Lovastatin 洛伐司他汀

CAS 75330-75-5 MFCD00072164

化学结构图

75330-75-5
SMILES: CC[C@@H](C)C(=O)O[C@@H]1C[C@H](C)C[C@H]2C=C[C@@H](C)[C@@H](CC[C@H]3C[C@H](O)CC(=O)O3)[C@@H]21 |&1:2,7,9,12,15,17,20,22,28|

化学属性

Mol. FormulaH2
Mol. Weight1
Melting Point175°C
TSCANo
Appearance +323°(C=0.5g溶于100ml乙腈)。UV最大吸收(甲醇)：229，237，246nm(耳三550，6250，430)。室温溶解度(mg/m1)：丙酮47，乙腈28，n-丁醇7，i-丁醇14，氯仿350，二甲基甲酰胺90，乙醇16，甲醇28，n-辛醇2，n-丙醇11，i-丙醇20，水0.4×10 D 25 -3 。急性毒性LD 小鼠(mg/kg)：＞1000口服。 白色结晶，熔点174.5℃(氮气中)。[α] 50
Density1.12

别名和识别编码

Chemical NameLovastatin
CAS Number75330-75-5
Alfabeta NameHYDROXYOXOTETRAHYDROPYRANYLETHYLDIMETHYLHEXAHYDRONAPHTHALE HA824622371237881[]()---------------,,,,,,
MDL NumberMFCD00072164
Synonym Mevinolin 洛伐司他汀 洛伐他汀 Mevinacor 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--Methylcompactin Lovastatin Monacolin K MSD 803 6-alpha-Methylcompactin Lovastatin
PubChem Substance ID87560159
Reaxys-RN4720754
Merck Number5586
Chemical Name Translation洛伐司他汀
Beilstein Registry Number3631989
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分类

  • {SA} Abbott, Antitumor Agents, Application Index, Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Metabolism, Cancer Research, Cell Biology, Cell Signaling Enzymes, Cell Signaling and Neuroscience, Chemopreventive Agents, D to K, Drug and Xenobiotic Metabolism, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Enzymes, Inhibitors, and Substrates, Hydroxymethylglutaryl-CoA Reductase, Inhibitors, M, Mevalonate Pathway in Cancer, Multi-Drug Resistance and Drug Metabolism, Substrates,
  • {SNA} Abbott
  • {SNA} Abbott,
  • {Chemicalbook} 药物: 心脑血管药物: 降血脂药
  • {SNA} Abbott,

产品应用

  • 降胆固醇药物和HMG-CoA还原酶的竞争性抑制剂，一种对胆固醇合成的速率限制酶。阻止胆固醇和异戊二烯生产的关键化合物甲羟戊酸（mevalonate）生产。该产品是Pgp 和 CYP3A的底物。它增加细胞对抗癌药物的耐药性，如阿霉素，诱导骨髓瘤细胞凋亡。该产品诱导众多癌细胞凋亡，部分通过抑制Rho家族GTP酶。它会导致细胞周期在G1和G2/ M期被捕获。

相关文献及参考

  • [2]. Kah J, et al. Selective induction of apoptosis by HMG-CoA reductase inhibitors in hepatoma cells and dependence on p53 expression. Oncol Rep. 2012 Sep;28(3):1077-83.
  • [3]. Frishman WH, et al. Lovastatin: an HMG-CoA reductase inhibitor for lowering cholesterol. Med Clin North Am. 1989 Mar;73(2):437-48.
  • [4]. Tobert JA, et al. Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors. Nat Rev Drug Discov. 2003 Jul;2(7):517-26.
  • [5]. Ifergan I, et al. Statins reduce human blood-brain barrier permeability and restrict leukocyte migration: relevance to multiple sclerosis. Ann Neurol. 2006 Jul;60(1):45-55.
  • Merck: 14,5586
  • [1]. Alberts AW, et al. Discovery, biochemistry and biology of lovastatin. Am J Cardiol. 1988 Nov 11;62(15):10J-15J.
  • [1]. Alberts AW, et al. Discovery, biochemistry and biology of lovastatin. Am J Cardiol. 1988 Nov 11;62(15):10J-15J.
  • [2]. Kah J, et al. Selective induction of apoptosis by HMG

安全信息

Warnings IRRITANT
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
GHS Symbol
Hazard statements
  • H302 Harmful if swallowed 吞食有害
WGK Germany3
Signal word
RTECSEK7907000
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
Risk Statements
Packing GroupIII
Hazard Class9
Storage condition 储存温度2-8°C 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human
DOSE/DURATION           : 8750 ug/kg/14D-I
TOXIC EFFECTS :
   Behavioral - wakefulness
   Behavioral - altered sleep time (including change in righting reflex)
REFERENCE :
   CLPTAT Clinical Pharmacology and Therapeutics (St. Louis).  (C.V. Mosby Co.,
   11830 Westline Industrial Dr., St. Louis, MO 63146)  V.1-    1960-
   Volume(issue)/page/year: 50,730,1991

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 285 mg/kg/30W-I
TOXIC EFFECTS :
   Liver - hepatitis (hepatocellular necrosis), zonal
   Liver - liver function tests impaired
   Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
   IJMDAI Israel Journal of Medical Sciences.  (POB 1435, Jerusalem 91013,
   Israel)  V.1-    1965-  Volume(issue)/page/year: 28,101,1992

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   JANTAJ Journal of Antibiotics.  (Japan Antibiotics Research Assoc., 2-20-8
   Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan)  V.2-5, 1948-52;  V.21- 1968-
   Volume(issue)/page/year: 32,852,1979

TYPE OF TEST            : TDLo - Lowest published toxic

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 240 mg/kg/60W-I
TOXIC EFFECTS :
   Behavioral - muscle weakness
REFERENCE :
   APHRER Annals of Pharmacotherpy.  (Harvey Whitney Books Co., POB 42696,
   Cincinnati, OH 45242) V. 26-    1992-  Volume(issue)/page/year: 26,190,1992

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 9600 mg/kg
SEX/DURATION            : female 6-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - body wall
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 28,449,1983

Precautionary statements

其他信息

  • 易溶于氯仿，溶于丙酮，微溶于甲醇，不溶于水。

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  4. Carbonyl Compounds 羰基化合物
  5. Esters - Carbonyl Compounds
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Application Index - Enzymes, Inhibitors, and Substrates
  5. Cell Signaling Enzymes - Application Index
  6. Xenobiotics and Drug Metabolism - Cell Signaling Enzymes
  7. Substrates - Xenobiotics and Drug Metabolism
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Enzyme - Enzyme Inhibitors
  6. D to K - Enzyme Inhibitors by Enzyme
  7. Hydroxymethylglutaryl-CoA Reductase - D to K
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Multi-Drug Resistance and Drug Metabolism - Cell Signaling and Neuroscience
  5. Drug and Xenobiotic Metabolism - Multi-Drug Resistance and Drug Metabolism
  6. Substrates, Inducers, Inhibitors - Drug and Xenobiotic Metabolism
  1. Medical Research Areas
  2. Metabolism
  3. HMG-CoA Reductase (HMGCR)  (HMG-CoA还原酶)

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