每周分子 | Molecule of the Week

Original ACS美国化学会 ACS美国化学会 2022-07-01

每周分子: ‍呋喃妥因

Molecule of the Week: Nitrofurantoin

呋喃妥因是一种抗菌药物，主要用于治疗泌尿道和膀胱感染。它已经以二十多个商品名出售，包括Macrobid；但现在，大多产品都为仿制药。

1952年，Kenyon J. Hayes在长期停业的伊顿实验室¹（纽约州诺威奇）获得了第一项合成呋喃妥因的美国专利。这种药物于1953年问世。在Benjamin E. Blass于2015年出版的《药物发现与开发基本原理》一书中，因为呋喃妥因的较长市场生命力，而被称为是“一种令人惊讶的成功药物”。

在2018年，爆发了关于呋喃妥因液体制剂成本的争议。只有两家美国公司Nostrum Laboratories（美国密苏里州，堪萨斯城）和Casper Pharma（美国新泽西州东布朗斯维克）在生产该制剂，但是他们都大幅提高了该制剂的价格：Nostrum从现在的每瓶475美元提高到2,393美元每瓶，Casper则提高到2,800美元每瓶。毋庸置疑，一场骚动接踵而至，对医药行业价格改革的要求越来越高，这是美国国会和其他地方非常关注的问题。

呋喃妥因信息速览

CAS登记号	67-20-9
分子式	C₈H₆N₄O₅
摩尔质量	238.16 g/mol
外观	黄色或者橘黄色晶体或者粉末
熔点	≈272 ºC (dec.)
水溶性	80 mg/L

呋喃妥因危害信息

GHS 分类*: 急性毒性，口服，分类4
H302—吞咽有害
GHS 分类: 皮肤致敏，分类1
H317—可能引起过敏性皮肤反应
GHS : 呼吸过敏，分类1
H334—吸入可能导致过敏或哮喘症状或呼吸困难

【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。

Nitrofurantoin is an antibacterial medication used primarily to treat urinary tract and bladder infections. It has been sold under more than two dozen trade names, including Macrobid; but it is now almost always supplied as a generic.

The first US patent on the synthesis of nitrofurantoin was awarded in 1952 to Kenyon J. Hayes at the long-defunct Eaton Laboratories¹ (Norwich, NY). The drug was introduced in 1953. In his 2015 book Basic Principles of Drug Discovery and Development, Benjamin E. Blass called nitrofurantoin “a surprisingly successful drug” because of its market longevity.

In 2018, a controversy erupted over the cost of the liquid formulation of nitrofurantoin. The only two US companies that produce the formulation, Nostrum Laboratories (Kansas City, MO) and Casper Pharma (East Brunswick, NJ), dramatically increased their prices: Nostrum, from the already expensive US$475 per bottle, to $2,393 and Casper to $2,800. Needless to say, an uproar ensued, heightening demands for pharma industry price reforms, an issue of much concern in the US Congress and elsewhere.

1. You can purchase vintage postcards of the Eaton buildings on Amazon and other online sellers.

Nitrofurantoin fast facts

CAS Reg. No.	67-20-9
Empirical formula	C₈H₆N₄O₅
Molar mass	238.16 g/mol
Appearance	Yellow to orange crystals or powder
Melting point	≈272 ºC (dec.)
Water solubility	80 mg/L

Nitrofurantoin hazard information

GHS classification*: acute toxicity, oral, category 4
H302—Harmful if swallowed
GHS classification: skin sensitization, category 1
H317—May cause an allergic skin reaction
GHS classification: respiratory sensitization, category 1
H334—May cause allergy or asthma symptoms or breathing difficulties if inhaled

*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.

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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