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酮洛芬

酮洛芬用途

Ketoprofen 是一种非甾体抗炎剂,能够有效地抑制 COX 的活性,在人血单核细胞中,对 COX-1 和 COX-2 的 IC50 值分别为 2 nM 和 26 nM。

酮洛芬名称

[ CAS 号 ]:
22071-15-4

[ 中文名 ]:
酮基布洛芬

[ 英文名 ]:
ketoprofen

[中文别名 ]:

[英文别名 ]:

2-(3-benzoyl-phenyl)propionic acid
Ketoprophene
Ketopron
UNII:90Y4QC304K
Epatec
Lertus
Ketoprofen
Dexal
Menamin
Meprofen

酮洛芬生物活性

[ 描述 ]:

Ketoprofen 是一种非甾体抗炎剂,能够有效地抑制 COX 的活性,在人血单核细胞中,对 COX-1 和 COX-2 的 IC50 值分别为 2 nM 和 26 nM。

[ 相关类别 ]:

研究领域 >> 炎症/免疫

[ 靶点 ]

COX-1:2 nM (IC50, in human blood monocytes)

COX-2:26 nM (IC50, in human blood monocytes)

[体外研究]

酮洛芬(化合物2)是一种非甾体类抗炎药,作为COX的有效抑制剂,人血单核细胞中COX-1和COX-2的IC50分别为2 nM和26 nM [1]。

[体内研究]

酮洛芬(0.32-10 mg/kg,sc)剂量依赖性地抑制酸诱导的嵌套抑制(IC50,2.05 mg/kg),并以0.1-10 mg/kg逆转CFA诱导的这种抑郁症,IC50为0.18小鼠中的mg/kg [2]。

[动物实验]

首先，评估酮洛芬（0.1-1.0mg / kg）和吗啡（0.1-1.0mg / kg）阻断U69,593诱导的嵌套抑制的有效性。对于这些研究，在筑巢前30分钟施用酮洛芬或吗啡，在筑巢前15分钟施用1.0mg / kg U69,593，并且在六只小鼠的组中测试每组条件[2]。

[参考文献]

[1]. Palomer A, et al. Structure-based design of cyclooxygenase-2 selectivity into ketoprofen. Bioorg Med Chem Lett. 2002 Feb 25;12(4):533-7.

[2]. Negus SS, et al. Effects of ketoprofen, morphine, and kappa opioids on pain-related depression of nesting in mice. Pain. 2015 Jun;156(6):1153-60.

[相关活性小分子]

酮洛芬物理化学性质

[ 密度 ]:
1.2±0.1 g/cm3

[ 沸点 ]:
431.3±28.0 °C at 760 mmHg

[ 熔点 ]:
93-96°C

[ 分子式 ]:
C₁₆H₁₄O₃

[ 分子量 ]:
254.281

[ 闪点 ]:
228.8±20.5 °C

[ 精确质量 ]:
254.094299

[ PSA ]:
54.37000

[ LogP ]:
2.81

[ 外观性状 ]:
白色结晶粉末

[ 蒸汽压 ]:
0.0±1.1 mmHg at 25°C

[ 折射率 ]:
1.592

[ 储存条件 ]:
通风低温干燥,与库房食品原料分开存放

[ 水溶解性 ]:
水溶性：实际上不溶；易溶于：甲醇；可溶于：乙醚,氯仿,二甲基甲酰胺,乙醇,丙酮

酮洛芬MSDS

酮洛芬毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UE7570000

CHEMICAL NAME :: Propionic acid, 2-(3-benzoylphenyl)-

CAS REGISTRY NUMBER :: 22071-15-4

LAST UPDATED :: 199801

DATA ITEMS CITED :: 23

MOLECULAR FORMULA :: C16-H14-O3

MOLECULAR WEIGHT :: 254.30

WISWESSER LINE NOTATION :: QVY1&R CVR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 5714 ug/kg

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), zonal Liver - jaundice (or hyperbilirubinemia) hepatocellular Nutritional and Gross Metabolic - body temperature increase

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 714 ug/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 80 mg/kg/10D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 300 mg/kg/15D-I

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes Behavioral - headache Gastrointestinal - nausea or vomiting

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 62400 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 350 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Rectal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 84 mg/kg

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from small intestine Gastrointestinal - peritonitis

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 360 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 550 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 450 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg/30D-C

TOXIC EFFECTS :: Endocrine - changes in spleen weight Blood - other changes Related to Chronic Data - changes in testicular weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1080 mg/kg/26W-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Gastrointestinal - other changes Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Rectal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 300 mg/kg/30D-C

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 900 mg/kg/5D-I

TOXIC EFFECTS :: Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1092 mg/kg/13W-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from duodenum Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 mg/kg

SEX/DURATION :: female 21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 50 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 393,123,1997

酮洛芬安全信息

[ 符号 ]:

GHS06

[ 信号词 ]:
Danger

[ 危害声明 ]:
H301-H315-H319-H335

[ 警示性声明 ]:
P261-P301 + P310-P305 + P351 + P338

[ 个人防护装备 ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ 危害码 (欧洲) ]:
T: Toxic;

[ 风险声明 (欧洲) ]:
R25;R36/37/38

[ 安全声明 (欧洲) ]:
S26-S45-S36/37/39

[ 危险品运输编码 ]:
2811

[ RTECS号 ]:
UE7570000

[ 包装等级 ]:
III

[ 危险类别 ]:
6.1(b)

[ 海关编码 ]:
2916392000

酮洛芬合成路线

酮洛芬上下游产品

酮洛芬上游产品

酮洛芬下游产品

酮洛芬制备

1. 5-(2-甲基-1,3-二烷-2-基)-7-苯基苯并[c]异唑的制备

在反应瓶中加入对硝基苯乙酮100g(0.60mol)、苯500ml、乙二醇123ml(136.96g,2.20mol)、对甲苯磺酸(p-TsOH)1.5g(7.90mmol),装置分水器,搅拌加热至回流,利用苯与水共沸带水,并分出水,搅拌回流15h.加入苯100ml,静置30min.下层(醇层)趁热用苯20ml提取.合并苯层,减压蒸出苯并回收,降温至35ºC, 加入含NaOH124g的95%乙醇500ml,搅拌,在30min内于45ºC滴加苯乙腈74ml(0.60mol),滴毕,于57~60ºC搅拌反应7h.降至室温,静置过夜.搅拌下加水350ml,继续搅拌30min.过滤,滤饼用水洗至中性,抽干,于80 ºC干燥,得浅黄色固体5-(2-甲基-1,3-二烷-2-基)-7-苯基苯并[c]异唑149.7g,收率87.9%,mp136~138ºC(文献[13]报道mp137~138 ºC)

2. 2-氨基-5-乙酰基二苯甲酮的制备

在反应瓶中加入化合物5-(2-甲基-1,3-二烷-2-基)-7-苯基苯并[c]异唑50g(0.2mol)、95%乙醇400ml和36%盐酸8ml(0.1mol),搅拌升温至60~70 ºC,保温搅拌反应30min降温至40ºC以下,加入60~80目铁粉47g(0.90mol),缓慢搅拌升温至回流#回流反应2h, 降温至70 ºC, 用固体NaOH调至pH7.2~7.5,趁热过滤,滤液减压回收乙醇.降至室温析晶,过滤,滤饼用少量乙醇和水洗涤,抽干,于80ºC干燥,得黄色固体2-氨基-5-乙酰基二苯甲酮39.1g, 收率91.9%,mp154~156 ºC(文献[13]报道mp152~154 ºC)

3. 3-乙酰基二苯甲酮的制备

在反应瓶中加入化合物2-氨基-5-乙酰基二苯甲酮26g(0.10mol)、乙醇60ml和浓H2SO4 14ml,降温至15 ºC, 搅拌下慢加入亚硝酸钠8.5g(0.10mol)的水(100ml)溶液,装上冷凝管后缓慢升温,有大量氨气逸出,改水浴为油浴加热、回流装置改为分馏装置,小心蒸除乙及乙醛,温度达80 ºC时停止蒸馏.降温至室温,用苯(50ml×2) 提取,提取液先用少量水洗涤,再用5%NaOH水溶液洗涤,最后用水洗涤至中性,用无水CaCl2干燥#过滤,滤液用常压蒸除溶剂,减压蒸馏#收集152~156 ºC/30Pa馏分,得浅黄色液体3-乙酰基二苯甲酮20.7g,收率84.9%(文献[14]报道化合物3-乙酰基二苯甲酮bp151~154 ºC/27Pa)

4. 3-苯甲酰基-α-甲基-苯乙酸(酮洛芬)的合成

在反应瓶中加入化合物3-乙酰基二苯甲酮168.g(75.00mmol)、氯乙酸异丙酯[10.3g(75.00mmol)的异丙醇(75ml)溶液,搅拌滴加含异丙醇钠6.6g(85.5mmol)的异丙醇溶液60ml.滴毕,搅拌回流反应2h.加入30%NaOH溶液600ml,继续搅拌反应2h.降至室温,用盐酸调至pH2,搅拌回流脱羧1h.降至40 ºC,滴加重铬酸钾和硫酸的水溶液(1:4)至溶液变绿为止.用石油醚提取3次,合并有机层(醚层),水洗至pH6.8,用10%NaOH水溶液调至pH10,将水层降温至8 ºC,用6mol/L盐酸缓慢调至pH2,过滤,滤饼经水洗涤,抽干,干燥,得白色结晶性粉末3-苯甲酰基-α-甲基-苯乙酸(酮洛芬)12.4g,收率65.1%,mp94~96 ºC.

酮洛芬海关

[ 海关编码 ]: 2918300090

[ 中文概述 ]:
2918300090 其他含醛基或酮基不含其他含氧基羧酸（包括酸酐、酰卤化物、过氧化物和过氧酸及该税号的衍生物）. 增值税率:17.0% 退税率:9.0% 监管条件:无最惠国关税:6.5% 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2918300090 other carboxylic acids with aldehyde or ketone function but without other oxygen function, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

酮洛芬文献

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...

Convenient QSAR model for predicting the complexation of structurally diverse compounds with β-cyclodextrins

Bioorg. Med. Chem. 17 , 896-904, (2009)

This paper reports a QSAR study for predicting the complexation of a large and heterogeneous variety of substances (233 organic compounds) with beta-cyclodextrins (beta-CDs). Several different theoret...

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酮洛芬