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 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
[edit]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
[edit]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
[edit]- ^ a b c "Fosenazide". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS). 2 April 2025.
- ^ Elks J, Ganellin CR (2000). Dictionary of Drugs: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-0-412-46630-4.
- ^ a b Yu H, Yang H, Shi E, Tang W (December 2020). "Development and Clinical Application of Phosphorus-Containing Drugs". Medicine in Drug Discovery. 8: 100063. doi:10.1016/j.medidd.2020.100063. PMC 7445155. PMID 32864606.
- ^ Zainkonnikova IV, Val'dman AV, Kozlovskaia MM, Rzhevskaia GF (1980). "[Pharmacological characteristics of the tranquilizing action of hydiphen]". Farmakologiia i Toksikologiia (in Russian). 43 (4): 334–338. PMID 7439361.
- ^ Val'dman AV, Kozlovskaia MM, Zaikonnikova IV, Bravkov MF, Rzhevskaia GF (March 1980). "[Effect of gidifen on behavior and hemodynamic signs of an emotionally stressful reaction]". Biulleten' Eksperimental'noi Biologii I Meditsiny (in Russian). 89 (3): 310–312. 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).
- ^ Kazan National Research Technological University, Sayfutdinova M, Shatalova N, Ivanova S, Gavrilova E, Kazan National Research Technological University (2025). "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. doi:10.55421/1998-7072_2025_28_1_45.
- ^ Kokuev AO, Sukhorukov AY (13 April 2023). "Michael addition of P-nucleophiles to azoalkenes provides simple access to phosphine oxides bearing an alkylhydrazone moiety". Frontiers in Chemistry. 11: 1177680. Bibcode:2023FrCh...1177680K. doi:10.3389/fchem.2023.1177680. PMC 10133514. PMID 37123875.
