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辛伐他汀，斯伐他汀

辛伐他汀，斯伐他汀用途

Simvastatin 是一种竞争性的 HMG-CoA reductase 抑制剂,Ki 值为 0.2 nM。

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辛伐他汀，斯伐他汀名称

[ CAS 号 ]:
79902-63-9

[ 中文名 ]:
辛伐他汀

[ 英文名 ]:
Simvastatin

[中文别名 ]:

[英文别名 ]:

Lipex
Velostatin
ZOCOR
Simvotin
Corolin
MFCD00072007
Cholestat
Colemin
Coledis
Simvastatin

辛伐他汀，斯伐他汀生物活性

[ 描述 ]:

Simvastatin 是一种竞争性的 HMG-CoA reductase 抑制剂,Ki 值为 0.2 nM。

[ 相关类别 ]:

信号通路 >> 自噬 >> 自噬

信号通路 >> 代谢酶/蛋白酶 >> HMG-CoA还原酶(HMGCR)

信号通路 >> 自噬 >> 自噬

研究领域 >> 心血管疾病

[ 靶点 ]

Ki: 0.2 nM (HMG-CoA reductase)[1]

[体外研究]

在用于细胞测定之前,辛伐他汀需要在EtOH处理中被NaOH活化。辛伐他汀抑制小鼠LM细胞,大鼠H4II E细胞和人Hep G2细胞的胆固醇合成,IC50分别为19.3 nM,13.3 nM和15.6 nM [1]。辛伐他汀在30分钟内引起Akt丝氨酸473磷酸化的剂量依赖性增加,最大磷酸化发生在1.0μM。辛伐他汀(1.0μM)增强内源性Akt底物内皮型一氧化氮合酶(eNOS)的磷酸化,抑制无血清培养基发生凋亡并加速血管结构形成[2]。辛伐他汀显示出抗炎作用,减少抗CD3 /抗CD28抗体刺激的PB衍生的单核细胞和来自类风湿性关节炎血液的滑膜流体细胞的增殖,以及10μM的IFN-γ释放。辛伐他汀(10μM)也可通过约30％的途径阻断由同源相互作用诱导的细胞介导的巨噬细胞TNF-γ释放[3]。辛伐他汀(5μM)显着降低星形胶质细胞和神经母细胞瘤细胞中ABCA1的表达,星形胶质细胞中载脂蛋白E的表达,并增加SK-N-SH细胞中细胞周期蛋白依赖性激酶5和糖原合成酶激酶3β的表达[7]。

[体内研究]

辛伐他汀通过口服给药抑制放射性标记的乙酸盐转化为胆固醇,IC50为0.2 mg/kg [1]。辛伐他汀(4毫克/天,口服13周)将胆固醇诱导的总胆固醇,低密度脂蛋白胆固醇和高密度脂蛋白胆固醇的增加恢复到正常水平的兔子喂养富含动脉粥样硬化的胆固醇饮食[4]。辛伐他汀(6 mg/kg)可增加喂食含0.25％胆固醇饮食的兔子的LDL受体依赖性结合和肝脏LDL受体数量[5]。辛伐他汀不依赖于其对血浆胆固醇水平的影响而影响炎症。辛伐他汀(20 mg/kg /天)导致病变中巨噬细胞含量减少1.3倍,血管细胞粘附分子-1,白细胞介素-1β和组织因子表达减少2倍,并伴有病变增加2.1倍动脉粥样硬化饮食中食用的食蟹猴平滑肌细胞和胶原蛋白含量[6]。

[激酶实验]

为了在体外评估Akt蛋白激酶活性，使用山羊多克隆抗Akt1抗体将底物（2μg组蛋白H2B或25μgeNOS肽）与从细胞裂解物中免疫沉淀的Akt一起温育。加入辛伐他汀后，激酶反应开始，最终浓度为ATP（50μM），含有10μCi的32P-γATP，二硫苏糖醇（1 mM），HEPES缓冲液（20 mM，pH 7.4），MnCl2（10 mM），MgCl2 （10mM）。在30℃温育30分钟后，在SDS-PAGE（15％）和放射自显影后观察到磷酸化的组蛋白H2B。为了估计32P掺入eNOS肽的程度，通过点样到磷酸纤维素盘式过滤器上测量每种反应混合物，并通过切伦科夫计数测量掺入的磷酸盐的量。野生型肽序列是1174-RIRTQSFSLQERHLRGAVPWA-1194，突变体eNOS肽是相同的，除了丝氨酸1179被丙氨酸取代[3]。

[细胞实验]

来自四个不同供体的原代人星形胶质细胞由从合法流产的胎儿获得的组织制备。将原代人星形胶质细胞和SK-N-SH神经母细胞瘤细胞系（ATCC）接种在6孔板上，分别在37℃，5％CO 2下培养于补充有5％或8％胎牛血清的DMEM中，直至80％汇合。为了测量基线处的基因表达水平，仅洗涤细胞并制备RNA并如下所述进行测定。在从两个供体获得的原代人星形胶质细胞中测量星形胶质细胞中的基线基因表达水平。出于实验目的，将细胞在无血清条件下孵育。从四个供体获得原代人星形胶质细胞。基于初步的时间依赖性研究，48小时孵育用于所有实验。基于剂量反应研究，我们的大多数实验使用以下浓度的活性化合物进行：5μM的辛伐他汀，10μM的普伐他汀，50μM的甲羟戊酸，以及10μM的GGPP和FPP。孵育后，彻底清洗细胞以去除死细胞和细胞碎片，并准备进行进一步分析[7]。

[动物实验]

猴子[1] 39只成年雄性食蟹猴最初喂食中度致动脉粥样化饮食，每卡路里含有0.28毫克胆固醇，其中16.7％来自蛋白质，45.1％来自脂质，38.1％来自碳水化合物。在使用致动脉粥样化饮食3个月后，将猴子分成3组（每组n = 13），其总血浆胆固醇（TPC），LDL-C和HDL胆固醇（HDL-C）浓度相当;这些组消耗致动脉粥样硬化饮食并接受他汀类药物（或对照）治疗15个月。对照猴子喂食致动脉粥样硬化饮食，不添加他汀类药物。 Prava处理的猴子每天添加40mg Prava / kg体重，添加到致动脉粥样化饮食中。辛伐他汀治疗的猴子每天消耗20毫克辛伐他汀/千克体重[1]。

[参考文献]

[1]. Slater, E.E., et al. Mechanism of action and biological profile of HMG CoA reductase inhibitors. A new therapeutic alternative. Drugs, 1988. 36 Suppl 3: p. 72-82.

[2]. Kureishi, Y., et al. The HMG-CoA reductase inhibitor simvastatin activates the protein kinase Akt and promotes angiogenesis in normocholesterolemic animals. Nat Med, 2000. 6(9): p. 1004-10.

[3]. Leung BP, et al. A novel anti-inflammatory role for simvastatin in inflammatory arthritis. J Immunol. 2003 Feb 1;170(3):1524-30.

[4]. Kobayashi M, et al. Preventive effect of MK-733 (simvastatin), an inhibitor of HMG-CoA reductase, on hypercholesterolemia and atherosclerosis induced by cholesterol feeding in rabbits. Jpn J Pharmacol. 1989 Jan;49(1):125-33.

[5]. Ishida F, et al. Comparative effects of simvastatin (MK-733) and pravastatin (CS-514) on hypercholesterolemia induced by cholesterol feeding in rabbits. Biochim Biophys Acta. 1990 Feb 23;1042(3):365-73.

[6]. Sukhova GK, et al. Statins reduce inflammation in atheroma of nonhuman primates independent of effects on serum cholesterol. Arterioscler Thromb Vasc Biol. 2002 Sep 1;22(9):1452-8.

[7]. Weijiang Dong, et al. Differential effects of simvastatin and pravastatin on expression of Alzheimer’s disease-related genes in human astrocytes and neuronal cells. J Lipid Res. 2009 Oct; 50(10): 2095-2102.

[8]. Liu Z, et al. Pretreatment Donors after Circulatory Death with Simvastatin Alleviates Liver Ischemia Reperfusion Injury through a KLF2-Dependent Mechanism in Rat. Oxid Med Cell Longev. 2017;2017:3861914.

[相关活性小分子]

辛伐他汀，斯伐他汀物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
564.9±50.0 °C at 760 mmHg

[ 熔点 ]:
139 °C

[ 分子式 ]:
C₂₅H₃₈O₅

[ 分子量 ]:
418.566

[ 闪点 ]:
184.8±23.6 °C

[ 精确质量 ]:
418.271912

[ PSA ]:
72.83000

[ LogP ]:
4.41

[ 外观性状 ]:
白色至灰白色结晶粉末

[ 蒸汽压 ]:
0.0±3.5 mmHg at 25°C

[ 折射率 ]:
1.530

[ 储存条件 ]:
库房低温,通风,干燥,闭光

辛伐他汀，斯伐他汀MSDS

详细MSDS(安全技术说明书)

辛伐他汀，斯伐他汀毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: EK7798000

CHEMICAL NAME :: Butanoic acid, 2,2-dimethyl-, 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, (1S-(1-alpha,3-alpha,7- beta,8-beta(2S*,4S*),8a-beta))-

CAS REGISTRY NUMBER :: 79902-63-9

LAST UPDATED :: 199612

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C25-H38-O5

MOLECULAR WEIGHT :: 418.63

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 2800 ug/kg/7D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Liver - jaundice (or hyperbilirubinemia) hepatocellular Liver - liver function tests impaired

REFERENCE :: MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 155,61,1991

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 108 mg/kg/77W-I

TOXIC EFFECTS :: Behavioral - muscle weakness Lungs, Thorax, or Respiration - acute pulmonary edema Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: ANZJB8 Australian and New Zealand Journal of Medicine. (Modern Medicine of Australia Pty., Ltd., 100 Pacific Highway, North Sydney, 2060, Australia) V.1- 1971- Volume(issue)/page/year: 25,745,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4438 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 705 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - muscle contraction or spasticity

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 672 mg/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 798 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - muscle contraction or spasticity

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1009 mg/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,95,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9275 mg/kg/53W-I

TOXIC EFFECTS :: Brain and Coverings - changes in brain weight Liver - changes in liver weight Endocrine - changes in thyroid weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,103,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17640 mg/kg/14W-I

TOXIC EFFECTS :: Blood - changes in bone marrow (not otherwise specified) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Related to Chronic Data - death

REFERENCE :: YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 43,259,1992

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 120 mg/kg/12D-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: PHTOEH Pharmacology and Toxicology (Copenhagen). (Munksgaard International Pub., POB 2148, DK-1016 Copenhagen K, Denmark) V.60- 1987- Volume(issue)/page/year: 77,391,1995 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 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)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,143,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 480 mg/kg

SEX/DURATION :: female 6-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,143,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 350 mg/kg

SEX/DURATION :: female 15-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 39,169,1990

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辛伐他汀，斯伐他汀安全信息

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xi: Irritant;

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
26-36

[ 危险品运输编码 ]:
3077

[ RTECS号 ]:
EK7798000

[ 包装等级 ]:
III

[ 危险类别 ]:
9

辛伐他汀，斯伐他汀合成路线

详细合成路线

辛伐他汀，斯伐他汀上下游产品

辛伐他汀，斯伐他汀上游产品

辛伐他汀，斯伐他汀下游产品

辛伐他汀，斯伐他汀制备

洛伐他汀(Lovastatin)(I，50.30g，0.124mo1)和正丁胺(42ml，0.42mo1)，在25℃：混合，然后在80℃下加热1h。冷却25℃，减压蒸出过量的正丁胺，得59.4g化合物(Ⅱ)，收率100%，直接用于下步反应。
上述得到化合物(Ⅱ)的粗品，在25℃溶于132ml二甲基甲酰胺，加人咪唑(19.59g，0.288mo1)和叔丁基二甲基氯化硅(TBSCl，44.4g，0.288mo1)，在60℃下加热6h。冷至12℃，加入无水甲醇(5.8ml，0.143mo1)，在15℃下搅拌30min，加入1.5 L环己烷和750ml 5%碳酸氢钠溶液，剧烈搅拌。分层，分出环己烷层，用750ml 5%碳酸氢钠溶液和750ml水洗。在常压浓缩至．580ml，再加入经分子筛干燥的600ml四氢呋喃，再常压浓缩至870ml。HPLC显示其中有86.9g化合物(Ⅲ)，收率99%，直接用于下步反应。
经分子筛干燥的吡咯烷(25.1ml，0.301mo1)和192ml四氢呋喃混合，冷至-18℃，加入正丁基锂的己烷溶液(1.60mol/L，181ml，0.290mo1)，维持在-10℃，约15min加毕，然后在-20℃再反应15min。如此得到的吡咯烷基锂溶液，冷至-20℃备用。将上述得到的化合物(Ⅲ)的四氢呋喃-环己烷溶液冷至-35℃，在剧烈搅拌下，加入冷至-20℃的吡咯烷基锂溶液，维持在-30℃。加毕，在-35～-30℃搅拌2h，然后一次性加入碘甲烷(12.2ml，0.196mo1)，此时因放热反应，温度会升至20℃，再冷至-30℃，并在此温度搅拌1h。升至-10℃，再搅拌20min。加入550ml水，剧烈搅拌10min，分出有机层，用550ml 10℃的1mol/L盐酸洗。减压浓缩至20%体积，其中含化合物(Ⅳ)，直接用于下步反应。
往上述得到的化合物(Ⅳ)的溶液中加入690ml甲醇，再加入45.7ml水和甲磺酸(1.5ml，0.023mo1)，在30℃搅拌5h，即形成化合物(V)，直接用于下步反应。
往上述得到的化合物(V)的溶液中，在25℃加入373ml 2mol/L氢氧化钠溶液，在常压下加热，并进行蒸馏，当气相温度达到72～73℃，液相温度达到78～80℃时，不再收集蒸出馏。剩下的溶液搅拌回流2h，再冷至40℃。减压蒸出大部分甲醇，再加入228ml水加以稀释。冷至10℃，用3mol/L盐酸调至PH=6～7。加入990ml乙酸乙酯，用3mol/L盐酸继续调至Ph=5.0。搅拌后分层，分出乙酸乙酯层，加入225ml甲醇。在1h中，加入75ml氨水-甲醇(1：3)的溶液，然后在45℃搅拌15min。在2.5h中，缓慢冷至-10℃，并在-10℃：搅拌1～2h。滤出铵盐(Ⅵ)结晶，用冷的乙酸乙酯-甲醇(3.5：1)洗，在35℃干燥过夜，得51.37铵盐(Ⅵ)，收率90.9％(以洛伐他汀计)。用乙腈重结晶可得到分析用的样品。
将该铵盐(Ⅵ)的粗品悬浮于1.03L甲苯中，通入氮气于100℃加热6h。冷至25℃，加入2.5g Darco KB，在25℃搅拌30min。过滤，滤液减压浓缩至油状物，加入140ml环己烷，再浓缩。再加入600ml环己烷，回流全溶。冷至10℃，搅拌1h。过滤收集结晶，用250ml冷环己烷洗，真空30～35℃干燥，得44.6g辛伐他丁，收率94.2%。以甲醇-水重结晶，得到分析用的样品。

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辛伐他汀，斯伐他汀文献

Environmental friendly method for urban wastewater monitoring of micropollutants defined in the Directive 2013/39/EU and Decision 2015/495/EU.

J. Chromatogr. A. 1418 , 140-9, (2015)

The fate and removal of organic micropollutants in the environment is a demanding issue evidenced by the recent European policy. This work presents an analytical method for the trace quantification of...

Oxysterols synergize with statins by inhibiting SREBP-2 in ovarian cancer cells.

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Determine mechanisms responsible for enhanced statin efficacy in a novel statin combination we name STOX (STatin-OXysterol).Ovarian cancer cell lines were treated with combinations of statins and oxys...

Autocrine secretion of 15d-PGJ2 mediates simvastatin-induced apoptotic burst in human metastatic melanoma cells.

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Despite new therapeutic approaches, metastatic melanomas still have a poor prognosis. Statins reduce low-density lipoprotein cholesterol and exert anti-inflammatory and anti-proliferative actions. We ...

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