Chemistry:Fosenazide
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| Other names | Gidifen, Fosfabenzid, Hydifen |
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| Formula | C14H15N2O2P |
| Molar mass | 274.260 g·mol−1 |
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Fosenazid (Gidifen, Фозеназид) is a tranquilizer with notable central nicotinic-cholinolytic, antiadrenergic, and antiserotonin effects.[1][2] Fosenazide is currently prescribed only in Russia, where it is used specifically for the treatment of alcohol withdrawal syndrome.[1] Its unique chemical structure and pharmacological profile distinguish it from other neuroactive agents, with strong inhibitory activity against adrenaline and serotonin systems.[1][3]
Fosenazide is an organophosphorus-containing medicine,[3] and contains an acylhydrazine functional group.
Pharmacology
Gidifen has a tranquilizing activity.[4] The drug has an antihypertensive action and reduces tachycardia caused by the emotional stress. It has a selective anti-phobic and anti-aggressive ("serenic/ataractic/psycholeptic") action and does not produce ataxia.[5]
It is patented for psychic and nervous disorders.[6]
Synthesis
The synthesis has been discussed:[7][8] & in a USA patent:[9] Precursor:[10][11] Soviet patents:[12][13][14][15] Swiss patent:[16]
Diphenylphosphinic acid [1707-03-5] (1) is reacted with ethyl chloroacetate (2) in the presence of hexamethyldisilazane and trimethylchlorosilane to give Diphenylphosphinyl acetic acid ethyl ester i.e. ethyl (diphenylphosphoryl)acetate [6361-05-3] (3). Further reaction with hydrazine gives the required Fosenazide (4).
An entirely new synthesis pathway was identified in 2025.[17][18]
References
- ↑ 1.0 1.1 1.2 "Fosenazide". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). 2 April 2025. https://drugs.ncats.io/drug/16C19Z7F4I.
- ↑ Dictionary of Drugs: Chemical Data, Structures and Bibliographies. Springer. 2000. ISBN 978-0-412-46630-4.
- ↑ 3.0 3.1 "Development and Clinical Application of Phosphorus-Containing Drugs". Medicine in Drug Discovery 8. December 2020. doi:10.1016/j.medidd.2020.100063. PMID 32864606.
- ↑ "[Pharmacological characteristics of the tranquilizing action of hydiphen]" (in Russian). Farmakologiia i Toksikologiia 43 (4): 334–338. 1980. PMID 7439361.
- ↑ "[Effect of gidifen on behavior and hemodynamic signs of an emotionally stressful reaction]" (in Russian). Biulleten' Eksperimental'noi Biologii I Meditsiny 89 (3): 310–312. March 1980. PMID 7190040.
- ↑ Grigory Yakovlevitsch Avrutzky, et al. DE2751389 (1979 to KZ G MEDICINSKIJ I IM S V KURA, KZ KHIM TEKH INST KIROVA).
- ↑ Razumov, A.I. et al, Zh. Obshch. Khim., 1967, 37, 421 (Engl. transl. p. 393); 1976,46, 1412 (Engl. transl. p. 1388).
- ↑ Razumov, A.I. et al, Zh. Prikl. Khim. (Leningrad), 1983, 56, 342 (Engl. transl. p. 325).
- ↑ Alexandr I. Razumov, et al. US4162264 (1971).
- ↑ Natalia Alexandrovna Bondarenko, et al. SU1616922 (1990).
- ↑ Natalia Alexandrovna Bondarenko, et al. SU1576535 (1990).
- ↑ , SU362025 (1972).
- ↑ Александр Иванович Разумов, et al. SU741876 (1980 to).
- ↑ , SU404828 (1973).
- ↑ AI Razumov, et al. SU467593 (1991).
- ↑ Alexandr Ivanovich Razumov, et al. CH631182 (1982).
- ↑ "Synthetic Possibility of Using Imidazolium Ionic Liquids, Hydrazides and Esters of Halogenated Carboxylic Acids in the Arbuzov Reaction to Obtain Fosenazide and ITS Hydrochloride". Herald of Technological University 28 (1): 45–49. 2025. doi:10.55421/1998-7072_2025_28_1_45. https://www.elibrary.ru/item.asp?id=80272423.
- ↑ "Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety". Frontiers in Chemistry 11. 13 April 2023. doi:10.3389/fchem.2023.1177680. PMID 37123875. Bibcode: 2023FrCh...1177680K.
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