-1.7 hours expand 查看数据来源
代谢
hepatic (CYP3A substrate) expand 查看数据来源
蛋白结合率
>95% expand 查看数据来源
法定药品分级
Rx-only (US) expand 查看数据来源
妊娠期药物分类
X (US) expand 查看数据来源
相关基因信息
human ... HMGCR(3156)rat ... Hmgcr(25675) expand 查看数据来源
生物活性机理
Inhibitor of cholesterol biosynthesis expand 查看数据来源
Potent inhibitor of HMG-CoA expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95% expand 查看数据来源
97% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
生物来源
Metab. of Aspergillus terreus and Monascus ruber expand 查看数据来源
应用领域
Antihyperlipidaemic agent expand 查看数据来源
产品质量级别
PREMIUM expand 查看数据来源
Empirical Formula (Hill Notation)
C24H36O5 expand 查看数据来源

详细说明

详细说明

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich DrugBank DrugBank TRC TRC
Sigma Aldrich -  M2147 external link
Biochem/physiol Actions
Lovastatin is a cholesterol lowering drug and competitive inhibitor of HMG-CoA reductase, a rate limiting enzyme in cholesterol synthesis. Blocks the production of mevalonate, a critical compound in the production of cholesterol and isoprenoids. This product is a substrate of Pgp and CYP3A. It increases cellular resistance to anticancer agents such as doxorubicin and induces apoptosis in myeloma cells. The roles of Pgp and CYP3A, possible connection between drug resistance, regulation of the mevalonate pathway, and iosprenylation of signaling proteins in these observations remain to be resolved. The product induces apoptosis in numerous cancer cell lines perhaps, in part, by inhibiting the isoprenylation of Rho family GTPases. It causes cell cycle arrest in G1 and G2/M phases.
DrugBank -  DB00227 external link
Item Information
Drug Groups approved; investigational
Description Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6’ position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today.
Indication For management as an adjunct to diet to reduce elevated total-C, LDL-C, apo B, and TG levels in patients with primary hypercholesterolemia and mixed dyslipidemia. For primary prevention of coronary heart disease and to slow progression of coronary atherosclerosis in patients with coronary heart disease.
Pharmacology The primary cause of cardiovascular disease is atherosclerotic plaque formation. Sustained elevations of cholesterol in the blood increase the risk of cardiovascular disease. Lovastatin lowers hepatic cholesterol synthesis 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. At therapeutic doses, lovastatin decreases serum LDL cholesterol by 29-32%, increases high density lipoprotein (HDL) cholesterol by 4.6-7.3%, and decrease triglyceride levels by 2-12%. 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 LD50>1000 mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Undergoes first pass hydrolysis to active metabolites β-hydroxyacid and 6'-hydroxy dervative.
Absorption < 5%. Time to peak serum concentration is 2-4 hours.
Half Life 5.3 hours
Protein Binding > 95%
Elimination Lovastatin undergoes extensive first-pass extraction in the liver, its primary site of action, with subsequent excretion of drug equivalents in the bile. 83% of the orally administered dose is excreted in bile and 10% is excreted in urine.
References
Bobek P, Ozdin L, Galbavy S: Dose- and time-dependent hypocholesterolemic effect of oyster mushroom (Pleurotus ostreatus) in rats. Nutrition. 1998 Mar;14(3):282-6. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals -  L472225 external link
An antihypercholesterolemic agent. A fungal metabolite, which is a potent inhibitor of HMG-CoA reductase.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Alberts et al (1980) Mevinolin: a highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent. Proc.Natl.Acad.Sci.USA 77 3957.
  • Bilheimer, D.W., et al.: Proc. Nat. Acad. Sci. USA, 80, 4124 (1983)
  • Bobek P, Ozdin L, Galbavy S: Dose- and time-dependent hypocholesterolemic effect of oyster mushroom (Pleurotus ostreatus) in rats. Nutrition. 1998 Mar;14(3):282-6. Pubmed
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