每周分子 | Molecule of the Week

Original ACS 美国化学会 ACS美国化学会 2022-07-01

收录于合集 #每周分子 110个

每周分子: 氯霉素

Molecule of the Week: Chloramphenicol

氯霉素是一种历史悠久的抗生素，上世纪40年代末，由Parke–Davis(底特律)、伊利诺伊大学(厄巴纳-香槟分校)和耶鲁大学(纽黑文，CT)的研究人员从土壤细菌委内瑞拉链霉菌中分离出来。它最初被称为chloromycetin。

1949年7月，Parke–Davis研究小组公布了这种化合物的结构，然后这种化合物获得了其通用名——氯霉素; Parke–Davis将chloromycetin作为氯霉素的商品名。该小组同时宣布了氯霉素的实验室合成方法。这是第一个全合成的抗生素。

多年来，氯霉素一直被用于治疗结膜炎、脑膜炎、霍乱和伤寒。它对大肠杆菌、葡萄球菌和沙门氏菌等细菌都有活性。

氯霉素会产生一些严重的副作用，包括再生障碍性贫血、神经毒性和一些癌症。1991年，美国停止使用其口服制剂，因为它与再生障碍性贫血有关。2007年，世界卫生组织将其列为一种可能的人类致癌物。

氯霉素仍在美国和其他国家作为注射剂使用。它是作为水溶性更强的前药氯霉素单琥珀酸盐静脉注射的。静脉注射的剂量比口服的大，因为大部分酯在体内水解之前就被消除了。另一种前药棕榈酸氯霉素是口服的，但像母体化合物一样，它在美国不再被批准使用。

氯霉素信息速览

CAS 登记号	56-75-7
SciFinder命名	Acetamide, 2, 2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-
分子式	C₁₁H₁₂Cl₂N₂O₅
摩尔质量	323.13 g/mol
外观	白色到淡黄色的针状、饼状或粉末
熔点	150.5–151.5 ºC
水溶性	2.5 g/L

氯霉素危害信息

危害等级*：致癌性，类别2
H351 - 疑似致癌

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

Chloramphenicol is a venerable antibiotic that was isolated from the soil bacterium Streptomyces venezuelae in the late 1940s by researchers at Parke–Davis (Detroit), the University of Illinois (Urbana–Champaign), and Yale University (New Haven, CT). It was originally called chloromycetin.

In July 1949, the Parke–Davis team published the structure of the compound, which then was given the generic name chloramphenicol; Parke–Davis adopted Chloromycetin as its trade name. The group simultaneously announced a laboratory synthesis of chloramphenicol. It was the first totally synthetic antibiotic.

Over the years, chloramphenicol has been used to treat conjunctivitis, meningitis, cholera, and typhoid fever. It is active against bacteria such as Escherichia coli, Staphylococcus spp., and Salmonella spp.

Chloramphenicol can produce some serious adverse effects, including aplastic anemia, neurotoxicity, and some cancers. In 1991, the United States discontinued the use of the oral formulation because of its association with aplastic anemia. In 2007, the World Health Organization classified it as a probable human carcinogen.

Chloramphenicol is still being used in the United States and other countries as an injectable. It is administered intravenously as the more water-soluble prodrug chloramphenicol monosuccinate. Intravenous dosages are greater than oral ones because much of the ester is eliminated before the body can hydrolyze it. Another prodrug, chloramphenicol palmitate, is given orally, but like the parent compound, it is no longer approved for use in the United States.

Chloramphenicol fast facts

CAS Reg. No.	56-75-7
SciFinder nomenclature	Acetamide, 2, 2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-
Empirical formula	C₁₁H₁₂Cl₂N₂O₅
Molar mass	323.13 g/mol
Appearance	White to pale yellow needles, plates, or powder
Melting point	150.5–151.5 ºC
Water solubility	2.5 g/L

Chloramphenicol hazard information

Hazard class*：Carcinogenicity, category 2
H351—Suspected of causing cancer

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

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