Chemistry:Amezinium metilsulfate
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| Routes of administration | Oral |
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| Formula | C12H15N3O5S |
| Molar mass | 313.33 g·mol−1 |
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Amezinium metilsulfate (INN, sold under the brand name Regulton, is a sympathomimetic drug which is widely used in the treatment of orthostatic hypotension in Japan.[1][2][3][4]
Pharmacology
Pharmacodynamics
Amezinium metilsulfate has a unique mechanism of action of acting as a dual monoamine oxidase inhibitor (MAOI) and norepinephrine reuptake inhibitor (NRI).[3][2][4]
Chemistry
Synthesis
This drug is made from 2-butyne-1,4-diol starting material with chloridazon (de) as an intermediate.
The halogenation of 2-butyne-1,4-diol (1) with chlorine gives mucochloric acid (2). Treatment with phenylhydrazine (3) gives 1-phenyl-4,5-dichloro-6-pyridazone (4). Addition of ammonia leads to chloridazon (5). Catalytic hydrogenation yields 5-amino-2-phenylpyridazin-3-one (6). Alkylation with dimethyl sulfate completes the synthesis of amezinium metisulfate (7).
See also
- List of investigational orthostatic intolerance drugs
References
- ↑ "Delving into the Latest Updates on Amezinium Metilsulfate with Synapse". 28 October 2025. https://synapse.patsnap.com/drug/1f67adced076461b9913840f13aeb092.
- ↑ 2.0 2.1 "From depression to neurodegeneration and heart failure: re-examining the potential of MAO inhibitors". Expert Rev Clin Pharmacol 5 (4): 413–425. July 2012. doi:10.1586/ecp.12.29. PMID 22943121. "Amezinium metilsulfate (risumic, supratonin, amezinin and ryzmilate) is an indirectly acting sympathomimetic drug available in Japan, which reversibly inhibits intraneuronal MAO-A and MAO-B, as well as the reuptake of NE at postganglionic sympathetic terminals [120,121]. Amezinium is indicated for the treatment of essential hypotension, orthostatic hypotension and hypotension during dialysis [208].".
- ↑ 3.0 3.1 "Treatment of orthostatic hypotension". Curr Opin Pharmacol 2 (6): 740–747. December 2002. doi:10.1016/s1471-4892(02)00213-8. PMID 12482740. "Amezinium metilsulfate is one of the most popular drugs in Japan for the treatment of OH. It has a unique mechanism of vasoconstriction. The drug inhibits monoamine oxidase (MAO) activity and norepinephrine (noradrenaline) uptake, and, therefore, enhances norepinephrine activity resulting in an increase in blood pressure [59]. Amezinium is especially recommended [60,61] in selected patients with asympathotonic (deficiency of sympathetic stimulation) OH [62••].".
- ↑ 4.0 4.1 "Treatment of neurogenic orthostatic hypotension with amezinium metilsulfate, a new indirect sympathomimetic drug". Neurology 38 (7): 1095–1099. July 1988. doi:10.1212/wnl.38.7.1095. PMID 3386828.
- ↑ "Amezinium metilsulfate". Drugs of the Future 6 (4): 207. 1981. doi:10.1358/dof.1981.006.04.199346.
- ↑ "Amezinium. Synthesis and radioactive labelling". Arzneimittel-Forschung 31 (9a): 1529–1533. 1981. PMID 7197967.
- ↑ "Heterocyclic hydrazines and hydrazones. II. Synthesis of hydrazino derivatives and of hydrazones in the thiazolo[4,5-d]pyridazin-7-ones". Bulletin de la Société Chimique de France 12 (2): 3324–3330.
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