69-53-4

• 常用中文名：氨苄西林
• 常用英文名：Ampicillin
• CAS号：69-53-4
• 分子式：C₁₆H₁₉N₃O₄S
• 分子量：349.405
• 相关类别： 原料药 抗生素类药物 青霉素类药
• 发布时间：2018-02-05 08:00:00
• 更新时间：2026-07-12 11:37:19
• Ampicillin是一种广谱β-内酰胺抗生素,适用于各种革兰氏阳性和革兰氏阴性菌。
• 药品为广谱半合成青霉素，毒性极低。抗菌谱与青霉素相似，对青霉素敏感的细菌效力较低，对草绿色链球菌的抗菌作用与青霉素相仿或略强。对白喉杆菌、破伤风杆菌和放线菌其效能基本和青霉素相同。对肠球菌及李斯特菌的作用则优于苄青霉素。对耐药葡萄球菌及其它能产生青霉素酶的细菌均无抗菌作用。对革兰阴性菌有效，但易产生耐药性。
  药品主要用于敏感菌所致的泌尿系统、呼吸系统、胆道、肠道感染以及脑膜炎、心内膜炎等。
  主要用于伤寒、副伤寒的治疗；也用于泌尿道、呼吸道感染。

名称

• 中文名: 氨苄西林
• 英文名: ampicillin
• 中文别名: 氨苄西林，六水; 甲苯磺酸磺胺嘧啶杂质B; 哌拉西林杂质A(氨苄西林、舒他西林杂质C); 原料氨苄西林; 氨基青霉素; 舒他西林杂质C(氨苄西林、哌拉西林杂质A); 广谱青霉素类抗生素; 哌拉西林杂质A; 氨苄西林杂质25; 哌拉西林杂质A(氨苄西林对照品)、无水氨苄西林(对照品); 无水氨苄西林(氨苄青霉素); 哌拉西林杂质A(氨苄西林对照品); 氨苄西林对照品; 苯明西林; 氨苄西林无水物; D(-)6-(α-氨基-苯乙酰胺)青霉烷酸; 氨苄西林(氨苄青霉素)检测标准品; 氨苄青霉素 标准品; 哌拉西林杂质A /BP); 哌拉西林杂质A(氨苄西林、舒达西林杂质C); 氨苄青霉素; 氨苄西林(氨苄西林三水酸); 氨苄青霉素-D5; (2S,5R,6R)-3,3-二甲基-6-[(R)-2-氨基-2-苯乙氨基]-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷; 氨苄西林-4 原料药; 氨苄青霉素/氨苄西林; 氨苄青霉素溶液,100PPM; 氨苄西林:广谱青霉素类抗生素; 哌拉西林 杂质 A(氨苄青霉素、舒他霉素 杂质 C); 舒达西林杂质C; 无水氨苄西林; 氨苄西林(无水) 标准品; 氨苄西林三水,氨苄青霉素; 氨比西林(+4℃); 舒他西林杂质C; 氨苄西林/氨苄青霉素; 氨苄青霉素/A1A; 赛米西林; (2S,5R,6R)-3,3-二甲基-6-[(R)-2-氨基-2-苯乙酰氨基]-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-甲酸; 哌拉西林钠杂质A; 氨卞西林; 氨苄西林(限制); 盐酸巴氨苄西林杂质I; 氨苄西林杂质O脱羧; 安比西林; 氨苄青霉素/2S,5R,6R)-3,3-二甲基-6-[D-(-)-2-氨基-2-苯乙酰氨基]-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-甲酸; 托西酸舒他西林杂质; (2S,5R,6R)-6-[[(2R)-2-氨基-2-苯基乙酰基]氨基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷 2-羧酸; 氨苄青霉素-D5 (非对映体的混合物); 氨苄西林,SULTAMICILLIN 杂质C; 苄那消; 水溶氨苄西林; 沙维西林; (2S,5R,6R)-6-((R)-2-氨基-2-苯乙酰胺基)-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2- 羧酸 (哌拉西林杂质)
• 英文别名: 6-(d(-)-alpha-aminophenylacetamido)penicillanicacid; AMPICILLIN READY MADE SOLUTION; 6-[d(-)-alpha-aminophenylacetamido]penicillanicacid; ampicillinanhydrate; [2s-[2alpha,5alpha,6beta(s)]]-o]-3-dimethyl-7-oxo; AmpiciL; ampicin; ab-pc; AMPICILIN 3-HYDRATE; ampimed; 6-[d-(2-amino-2-phenylacetamido)]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0; ampy-penyl; amplital; (2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7 -oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic Acid; MFCD00072036; amplisom; p-50; Rosampline; qidamp; ay-6108; 4-thia-1-azabicyclo[3.2.0]htane-2-cboxylicacid,6-[(aminophenylacetyl)amin; aminobenzylpenicillin; Misilan; Ampicillin -4 Phmaceutical Raw Material Manufacturer; EINECS 200-709-7; 4-Thia-1-azabicyclo3.2.0htane-2-cboxylic acid, 6-(2R)-aminophenylacetylamino-3,3-dimethyl-7-oxo-, (2S,5R,6R); Nonane-1,9-diamine; Ampicillinbase; amfipen; ampi-bol; amblosin; 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0]htane-2-cboxylic acid trihydrate; binotal; ampicillin soluble powder; Unasyn; D(-)-ALPHA-AMINOBENZYLPENICILLIN TRIHYDRATE; AMPICILLIN ANHYDROUS CRYSTALLINE; Ampicillin-d5 (Mixture of Diastereomers); D(-)-aplha-aminobenzylpenicillin; Albipen; Ampicillin/Sulbactam,(1:x); Sultamicillin Impurity C (Ampicillin, Piperacillin Impurity A); SBT/ABPC; Wymox; 6-[D-ALPHA-AMINOPHENYLACETAMIDO]PENICILLANIC ACID TRIHYDRATE; Sultamicillin Impurity 3（Sultamicillin Impurity C）; (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; ampicillina; AMPICILLIN, ANHYDROUS MM(CRM STANDD); D(-)-ALPHA-AMINOBENZYLPENICILLIN; Ampicilin Trihydrate; Penstabil; ALPHA-AMINOBENZYLPENICILLIN, TRIHYDRATE; adobacillin; Piperacillin Impurity 1 Impurity A); (2S,5R,6R)-6-[(R)-2-Amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]htane-2-cboxylic acid; (aminophenylmethyl)-penicilli; ampicillinanhydrous; 6-(D-[-]-α-Aminophenylacetamido) penicillanic acid; ampicillinacid; amipenixs; ampipenin; Aminobenzylpenicillin/sulbactam; Piperacillin Impurity A (Ampicillin, Sultamicillin Impurity C)

物化性质

• 密度: 1.6±0.1 g/cm3
• 沸点: 644.5±65.0 °C at 760 mmHg
• 熔点: 198-200 °C (dec.)(lit.)
• 分子式: C₁₆H₁₉N₃O₄S
• 分子量: 349.405
• 闪点: 343.6±34.3 °C
• 精确质量: 349.109619
• PSA: 138.03000
• LogP: 1.65
• 外观性状: 结晶固体
• 蒸汽压: 0.0±2.0 mmHg at 25°C
• 折射率: 1.724
• 储存条件:

  本品应密封于4℃干燥保存。有效期2年半。

• 稳定性: Stable, but may be moisture sensitive. Incopmpatible with strong oxidizing agents.
• 水溶解性: NH4OH 1 M: 50 mg/mL, clear, colorless
• 分子结构:

  1、 摩尔折射率：89.94

  2、 摩尔体积（cm³/mol）：239.3

  3、 等张比容（90.2K）：702.7

  4、 表面张力（dyne/cm）：74.3

  5、 极化率（10-24cm3）：35.65

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:3

  3.氢键受体数量:6

  4.可旋转化学键数量:4

  5.互变异构体数量:4

  6.拓扑分子极性表面积138

  7.重原子数量:24

  8.表面电荷:0

  9.复杂度:562

  10.同位素原子数量:0

  11.确定原子立构中心数量:4

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：白色结晶性粉末。味微苦。

  2. 密度（g/mL,25/4℃）： 未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：200～202

  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，C＝1，水中）：+250±5

  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：溶于稀酸和稀碱，微溶于水，几乎不溶于氯仿、96%的乙醇、乙醚和固定油中。

生物活性

• 描述: Ampicillin是一种广谱β-内酰胺抗生素,适用于各种革兰氏阳性和革兰氏阴性菌。
• 相关类别:
  信号通路 >> 抗感染 >> 细菌
  研究领域 >> 感染
• 体外研究: 氨苄青霉素以剂量依赖性方式抑制猪源大肠杆菌的生长。氨苄青霉素的有效抑制浓度为2.5 uG/mL [1]。
• 体内研究: 氨苄西林在减轻11周龄猪出血性肠炎的症状方面非常有效[1]。氨苄西林在胆汁中产生的最大浓度是血清中的两倍。口服给药后氨苄西林的峰值浓度是门静脉血液中的两倍,高于外周血[2]。氨苄西林提供针对缺血再灌注脑损伤的神经保护作用。氨苄青霉素降低MMP的活性并增加GLT-1的表达水平。氨苄青霉素预处理可显着降低全脑前脑缺血后内侧海马细胞死亡[3]。
• 动物实验: 小鼠：将氨苄青霉素溶于生理盐水中。用氟烷麻醉雄性C57BL / 6小鼠，并进行双侧颈总动脉闭塞40分钟。在短暂的前脑缺血之前，每天施用氨苄青霉素（200mg / kg，腹膜内[ip]）或青霉素G（6,000U / kg或20,000U / kg，ip），持续5天。在对照动物中，以相同的体积和时间表给予盐水[3]。
• 参考文献:

  [1]. Chopra SL, et al. Effect of Ampicillin on E. Coli of Swine Origin. Can J Comp Med Vet Sci. 1963 Sep;27(9):223-7.

  [2]. Lund B, et al. Ampicillin in portal and peripheral blood and bile after oral administration of ampicillin andpivampicillin. Eur J Clin Pharmacol. 1974;7(2):133-5.

  [3]. Lee KE, et al. The neuroprotective mechanism of ampicillin in a mouse model of transient forebrain ischemia. Korean J Physiol Pharmacol. 2016 Mar;20(2):185-92.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : XH8350000 CHEMICAL NAME : 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-amino-2-phenylacetamido)-3,3- dimethyl-7-oxo-, D-(-)- CAS REGISTRY NUMBER : 69-53-4 LAST UPDATED : 199806 DATA ITEMS CITED : 31 MOLECULAR FORMULA : C16-H19-N3-O4-S MOLECULAR WEIGHT : 349.44 WISWESSER LINE NOTATION : T45 ANV ESTJ CMVYZR& F1 F1 GVQ -D HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - man DOSE/DURATION : 400 mg/kg/4W-I TOXIC EFFECTS : Blood - agranulocytosis Blood - other changes Nutritional and Gross Metabolic - body temperature increase TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 160 mg/kg/4D-I TOXIC EFFECTS : Blood - agranulocytosis Blood - thrombocytopenia TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >5 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 : 4500 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >5 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 : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 6200 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 : Parenteral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >3 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 : Unreported 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 : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >5 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 - mouse DOSE/DURATION : 3250 mg/kg TOXIC EFFECTS : Brain and Coverings - recordings from specific areas of CNS Behavioral - somnolence (general depressed activity) TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >5 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 : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 4600 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 : 380 mg/kg TOXIC EFFECTS : Behavioral - hallucinations, distorted perceptions Behavioral - excitement Musculoskeletal - changes in teeth and supporting structures TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Parenteral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >3 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 : Unreported SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 28 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - cat DOSE/DURATION : >100 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 : Unreported SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 7500 ug/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 : Oral DOSE : 2500 mg/kg SEX/DURATION : female 4-13 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death MUTATION DATA TYPE OF TEST : Cytogenetic analysis TEST SYSTEM : Human Lymphocyte DOSE/DURATION : 28 mg/L REFERENCE : HUTODJ Human Toxicology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants., RG 21 2XS, UK) V.1- 1981- Volume(issue)/page/year: 3,173,1984 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,153,1990 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,153,1990 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,153,1990 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.1 mg/m3 JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81707 No. of Facilities: 1320 (estimated) No. of Industries: 2 No. of Occupations: 4 No. of Employees: 2942 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81707 No. of Facilities: 1250 (estimated) No. of Industries: 2 No. of Occupations: 13 No. of Employees: 42346 (estimated) No. of Female Employees: 32858 (estimated)

安全

• 符号: GHS07, GHS08
• 信号词: Danger
• 危害声明: H315-H317-H319-H334-H335
• 警示性声明: P261-P280-P284-P304 + P340-P305 + P351 + P338-P342 + P311
• 个人防护装备: dust mask type N95 (US);Eyeshields;Faceshields;Gloves
• 危害码 (欧洲): Xn:Harmful
• 风险声明 (欧洲): R36/37/38;R42/43
• 安全声明 (欧洲): S22-S26-S36/37
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: XH8425000
• 包装等级: I; II; III
• 海关编码: 2941109200

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制备

先将D（-）-苯甘氨酸的侧链羧酸用氯化剂PCI5。做成酰氯，再与6-APA进行缩合反应而得。在反应罐中加入丙酮和水，降温到-5－-10℃时加入6-APA，再加盐酸苯甘氨酰氯，反应0.5h后用10%氢氧化钠调节pH至3.5。反应物用甲苯萃取。取水层，用10%氨水调节pH值约3.0。用活性炭脱色，并过滤。滤液再用氨水调节使pH为4.8。静置，然后过滤，用丙酮洗涤，在40℃以下进行真空干燥得产品。

海关

海关编码	2941109200