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  4. 奈替米星

奈替米星

  • 基本信息
  • 制备方法及用途
  • 物化性质
  • 毒理性
  • 结构与计算化学
  • 上游产品

奈替米星 基本信息

中文名称：
奈替米星 
中文别名：
奈替米星;
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 
英文名称：
D-Streptamine,O-3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(1®6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1®4)]-2-deoxy-N1-ethyl-
英文别名：
netilmycin;
netilyn;
netillin;
ntl;
NETILMICIN;
1-N-ethylsisomicin;
ntromycin;
netroymcin;
certomycin;
vectacin;
nettacin;
ntromicine 
CAS No.：
56391-56-1
分 子 式：

C21H41N5O7

分 子 量：
475.58
精确分子量：
475.30100
PSA：
199.73000
EINECS：
260-146-8
InChI：
The Key: CIDUJQMULVCIBT-MQDUPKMGSA-N
危险品标志：

 

风险术语：

 

安全术语：

 

分子结构式：
SDS：
查看

奈替米星 制备方法及用途

制备方法

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。

合成制备方法

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。

用途简介

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。

用途

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。

奈替米星 物化性质

密度：
1.32g/cm3
沸点：
684.3ºC at 760mmHg
闪点：
367.7ºC
折射率：
1.597
其它信息：

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。

奈替米星 毒理性

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
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。

奈替米星 分子结构与计算化学数据

分子结构数据

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

奈替米星 上游产品

3,2',6'-tri-N-acetylsisomicin 西索米星

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