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：地塞米松

Molecule of the Week: Dexamethasone

地塞米松是一种久负盛名的皮质类固醇药物，用于治疗多种疾病。维基百科认为是梅奥诊所(Mayo Clinic, Rochester, MN明尼苏达州罗彻斯特)的Philip S. Hench医生及其同事们于1957年首次制备了这种药物；但是没有引用同行评议的参考文献。(Hench因发现可的松而成为1950年诺贝尔生理学或医学奖的共同获奖者。)

第二年，默克公司(Merck)的Glen E. Arth及其同事们报道了地塞米松的合成，这是他们研究新的甾体抗炎药的一部分。一个月后，Eugene P. Oliveto和来自Schering (Bloomfield, NJ)及马萨诸塞州综合医院(波士顿)的共同作者们发表了一篇不同的有关地塞米松合成的论文。1961年，另外两家制药公司获得了地塞米松合成的专利权。

地塞米松已被用于治疗过敏、脑肿胀、肺结核、自身免疫性疾病和几种肺部疾病。它的通用性促使世界卫生组织将其列入基本药物标准清单。但是地塞米松有许多副作用，包括引起痤疮、眩晕等。

地塞米松的多种医学用途促使研究人员将其用于COVID-19患者，这或许并不令人惊讶。在英国一项名为“康复(COVID-19治疗的随机评估)”的研究中，超过1.1万名重症患者接受了几种治疗方法中的一种，包括口服或注射地塞米松。在接受地塞米松治疗的约2100名患者中，使用呼吸机的患者的死亡人数比对照组少三分之一。那些需要氧气而不需要呼吸机的患者的死亡率降低了20%。

截至2020年6月22日，这项研究的结果还没有经过同行评议。

地塞米松信息速览

CAS登记号	50-02-2
SciFinder命名	Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11β,16α)-
分子式	C₂₂H₂₉FO₅
摩尔质量	392.46 g/mol
外观	白色或者灰白色粉末
沸点	262–264 ºC
水溶性	89 g/L

地塞米松危害信息

危险等级*：生殖毒性，分类1B
H360DF-可能损害胎儿; 怀疑破坏生育能力

【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。

Dexamethasone is a venerable corticosteroid medication that has been used against a wide range of diseases and conditions. Wikipedia credits the first preparation of the drug in 1957 to physician Philip S. Hench and co-workers at the Mayo Clinic (Rochester, MN); but no peer-reviewed references are cited. (Hench was a co-winner of the 1950 Nobel Prize for Physiology or Medicine for the discovery of cortisone.)

The following year, Glen E. Arth and colleagues at Merck (Rahway, NJ) reported the synthesis of dexamethasone as part of their search for new steroidal anti-inflammatory medicines. One month later, Eugene P. Oliveto and coauthors at Schering (Bloomfield, NJ) and Massachusetts General Hospital (Boston) published a different synthesis. Patents describing dexamethasone syntheses were awarded to two other drug companies in 1961.

Dexamethasone has been used to treat allergies, brain swelling, tuberculosis, autoimmune conditions, and several lung diseases. Its versatility prompted the World Health Organization to include it in its Model List of Essential Medicines. But dexamethasone has many adverse side effects that range from acne to vertigo.

Perhaps it is not surprising that the variety of dexamethasone’s medical uses has led researchers to administer it to COVID-19 patients. In a British study called RECOVERY (for Randomised Evaluation of COVID-19 Therapy), more than 11,000 patients with serious cases of the disease were given one of several treatments, including oral or injected dexamethasone. Of the approximately 2100 subjects given dexamethasone, the patients on ventilators had one-third fewer deaths compared with control subjects. Those who required oxygen without a ventilator had about 20% fewer deaths.

It should be noted that as of June 22, 2020, the study’s results had not been peer-reviewed.

Dexamethasone fast facts

CAS Reg. No.	50-02-2
SciFinder nomenclature	Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17,21-trihydroxy-16-methyl-, (11β,16α)-
Empirical formula	C₂₂H₂₉FO₅
Molar mass	392.46 g/mol
Appearance	White to off-white crystalline powder
Boiling point	262–264 ºC
Water solubility	89 g/L

Dexamethasone hazard information

Hazard class: Reproductive toxicity, category 1B
H360DF-May damage the unborn child; suspected of damaging fertility

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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