CGP-20712

Details

Stereochemistry	RACEMIC
Molecular Formula	C23H25F3N4O5
Molecular Weight	494.4636
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C=C(N=C1C2=CC=C(OCC(O)CNCCOC3=CC=C(O)C(=C3)C(N)=O)C=C2)C(F)(F)F

InChI

InChIKey=GKJZEKSHCJELPL-UHFFFAOYSA-N

InChI=1S/C23H25F3N4O5/c1-30-12-20(23(24,25)26)29-22(30)14-2-4-16(5-3-14)35-13-15(31)11-28-8-9-34-17-6-7-19(32)18(10-17)21(27)33/h2-7,10,12,15,28,31-32H,8-9,11,13H2,1H3,(H2,27,33)

HIDE SMILES / InChI

Molecular Formula	C23H25F3N4O5
Molecular Weight	494.4636
Charge	0
Count

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23614528	Antagonist 2778		9.48 null [pKd]
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23614528	Antagonist 2778		5.98 null [pKd]

PubMed

Title	Date	PubMed
The receptor binding profile of the new antihypertensive agent nebivolol and its stereoisomers compared with various beta-adrenergic blockers.	1988 Dec	2462161
Atypical beta-adrenergic receptor in 3T3-F442A adipocytes. Pharmacological and molecular relationship with the human beta 3-adrenergic receptor.	1991 Oct 25	1682311
Pre- and postganglionic stimulation-induced noradrenaline overflow is markedly facilitated by a prejunctional beta 2-adrenoceptor-mediated control mechanism in the pithed rat.	1994 Jun	7969507
Carazolol: a potent, selective beta 3-adrenoceptor agonist.	1995 Nov 30	8719421
SR59230A blocks beta3-adrenoceptor-linked modulation of upcoupling protein-1 and leptin in rat brown adipocytes.	1998 Jul 3	9718277
Selective activation of beta3-adrenoceptors by octopamine: comparative studies in mammalian fat cells.	1999 Apr	10344530
Potent and selective human beta(3)-adrenergic receptor antagonists.	1999 Aug	10411574
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.	1999 Feb 19	10079020
Opposing effects of beta(1)- and beta(2)-adrenergic receptors on cardiac myocyte apoptosis : role of a pertussis toxin-sensitive G protein.	1999 Nov 30	10577992
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.	2001 Jan	11159692
Constitutive activity of the human beta(1)-adrenergic receptor in beta(1)-receptor transgenic mice.	2001 Oct	11562432
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002 Jan	11815381
Bone marrow-derived regenerated cardiomyocytes (CMG Cells) express functional adrenergic and muscarinic receptors.	2002 Jan 22	11804996
Physiological antagonism between ventricular beta 1-adrenoceptors and alpha 1-adrenoceptors but no evidence for beta 2- and beta 3-adrenoceptor function in murine heart.	2002 May	12010770
Beta 1-adrenoceptor selectivity of nebivolol and bisoprolol. A comparison of [3H]CGP 12.177 and [125I]iodocyanopindolol binding studies.	2003 Jan 26	12535855
Function of beta1-adrenoceptors and mRNA expression of beta1- and beta2-adrenoceptors in guinea-pig esophagus.	2003 Jul 18	12877941
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor.	2003 Jun	12761341
Regeneration of cardiomyocytes from bone marrow: Use of mesenchymal stem cell for cardiovascular tissue engineering.	2003 Mar	19002953
Beta-adrenergic receptor blockade modulates Bcl-X(S) expression and reduces apoptosis in failing myocardium.	2003 May	12738230
Functional and molecular characterization of beta-adrenoceptors in the internal anal sphincter.	2003 May	12606629
Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.	2004 Feb	14730417
Functional characterization of the beta-adrenergic receptor subtypes expressed by CA1 pyramidal cells in the rat hippocampus.	2005 Aug	15908513
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.	2005 Feb	15655528
Agonist-specific activation of the beta2-adrenoceptor/Gs-protein and beta2-adrenoceptor/Gi-protein pathway in adult rat ventricular cardiomyocytes.	2006 Apr	16474418
Carvedilol blocks beta2- more than beta1-adrenoceptors in human heart.	2006 Jan	16225854
Recruitment of functionally active heart beta2-adrenoceptors in the initial phase of endotoxic shock in pithed rats.	2006 Nov	17047523
Histamine augments beta2-adrenoceptor-induced cyclic AMP accumulation in human prostate cancer cells DU-145 independently of known histamine receptors.	2007 Mar 15	17196553
Catecholamines relax detrusor through beta 2-adrenoceptors in mouse and beta 3-adrenoceptors in man.	2009 Jan	18820136

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:51:51 GMT 2023` Edited by `admin` on `Sat Dec 16 09:51:51 GMT 2023`
Record UNII	SIO2UEZ19H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CGP-20712

Common Name

English

BENZAMIDE, 2-HYDROXY-5-(2-((2-HYDROXY-3-(4-(1-METHYL-4-(TRIFLUOROMETHYL)-1H-IMIDAZOL-2-YL)PHENOXY)PROPYL)AMINO)ETHOXY)-, (±)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

2685