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
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 |
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PubMed
Title | Date | PubMed |
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ETA receptor-mediated constrictor responses to endothelin peptides in human blood vessels in vitro. | 1995 May |
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Endothelin-1 binding to endothelin receptors in the rat anterior pituitary gland: possible formation of an ETA-ETB receptor heterodimer. | 2002 Apr |
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Actions of endothelin and corticotropin releasing factor in the guinea-pig ileum: no evidence for an interaction with capsaicin-sensitive neurons. | 2003 Aug |
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Endothelin receptor blockade inhibits molecular effectors of Kaposi's sarcoma cell invasion and tumor growth in vivo. | 2003 Aug |
|
Endothelin-1 inhibits TNF alpha-induced iNOS expression in 3T3-F442A adipocytes. | 2003 Jul |
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Developmental changes in the functional, biochemical and molecular properties of rat bladder endothelin receptors. | 2003 May |
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Endothelin ET(A) but not ET(B) receptors mediate contraction of common bile duct. | 2003 May 15 |
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Endothelin 1 versus endothelin 3 in the development of the slow force response to myocardial stretch. | 2005 Apr |
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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 |
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Modulation of the myocardial effects of selective ETB receptor stimulation and its implications for heart failure. | 2005 Sep |
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Ethanol consumption enhances endothelin-1-induced contraction in the isolated rat carotid. | 2006 Aug |
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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 |
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Vehicular emissions induce vascular MMP-9 expression and activity associated with endothelin-1-mediated pathways. | 2009 Apr |
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Endothelin-1 promotes osteosarcoma cell invasion and survival against cisplatin-induced apoptosis. | 2011 Nov |
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Irregular electrical activation of intrinsic cardiac adrenergic cells increases catecholamine-synthesizing enzymes. | 2011 Sep 30 |
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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
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S2A8YZM151
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DB12054
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443289
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136553-81-6
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DTXSID70929476
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BQ-123
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)