37517-28-5

• 常用中文名：阿米卡星
• 常用英文名：Amikacin
• CAS号：37517-28-5
• 分子式：C₂₂H₄₃N₅O₁₃
• 分子量：585.602
• 相关类别： 原料药 抗生素类药物 氨基糖苷类药
• 发布时间：2018-10-04 12:15:24
• 更新时间：2024-01-02 15:46:59
• 阿米卡星(BAY 41-6551)是卡那霉素的半合成类似物,对大多数革兰氏阴性细菌(包括庆大霉素和妥布霉素耐药菌株)非常有效。阿米卡星(BAY 41-6551)具有耳毒性和肾毒性[1][2]。

名称

• 中文名: 阿米卡星
• 英文名: amikacin
• 中文别名: 氨基羟丁基卡那霉素A; 阿米卡星(丁胺卡那霉素)二水合物; 抗菌素BBK8
• 英文别名: Butanamide, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2S)-; Butanimidic acid, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (1E,2S)-; kaminax; (2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-a-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-a-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide; novamin; 1-N-[L(-)-4-Amino-2-hydroxybutyryl]kanamycin A; mikavir; D-Streptamine; AMIKACIN; bb-k8; Amikin; EINECS 253-538-5; butanamide, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-a-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-a-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2S)-; (1E,2S)-4-Amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanimidic acid; Amikacin Base; Fabianol; lukadin; Biklin; amiklin; (2S)-4-Amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide; O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1®6)-O-[6-amino-6-deoxy-a-D-glucopyranosyl-(1®4)]-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-D-streptamine; AMK

物化性质

• 密度: 1.6±0.1 g/cm3
• 沸点: 981.8±65.0 °C at 760 mmHg
• 熔点: 203-204ºC (sesquihydrate)
• 分子式: C₂₂H₄₃N₅O₁₃
• 分子量: 585.602
• 闪点: 547.6±34.3 °C
• 精确质量: 585.285706
• PSA: 331.94000
• LogP: -3.34
• 外观性状: 白色粉末
• 蒸汽压: 0.0±0.6 mmHg at 25°C
• 折射率: 1.664
• 储存条件:

  密封、阴凉、干燥保存

• 稳定性:

  常规情况下不会分解，没有危险反映

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：-7.9

  2、 氢键供体数量：13

  3、 氢键受体数量：17

  4、 可旋转化学键数量：10

  5、 拓扑分子极性表面积（TPSA）：332

  6、 重原子数量：40

  7、 表面电荷：0

  8、 复杂度：819

  9、 同位素原子数量：0

  10、 确定原子立构中心数量：16

  11、 不确定原子立构中心数量：0

  12、 确定化学键立构中心数量：0

  13、 不确定化学键立构中心数量：0

  14、 共价键单元数量：1

• 更多:

  1. 性状： 未确定

  2. 密度（g/mL,20 ºC）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）： 未确定

  4. 熔点（ºC）： 未确定

  5. 沸点（ºC,17mm hg）： 未确定

  6. 沸点（ºC,91kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）： 未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）： 未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：未确定

生物活性

• 描述: 阿米卡星(BAY 41-6551)是卡那霉素的半合成类似物,对大多数革兰氏阴性细菌(包括庆大霉素和妥布霉素耐药菌株)非常有效。阿米卡星(BAY 41-6551)具有耳毒性和肾毒性[1][2]。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 参考文献:

  [1]. Edson, R.S. and C.L. Terrell, The aminoglycosides. Mayo Clin Proc, 1999. 74(5): p. 519-28.

  [2]. Ristuccia AM, et al. An overview of amikacin. Ther Drug Monit. 1985;7(1):12-25.

  [3]. Siân R Kitcher, et al. ORC-13661 Protects Sensory Hair Cells From Aminoglycoside and Cisplatin Ototoxicity. JCI Insight. 2019 Aug 8;4(15):e126764.

MSDS

Section 1. Chemical Product and Company Identification Amikacin Common Name/ Trade Name Amikacin Section 4. First Aid Measures Eye ContactCheck for and remove any contact lenses. In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical attention if irritation occurs. Skin ContactWash with soap and water. Cover the irritated skin with an emollient. Get medical attention if irritation develops. Serious Skin ContactNot available. InhalationIf inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical attention. Serious InhalationNot available. IngestionDo NOT induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Loosen tight clothing such as a collar, tie, belt or waistband. Get medical attention if symptoms appear. Serious IngestionNot available. Section 5. Fire and Explosion Data Flammability of the Product May be combustible at high temperature. Auto-Ignition Temperature Not available. Flash PointsNot available. Flammable LimitsNot available. Products of CombustionThese products are carbon oxides (CO, CO2). Fire Hazards in Presence of Slightly flammable to flammable in presence of heat. Various SubstancesNon-flammable in presence of shocks. Explosion Hazards in Presence Slightly explosive in presence of open flames and sparks. Non-explosive in presence of shocks. of Various Substances SMALL FIRE: Use DRY chemical powder. Fire Fighting Media and InstructionsLARGE FIRE: Use water spray, fog or foam. Do not use water jet. As with most organic solids, fire is possible at elevated temperatures Special Remarks on Fire Hazards Special Remarks on Explosion Fine dust dispersed in air in sufficient concentrations, and in the presences of an ignition source is a potential dust Hazardsexplosion hazard. Section 6. Accidental Release Measures Small SpillUse appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by spreading water on the contaminated surface and dispose of according to local and regional authority requirements. Large SpillUse a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water on the contaminated surface and allow to evacuate through the sanitary system. Amikacin Section 7. Handling and Storage PrecautionsKeep away from heat. Keep away from sources of ignition. Do not ingest. Do not breathe dust. If ingested, seek medical advice immediately and show the container or the label. StorageKeep container tightly closed. Keep container in a cool, well-ventilated area. Section 8. Exposure Controls/Personal Protection Engineering ControlsUse process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants below the exposure limit. Personal Protection Safety glasses. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Gloves. Personal Protection in Case of Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used a Large Spillto avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this product. Exposure LimitsNot available. Section 9. Physical and Chemical Properties Physical state and appearance Solid. (Powdered solid.)OdorNot available. TasteNot available. Molecular Weight585.6 g/mole ColorWhite. pH (1% soln/water)Not available. Boiling PointNot available. Melting Point214°C (417.2°F) Critical TemperatureNot available. Not available. Specific Gravity Vapor PressureNot applicable. Vapor DensityNot available. VolatilityNot available. Odor ThresholdNot available. Not available. Water/Oil Dist. Coeff. Ionicity (in Water)Not available. Not available. Dispersion Properties SolubilityNot available. Section 10. Stability and Reactivity Data StabilityThe product is stable. Not available. Instability Temperature Conditions of InstabilityExcess heat, dust generation, incompatible materials Incompatibility with variousReactive with oxidizing agents. substances CorrosivityNot available. Amikacin Special Remarks onNot available. Reactivity Special Remarks onNot available. Corrosivity PolymerizationWill not occur. Section 11. Toxicological Information Routes of EntryInhalation. Ingestion. Toxicity to AnimalsAcute oral toxicity (LD50): >6000 mg/kg [Mouse]. Chronic Effects on Humans May cause damage to the following organs: kidneys, ears. Other Toxic Effects onSlightly hazardous in case of skin contact (irritant), of ingestion, of inhalation. Humans Special Remarks onNot available. Toxicity to Animals Special Remarks onMay cause adverse reproductive effects and birth defects (teratogenic) Chronic Effects on Humans Special Remarks on otherAcute Potential Health Effects: Toxic Effects on HumansSkin: May cause skin irritation. Eyes: May cause eye irritation. Inhalation: May cause respiratory tract irritation. Ingestion: May cause irritation of the digestive tract. May affect the nervous system (flaccid paralysis without anesthesia). Chronic Potential Health Effects: Ingestion: Prologned or repeated ingestion may cause kidney damage, and may affect the blood, and metabolism (weight loss), hearing (nerve deafness, change in cochlear structure or function). Aminoglycosides are associated with significant nephrotoxicity and/or ototoxicity. Section 12. Ecological Information EcotoxicityNot available. Not available. BOD5 and COD Possibly hazardous short term degradation products are not likely. However, long term degradation products may Products of Biodegradation arise. Toxicity of the ProductsThe product itself and its products of degradation are not toxic. of Biodegradation Special Remarks on theNot available. Products of Biodegradation Section 13. Disposal Considerations Waste DisposalWaste must be disposed of in accordance with federal, state and local environmental control regulations. Amikacin Section 14. Transport Information DOT ClassificationNot a DOT controlled material (United States). IdentificationNot applicable. Not applicable. Special Provisions for Transport DOT (Pictograms) Section 15. Other Regulatory Information and Pictograms No products were found. Federal and State Regulations CaliforniaCalifornia prop. 65: This product contains the following ingredients for which the State of California has found to cause cancer which would require a warning under the statute: No products were found. Proposition 65 Warnings California prop. 65: This product contains the following ingredients for which the State of California has found to cause birth defects which would require a warning under the statute: No products were found. Other RegulationsOSHA: Hazardous by definition of Hazard Communication Standard (29 CFR 1910.1200). EINECS: This product is on the European Inventory of Existing Commercial Chemical Substances. WHMIS (Canada) Not controlled under WHMIS (Canada). Other Classifications DSCL (EEC)This product is not classified according S24/25- Avoid contact with skin and eyes. to the EU regulations.S36/37/39- Wear suitable protective clothing, gloves and eye/face protection. Health Hazard HMIS (U.S.A.)1 National Fire Protection 1 Flammability 1 Association (U.S.A.) Fire Hazard 1 0 Reactivity Health Reactivity 0 Specific hazard Personal Protection E WHMIS (Canada) (Pictograms) DSCL (Europe) (Pictograms) TDG (Canada) (Pictograms) ADR (Europe) (Pictograms) Amikacin Protective Equipment Gloves. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1、急性毒性：小鼠注射LD50：280 mg/kg； 小鼠肌肉LD50：6200 mg/kg。 小鼠经口LD50：>6 gm/kg； 小鼠皮下LD50：6200 mg/kg； 小鼠腹腔LD50：750 mg/kg； 其托多剂量毒性数据 大鼠皮下TDLo：5040 mg/kg； 大鼠肌肉TDLo：3150 mg/kg； 豚鼠皮下TDLo：4500 mg/kg； 豚鼠肌肉TDLo：5600 mg/kg； 繁殖数据 兔子肌肉TDLo：90 mg/kg； 生态学数据: 对水是稍微有危害的不要让未稀释或大量的产品接触地下水、水道或者污水系统，若无政府许可，勿将材料排入周围环境。 CHEMICAL IDENTIFICATION RTECS NUMBER : WK1955000 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))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)- CAS REGISTRY NUMBER : 37517-28-5 LAST UPDATED : 199612 DATA ITEMS CITED : 12 MOLECULAR FORMULA : C22-H43-N5-O13 MOLECULAR WEIGHT : 585.70 WISWESSER LINE NOTATION : T6OTJ CQ DZ EQ F1Q BO- DL6TJ AZ CQ EMVYQ2Z BO- BT6OTJ CQ DQ EQ F1Z -S HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >6 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,415,1975 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 750 mg/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) REFERENCE : AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 13,41,1978 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 6200 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,415,1975 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 280 mg/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: 43,858,1990 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 6200 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,415,1975 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 5040 mg/kg/14D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) REFERENCE : JEPTDQ Journal of Environmental Pathology and Toxicology. (Park Forest South, IL) V.1-5(3), 1977-81(?). For publisher information, see JEPOEC. Volume(issue)/page/year: 4(5-6),277,1980 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3150 mg/kg/21D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 33(Suppl 5),47,1985 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 4500 mg/kg/20D-I TOXIC EFFECTS : Sense Organs and Special Senses (Ear) - changes in cochlear structure or function REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 65,222,1982 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 5600 mg/kg/4W-I TOXIC EFFECTS : Sense Organs and Special Senses (Ear) - changes in vestibular functions Sense Organs and Special Senses (Ear) - changes in cochlear structure or function Nutritional and Gross Metabolic - weight loss or decreased weight gain REFERENCE : NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 33(Suppl 5),90,1985 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 90 mg/kg SEX/DURATION : female 8-16 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - body wall REFERENCE : JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,366,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3198 No. of Facilities: 312 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 15838 (estimated) No. of Female Employees: 12302 (estimated)

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): 26-36
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: WK1955000

合成路线

39831-55-5 ~% 37517-28-5

文献：WO2010/30690 A1, ; Page/Page column 17-18 ; WO 2010/030690 A1

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