Amezinium metilsulfate: Difference between revisions

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			{{Short description\|Chemical compound}}
	{{drugbox
			{{Drugbox
	\| Verifiedfields = changed		\| Verifiedfields = changed
		⚫	\| verifiedrevid = 456687368
	\| Watchedfields = changed
		⚫	\| IUPAC_name = 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
⚫	\| UNII_Ref = {{fdacite\|changed\|FDA}}
			\| image = Structural formula of amezinium metilsulfate.svg
⚫	\| UNII = 03NR868ICX

⚫	\| verifiedrevid = ~~399504585~~
			<!--Clinical data-->
⚫	\| IUPAC_name = 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
			\| tradename =
	\| image = Amezinium metilsulfate.png
			\| Drugs.com = {{drugs.com\|international\|amezinium-metilsulfate}}
		⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
		⚫	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
		⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
		⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	\| legal_status = Rx-only
		⚫	\| routes_of_administration = Oral

			<!--Pharmacokinetic data-->
		⚫	\| bioavailability =
		⚫	\| protein_bound =
		⚫	\| metabolism =
		⚫	\| elimination_half-life =
		⚫	\| excretion =

			<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|changed\|??}}
		⚫	\| CAS_number = 30578-37-1
		⚫	\| ATC_prefix = C01
		⚫	\| ATC_suffix = CA25
		⚫	\| ATC_supplemental =
		⚫	\| PubChem = 71926
			\| ChEBI = 31201
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 2106667
		⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| DrugBank =
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 64937		\| ChemSpiderID = 64937
		⚫	\| UNII_Ref = {{fdacite\|changed\|FDA}}
	\| InChI = 1/C11H11N3O.CH4O4S/c1-15-11-7-9(12)8-13-14(11)10-5-3-2-4-6-10;1-5-6(2,3)4/h2-8,12H,1H3;1H3,(H,2,3,4)
		⚫	\| UNII = 03NR868ICX
	\| InChIKey = ZEASXVYVFFXULL-UHFFFAOYAG
		⚫	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| smiles1 = S(=O)(=O)OC.O(c1(ncc(N)c1)c2ccccc2)C
		⚫	\| KEGG = D01304

			<!--Chemical data-->
		⚫	\| chemical_formula =
		⚫	\| C=12 \| H=15 \| N=3 \| O=5 \| S=1
		⚫	\| smiles = COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O)
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C11H11N3O.CH4O4S/c1-15-11-7-9(12)8-13-14(11)10-5-3-2-4-6-10;1-5-6(2,3)4/h2-8,12H,1H3;1H3,(H,2,3,4)		\| StdInChI = 1S/C11H11N3O.CH4O4S/c1-15-11-7-9(12)8-13-14(11)10-5-3-2-4-6-10;1-5-6(2,3)4/h2-8,12H,1H3;1H3,(H,2,3,4)
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = ZEASXVYVFFXULL-UHFFFAOYSA-N		\| StdInChIKey = ZEASXVYVFFXULL-UHFFFAOYSA-N
⚫	\| CAS_number = 30578-37-1
	\| CAS_supplemental =
⚫	\| ATC_prefix = C01
⚫	\| ATC_suffix = CA25
⚫	\| ATC_supplemental =
⚫	\| PubChem = 71926
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| DrugBank =
⚫	\| KEGG_Ref = {{keggcite\|~~changed~~\|kegg}}
⚫	\| KEGG = D01304
⚫	\| chemical_formula =
⚫	\| C=12 \| H=15 \| N=3 \| O=5 \| S=1
	\| molecular_weight = 313.32 g/mol
⚫	\| smiles = COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O)
⚫	\| bioavailability =
⚫	\| protein_bound =
⚫	\| metabolism =
⚫	\| elimination_half-life =
⚫	\| excretion =
⚫	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category=
⚫	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫	\| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	\| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	\| legal_status = Rx-only
⚫	\| routes_of_administration = Oral
	}}		}}

	'''Amezinium metilsulfate''' (], trade name '''Regulton''') is a ] drug used for the treatment of low ]. It has multiple mechanisms, including stimulation of ] and ]s and inhibition of ] and ] uptake.<ref>{{~~pmid~~\|6873182}}</ref><ref>{{~~pmid~~\|7197970}}</ref>		'''Amezinium metilsulfate''' (], trade name '''Regulton''') is a ] drug used for the treatment of low ]. It has multiple mechanisms, including stimulation of ] and ]s and inhibition of ] and ] uptake.<ref>{{cite journal \| vauthors = Araújo D, Caramona MM, Osswald W \| title = On the mechanism of action of amezinium methylsulphate on the dog saphenous vein \| journal = European Journal of Pharmacology \| volume = 90 \| issue = 2–3 \| pages = 203–14 \| date = June 1983 \| pmid = 6873182 \| doi = 10.1016/0014-2999(83)90238-8 }}</ref><ref>{{cite journal \| vauthors = Lenke D, Gries J, Kretzschmar R \| title = Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action \| journal = Arzneimittel-Forschung \| volume = 31 \| issue = 9a \| pages = 1558–65 \| year = 1981 \| pmid = 7197970 }}</ref>

	==~~References~~==		==Synthesis==
			This antidepressant is made from ] starting material.
			Synthesis:<ref>{{cite journal \| vauthors = Unterhalt B \| title = Amezinium metilsulfate \| journal = Drugs of the Future \| date = 1981 \| volume = 6 \| issue = 4 \| pages = 207 \| doi = 10.1358/dof.1981.006.04.199346 }}</ref><ref>{{cite journal \| vauthors = Reicheneder F, Burger TF, König H, Kropp R, Lietz H, Thyes M, Wiersdorff WW \| title = Amezinium. Synthesis and radioactive labelling \| journal = Arzneimittel-Forschung \| volume = 31 \| issue = 9a \| pages = 1529–1533 \| date = 1981 \| pmid = 7197967 }}</ref><ref>{{cite journal \| vauthors = Beljean M, Pays M \| title = Heterocyclic hydrazines and hydrazones. II. Synthesis of hydrazino derivatives and of hydrazones in the thiazolopyridazin-7-ones \| journal = Bulletin de la Societe Chimique de France \| volume = 12 \| issue = 2 \| pages = 3324–3330 }}</ref>]]
			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 completed the synthesis of Amezinium metisulfate (7).

			== References ==
	{{reflist}}		{{reflist}}

	{{Cardiac stimulants excluding cardiac glycosides}}		{{Cardiac stimulants excluding cardiac glycosides}}

			]
	]		]
			]


	{{cardiovascular-drug-stub}}		{{cardiovascular-drug-stub}}

	]

Latest revision as of 07:17, 23 December 2024

Chemical compound Pharmaceutical compound

Amezinium metilsulfate
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	C01CA25 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
CAS Number	30578-37-1
PubChem CID	71926
ChemSpider	64937
UNII	03NR868ICX
KEGG	D01304
ChEBI	CHEBI:31201
ChEMBL	ChEMBL2106667
CompTox Dashboard (EPA)	DTXSID00184657
ECHA InfoCard	100.045.665
Chemical and physical data
Formula	C₁₂H₁₅N₃O₅S
Molar mass	313.33 g·mol
3D model (JSmol)	Interactive image
SMILES COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O)
InChI InChI=1S/C11H11N3O.CH4O4S/c1-15-11-7-9(12)8-13-14(11)10-5-3-2-4-6-10;1-5-6(2,3)4/h2-8,12H,1H3;1H3,(H,2,3,4) Key:ZEASXVYVFFXULL-UHFFFAOYSA-N
(what is this?) (verify)

Amezinium metilsulfate (INN, trade name Regulton) is a sympathomimetic drug used for the treatment of low blood pressure. It has multiple mechanisms, including stimulation of alpha and beta-1 receptors and inhibition of noradrenaline and tyramine uptake.

Synthesis

This antidepressant is made from Chloridazon starting material.

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 completed the synthesis of Amezinium metisulfate (7).

References

Araújo D, Caramona MM, Osswald W (June 1983). "On the mechanism of action of amezinium methylsulphate on the dog saphenous vein". European Journal of Pharmacology. 90 (2–3): 203–14. doi:10.1016/0014-2999(83)90238-8. PMID 6873182.
Lenke D, Gries J, Kretzschmar R (1981). "Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action". Arzneimittel-Forschung. 31 (9a): 1558–65. PMID 7197970.
Unterhalt B (1981). "Amezinium metilsulfate". Drugs of the Future. 6 (4): 207. doi:10.1358/dof.1981.006.04.199346.
Reicheneder F, Burger TF, König H, Kropp R, Lietz H, Thyes M, Wiersdorff WW (1981). "Amezinium. Synthesis and radioactive labelling". Arzneimittel-Forschung. 31 (9a): 1529–1533. PMID 7197967.
Beljean M, Pays M. "Heterocyclic hydrazines and hydrazones. II. Synthesis of hydrazino derivatives and of hydrazones in the thiazolopyridazin-7-ones". Bulletin de la Societe Chimique de France. 12 (2): 3324–3330.

Cardiac stimulants excluding cardiac glycosides (C01C)

Adrenergic and
dopaminergic agents

Adrenergic agonists

α	Denopamine Metaraminol Methoxamine Midodrine Norfenefrine Oxedrine Phenylephrine
β	Arbutamine Dobutamine Isoprenaline Prenalterol
mixed	Amezinium metilsulfate Droxidopa Epinephrine # Etilefrine Norepinephrine

Dopamine agonists

Fenoldopam

Both

Unknown/ungrouped

Phosphodiesterase inhibitors (PDE3I)

Other cardiac stimulants

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

This drug article relating to the cardiovascular system is a stub. You can help Misplaced Pages by expanding it.

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