Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C31H42N6O7 |
Molecular Weight | 610.7012 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C[C@@H]1NC(=O)[C@H](NC(=O)[C@@H]2CCCN2C(=O)[C@@H](CC(O)=O)NC(=O)[C@@H](CC3=CNC4=CC=CC=C34)NC1=O)C(C)C
InChI
InChIKey=VYCMAAOURFJIHD-PJNXIOHISA-N
InChI=1S/C31H42N6O7/c1-16(2)12-21-27(40)33-22(13-18-15-32-20-9-6-5-8-19(18)20)28(41)35-23(14-25(38)39)31(44)37-11-7-10-24(37)29(42)36-26(17(3)4)30(43)34-21/h5-6,8-9,15-17,21-24,26,32H,7,10-14H2,1-4H3,(H,33,40)(H,34,43)(H,35,41)(H,36,42)(H,38,39)/t21-,22+,23+,24-,26+/m0/s1
Molecular Formula | C31H42N6O7 |
Molecular Weight | 610.7012 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
BQ-123 is a selective endothelin receptor-1 antagonist; it is used as a biochemical tool in the study of endothelin receptor function. BQ-123 was suspected to contribute to the regulation of vascular tone humans. However, a study involving young normotensive subjects did not demonstrate any major role for BQ-123 regulation of vascular tone.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8437512
Curator's Comment: Known to be CNS non-penetrant in rats. Human data not available
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8809172
Curator's Comment: BQ-123 originally isolated from microbial sources by Banyu investigators
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P25101|||Q16433 Gene ID: 1909.0 Gene Symbol: EDNRA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7690094 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
[Demonstration of a vasopressor role of endogenous endothelin after inhibition of nitric oxide synthesis in rats]. | 1995 Aug |
|
ETA receptor-mediated constrictor responses to endothelin peptides in human blood vessels in vitro. | 1995 May |
|
Endothelin receptor-mediated Ca2+ mobilization and contraction in bovine oviductal arteries: comparison with noradrenaline and potassium. | 1997 Oct |
|
Endothelin ETA receptors subtype mediates phosphoinositide hydrolysis in adrenal medulla. | 1997 Sep |
|
Role of endothelin-1 in the active constriction of human atherosclerotic coronary arteries. | 2001 Sep 4 |
|
Endothelin-1 binding to endothelin receptors in the rat anterior pituitary gland: possible formation of an ETA-ETB receptor heterodimer. | 2002 Apr |
|
Stimulation of catecholamine biosynthesis via the protein kinase C pathway by endothelin-1 in PC12 rat pheochromocytoma cells. | 2002 Mar 1 |
|
Et-A receptor antagonist BQ123 prevents radiocontrast media-induced renal medullary hypoxia. | 2003 Jan |
|
Endothelin-1-induced responses in isolated mouse vessels: the expression and function of receptor types. | 2004 Aug |
|
Obligatory role for endogenous endothelin in mediating the hypertrophic effects of phenylephrine and angiotensin II in neonatal rat ventricular myocytes: evidence for two distinct mechanisms for endothelin regulation. | 2004 Jul |
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Ventricular nonmyocytes inhibit doxorubicin-induced myocyte apoptosis: involvement of endogenous endothelin-1 as a paracrine factor. | 2004 May |
|
Endothelins induce ETB receptor-mediated mechanical hypernociception in rat hindpaw: roles of cAMP and protein kinase C. | 2004 Oct 6 |
|
Endothelin upregulates the expression of vasopressin V2 mRNA in the inner medullary collecting duct of the rat. | 2004 Sep |
|
Endothelin 1 versus endothelin 3 in the development of the slow force response to myocardial stretch. | 2005 Apr |
|
Endothelin receptors in lower esophageal sphincter circular smooth muscle. | 2005 Apr 15 |
|
Endothelin-1 receptor antagonist BQ123 prevents pulmonary artery hypertension induced by low ambient temperature in broilers. | 2005 Dec |
|
Intercellular communication via gap junctions in activated rat hepatic stellate cells. | 2005 Feb |
|
Chronic endothelin exposure inhibits connexin43 expression in cultured cortical astroglia. | 2005 Feb 1 |
|
Endothelin isoforms and the response to myocardial stretch. | 2005 Jun |
|
Cyclo-oxygenase-2, endothelium and aortic reactivity during deoxycorticosterone acetate salt-induced hypertension. | 2005 May |
|
Functional characterization and expression of endothelin receptors in rat carotid artery: involvement of nitric oxide, a vasodilator prostanoid and the opening of K+ channels in ETB-induced relaxation. | 2005 Nov |
|
Modulation of the myocardial effects of selective ETB receptor stimulation and its implications for heart failure. | 2005 Sep |
|
ETa-receptor blockade, but not ACE inhibition, blunts retinal vessel response during isometric exercise. | 2006 Apr |
|
Ethanol consumption enhances endothelin-1-induced contraction in the isolated rat carotid. | 2006 Aug |
|
Involvement of endothelium and endothelin-1 in lead-induced smooth muscle cell dysfunction in rats. | 2006 Feb |
|
Leptin regulates cardiomyocyte contractile function through endothelin-1 receptor-NADPH oxidase pathway. | 2006 Feb |
|
Contribution of endothelin receptors and cyclooxygenase-derivatives to the altered response of the rabbit renal artery to endothelin-1 in diabetes. | 2006 Mar 18 |
|
Regulation of dHAND protein expression by all-trans retinoic acid through ET-1/ETAR signaling in H9c2 cells. | 2006 Oct 1 |
|
Mechanisms of direct peritoneal resuscitation-mediated splanchnic hyperperfusion following hemorrhagic shock. | 2007 Apr |
|
NADPH oxidase mediates angiotensin II-induced endothelin-1 expression in vascular adventitial fibroblasts. | 2007 Sep 1 |
|
Molecular analysis of cocaine-induced endothelial dysfunction: role of endothelin-1 and nitric oxide. | 2008 Dec |
|
Central endothelin: effects on vasopressin and the arterial baroreflex in doxorubicin heart failure rats. | 2008 Jun |
|
Aldosterone induces interleukin-18 through endothelin-1, angiotensin II, Rho/Rho-kinase, and PPARs in cardiomyocytes. | 2008 Sep |
|
Vehicular emissions induce vascular MMP-9 expression and activity associated with endothelin-1-mediated pathways. | 2009 Apr |
|
Role of ET(A) and ET(B) endothelin receptors on endothelin-1-induced potentiation of nociceptive and thermal hyperalgesic responses evoked by capsaicin in rats. | 2009 Jul 3 |
|
Simvastatin stimulates production of the antiapoptotic protein Bcl-2 via endothelin-1 and NFATc3 in SH-SY5Y cells. | 2010 Jun |
|
Endothelin-1 promotes osteosarcoma cell invasion and survival against cisplatin-induced apoptosis. | 2011 Nov |
|
Irregular electrical activation of intrinsic cardiac adrenergic cells increases catecholamine-synthesizing enzymes. | 2011 Sep 30 |
|
Selective ET(A) receptor blockade protects against cisplatin-induced acute renal failure in male rats. | 2014 May 5 |
|
BQ-123 prevents LPS-induced preterm birth in mice via the induction of uterine and placental IL-10. | 2015 Feb 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12049621
double-blind randomized study: 50 nmol/min for 60 min, or 300 nmol/min for 5 min followed by saline for 55 min
Route of Administration:
Intra-arterial
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:31:12 GMT 2023
by
admin
on
Fri Dec 15 16:31:12 GMT 2023
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Record UNII |
S2A8YZM151
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Record Status |
Validated (UNII)
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Record Version |
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DB12054
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DTXSID70929476
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BQ-123
Created by
admin on Fri Dec 15 16:31:12 GMT 2023 , Edited by admin on Fri Dec 15 16:31:12 GMT 2023
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