氨苄西林

氨苄西林用途

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。

氨苄西林作用

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。

氨苄西林名称

[ CAS 号 ]:
69-53-4

[ 中文名 ]:
氨苄西林

[ 英文名 ]:
Ampicillin

[中文别名 ]:

[英文别名 ]:

amfipen
qidamp
ay-6108
binotal
Wymox
Unasyn
MFCD00072036
p-50
ab-pc
EINECS 200-709-7

氨苄西林生物活性

[ 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.

[相关活性小分子]

氨苄西林物理化学性质

[ 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 ]:
库房通风低温干燥

[ 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

氨苄西林毒性和生态

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)

氨苄西林安全信息

[ 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

氨苄西林合成路线

详细合成路线

氨苄西林上下游产品

氨苄西林上游产品

氨苄西林下游产品

氨苄西林制备

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。

氨苄西林海关

[ 海关编码 ]: 2941109200

氨苄西林文献

Fine mapping and characterization of the L-polymerase-binding domain of the respiratory syncytial virus phosphoprotein.

J. Virol. 89(8) , 4421-33, (2015)

The minimum requirement for an active RNA-dependent RNA polymerase of respiratory syncytial virus (RSV) is a complex made of two viral proteins, the polymerase large protein (L) and the phosphoprotein...

BBS4 directly affects proliferation and differentiation of adipocytes.

Cell. Mol. Life Sci. 71(17) , 3381-92, (2014)

BBS4 is one of several proteins whose defects cause Bardet-Biedl syndrome (BBS), a multi-systemic disorder, manifesting with marked obesity. BBS4 polymorphisms have been associated with common non-syn...

An HD-domain phosphodiesterase mediates cooperative hydrolysis of c-di-AMP to affect bacterial growth and virulence.

Proc. Natl. Acad. Sci. U. S. A. 112(7) , E747-56, (2015)

The nucleotide cyclic di-3',5'- adenosine monophosphate (c-di-AMP) was recently identified as an essential and widespread second messenger in bacterial signaling. Among c-di-AMP-producing bacteria, al...

更多文献

氨苄西林相关知识

【氨苄西林】-说明书-作用-氨苄西林胶囊副作用

2018-12-25 17:23:42

导读：氨苄西林（Ampicillin-Xincat），商品名伊西德胶囊。感冒继发感染，支气感炎，肺炎等胆囊及胆道感染，急性胃肠炎、细菌性痢疾、伤寒及副伤寒淋病、非淋病性尿路感染等蜂窝组织炎、皮肤溃疡感染等败血症、脑膜炎、心内膜炎、腹膜及腹腔内感染、白喉、百日咳等。本药品被归类到胰腺炎等药品...