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
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
DescriptionCurator'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
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.
Approval Year
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 |
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| Release of norepinephrine from human ovary: coupling to steroidogenic response. | 2001 Jul |
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| Enhanced cardiac L-type calcium current response to beta2-adrenergic stimulation in heart failure. | 2001 Jul |
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| 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 |
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| Beta(2)-adrenergic receptor agonists increase intracellular free Ca(2+) concentration cycling in ventricular cardiomyocytes through p38 and p42/44 MAPK-mediated cytosolic phospholipase A(2) activation. | 2001 Oct 26 |
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| Effects of glucose and 2-deoxyglucose on memory formation in the chick: interaction with beta(3)-adrenoceptor agonists. | 2002 |
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| Phosphatidylinositol 3-kinase functionally compartmentalizes the concurrent G(s) signaling during beta2-adrenergic stimulation. | 2002 Jul 12 |
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| Characterization of the beta-adrenoceptor subtype involved in mediation of glucose transport in L6 cells. | 2002 Sep |
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| Regulation of myocardial contractility and cell size by distinct PI3K-PTEN signaling pathways. | 2002 Sep 20 |
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| High spinal anesthesia for cardiac surgery: effects on beta-adrenergic receptor function, stress response, and hemodynamics. | 2003 Feb |
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| Opposite action of beta1- and beta2-adrenergic receptors on Ca(V)1 L-channel current in rat adrenal chromaffin cells. | 2003 Jan 1 |
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| New insights into beta2-adrenoceptor signaling in the adult rat heart. | 2003 Mar |
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| beta2-Adrenergic signaling in human heart: shift from the cyclic AMP to the arachidonic acid pathway. | 2003 Nov |
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| Enhanced G(i) signaling selectively negates beta2-adrenergic receptor (AR)--but not beta1-AR-mediated positive inotropic effect in myocytes from failing rat hearts. | 2003 Sep 30 |
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| Beneficial effects of chronic pharmacological manipulation of beta-adrenoreceptor subtype signaling in rodent dilated ischemic cardiomyopathy. | 2004 Aug 31 |
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| Characterization of agonist stimulation of cAMP-dependent protein kinase and G protein-coupled receptor kinase phosphorylation of the beta2-adrenergic receptor using phosphoserine-specific antibodies. | 2004 Jan |
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| The cytosolic phospholipase A2 pathway, a safeguard of beta2-adrenergic cardiac effects in rat. | 2005 May 13 |
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| Temporal dynamics of inotropic, chronotropic, and metabolic responses during beta1- and beta2-AR stimulation in the isolated, perfused rat heart. | 2005 Sep |
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| Multiple signalling pathways involved in beta2-adrenoceptor-mediated glucose uptake in rat skeletal muscle cells. | 2006 Feb |
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| Endurance exercise training attenuates cardiac beta2-adrenoceptor responsiveness and prevents ventricular fibrillation in animals susceptible to sudden death. | 2006 Jun |
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| Agonist effects of zinterol at the mouse and human beta(3)-adrenoceptor. | 2006 May |
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| (-)-Adrenaline elicits positive inotropic, lusitropic, and biochemical effects through beta2 -adrenoceptors in human atrial myocardium from nonfailing and failing hearts, consistent with Gs coupling but not with Gi coupling. | 2007 Mar |
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| beta2-Adrenergic receptor agonists stimulate L-type calcium current independent of PKA in newborn rabbit ventricular myocytes. | 2007 Nov |
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| Beta2- and beta3-adrenoceptors activate glucose uptake in chick astrocytes by distinct mechanisms: a mechanism for memory enhancement? | 2007 Nov |
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| Energy metabolism and memory processing: role of glucose transport and glycogen in responses to adrenoceptor activation in the chicken. | 2008 Jun 15 |
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| Arrhythmogenic effects of beta2-adrenergic stimulation in the failing heart are attributable to enhanced sarcoplasmic reticulum Ca load. | 2008 Jun 6 |
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| The beta3-adrenoceptor agonist 4-[[(Hexylamino)carbonyl]amino]-N-[4-[2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]-phenyl]-benzenesulfonamide (L755507) and antagonist (S)-N-[4-[2-[[3-[3-(acetamidomethyl)phenoxy]-2-hydroxypropyl]amino]-ethyl]phenyl]benzenesulfonamide (L748337) activate different signaling pathways in Chinese hamster ovary-K1 cells stably expressing the human beta3-adrenoceptor. | 2008 Nov |
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| Laminin enhances beta(2)-adrenergic receptor stimulation of L-type Ca(2+) current via cytosolic phospholipase A(2) signalling in cat atrial myocytes. | 2009 Oct 15 |
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| Tissue functions mediated by beta(3)-adrenoceptors-findings and challenges. | 2010 Aug |
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| The selectivity of beta-adrenoceptor agonists at human beta1-, beta2- and beta3-adrenoceptors. | 2010 Jul |
|
| A full pharmacological analysis of the three turkey β-adrenoceptors and comparison with the human β-adrenoceptors. | 2010 Nov 30 |
Patents
Sample Use Guides
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
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NCI_THESAURUS |
C48149
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37990
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CHEMBL1243407
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SUB00165MIG
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ZINTEROL
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37000-20-7
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100000078769
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7167N7AJJR
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C152958
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C002904
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4301
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DTXSID70865845
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
