Chemistry:Quifenadine
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| Trade names | Fencarol |
| Other names | 3-Quinuclidinyldiphenylmethanol |
| Routes of administration | Oral (tablets), IM injection |
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| Pharmacokinetic data | |
| Bioavailability | 45% (Tmax = 1 hour)[1] |
| Metabolism | Liver |
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| Formula | C20H23NO |
| Molar mass | 293.410 g·mol−1 |
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Quifenadine (Russian: хифенадин, trade name: Phencarol, Фенкарол) is a 2nd generation antihistamine drug, marketed mainly in post-Soviet countries.[2][3] Chemically, it is a quinuclidine derivative.
The drug has antiarrhythmic properties, probably due to the presence of a quinuclidine nucleus in the molecule's core. It acts as a calcium channel blocker and influences the activity of potassium channels.[clarification needed] In children with cardiac arrhythmia, combination therapy with quifenadone and either amiodarone or propafenone was found to be more effective than monotherapy with either amiodarone or propafenone.[4]
Quifenadine is a derivative of quinuclidylcarbinol, which reduces the effects of histamine on organs and systems. Quifenadine is a competitive blocker of H1 receptors. In addition, it activates the diamine oxidase enzyme, which breaks down about 30% of endogenous histamine. This explains the effectiveness of quifenadine in patients insensitive to other antihistamines. The antihistaminic qualities of quifenadine are associated with the presence of a cyclic quinuclidine core in the structure and the distance between the diphenylcarbinol group and the nitrogen atom. In terms of antihistaminic activity and duration of action, quifenadine is superior to diphenhydramine. Quifenadine reduces the toxic effect of histamine, eliminates or weakens its bronchoconstrictor effect and spasmodic effect on the smooth muscles of the intestines, has a moderate antiserotonin and weak cholinolytic effect, has well-defined antipruritic and desensitizing properties. Quifenadine weakens the hypotensive effect of histamine and its effect on capillary permeability, does not directly affect cardiac activity and blood pressure, does not have a protective effect in aconitine arrhythmias.[5]
Indications
- Allergic rhinitis
- Acute and chronic urticaria
- Angioedema
- Dermatitis
- Atopic dermatitis
- Pruritus[1]
Synthesis
Same precursor as for mequitazine. Use patent:[6]
The Grignard reaction between methylquinuclidine-3-carboxylate [38206-86-9] (1) and phenylmagnesium bromide (2) gave the benzhydryl alcohol product ~29% yield. The ethyl ester is cas: [6238-33-1]
References
- ↑ 1.0 1.1 "Fencarol (quifenadine) Tablets, for Oral Use. Full Prescribing Information" (in ru). http://grls.rosminzdrav.ru/ImgInstr.aspx?folder=ScanVavilova&Filepath=\Vneseno_v_Grls\442006\IP&idReg=86466&isOld=1&fileType=jpg&pfolder=2.
- ↑ "Quifenadine". https://www.drugs.com/international/quifenadine.html.
- ↑ "The antiarrhythmic properties of quifenadine, H1-histamine receptor blocker in children with premature beats: a randomized controlled pilot trial". American Journal of Therapeutics 17 (4): 396–401. 2010. doi:10.1097/MJT.0b013e3181a86987. PMID 19487925.
- ↑ "Эффективность Фенкарола В Сочетании С Традиционными Противоаритмическими Средствами При Экстрасистолии У Детей" (in ru). RUDN Journal of Medicine (3): 46–51. 2008-09-01. ISSN 2313-0245. http://journals.rudn.ru/medicine/article/view/3654. Retrieved 18 November 2020.
- ↑ "Quifenadine". https://compendium.com.ua/dec/268385/.
- ↑ Mikhail Davydovich Mashkovsky, et al. U.S. Patent 4,117,139 (1978).
- ↑ "Discovery of novel 1-azoniabicyclo[2.2.2]octane muscarinic acetylcholine receptor antagonists". Journal of Medicinal Chemistry 52 (8): 2493–2505. April 2009. doi:10.1021/jm801601v. PMID 19317446.
- ↑ Micail Emmanuilovic Kaminka, DE patent 2502916 (1975 to VSESOJUZNYJ NAUCNO-ISSLEDOVATEL'SKIJ CHIMIKO-FARMACEVTICESKIJ INSTITUT IMENI SERGO ORDZONIKIDZE MOSKAU/MOSKVA SU).
- ↑ , U.S. Patent 2,901,486 (1959).
- ↑ Harry J. Wadsworth, et al. U.S. Patent 5,091,397 (1992 to Beecham Group PLC).
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