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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
Structure of BQ-123

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

HIDE SMILES / InChI

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

Curator's Comment: Known to be CNS non-penetrant in rats. Human data not available

Originator

Curator's Comment: BQ-123 originally isolated from microbial sources by Banyu investigators

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P25101|||Q16433
Gene ID: 1909.0
Gene Symbol: EDNRA
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
[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
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
Patents

Sample Use Guides

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:31:12 GMT 2023
Edited
by admin
on Fri Dec 15 16:31:12 GMT 2023
Record UNII
S2A8YZM151
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BQ-123
Common Name English
CYCLO(D-.ALPHA.-ASPARTYL-L-PROLYL-D-VALYL-L-LEUCYL-D-TRYPTOPHYL)
Systematic Name English
CYCLO(D-TRP-D-ASP-PRO-D-VAL-LEU)
Common Name English
2-((3R,6R,9S,12R,15S)-6-(1H-INDOL-3-YLMETHYL)-9-(2-METHYLPROPYL)-2,5,8,11,14-PENTAOXO-12-PROPAN-2-YL-1,4,7,10,13-PENTAZABICYCLO(13.3.0)OCTADECAN-3-YL)ACETIC ACID
Systematic Name English
BQ123
Code English
Code System Code Type Description
FDA UNII
S2A8YZM151
Created by admin on Fri Dec 15 16:31:12 GMT 2023 , Edited by admin on Fri Dec 15 16:31:12 GMT 2023
PRIMARY
DRUG BANK
DB12054
Created by admin on Fri Dec 15 16:31:12 GMT 2023 , Edited by admin on Fri Dec 15 16:31:12 GMT 2023
PRIMARY
PUBCHEM
443289
Created by admin on Fri Dec 15 16:31:12 GMT 2023 , Edited by admin on Fri Dec 15 16:31:12 GMT 2023
PRIMARY
CAS
136553-81-6
Created by admin on Fri Dec 15 16:31:12 GMT 2023 , Edited by admin on Fri Dec 15 16:31:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID70929476
Created by admin on Fri Dec 15 16:31:12 GMT 2023 , Edited by admin on Fri Dec 15 16:31:12 GMT 2023
PRIMARY
WIKIPEDIA
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
PRIMARY
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