sodium cephalothin | 58-71-9

• 物质功能分类: 原料药 - 抗生素类药物 - 头孢菌素类药
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: sodium cephalothin
• 英文别名: cephalothin sodium；cephalothin sodium salt；sodium;N-[(6R,7R)-3-(acetyloxymethyl)-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]-2-thiophen-2-ylethanimidate
• CAS: 58-71-9
• 化学式: C₁₆H₁₅N₂O₆S₂*Na
• 分子量: 418.427
• InChiKey: VUFGUVLLDPOSBC-XRZFDKQNSA-M

物化性质

• 熔点：
  240°C
• 比旋光度：
  D +135° (c = 1.0 in water)
• 溶解度：
  H2O：50 mg/mL，清澈，淡黄色
• 碰撞截面：
  183.1 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  -3.74
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  169
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S36/37
• 危险类别码：
  R42/43
• WGK Germany：
  2
• 海关编码：
  3003201900
• 危险品运输编号：
  NONH for all modes of transport
• RTECS号：
  XI0388300
• 储存条件：
  本品应密封存放于4℃、干燥且避光的环境中。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Cefalotin sodium salt
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H334: May cause allergy or asthma symptoms or breathing difficulties if inhaled
H317: May cause an allergic skin reaction
P285: In case of inadequate ventilation wear respiratory protection
P280: Wear protective gloves/protective clothing/eye protection/face protection
P342+P311: If experiencing respiratory symptoms: Call a POISON CENTER or doctor/physician
P363: Wash contaminated clothing before reuse
P304+P341: IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position
comfortable for breathing

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Section 3. Composition/information on ingredients.
Ingredient name: Cefalotin sodium salt
CAS number: 58-71-9

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C16H15N2O6S2.Na
Molecular weight: 418.4

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

头孢噻吩钠简介

头孢噻吩钠，又称噻孢霉素，是第一代头孢菌素类抗生素。主要用于治疗金黄色葡萄球菌和链球菌感染，也适用于革兰阴性菌引起的尿路感染。由于其对金黄色葡萄球菌有较强的抗菌活性，并且对青霉素酶稳定，因此常被用作抗葡萄球菌感染的药物，特别是用于治疗由金黄色葡萄球菌引发的菌血症和心内膜炎。此外，在溶血性链球菌和肺炎球菌感染时，也可替代青霉素使用，但其疗效较青霉素略差且价格较高。

药理作用

头孢噻吩钠对革兰阳性菌具有强大的抗菌活性，特别是对于青霉素敏感和耐药的金黄色葡萄球菌（除了耐甲氧西林金黄色葡萄球菌），其效果优于第二代和第三代头孢菌素。然而，它对革兰阴性杆菌产生的β-内酰胺酶不稳定，在治疗革兰阴性菌时效果不如第二代和第三代头孢菌素。具体而言：

1. 该药物对产青霉素酶和不产青霉素酶的金黄色葡萄球菌、化脓性链球菌、肺炎链球菌、B组溶血性链球菌、草绿色链球菌、表皮葡萄球菌、白喉杆菌及炭疽杆菌高度敏感，其最低抑菌浓度（MIC）为0.06～1μg/ml。
2. 对革兰阴性菌的作用较差，仅对流感杆菌、脑膜炎球菌、卡他莫拉菌和淋球菌高度敏感，而大肠杆菌、克雷白菌属、沙门菌属、志贺菌属、奇异变形杆菌中度敏感。其余多数革兰阴性杆菌对该药物耐药。

适应症

头孢噻吩钠主要用于治疗由耐青霉素G菌株引起的感染，包括泌尿系感染、心肌内膜炎、脑膜炎、前列腺炎、胆道感染及猩红热等。

不良反应

头孢噻吩钠可能出现以下不良反应：

1. 皮疹、嗜酸粒细胞增多、药物热和血清病样反应。
2. 胃肠道不适，如恶心和呕吐；罕见情况下可能导致由艰难梭菌引发的血栓性静脉炎。
3. 局部注射疼痛。
4. 静脉滴注后血栓性静脉炎发生率较高。
5. 用药剂量超过6g时，可能发生血栓性静脉炎，通常在用药后3天内出现。
6. 肾功能减退患者使用大剂量药物时可能出现惊厥现象。
7. 其他不良反应包括局部疼痛和注射部位炎症。

化学性质

头孢噻吩（碱）熔点为160-160.5℃，而其钠盐为白色结晶性粉末，易溶于水且微溶于乙醇，不溶于氯仿或乙醚。水溶液在低温条件下较为稳定，几乎无臭。

用途

头孢噻吩钠是一种广谱繁殖期杀菌型抗生素，用于治疗由耐青霉素G的细菌引起的感染，如呼吸系统、胆道、泌尿道感染、金黄色葡萄球菌性脑膜炎、心内膜炎、败血症、扁桃体炎、骨髓炎和猩红热等。

生产方法

以发酵生产的头孢菌素C为原料，经保护性水解得到7-氨基头孢烷酸（7-ACA），然后与噻吩乙酰氯缩合。所得产物通过乙酸丁酯提取，并采用活性炭进行脱色处理。最后加入甲醇醋酸钠成盐结晶而获得头孢噻吩钠。

类别和安全性 性质

• 头孢噻吩钠属于有毒物品，但其毒性较低。

毒性分级

• 口服大鼠LD50: >10000毫克/公斤；口服小鼠LD50: > 10000毫克/公斤。

火灾危险特性

• 头孢噻吩钠可燃，在火场会释放氮氧化物、硫氧化物和氧化钠的辛辣刺激烟雾。

储运条件

• 库房应低温通风，保持干燥。

灭火方法

• 可用水、二氧化碳或干粉灭火器进行扑救。沙土也可作为辅助手段。

反应信息

• 作为反应物：
  描述：

  sodium cephalothin 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 0.04h， 以80%的产率得到(6R-反式)-3-(羟基甲基)-8-氧代-7-(2-噻吩基乙酰氨基)-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-羧酸
  参考文献：
  名称：

  用于 ADEPT 方法的头孢烯衍生物的合成和总 1H-和 13C-NMR 归属

  摘要：

  我们报告了 5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxy-3-[[[(4''-nitrophenoxy)carbonyl]oxy]-[[[(4''-nitrophenoxy)carbonyl]oxy]-的合成和总核磁共振表征甲基]-8-oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethylester-5-dioxide (5)，一种新的头孢菌素衍生物。该化合物可用作多种含有氨基的药物的载体。中间产物5-硫杂-1-氮杂双环[4.2.0]oct-2-烯-2-羧酸-3-[4-(6-甲氧基喹啉-8-基氨基)戊基氨基甲酸甲酯]-8-的制备oxo-7-[(2-thienyloxoacetyl)amino]-diphenylmethylester-5-dioxide (6)，以及抗疟伯氨喹前药 5-thia-1-azabicyclo[4

  DOI：

  10.3390/molecules13040841
• 作为产物：
  描述：

  头孢噻吩 在 sodium 2-ethylhexanoic acid 作用下， 以 丙酮 为溶剂， 以26%的产率得到sodium cephalothin
  参考文献：
  名称：

  Synthesis of 3-functionalised cephalosporins by photoinitiated bromination

  摘要：

  DOI：

  10.1016/s0040-4020(01)88547-1

文献信息

• [EN] ISOTHIAZOLOQUINOLONES AND RELATED COMPOUNDS AS ANTI-INFECTIVE AGENTS<br/>[FR] ANTI-INFECTIEUX A BASE D'ISOTHIAZOLOQUINOLONES ET DE SELS CORRESPONDANTS
  申请人：ACHILLION PHARMACEUTICALS INC

  公开号：WO2005019228A1

  公开（公告）日：2005-03-03

  The invention provides compounds and salts of Formula (I) and Formula (II): which possess antimicrobial activity. The invention also provides novel synthetic intermediates useful in making compounds of Formula (I) and Formula (II). The variables A1, R2, R3, R5, R6, R7, A8 and R9 are defined herein. Certain compounds of Formula (I) and Formula (II) disclosed herein are potent and selective inhibitors of bacterial DNA synthesis and bacterial replication. The invention also provides antimicrobial compositions, including pharmaceutical compositions, containing one or more compounds of Formula (I) or Formula (II) and one or more carriers, excipients, or diluents. Such compositions may contain a compound of Formula (I) or Formula (II) as the only active agent or may contain a combination of a compound of Formula (I) or Formula (II) and one or more other active agents. The invention also provides methods for treating microbial infections in animals.

  本发明提供了具有抗菌活性的公式(I)和公式(II)的化合物及盐类：本发明还提供了用于制造公式(I)和公式(II)化合物的新的合成中间体。变量A1、R2、R3、R5、R6、R7、A8和R9在此文中定义。本文披露的某些公式(I)和公式(II)化合物是细菌DNA合成和细菌复制的强效和选择性抑制剂。本发明还提供了含有一种或多种公式(I)或公式(II)化合物以及一种或多种载体、辅料或稀释剂的抗菌组合物，包括药物组合物。这样的组合物可以只含有公式(I)或公式(II)的化合物作为唯一的活性成分，也可以含有公式(I)或公式(II)的化合物与一种或多种其他活性成分的组合。本发明还提供了用于治疗动物微生物感染的方法。
• Beta-lactam antibiotics
  申请人：——

  公开号：US20020115642A1

  公开（公告）日：2002-08-22

  The present invention provides compositions comprising improved beta-lactam antibiotics and methods for applying these compositions to inhibit the growth of microbial infections. The improved antibiotics are capable of inhibiting the growth of both antibiotic sensitive and antibiotic resistant microorganisms In addition, the invention provides methods for treating a subject infected with a microorganism by administering the compositions of the invention.

  本发明提供了包含改进的β-内酰胺类抗生素的组成物，以及将这些组成物应用于抑制微生物感染生长的方法。这些改进的抗生素能够抑制对抗生素敏感和抗生素耐药微生物的生长。此外，本发明还提供了通过施用本发明的组成物来治疗被微生物感染的主体的方法。
• [EN] GOLD COMPOUNDS AND THEIR USE IN THERAPY<br/>[FR] COMPOSÉS D'OR ET LEUR UTILISATION DANS LE CADRE D'UNE THÉRAPIE
  申请人：AUSPHERIX LTD

  公开号：WO2018220171A1

  公开（公告）日：2018-12-06

  Compound of formula (I) and pharmaceutically acceptable salts and solvates thereof are described, wherein: Px selected from (P1), (P2) or (P3); The compounds are useful in the prevention or treatment of a bacterial infection.

  描述了化合物的公式（I）及其药用可接受的盐和溶剂化合物，其中：Px选自（P1）、（P2）或（P3）；这些化合物在预防或治疗细菌感染方面是有用的。
• Cephalosporins
  申请人：Hoffmann-La Roche Inc.

  公开号：US04091211A1

  公开（公告）日：1978-05-23

  Cephalosporins represented by the formula X-S-Y wherein X is a deacetoxycephalosporinyl group and Y is a 6-membered heterocyclic group containing 1-3 nitrogens at least one of which is substituted and at least one of which is adjacent to a carbonyl group, said heterocyclic group containing one or more ring substituents and being characterized by being non-aromatic and not enolizable to an aromatic form.

  头孢菌素的结构式为X-S-Y，其中X是去乙酰头孢菌素基团，Y是含有1-3个氮原子的6元杂环基团，其中至少一个被取代，至少一个邻近一个羰基，所述杂环基团含有一个或多个环取代基，其特点是非芳香性且不能转变为芳香形式。
• [EN] ANTIFUNGAL COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS ANTI-FONGIQUES ET UTILISATIONS ASSOCIÉES
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2017143230A1

  公开（公告）日：2017-08-24

  Provided herein are compounds (e.g., compounds of Formulae (I), (II), and (III)) which are anti-fungal agents and can be used in the treatment of diseases, including infectious diseases. The invention provides methods of treating diseases in a subject (e.g., infectious diseases such as fungal infections), and methods of killing or inhibiting the growth of fungi in or on a subject or biological sample. The compounds may be used in subjects, in clinical settings, or in agricultural settings.

  本发明提供了化合物（例如，公式(I)、(II)和(III)的化合物），这些化合物是抗真菌剂，可用于治疗包括传染性疾病在内的疾病。本发明还提供了在主体（例如，真菌感染等传染性疾病）中治疗疾病的方法，以及杀死或抑制主体或生物样本内或上的真菌生长的方法。这些化合物可用于主体、临床环境或农业环境。