What molecule am I?
Digoxin is a secondary glycoside produced by plants in the Digitalis (foxglove) genus that were used for medicinal purposes as long ago as the 18th century. In 1930, Sydney Smith at Burroughs Wellcome (London) .听
The US Food and Drug Administration approved the use of digoxin as a heart-disease medication in the late 1990s. It has been prescribed ever since under trade names such as Lanoxin for atrial fibrillation and heart failure. Digoxin, however, has a ; and drug interactions and adverse side effects are common. It has shown efficacy against some cancers, but other studies indicated that patients on digoxin have an increased risk of developing cancer.
Overdose is often fatal, as shown in the hazard information table. In 2003, a hospital nurse pleaded guilty to killing as many as 40 patients with digoxin and other heart medications.
Digoxin should not be confused with digitoxin1, which has one fewer hydroxyl group and is also a heart medication. For a new wrinkle on digoxin, see Molecule of the Future below.
1. CAS Reg. No. 71-63-6.
Digoxin ether听hazard information
| Hazard class* | GHS code and hazard statement | |
|---|---|---|
| Acute toxicity, oral , category 2 | H300鈥擣atal if swallowed听 |  |
| Acute toxicity, inhalation , category 3 | H331鈥擳oxic if inhaled | |
| Carcinogenicity, category 2 | H351鈥擲uspected of causing cancer |  |
| Specific target organ toxicity, repeated exposure, category 2 | H373鈥擬ay cause damage to organs through prolonged or repeated exposure | |
*Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.
Molecule of the Future
According to Xiang-Guo Hu, Chu-Yi Yu, and colleagues at Jiangxi Normal University (Nanchang, China) and the Chinese Academy of Sciences (Beijing), 鈥淭he modification of carbohydrates with fluorine can profoundly affect molecules鈥� chemical and physical properties such as conformation, lipophilicity, and stability.鈥� In December 2021, they reported the development of a scalable, stereoselective, de novo synthesis听 of C2-fluorinated Digitalis-type oligosaccharides, including digoxin.
The key steps in the authors鈥� synthesis were a Sharpless kinetic resolution and an organocatalytic fluorination of an aldehyde intermediate. The fluorinated digoxin1 was completed in 10 steps after the fluorination reaction.
It turned out that the fluorinated derivative exhibited 鈮�10 times less cytotoxicity toward A549 non鈥搒mall-cell lung cancer cells than original digoxin. This result demonstrated that adding the fluorine atom indeed affected biological activity, which the authors state is worthy of additional research.
1. CAS Reg. No. 2769846-71-9.
Molecule of the Future
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Digoxin fast facts
| CAS Reg. No. | 20830-75-5 |
nomenclature | Card-20(22)-enolide, 3-[(O-2,6-诲颈诲别辞虫测-尾-D-ribo-丑别虫辞辫测谤补苍辞蝉测濒-(1鈫�4)-O-2,6-诲颈诲别辞虫测-尾-D-ribo-丑别虫辞辫测谤补苍辞蝉测濒-(1鈫�4)-2,6-诲颈诲别辞虫测-尾-D-ribo-hexopyranosyl) oxy]-12,14-dihydroxy-, (3尾,5尾,12尾)- |
| Empirical formula | C41H64O14 |
| Molar mass | 780.94 g/mol |
| Appearance | White crystals or powder |
| Melting point | 230鈥�265 掳C (dec.) |
| Water solubility | 65 mg/L |
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