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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
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
ETA receptor-mediated constrictor responses to endothelin peptides in human blood vessels in vitro.
1995 May
Endothelin-1 binding to endothelin receptors in the rat anterior pituitary gland: possible formation of an ETA-ETB receptor heterodimer.
2002 Apr
Actions of endothelin and corticotropin releasing factor in the guinea-pig ileum: no evidence for an interaction with capsaicin-sensitive neurons.
2003 Aug
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
Developmental changes in the functional, biochemical and molecular properties of rat bladder endothelin receptors.
2003 May
Endothelin ET(A) but not ET(B) receptors mediate contraction of common bile duct.
2003 May 15
Endothelin 1 versus endothelin 3 in the development of the slow force response to myocardial stretch.
2005 Apr
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
Ethanol consumption enhances endothelin-1-induced contraction in the isolated rat carotid.
2006 Aug
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
Vehicular emissions induce vascular MMP-9 expression and activity associated with endothelin-1-mediated pathways.
2009 Apr
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
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
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
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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
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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
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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
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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
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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
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