ZINTEROL

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H26N2O4S
Molecular Weight	378.486
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=XJBCFFLVLOPYBV-UHFFFAOYSA-N

InChI=1S/C19H26N2O4S/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

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	( + / - )

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
beta-Adrenergic receptor stimulation of L-type Ca2+ channels in rabbit portal vein myocytes involves both alphas and betagamma G protein subunits.	2001 Feb 15	11179395
Enhanced cardiac L-type calcium current response to beta2-adrenergic stimulation in heart failure.	2001 Jul	11408541
Murine ventricular L-type Ca(2+) current is enhanced by zinterol via beta(1)-adrenoceptors, and is reduced in TG4 mice overexpressing the human beta(2)-adrenoceptor.	2001 May	11325796
Phosphatidylinositol 3-kinase functionally compartmentalizes the concurrent G(s) signaling during beta2-adrenergic stimulation.	2002 Jul 12	12114321
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
Tissue functions mediated by beta(3)-adrenoceptors-findings and challenges.	2010 Aug	20517594
The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors.	2010 Jul	20590599
A full pharmacological analysis of the three turkey β-adrenoceptors and comparison with the human β-adrenoceptors.	2010 Nov 30	21152092

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 15:49:37 GMT 2023` Edited by `admin` on `Fri Dec 15 15:49:37 GMT 2023`
Record UNII	7167N7AJJR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZINTEROL

Official Name

English

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

Systematic Name

English

zinterol [INN]

Common Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C48149