ZINTEROL HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H26N2O4S.ClH
Molecular Weight	414.947
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CC(C)(CC1=CC=CC=C1)NCC(O)C2=CC(NS(C)(=O)=O)=C(O)C=C2

InChI

InChIKey=LVNUBJDWJFOMKH-UHFFFAOYSA-N

InChI=1S/C19H26N2O4S.ClH/c1-19(2,12-14-7-5-4-6-8-14)20-13-18(23)15-9-10-17(22)16(11-15)21-26(3,24)25;/h4-11,18,20-23H,12-13H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula	C19H26N2O4S
Molecular Weight	378.486
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4144240
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/39574 | https://www.ncbi.nlm.nih.gov/pubmed/8974046 | https://www.ncbi.nlm.nih.gov/pubmed/16601951 | https://www.ncbi.nlm.nih.gov/pubmed/11325796

Zinterol (MJ-9184-1) is an beta-adregenrgic agonist demostrated activity toward beta1-3 receptors. Oral zinterol caused a fast-appearing and long-lasting bronchodilator effect in patients with with stable chronic obstructive lung disease, however it seems development of zinterol was discontitued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11325796	Agonist 2678
Beta-3 adrenergic receptor 49 Target ID: CHEMBL246 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16601951	Agonist 2678
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8001277 \| https://www.ncbi.nlm.nih.gov/pubmed/8974046 \| https://www.ncbi.nlm.nih.gov/pubmed/4144240	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic obstructive pulmonary disease 174 Sources: https://www.google.com/patents/US3919424 https://www.ncbi.nlm.nih.gov/pubmed/39574	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Enhanced cardiac L-type calcium current response to beta2-adrenergic stimulation in heart failure.	2001 Jul	11408541
Regulation of myocardial contractility and cell size by distinct PI3K-PTEN signaling pathways.	2002 Sep 20	12297047
New insights into beta2-adrenoceptor signaling in the adult rat heart.	2003 Mar	12618231
Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells.	2006 Feb	16415914
Endurance exercise training attenuates cardiac beta2-adrenoceptor responsiveness and prevents ventricular fibrillation in animals susceptible to sudden death.	2006 Jun	16387787

Patents

Sample Use Guides

In Vivo Use Guide

In double-blind cross-over study including placebo, 0.25 mg and 0.50 mg zinterol (MJ-9184-1) and involving ten patients with stable chronic obstructive lung disease with reversible airways obstruction, MJ-9184-1 caused a fast-appearing and long-lasting bronchodilator effect. The oral intake of 0.50 mg MJ-9184-1, compared to 0.25 mg, caused a more rapid effect and a more pronounced bronchodilation; 0.50 mg MJ-9184-1 also caused some elevation of the pulse rate. The effect was not seen after 0.25 mg MJ-9184-1.

Route of Administration: Oral

In Vitro Use Guide

Zinterol caused positive inotropic and lusitropic effects in the isolated human right atrial appendage with EC50 values of 3 and 2 nM, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:40:57 GMT 2023` Edited by `admin` on `Fri Dec 15 17:40:57 GMT 2023`
Record UNII	569D41K4F5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZINTEROL HYDROCHLORIDE

Official Name

English

5'-(2-((.ALPHA.,.ALPHA.-DIMETHYLPHENETHYL)AMINO)-1-HYDROXYETHYL)-2'-HYDROXYMETHANESULFONANILIDE MONOHYDROCHLORIDE

Systematic Name

English

ZINTEROL HYDROCHLORIDE [USAN]

Common Name

English

ZINTEROL HCL

Common Name

English

MJ 9184-1

Code

English

METHANESULFONAMIDE, N-(5-(2-((1,1-DIMETHYL-2-PHENYLETHYL)AMINO)-1-HYDROXYETHYL)-2-HYDROXYPHENYL)-, MONOHYDROCHLORIDE

Common Name

English

MJ-9184-1

Code

English

NSC-284704

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C48149