ampicillin sodium | 69-52-3

• 物质功能分类: 原料药 - 抗生素类药物 - 青霉素类药
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: ampicillin sodium
• 英文别名: sodium ampicillin；Sodium [2S-(2α,5α,6β(S*))]-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate；ampicillin sodium salt；Ampicillin, Na-Salz；sodium;2-amino-N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl)-2-phenylethanimidate
• CAS: 69-52-3
• 化学式: C₁₆H₁₈N₃O₄S*Na
• 分子量: 371.392
• InChiKey: KLOHDWPABZXLGI-UHFFFAOYSA-M

物化性质

• 熔点：
  215 °C (dec.)(lit.)
• 比旋光度：
  +246～+272°
• 溶解度：
  在水中的溶解度50 mg/mL，澄清，非常淡黄色

计算性质

• 辛醇/水分配系数(LogP)：
  -4.01
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S22,S26,S36,S36/37,S45
• 危险类别码：
  R42/43
• WGK Germany：
  2
• 海关编码：
  2941101900
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  XH8400000
• 危险标志：
  GHS08
• 危险性描述：
  H317,H334
• 危险性防范说明：
  P261,P280,P342 + P311
• 储存条件：
  本品应密封在4℃干燥处保存，有效期为2年半。

SDS

Name:	Ampicillin Sodium Salt Material Safety Data Sheet
Synonym:	Alpen-N; Amcill-S; D-Alpha-aminobenxylpenicillin sodium salt; Ampicillin sodium sal
CAS:	69-52-3

Section 1 - Chemical Product MSDS Name:Ampicillin Sodium Salt Material Safety Data Sheet
Synonym:Alpen-N; Amcill-S; D-Alpha-aminobenxylpenicillin sodium salt; Ampicillin sodium sal

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
69-52-3	Ampicillin Sodium	100	200-708-1

Hazard Symbols: XN
Risk Phrases: 36/37/38 42/43

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin. May cause sensitization by inhalation and skin contact.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material.
May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May cause allergic respiratory reaction. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with skin and eyes. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 69-52-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white to off-white
Odor: none reported
pH: 8.0-10.0 @ 1% solu.
Vapor Pressure: Not applicable.
Viscosity: Not applicable.
Boiling Point: Not available.
Freezing/Melting Point: 419 deg F
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Very soluble in water.
Specific Gravity/Density: Not available.
Molecular Formula: C16H18N3O4SNa
Molecular Weight: 371.1935

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
High temperatures, incompatible materials, dust generation, moisture.
Incompatibilities with Other Materials:
Strong oxidizers.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 69-52-3: XH8400000 LD50/LC50:
CAS# 69-52-3: Oral, mouse: LD50 = >5314 mg/kg; Oral, rat: LD50 = >5314 mg/kg.
Carcinogenicity:
Ampicillin Sodium - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
R 42/43 May cause sensitization by inhalation and
skin contact.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 69-52-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 69-52-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 69-52-3 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

广谱青霉素——氨苄西林钠

氨苄西林钠是一种广谱青霉素，其抗菌谱较青霉素更广。它对部分革兰阴性杆菌（如流感嗜血杆菌、大肠埃希菌、奇异变形杆菌）也具有抗菌活性，并且与青霉素一样对抗革兰阳性球菌有效。不过，氨苄西林钠也可被细菌产生的青霉素酶水解失活。

临床上主要用于治疗敏感细菌引起的呼吸道感染、尿路感染、胃肠道感染、皮肤软组织感染、脑膜炎、败血症及心内膜炎等疾病，并且是肠球菌感染的首选药物。

化学性质

氨苄西林钠为白色或类白色的粉末或结晶。易溶于水，略溶于乙醇，不溶于乙醚。具有吸湿性，在室温下逐渐变黄并产生混浊，效价随之下降。无臭味微苦。

用途

氨苄西林钠属半合成的广谱青霉素，主要用于治疗对青霉素敏感的革兰氏阳性球菌、大肠杆菌、变形杆菌、沙门氏菌及痢疾杆菌等所致感染。

生产方法

通过氨苄青霉素成盐制备而成：将氨苄青霉素混悬于水中，用氢氧化钠溶液调节pH值至9后溶解并过滤。滤液经过活性炭脱色与低温干燥处理后即可得到产品。

类别

有毒物品

毒性分级

低毒

急性毒性

• 大鼠口服LD₅₀：＞5314毫克/公斤
• 小鼠口服LD₅₀：＞5314毫克/公斤

可燃性危险特性

燃烧时产生有毒的氧化钠、氮氧化物和硫氧化物气体。

储运特性

应保存于通风干燥的地方，并避免高温。

反应信息

• 作为反应物：
  描述：

  ampicillin sodium 、 乙酰乙酸乙酯 以 异丙醇 为溶剂， 反应 3.0h， 以75%的产率得到N-(1-methyl-2-ethoxycarbonylvinyl)ampicillin sodium
  参考文献：
  名称：

  兔体内氨基酸样β-内酰胺类抗生素烯胺前药的口服和直肠给药生物药物研究。

  摘要：

  氨苄西林、阿莫西林和头孢氨苄的烯胺衍生物是在温和条件下与乙酰乙酸乙酯反应制备的。通过测量核磁共振（NMR）光谱，确定了这些化合物的烯胺结构。这些化合物在体外水溶液中很容易水解，随着 pH 值的降低，水解速度加快。烯胺衍生物的 Rf 和迁移率的测定结果表明，烯胺衍生物比相应的母药更亲脂。对兔子口服和直肠给药后这些原药的生物利用度进行了研究。口服相应的烯胺原药后，母体抗生素的生物利用度并没有提高。然而，直肠给药相应的烯胺原药后，氨苄西林和阿莫西林的生物利用度明显提高。兔子口服后，生物利用度的提高超过了母药的生物利用度。研究发现，氨苄西林的烯胺原药可促进氨苄西林直肠吸收。因此，氨基酸类 β-内酰胺抗生素的烯胺衍生物似乎是临床上可能用作直肠给药原药的有趣候选药物。

  DOI：

  10.1248/cpb.29.1986
• 作为产物：
  描述：

  N-(1-methyl-2-ethoxycarbonylvinyl)ampicillin sodium 在 水 作用下， 生成 ampicillin sodium
  参考文献：
  名称：

  兔体内氨基酸样β-内酰胺类抗生素烯胺前药的口服和直肠给药生物药物研究。

  摘要：

  氨苄西林、阿莫西林和头孢氨苄的烯胺衍生物是在温和条件下与乙酰乙酸乙酯反应制备的。通过测量核磁共振（NMR）光谱，确定了这些化合物的烯胺结构。这些化合物在体外水溶液中很容易水解，随着 pH 值的降低，水解速度加快。烯胺衍生物的 Rf 和迁移率的测定结果表明，烯胺衍生物比相应的母药更亲脂。对兔子口服和直肠给药后这些原药的生物利用度进行了研究。口服相应的烯胺原药后，母体抗生素的生物利用度并没有提高。然而，直肠给药相应的烯胺原药后，氨苄西林和阿莫西林的生物利用度明显提高。兔子口服后，生物利用度的提高超过了母药的生物利用度。研究发现，氨苄西林的烯胺原药可促进氨苄西林直肠吸收。因此，氨基酸类 β-内酰胺抗生素的烯胺衍生物似乎是临床上可能用作直肠给药原药的有趣候选药物。

  DOI：

  10.1248/cpb.29.1986

文献信息

• SZYMANSKI, J.;ZUKOWSKI, E.;LEWANDOWSKI, J.;DZIEGIELEWSKI, K.;BUJNOWSKA, E+
  作者：SZYMANSKI, J.、ZUKOWSKI, E.、LEWANDOWSKI, J.、DZIEGIELEWSKI, K.、BUJNOWSKA, E+

  DOI：——

  日期：——
• BADAWI, A. M.;SELIEM, VIOLET R.;HAROUN, B.;SOLIMAN, H., ORIENT. J. CHEM., 4,(1988) N 2, 107-118
  作者：BADAWI, A. M.、SELIEM, VIOLET R.、HAROUN, B.、SOLIMAN, H.

  DOI：——

  日期：——
• Biopharmaceutical study on the oral and rectal administrations of enamine prodrugs of amino acid-like .BETA.-lactam antibiotics in rabbits.
  作者：TERUO MURAKAMI、HIROMU TAMAUCHI、MASARU YAMAZAKI、KAZUYOSHI KUBO、AKIRA KAMADA、NOBORU YATA

  DOI：10.1248/cpb.29.1986

  日期：——

  Enamine derivatives of ampicillin, amoxicillin and cephalexin were prepared by reacting the drugs with ethyl acetoacetate under mild conditions. The enamine structures of these compounds were determined by measurements of the nuclear magnetic resonance (NMR) spectra. The compounds were easily hydrolyzed in vitro in aqueous solution and the rate accelerated as the pH was lowered. The determination of Rf and rate of migration of the enamine derivatives showed that the enamine derivatives were more lipophilic than the corresponding parent drugs. The bioavailabilities of these prodrugs were studied following oral and rectal administrations in rabbits. The bioavailabilities of the parent antibiotics were not improved by the oral administration of the corresponding enamine prodrugs. However, the bioavailabilities of ampicillin and amoxicillin were markedly improved by rectal administration of the corresponding enamine prodrugs. The improved bioavailabilities exceeded those of the parent drugs following oral administration in rabbits. The enamine prodrug of ampicillin was found to promote the rectal absorption of ampicillin upon coadministration of these two drugs. Thus, enamine derivatives of amino acid-like β-lactam antibiotics appear to be interesting candidates for possible clinical use as prodrugs for rectal administration.

  氨苄西林、阿莫西林和头孢氨苄的烯胺衍生物是在温和条件下与乙酰乙酸乙酯反应制备的。通过测量核磁共振（NMR）光谱，确定了这些化合物的烯胺结构。这些化合物在体外水溶液中很容易水解，随着 pH 值的降低，水解速度加快。烯胺衍生物的 Rf 和迁移率的测定结果表明，烯胺衍生物比相应的母药更亲脂。对兔子口服和直肠给药后这些原药的生物利用度进行了研究。口服相应的烯胺原药后，母体抗生素的生物利用度并没有提高。然而，直肠给药相应的烯胺原药后，氨苄西林和阿莫西林的生物利用度明显提高。兔子口服后，生物利用度的提高超过了母药的生物利用度。研究发现，氨苄西林的烯胺原药可促进氨苄西林直肠吸收。因此，氨基酸类 β-内酰胺抗生素的烯胺衍生物似乎是临床上可能用作直肠给药原药的有趣候选药物。