78110-38-0

• 常用中文名：氨曲南
• 常用英文名：Aztreonam
• CAS号：78110-38-0
• 分子式：C₁₃H₁₇N₅O₈S₂
• 分子量：435.433
• 相关类别： 原料药 抗生素类药物 β-内酰胺酶抑制剂
• 发布时间：2018-02-07 08:00:00
• 更新时间：2024-01-02 13:05:04
• Aztreonam是单环β-内酰胺抗生素,与青霉素结合蛋白3(PBP-3)有较高亲和力。

名称

• 中文名: 氨曲南
• 英文名: aztreonam
• 中文别名: [2S-[2a,3b(Z)]]-2-[[[1-(2-氨基-4-噻唑基)-2-[(2-甲基-4-氧代-1-磺基-3-氮杂环丁烷基)氨基]-2-氧化亚乙基]氨基]氧代]-2-甲基丙酸; [2S-[2Α,3Β(Z)]]-2-[[[1-(2-氨基-4-噻唑基)-2-[(2-甲基-4-氧代-1-磺基-3-氮杂环丁基)氨基]-2-氧-1,1-亚乙基]氨基]氧基]-2-甲基丙酸
• 英文别名: 2-({[(1Z)-1-(2-Amino-1,3-thiazol-4-yl)-2-{[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino}-2-oxoethylidene]amino}oxy)-2-methylpropanoic acid; CAYSTON; Nebactam; [2S-[2a,3b(Z)]]-2-[[[1-(2-Amino-4-thiazolyl)-2-[(2-methyl-4-oxo-1-sulfo-3-azetidinyl)amino]-2-oxoethylidene]amino]oxy]-2-methylpropanoic Acid; Azteronam; SQ 26,776; (2S,3S)-3-{[(2Z)-2-(2-Ammonio-1,3-thiazol-4-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-2-methyl-4-oxoazetidine-1-sulfonate; MFCD00072145; sq26,776; Azactam; Primbactam; (2S,3S)-3-{[(2Z)-2-(2-Ammonio-1,3-thiazol-4-yl)-2-{[(2-carboxy-2-propanyl)oxy]imino}acetyl]amino}-2-methyl-4-oxo-1-azetidinesulfonate; EINECS 278-839-9; Aztreon; Azonam; Azthreonam; Propanoic acid, 2-[[[(1Z)-1-(2-amino-4-thiazolyl)-2-[[(2S,3S)-2-methyl-4-oxo-1-sulfo-3-azetidinyl]amino]-2-oxoethylidene]amino]oxy]-2-methyl-; Aztreonam; monobactam

物化性质

• 密度: 1.83
• 熔点: 227°C
• 分子式: C₁₃H₁₇N₅O₈S₂
• 分子量: 435.433
• 精确质量: 435.051849
• PSA: 238.20000
• LogP: -0.66
• 外观性状: 白色至灰白色晶体
• 折射率: 1.74
• 储存条件:

  存放在密封容器内，并放在阴凉，干燥处。

• 稳定性:

  指定条件下稳定，远离氧化物。

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：0.3

  2、 氢键供体数量：4

  3、 氢键受体数量：11

  4、 可旋转化学键数量：7

  5、 拓扑分子极性表面积（TPSA）：202

  6、 重原子数量：28

  7、 表面电荷：0

  8、 复杂度：808

  9、 同位素原子数量：0

  10、 确定原子立构中心数量：0

  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：白色结晶或者无色粉末。

  2. 密度（g/mL,25/4℃）： 1.83

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：227

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：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：溶于二甲基甲酰胺，微溶于甲醇，极微溶于乙醇，几不溶于甲苯、氯仿或乙酸乙酯。

生物活性

• 描述: Aztreonam是单环β-内酰胺抗生素,与青霉素结合蛋白3(PBP-3)有较高亲和力。
• 相关类别:
  信号通路 >> 抗感染 >> 细菌
  研究领域 >> 感染
• 参考文献:

  [1]. Kobayashi Y, et al. Synergy with aztreonam and arbekacin or tobramycin against Pseudomonas aeruginosa isolated from blood. J Antimicrob Chemother. 1992 Dec;30(6):871-2.

  [2]. Guay DR, et al. Aztreonam, a new monobactam antimicrobial. Clin Pharm. 1985 Sep-Oct;4(5):516-26.

毒性和生态

毒理学数据: 1、急性毒性：大鼠（口服）LD50：＞10mg/kg 大鼠（腹膜）LD50： 2,549 mg/kg 大鼠（皮下）LD50： 3,154 mg/kg 大鼠（静脉）LD50： 2,001 mg/kg 小鼠（口服）LD50： ＞10mg/kg 小鼠（腹膜）LD50： 2,897mg/kg 小鼠（皮下）LD50： 3,906mg/kg 小鼠（静脉）LD50： 1,963mg/kg 由于食盐的LD50是3,000 mg/kg，BPA的急性毒性程度与食盐同。 生态学数据: 通常对水是不危害的，若无政府许可，勿将材料排入周围环境。 CHEMICAL IDENTIFICATION RTECS NUMBER : UA2451400 CHEMICAL NAME : Propanoic acid, 2-(((1-(2-amino-4-thiazolyl)-2-((2-methyl-4-oxo-1-sul fo-3-azetidinyl)amino )- 2-oxoethylidene)amino)oxy)-2-methyl-, (2S-(2-alpha,3-beta(Z)))- CAS REGISTRY NUMBER : 78110-38-0 LAST UPDATED : 199612 DATA ITEMS CITED : 12 MOLECULAR FORMULA : C13-H17-N5-O8-S2 MOLECULAR WEIGHT : 435.47 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 REFERENCE : IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,474,1987 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2549 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease 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 1),143,1985 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3154 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease 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 1),143,1985 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2001 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea REFERENCE : KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 19,468,1985 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 18,474,1987 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 2897 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease 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 1),143,1985 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3906 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease 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 1),143,1985 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1963 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea 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 1),143,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 21 gm/kg/35D-I TOXIC EFFECTS : Kidney, Ureter, Bladder - changes in bladder weight Skin and Appendages - dermatitis, other (after systemic exposure) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases 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 1),169,1985 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 26250 mg/kg/35D-C TOXIC EFFECTS : Liver - changes in liver weight Blood - changes in erythrocyte (RBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases 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 1),149,1985 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 2970 mg/kg SEX/DURATION : female 7-17 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Newborn - live birth index (measured after birth) 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 1),203,1985 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 1100 mg/kg SEX/DURATION : female 7-17 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) 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 1),203,1985

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• 危害码 (欧洲): Xn
• 风险声明 (欧洲): 20/21/22-36/37/38
• 安全声明 (欧洲): S22-S24/25
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: UA2451400
• 海关编码: 2942000000

合成路线

330944-50-8 ~72% 78110-38-0

文献：BIOGAL GYOGYSZERGYAR RT.; TEVA PHARMACEUTICAL USA, INC. Patent: WO2004/13133 A1, 2004 ; Location in patent: Page 10 ;

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文献：Singh, Janak; Denzel, Theodor W.; Fox, Rita; Kissick, Thomas P.; Herter, Rolf; Wurdinger, Joseph; Schierling, Peter; Papaioannou, Chris G.; Moniot, Jerome L.; Mueller, Richard H.; Cimarusti, Christopher M. Organic Process Research and Development, 2002 , vol. 6, # 6 p. 863 - 868

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文献：US4826973 A1, ;

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文献：Singh, Janak; Denzel, Theodor W.; Fox, Rita; Kissick, Thomas P.; Herter, Rolf; Wurdinger, Joseph; Schierling, Peter; Papaioannou, Chris G.; Moniot, Jerome L.; Mueller, Richard H.; Cimarusti, Christopher M. Organic Process Research and Development, 2002 , vol. 6, # 6 p. 863 - 868

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文献：Organic Process Research and Development, , vol. 6, # 6 p. 863 - 868

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制备

以苏氨酸为原料，经氯化生成的酰氯再氨解生成酰胺，用氯甲酸苄酯对α-氨基进行保护，用甲磺酰氯对β-羟基进行酯化，用硫酸四丁基铵盐对酰胺基进行磺化，然后在碳酸氢钾作用下环合成氮杂环丁烷衍生物，再氢解脱去保护基生成3-氨基-2-甲基-4-氧代-1-磺基氮杂环丁烷。

上述得到的氮杂环丁烷衍生物和侧链噻唑衍生物脱水酰胺化，再水解脱去保护基得到氨曲南。

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海关编码	2942000000