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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Fosenazide (Gidifen, Hydifen) is a drug that behaves as a tranquilliser, antiepileptic agent, or anti-tubercular.[1] Gidifen may be a solution to alcoholism,[2] or for other neuropsychiatric disorders.
Fosenazide is an organophosphorus-containing medicine,[3] and includes an acylhydrazine functional grouping. It is prescribed in Russia for the treatment of alcohol withdrawal syndrome.[4]
Pharmacology
[edit]Gidifen has a tranquilizing activity.[5] 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.[6]
It is patented for psychic and nervous disorders.[7]
Synthesis
[edit]The synthesis has been discussed:[8][9] & in a USA patent:[10] Precursor:[11][12] Soviet patents:[13][14][15][16] Swiss patent:[17]
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.[18][19]
References
[edit]- ^ Dictionary of Drugs by J. Elks & C.R. Ganellin.
- ^ R.I. Tarasova, et al. RU2062099 (1995).
- ^ 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.
- ^ "NCATS Inxight Drugs — FOSENAZIDE". drugs.ncats.io. Retrieved 2025-06-14.
- ^ Zainkonnikova IV, Val'dman AV, Kozlovskaia MM, Rzhevskaia GF. Farmakologicheskaia kharakteristika trankviliziruiushchego deistviia gidifena [Pharmacological characteristics of the tranquilizing action of hydiphen]. Farmakol Toksikol. 1980 Jul-Aug;43(4):334-8. Russian. PMID: 7439361.
- ^ Val'dman AV, Kozlovskaia MM, Zaikonnikova IV, Bravkov MF, Rzhevskaia GF. Vliianie gidifena na povedenie i gemodinamicheskie proiavleniia émotsional'no-stressovoĭ reaktsii [Effect of gidifen on behavior and hemodynamic signs of an emotionally stressful reaction]. Biull Eksp Biol Med. 1980 Mar;89(3):310-2. Russian. 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.N.; Shatalova, N.I.; Ivanova, S.Yu.; Gavrilova, E.L.; 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, A. O., Sukhorukov, A. Yu. (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.
