56391-56-1

• 常用中文名：奈替米星
• 常用英文名：NETILMICIN
• CAS号：56391-56-1
• 分子式：C₂₁H₄₁N₅O₇
• 分子量：475.58000
• 相关类别： 原料药 抗生素类药物 氨基糖苷类药
• 发布时间：2018-02-04 08:00:00
• 更新时间：2025-08-20 20:25:58
• 为氨基糖苷类抗生素西梭霉素的衍生物。抗菌谱和庆大霉素、妥布霉素、西梭霉素、丁胺卡那霉素相似，但对金黄色葡萄球菌、肠道细菌更为有效，抑制绿脓杆菌、普罗威斯登菌则稍差。其最大的优点是对听觉神经及肾脏的毒性比临床常用的氨基糖苷类抗生素为小，对耐庆大霉素的肠道细菌及绿脓杆菌有高效。用于呼吸系统感染、皮肤软组织感染、泌尿系统感染、创面感染、骨关节感染、产后感染、胃肠道及胆道感染、败血症等。
• 本品属半合成氨基糖甙类抗生素，其抗菌谱广，对大肠肝菌、克霉伯菌属、肠肝菌属、沙雷菌属、枸橼酸杆菌属、变形杆菌属、沙门菌属、志贺菌属、嗜血质流感杆菌等具有高度抗菌活性；对缘脓杆菌等假单胞菌、普鲁威登菌和不动杆菌属等的某些菌株亦具有抗菌活性；对葡萄球菌属，包括甲氧西林敏感菌株和部分甲氧西林耐药菌株也具抗菌作用，对肺炎球菌、溶血性链球菌、粪肠球菌的抗菌作用较差。性状：本品为无色或几乎无色的澄明液体。

名称

• 中文名: 奈替米星
• 英文名: netilmycin
• 中文别名: O-3-脱氧-4-C-甲基-3-甲氨基-Β-L-阿拉伯吡喃糖苷基-(1→6)-O-[2,6-二氨基-2,3,4,6-四脱氧-Α-D-甘油糖-己-4-烯吡喃糖苷基-(1→4)]-2-脱氧-N1-乙基-D-链霉胺; 乙基紫苏霉素
• 英文别名: certomycin; ntromycin; netillin; 1-N-ethylsisomicin; ntl; NETILMICIN; vectacin; nettacin; netroymcin; ntromicine; EINECS 260-146-8; netilyn

物化性质

• 密度: 1.32g/cm3
• 沸点: 684.3ºC at 760mmHg
• 分子式: C₂₁H₄₁N₅O₇
• 分子量: 475.58000
• 闪点: 367.7ºC
• 精确质量: 475.30100
• PSA: 199.73000
• 折射率: 1.597
• 分子结构:

  1、 摩尔折射率：123.37

  2、 摩尔体积（cm³/mol）：371.4

  3、 等张比容（90.2K）：1031.0

  4、 表面张力（dyne/cm）：59.3

  5、 极化率（10-24cm3）：48.91

• 更多:

  1.性状：白色结晶性粉末

  2.溶解性：易溶于水，其水溶液较稳定。

毒性和生态

毒理学数据: 急性毒性LD50小鼠(mg/kg):40静脉注射,125腹腔注射,175皮下注射。 CHEMICAL IDENTIFICATION RTECS NUMBER : WK2285000 CHEMICAL NAME : D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopy ranosyl(1-6)-O-(2,6- diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enop yranosyl(1-4))-2-deox y-N(sup 1)-ethyl- CAS REGISTRY NUMBER : 56391-56-1 LAST UPDATED : 199612 DATA ITEMS CITED : 17 MOLECULAR FORMULA : C21-H41-N5-O7 MOLECULAR WEIGHT : 475.67 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Human DOSE/DURATION : 52 mg/kg/7D-C TOXIC EFFECTS : Kidney, Ureter, Bladder - other changes REFERENCE : CMAJAX Canadian Medical Association Journal. (Canadian Medical Assoc., POB 8650, Ottawa, ON K1G 0G8, Canada) V.1- 1911- Volume(issue)/page/year: 120,161,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 25200 ug/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Blood - hemorrhage REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 40 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 29,543,1986 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 500 mg/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Blood - hemorrhage REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 125 mg/kg TOXIC EFFECTS : Brain and Coverings - changes in circulation (hemorrhage, thrombosis, etc.) Lungs, Thorax, or Respiration - chronic pulmonary edema Blood - hemorrhage REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 207 mg/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Blood - hemorrhage REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 181 mg/kg TOXIC EFFECTS : Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Blood - hemorrhage REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 1350 mg/kg/15D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - other changes in urine composition Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Metabolism (Intermediary) - other proteins REFERENCE : AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 10,845,1976 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 322 mg/kg/2W-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 REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Unreported SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 560 mg/kg/14D-I TOXIC EFFECTS : Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) REFERENCE : CLREAS Clinical Research. (Slack Inc., 6900 Grove Rd., Thorofare, NJ 08086) V.6- 1958- Volume(issue)/page/year: 26,141A,1978 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 700 mg/kg/2W-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in bladder weight REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Primate - monkey DOSE/DURATION : 2100 mg/kg/21D-I TOXIC EFFECTS : Behavioral - ataxia Related to Chronic Data - death REFERENCE : JIDIAQ Journal of Infectious Diseases. (Univ. of Chicago Press, Journals Div., POB 37005, Chicago, IL 60637) V.1- 1904- Volume(issue)/page/year: 137,476,1978 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Mammal - cat DOSE/DURATION : 4200 mg/kg/30W-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) REFERENCE : TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 77,479,1985 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 31500 mg/kg/21D-I TOXIC EFFECTS : Related to Chronic Data - death REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 53,230,1983 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 2720 mg/kg SEX/DURATION : female 14 day(s) pre-mating female 1-20 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - other effects to embryo REFERENCE : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 45,145,1979 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 3040 mg/kg SEX/DURATION : female 6-22 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 : APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 45,145,1979 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 250 mg/kg SEX/DURATION : female 6-15 day(s) after conception TOXIC EFFECTS : Reproductive - Specific Developmental Abnormalities - musculoskeletal system REFERENCE : ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,816,1981

合成路线

66567-31-5 ~89% 56391-56-1

文献：Nagabhushan, Tattanahalli L.; Turner, William N.; Tsai, Hsinghan; Jaret, Robert S.; Schumacher, Doris; et al. Carbohydrate Research, 1984 , vol. 130, p. 243 - 250

66065-86-9 ~% 56391-56-1

文献：Carbohydrate Research, , vol. 130, p. 243 - 250

32385-11-8 ~% 56391-56-1

文献：Carbohydrate Research, , vol. 130, p. 243 - 250

66065-91-6 ~% 56391-56-1

文献：Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 2168 - 2185

66567-31-5 ~10% 66065-95-0 66065-95-0 56391-56-1 详细

文献：Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 2168 - 2185

66567-31-5 ~10% 32385-11-8 66065-95-0 56391-56-1 详细

文献：Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , p. 2168 - 2185

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66567-31-5 66065-86-9 32385-11-8
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制备

方法1：发酵法，产生菌为Micromonospora inyoensis 155OF-1G，由N-乙基-α-去氧-D-链霉胺发酵，提纯而得。
方法2：以西梭霉素为原料，调节Ph值为5，乙醛烷化再氰基氢硼化钠还原即得奈替米星。
方法3：部分氨上乙酰化的西梭霉素，用乙醛和氰基硼氢化钠引入乙基后，经碱性树脂脱去乙酰基，即得奈替米星。