54-05-7

• 常用中文名：氯喹
• 常用英文名：Chloroquine
• CAS号：54-05-7
• 分子式：C₁₈H₂₆ClN₃
• 分子量：319.872
• 相关类别： 原料药 抗寄生虫病药 抗疟药
• 发布时间：2018-05-09 08:00:00
• 更新时间：2025-08-25 19:17:53
• Chloroquine 是一种广泛用于治疗疟疾和类风湿性关节炎的抗疟疾和抗炎剂。Chloroquine 是 autophagy 和 toll-like receptors (TLRs) 的抑制剂。Chloroquine 有效抑制 SARS-CoV-2 (COVID-19) 感染 (EC50=1.13 μM)。

名称

• 中文名: 氯喹
• 英文名: chloroquine
• 英文别名: UNII:886U3H6UFF; Bemaco; (±)-Chloroquine; N-(7-Chloro-4-quinolinyl)-N,N-diethyl-1,4-pentanediamine; [3H]-Chloroquine; sn7618; N-(7-Chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine; CHLOROQUINE; 1,4-Pentanediamine, N-(7-chloro-4-quinolinyl)-N,N-diethyl-; 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-; N4-(7-Chloroquinolin-4-yl)-N1,N1-diethylpentane-1,4-diamine; Amokin; rp3377; N4-(7-chloroquinoline-4-yl)-N1,N1-diethyl-pentane-1,4-diamine; Imagon; Aralen; w7618; 3377 RP; win244

物化性质

• 密度: 1.1±0.1 g/cm3
• 沸点: 460.6±40.0 °C at 760 mmHg
• 熔点: 87ºC
• 分子式: C₁₈H₂₆ClN₃
• 分子量: 319.872
• 闪点: 232.3±27.3 °C
• 精确质量: 319.181519
• PSA: 28.16000
• LogP: 4.69
• 外观性状: 白色粉末
• 蒸汽压: 0.0±1.1 mmHg at 25°C
• 折射率: 1.592
• 储存条件: 0-10°C;存放于惰性气体之中;避免空气,加热

生物活性

• 描述: Chloroquine 是一种广泛用于治疗疟疾和类风湿性关节炎的抗疟疾和抗炎剂。Chloroquine 是 autophagy 和 toll-like receptors (TLRs) 的抑制剂。Chloroquine 有效抑制 SARS-CoV-2 (COVID-19) 感染 (EC50=1.13 μM)。
• 相关类别:
  信号通路 >> 免疫及炎症 >> Toll样受体(TLR)
  研究领域 >> 癌症
  信号通路 >> 抗感染 >> HIV
  信号通路 >> 抗感染 >> SARS冠状病毒
  信号通路 >> 自噬 >> 自噬
• 靶点:

  TLRs, HIV, SARS-CoV-2, Autophagy[1][2][3][4]

• 体外研究: 氯喹(CHQ,20μM)抑制IL-12p70的释放,降低激活的人单核细胞源性Langerhans样细胞(MoLC)Th1的启动能力。氯喹(20μM)增强IL-1诱导的MoLC分泌IL-23,随后增加CD4+T细胞释放IL-17A的能力[1]。氯喹(25μM)抑制MDA-MB-231细胞正常氧和缺氧时MMP-9mrna的表达。氯喹对MMP-2、MMP-9和MMP-13mrna表达具有细胞、剂量和缺氧依赖性[2]。使用IRS-954或氯喹抑制TLR7和TLR9可显著降低HuH7细胞体外增殖[3]。氯喹(0.01-100μM；48 h)在低微极浓度(EC50=1.13 μM)下能有效阻断病毒感染(SARS-CoV-2感染vero E6细胞)。氯喹通过提高病毒/细胞融合所需的内体pH值,以及干扰SARS-CoV细胞受体的糖基化来阻断病毒感染[4]。
• 体内研究: 氯喹(80mg/kg,i.p.)不能阻止原位小鼠模型中具有高或低TLR9表达水平的三阴性MDA-MB-231细胞的生长[2]。用IRS-954或氯喹抑制TLR7和TLR9可显著抑制小鼠异种移植瘤的生长。氯喹也显著抑制DEN/NMOR大鼠模型中的HCC发展[3]。
• 参考文献:

  [1]. Said A, et al. Chloroquine promotes IL-17 production by CD4+ T cells via p38-dependent IL-23 release by monocyte-derived Langerhans-like cells. J Immunol. 2014 Dec 15;193(12):6135-43.

  [2]. Tuomela J, et al. Chloroquine has tumor-inhibitory and tumor-promoting effects in triple-negative breast cancer. Oncol Lett. 2013 Dec;6(6):1665-1672.

  [3]. Mohamed FE, et al. Effect of toll-like receptor 7 and 9 targeted therapy to prevent the development of hepatocellular carcinoma. Liver Int. 2014 Jul 2. doi: 10.1111/liv.12626.

  [4]. Colson P, et al. Chloroquine and hydroxychloroquine as available weapons to fight COVID-19. Int J Antimicrob Agents. 2020;55(4):105932.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : VB2360000 CHEMICAL NAME : Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)- CAS REGISTRY NUMBER : 54-05-7 LAST UPDATED : 199707 DATA ITEMS CITED : 40 MOLECULAR FORMULA : C18-H26-Cl-N3 MOLECULAR WEIGHT : 319.92 WISWESSER LINE NOTATION : T66 BNJ EMY1&3N2&2 IG HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 24 mg/kg/12D-I TOXIC EFFECTS : Brain and Coverings - changes in surface EEG Behavioral - hallucinations, distorted perceptions Behavioral - changes in motor activity (specific assay) TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 110 mg/kg TOXIC EFFECTS : Cardiac - change in rate Cardiac - other changes Gastrointestinal - nausea or vomiting TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 3600 mg/kg/3Y TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - visual field changes Gastrointestinal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 86 mg/kg TOXIC EFFECTS : Cardiac - change in rate Cardiac - other changes Gastrointestinal - nausea or vomiting TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human DOSE/DURATION : 20 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - diplopia Behavioral - coma Vascular - BP elevation not characterized in autonomic section TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - child DOSE/DURATION : 37593 ug/kg TOXIC EFFECTS : Brain and Coverings - other degenerative changes Behavioral - convulsions or effect on seizure threshold Cardiac - change in rate TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 330 mg/kg TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 102 mg/kg TOXIC EFFECTS : Gastrointestinal - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 190 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 : 60 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 - mouse DOSE/DURATION : 311 mg/kg TOXIC EFFECTS : Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 66 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 : 150 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 : 21600 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 : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 71 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 - rabbit DOSE/DURATION : 75 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 - rabbit DOSE/DURATION : 8 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rabbit DOSE/DURATION : 20 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 : 560 mg/kg/14D-I TOXIC EFFECTS : Behavioral - food intake (animal) 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 - rat DOSE/DURATION : 9800 mg/kg/35W-C TOXIC EFFECTS : Behavioral - food intake (animal) Blood - changes in leukocyte (WBC) count Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 360 mg/kg/30D-I TOXIC EFFECTS : Behavioral - tremor Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases Related to Chronic Data - death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 420 mg/kg SEX/DURATION : female 1-42 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - urogenital system Reproductive - Specific Developmental Abnormalities - other developmental abnormalities TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 1155 mg/kg SEX/DURATION : female 6-39 week(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - eye/ear Reproductive - Effects on Newborn - other postnatal measures or effects TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported DOSE : 840 mg/kg SEX/DURATION : female 1-84 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral DOSE : 10500 mg/kg SEX/DURATION : female 1-15 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Specific Developmental Abnormalities - hepatobiliary system TYPE OF TEST : Specific locus test TYPE OF TEST : Sex chromosome loss and nondisjunction MUTATION DATA TYPE OF TEST : DNA damage TEST SYSTEM : Mammal - species unspecified Lymphocyte DOSE/DURATION : 500 umol/L REFERENCE : BBACAQ Biochimica et Biophysica Acta. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1947- Volume(issue)/page/year: 561,77,1979 *** REVIEWS *** IARC Cancer Review:Animal Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,47,1977 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 13,47,1977 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW PLMJAP Pahlavi Medical Journal. (Shiraz, Iran) V.1-9, 1970-78. Volume(issue)/page/year: 6,160,1975 TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 TOXICOLOGY REVIEW FNSCA6 Forensic Science. (Lausanne, Switzerland) V.1-11, 1972-78. For pub lisher information, see FSINDR. Volume(issue)/page/year: 2,67,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4820 No. of Facilities: 7 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 103 (estimated) No. of Female Employees: 52 (estimated)

安全

• 危害码 (欧洲): Xi
• 海关编码: 2933499090

合成路线

98519-65-4 140-80-7 ~76% 54-05-7

文献：Margolis, Brandon J.; Long, Kimberly A.; Laird, Dana L. T.; Ruble, J. Craig; Pulley, Shon R. Journal of Organic Chemistry, 2007 , vol. 72, # 6 p. 2232 - 2235

50-63-5 ~% 54-05-7

文献：Kuter, David; Benjamin, Stefan J.; Egan, Timothy J. Journal of Inorganic Biochemistry, 2014 , vol. 133, p. 40 - 49

86-99-7 ~% 54-05-7

文献：De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

108-42-9 ~% 54-05-7

文献：De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

86-47-5 ~% 54-05-7

文献：De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

16600-22-9 ~% 54-05-7

文献：De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

3412-99-5 ~% 54-05-7

文献：De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

114422-77-4 ~% 54-05-7 607-14-7

文献：Constantinidis, I.; Satterlee, James D. Journal of the American Chemical Society, 1988 , vol. 110, # 13 p. 4391 - 4395

86-98-6 140-80-7 ~% 54-05-7

文献：De; Byers; Krogstad Journal of Heterocyclic Chemistry, 1997 , vol. 34, # 1 p. 315 - 320

上下游产品

上游产品  10
98519-65-4 140-80-7 50-63-5 86-99-7
108-42-9 86-47-5 16600-22-9 3412-99-5
114422-77-4 86-98-6
下游产品  1
1476-52-4

海关

海关编码	2933499090
中文概述	2933499090. 其他含喹琳或异喹啉环系的化合物〔但未进一步稠合的〕. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%