AMEZINIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H12N3O
Molecular Weight	202.2325
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(N)=CN=[N+]1C2=CC=CC=C2

InChI

InChIKey=VXROHTDSRBRJLN-UHFFFAOYSA-O

InChI=1S/C11H11N3O/c1-15-11-7-9(12)8-13-14(11)10-5-3-2-4-6-10/h2-8,12H,1H3/p+1

HIDE SMILES / InChI

Molecular Formula	C11H11N3O
Molecular Weight	201.2245
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://ds-pharma.jp/product/risumic/pdf/risumic_tab_interv.pdf
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/6873182

Amezinium is a sympathomimetic used for its vasopressor effects in the treatment of hypotensive states. Amezinium inhibited monoamine oxidase (MAO) activity. Amezinium antagonized the response to tyramine and blocked neuronal uptake of noradrenaline. Side effects revealed are: palpitation, headache, nausea/vomiting, hot flashes, high blood pressure.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Amine oxidase [flavin-containing] A 14 Target ID: P58027 Gene ID: 403450.0 Gene Symbol: MAOA Target Organism: Canis lupus familiaris (Dog) (Canis familiaris) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6873182	Inhibitor 8297	5.0 µM [IC50]
Amine oxidase [flavin-containing] B 11 Target ID: Q7YRB7 Gene ID: 403451.0 Gene Symbol: MAOB Target Organism: Canis lupus familiaris (Dog) (Canis familiaris) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6873182	Inhibitor 8297	1.0 mM [IC50]
Alpha adrenergic receptor (Canis lupus) 2 Target ID: Alpha adrenergic receptor (Canis lupus) Sources: https://www.ncbi.nlm.nih.gov/pubmed/6873182	Blocker 537

Conditions

Condition	Modality	Targets	Highest Phase	Product
Essential hypotension 2 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00000102-001#00000102-001	Primary		Approved 8429	Risumic Approved Use Amezinium is indicated for the treatment of hypotensive states (essential hypotension, orthostatic hypotension). Launch Date 1991
Orthostatic hypotension 4 Sources: http://www.kegg.jp/medicus-bin/japic_med_product?id=00000102-001#00000102-001	Primary		Approved 8429	Risumic Approved Use Amezinium is indicated for the treatment of hypotensive states (essential hypotension, orthostatic hypotension). Launch Date 1991

PubMed

Title	Date	PubMed
Effect of midodrine on chlorpromazine-induced orthostatic hypotension in rabbits: comparison with amezinium, etilefrine and droxidopa.	2000 Dec	11145175
Pharmacological effect of amezinium on urethra and bladder of rabbits.	2001	11451005
[An autopsy case of pure autonomic failure with pathological features of Parkinson's disease].	2001 Jan	11433766
Determination of amezinium in plasma by RP HPLC and its application to bioequivalence studies.	2001 Sep-Oct	11876436
Amezinium metilsulfate, a sympathomimetic agent, may increase the risk of urinary retention in multiple system atrophy.	2003 Feb	12664248
Successful treatment of retrograde ejaculation with amezinium.	2003 May-Jun	12746100
[Cathecholamine].	2004 Jun	15250291
Differences in skin sympathetic involvements between two chronic autonomic disorders: multiple system atrophy and pure autonomic failure.	2009 Jun	18805037

Patents

Sample Use Guides

In Vivo Use Guide

Twice a day, 20 mg daily

Route of Administration: Oral

In Vitro Use Guide

Amezinium antagonized the response to tyramine and blocked neuronal uptake of noradrenaline m concentrations as low as 0.1 to 10 uM and therefore it was not surprising to find that in the presence of the lower concentration of Amezinium the effects of noradrenaline were potentiated (at the level of the ED50) by a factor of 3.5.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:00:56 GMT 2023` Edited by `admin` on `Fri Dec 15 17:00:56 GMT 2023`
Record UNII	T4VA39MO9X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AMEZINIUM

Common Name

English

Amezinium [WHO-DD]

Common Name

English

AMEZINIUM ION

Common Name

English

4-AMINO-6-METHOXY-1-PHENYLPYRIDAZINIUM

Systematic Name

English

AMEZINIUM CATION

Common Name

English

PYRIDAZINIUM, 4-AMINO-6-METHOXY-1-PHENYL-

Systematic Name

English

Code System Code Type Description

FDA UNII

T4VA39MO9X