59-01-8

• 常用中文名：卡那霉素碱
• 常用英文名：kanamycin
• CAS号：59-01-8
• 分子式：C₁₈H₃₆N₄O₁₁
• 分子量：484.499
• 相关类别： 医药中间体 杂环化合物 吡啶类化合物 乙基吡啶
• 发布时间：2018-07-10 18:11:40
• 更新时间：2026-07-04 08:01:49
• 卡那霉素(卡那霉霉素A)是一种口服活性抗菌剂(革兰氏阴性/阳性细菌),通过与70 S核糖体亚单位结合,抑制易位并导致编码错误。卡那霉素对结核分枝杆菌(敏感和耐药)和肺炎克雷伯菌均有良好的抑制活性,可用于结核病和肺炎的研究[1][2][3][4]。

名称

• 中文名: 卡那霉素碱
• 英文名: kanamycin A
• 中文别名: 卡那霉素杂质; 卡那霉素; 卡那辛; 卡那霉素A; 单硫酸卡那毒素; 单硫酸卡那霉素; 丁胺卡那霉素D; 阿米卡星杂质D; 阿米卡星杂质4; 卡那霉素/卡那霉素碱
• 英文别名: KANAMYCIN //BP; Amikacin Impurity 4（Amikacin Impurity D）; glucopyranoside,4,6-diamino-2-hydroxy-1,3-cyclohexylene3,6’diamino-3,6’-dideo; kanamycin from Streptomyces kanamyceticus; d-deoxydi; Kanamycins; Amikacin Impurity 4; 1-O-[(1R)-2α-Hydroxy-3β-(3-amino-3-deoxy-α-D-glucopyranosyloxy)-4α,6α-diaminocyclohexane-1β-yl]-6-amino-6-deoxy-α-D-glucopyranose; y-alpha-d-glucopyranosyl-)-2-deoxy; 6-O-(3-Amino-3-deoxy-α-D-glucopyranosyl)-4-O-(6-amino-6-deoxy-α-D-glucopyranosyl)-2-deoxy-D-strtamine; (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-bis(azanyl)-3-[(2S,3R,4S,5S,6R)-4-azanyl-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-oxane-3,4,5-triol; 4,6-Diamino-3-[(6-amino-6-deoxyhexopyranosyl)oxy]-2-hydroxycyclohexyl 3-amino-3-deoxyhexopyranoside; d-strtamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1.fwdw.6)-o-[6-amin; d-xydi; Amikacin Impurity D; o-6-deoxy-alpha-d-glucopyranosyl-(1.fwdw.)]-2-deoxy; (2R,3S,4S,5R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol; km(theantibiotic); KANAMYCIN BASE; Kanamycin A in water; gentamicin A; Kanamycin free base; KANAMYCIN; 4-O-(6-Amino-6-deoxy-α-D-glucopyranosyl)-6-O-(3-amino-3-deoxy-α-D-glucopyranosyl)-2-deoxy-D-strtamine; (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol; KANAMYCIN BASE ENTERPRISE STANDD; Kannamycin Monosulfate; KANAMYCIN A; kanamicina; KanamycinMonosulfateA; 4,6-diamino-2-hydroxy-1,3-cyclohexane3,6’diamino-3,6’-dideoxydi-alpha-d-gluc; 4,6-diamino-2-hydroxy-1,3-cyclohexane3,6’diamino-3,6’-dideoxydi-alpha-d-glucos; d.6-O-(3-amino-3-deoxy-α-d-glucopyranosyl)-4-O-(6-amino-6-deoxy-α-d-glucopyranosyl)-2-deoxy-d-strtamine(kanamycin); D-Strtamine, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-amino-6-deoxy-α-D-glucopyranosyl-(1→4)]-2-deoxy; Kanamycine; 4))-2-deoxy-y-alpha-d-glucopyranosyl-(; (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4,5-triol; glucopyranoside,4,6-diamino-2-hydroxy-1,3-cyclohexylene3,6’-diamino-3,6’-di

物化性质

• 密度: 1.6±0.1 g/cm3
• 沸点: 809.5±65.0 °C at 760 mmHg
• 分子式: C₁₈H₃₆N₄O₁₁
• 分子量: 484.499
• 闪点: 443.4±34.3 °C
• 精确质量: 484.238068
• PSA: 282.61000
• LogP: -2.58
• 蒸汽压: 0.0±6.5 mmHg at 25°C
• 折射率: 1.670

生物活性

• 描述: 卡那霉素(卡那霉霉素A)是一种口服活性抗菌剂(革兰氏阴性/阳性细菌),通过与70 S核糖体亚单位结合,抑制易位并导致编码错误。卡那霉素对结核分枝杆菌(敏感和耐药)和肺炎克雷伯菌均有良好的抑制活性,可用于结核病和肺炎的研究[1][2][3][4]。
• 相关类别:
  研究领域 >> 感染
  研究领域 >> 炎症/免疫
  信号通路 >> 抗感染 >> 细菌
• 体外研究: 卡那霉素(0.1-100μg/mL；2周)在体外对各种分枝杆菌菌株表现出良好的抗菌活性(MIC=1-5μg/mL)[1]。细胞活力测定[1]细胞系：分枝杆菌H37Rv、H2、H37RvR PAS、Ravenel、Kirchbergand和BCG。浓度：0.1-100μg/mL孵育时间：2周结果：对各种分枝杆菌(H37Rv、H2、H37RvR PAS、Ravenel和BCG)表现出良好的抗菌活性,Kirchbergand菌株的MIC分别为1μg/mL和5μg/mL。
• 体内研究: 卡那霉素(2,4 mg/kg；皮下注射；每日一次,每周6次,共3周)抑制小鼠肺和脾脏中牛结核杆菌的生长[1]。卡那霉素(1.25,5 mg/kg；皮下注射；单次(感染后3小时))抑制小鼠肺、气管和血液中肺炎克雷伯菌DT-s的增殖,并与给药剂量成比例,还增加了小鼠的存活率[2]。动物模型：近交系正常小鼠(14-16g；牛结核杆菌(Ravenel株)感染模型)[1]。剂量：2,4mg/kg给药：皮下注射；每天一次,每周6次,持续3周。结果：对小鼠体内尤其是肺结核的增殖有明显的抑制作用。动物模型：Slc:ICR雄性小鼠(4周龄；18-24克；肺炎克雷伯菌DT-S感染模型(通过气溶胶法))[2]。剂量：1.25,5mg/kg给药：皮下给药；单个(感染后3小时)。结果：与给药剂量成比例地抑制肺炎克雷伯菌DT-S在肺、气管和血液中的生长。在感染后第6天导致90%的存活率(阴性对照组：所有人在4天内死亡),并在48小时内(当剂量为5 mg/kg时)从小鼠的肺、气管和血液中清除肺炎克雷伯菌DT-S。
• 参考文献:

  [1]. YANAGISAWA K, et al. Studies on kanamycin, a new antibiotic against tubercle bacilli. I. Effect on virulent tubercle bacilli in vitro and in mice. J Antibiot (Tokyo). 1957 Nov;10(6):233-5.

  [2]. Nishi T, et al. Experimental respiratory tract infection with Klebsiella pneumoniae DT-S in mice: chemotherapy with kanamycin. Antimicrob Agents Chemother. 1980 Mar;17(3):494-505.

  [3]. Misumi M, et al. Interaction of kanamycin and related antibiotics with the large subunit of ribosomes and the inhibition of translocation. Biochem Biophys Res Commun. 1978 Sep 29;84(2):358-65.

  [4]. Misumi M, et al. Mechanism of inhibition of translocation by kanamycin and viomycin: a comparative study with fusidic acid. Biochem Biophys Res Commun. 1980 Jan 29;92(2):647-54.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : WK1962000 CHEMICAL NAME : D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-a mino-6-deoxy-alpha- D-glucopyranosyl-(1-4))-2-deoxy- CAS REGISTRY NUMBER : 59-01-8 BEILSTEIN REFERENCE NO. : 0061647 LAST UPDATED : 199706 DATA ITEMS CITED : 27 MOLECULAR FORMULA : C18-H36-N4-O11 MOLECULAR WEIGHT : 484.58 WISWESSER LINE NOTATION : T6OTJ CQ DZ EQ F1Q BO- BL6TJ AZ CQ EZ DO- BT6OTJ CQ DQ EQ F1Z HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >10 gm/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 : 1515 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 : 4070 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 : 437 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 : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1014 mg/kg TOXIC EFFECTS : Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis Lungs, Thorax, or Respiration - other changes TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 20700 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 - mouse DOSE/DURATION : 794 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 : 1350 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 : 115 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 : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 54 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 : Intracerebral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 33750 ug/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Cardiac - other changes Lungs, Thorax, or Respiration - respiratory depression TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rabbit 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 : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 1385 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 : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 960 mg/kg/4D-I TOXIC EFFECTS : Blood - changes in other cell count (unspecified) Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 12 gm/kg/30D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - changes in bladder weight Related to Chronic Data - death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 3600 mg/kg SEX/DURATION : female 1-12 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 3600 mg/kg SEX/DURATION : female 12-20 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 3500 mg/kg SEX/DURATION : female 12-18 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - eye/ear MUTATION DATA TYPE OF TEST : DNA repair TEST SYSTEM : Bacteria - Bacillus subtilis DOSE/DURATION : 27 ug/L REFERENCE : WATRAG Water Research. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 0BW, UK) V.1- 1967- Volume(issue)/page/year: 14,1613,1980 *** REVIEWS *** TOXICOLOGY REVIEW CLANA4 Clinical Anesthesia. (Philadelphia, PA 19103) V.1-11, 1963-76. Volume(issue)/page/year: 10(Pt 1),283,1973 TOXICOLOGY REVIEW MMWOAU Muenchener Medicinische Wochenschrift. (Munich, Fed. Rep. Ger.) V.33-115, 1886-1973. Volume(issue)/page/year: 115,1661,1973 TOXICOLOGY REVIEW INTEAG Internist. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1960- Volume(issue)/page/year: 15,7,1974 TOXICOLOGY REVIEW ARVPAX Annual Review of Pharmacology. (Palo Alto, CA) V.1-15, 1961-75. For publisher information, see ARPTDI. Volume(issue)/page/year: 5,447,1965 TOXICOLOGY REVIEW AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 38,409,1965

安全

• WGK德国: 2