每周分子 | Molecule of the Week
每周分子 | Molecule of the Week
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每周分子： 碘苷
Molecule of the Week: Idoxuridine
碘苷是脱氧尿苷和胸苷的碘化类似物。 1958 年，耶鲁大学 ( 纽黑文，康涅狄格州 ) 的 William H. Prusoff 首次合成了它。五年后，碘苷成为美国食品药品监督管理局批准的第一个抗病毒药物，用于局部治疗单纯疱疹性角膜炎 。
碘苷的溶液或软膏也被用于眼科。它不能内服，因为会引起心脏毒性 。
如果说碘苷是最古老的抗病毒药物，那什么是最新的抗病毒药物呢 ? lufotrelvir 1 就是其中的一款候选药物 ，这是辉瑞全球研发和其他机构的多个实验室研究人员于 2020 年公开的一种化合物。 Lufotrelvir 是一款治疗 COVID-19 的潜在药物，但与其他药物不同的是，它必须通过静脉注射。 Lufotrelvir 相对不太稳定，今年二月份，辉瑞公司的 Robert A. Singer 及其同事报道了它的改进合成方法 。
1. CAS 登记号：2468015-78-1
碘苷信息速览
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CAS 登记号 |
54-42-2 |
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CAS SciFinder命名 |
Uridine, 2′-deoxy-5-iodo- |
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分子式 |
C 9 H 11 IN 2 O 5 |
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摩尔质量 |
354.10 g/mol |
|
外观 |
白色晶体或粉末 |
|
熔点 |
170 - 263 °C |
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水溶性 |
2 g/L |
碘苷危害信息
GHS分类：急性毒性，口服，分类4 |
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H302-吞食有害 |
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GHS分类：急性毒性，皮肤，分类4 |
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H312-与皮肤接触有害 |
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GHS分类：皮肤腐蚀/刺激，分类2 |
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H315-引起皮肤刺激 |
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GHS分类：严重的眼损伤/眼刺激，分类2A |
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H319-引起严重的眼刺激 |
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GHS分类：急性毒性，吸入，分类4 |
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H332-吸入有害 |
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GHS分类：特定靶器官毒性，单次暴露，呼吸道刺激，分类3 |
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H335-可能引起呼吸道刺激 |
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GHS分类：生殖细胞诱变，分类2 |
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H341-疑似导致基因缺陷 |
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GHS分类：生殖毒性，分类2 |
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H361-疑会损害生育能力或胎儿 |
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【 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CAS SciFinder n 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 。
Idoxuridine is an iodinated analogue of the nucleosides deoxyuridine and thymidine. It was first synthesized by William H. Prusoff at Yale University (New Haven, CT) in 1958. Five years later, it became the first antiviral drug approved by the US Food and Drug admin126459646istration , for topical use against herpes simplex keratitis .
Idoxuridine in solution or ointment form also has ophthalmic applications. It cannot be admin126459646istered internally because it is cardiotoxic.
If idoxuridine is the oldest antiviral, what is the newest? One candidate is lufotrelvir 1 , a compound disclosed in 2020 by researchers at multiple laboratories of Pfizer Worldwide Research and Development and other institutions. Lufotrelvir is a potential treatment for COVID-19 , although, unlike some others, it must be admin126459646istered intravenously. This month, Robert A. Singer and co-workers at Pfizer (Groton, CT) reported an improved synthesis of the relatively unstable lufotrelvir .
1. CAS Reg. No. 2468015-78-1
Idoxuridine fast facts
|
CAS Reg. No. |
54-42-2 |
|
SciFinder nomenclature |
Uridine, 2′-deoxy-5-iodo- |
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Empirical formula |
C 9 H 11 IN 2 O 5 |
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Molar mass |
354.10 g/mol |
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Appearance |
White crystals or powder |
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Melting point |
Values reported from 170 to 263 °C |
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Water solubility |
2 g/L |
Idoxuridine hazard information
Acute toxicity, oral, category 4 |
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H302-Harmful if swallowed |
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Acute toxicity, dermal, category 4 |
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H312-Harmful in contact with skin |
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Skin corrosion/irritation, category 2 |
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H315-Causes skin irritation |
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Serious eye damage/eye irritation, category 2A |
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H319-Causes serious eye irritation |
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Acute toxicity, inhalation, category 4 |
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H332-Harmful if inhaled |
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Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 |
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H341-May cause respiratory irritation |
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Germ cell mutagenicity, category 2 |
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H341-Suspected of causing genetic defects |
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Reproductive toxicity, category 2 |
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H361-Suspected of damaging fertility or the unborn child |
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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 CAS SciFinder n . Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org .
每周分子Molecule of the Week ：苯甲腈
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