BQ-788

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H50N5O7.Na
Molecular Weight	663.7799
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCCC[C@@H](NC(=O)[C@@H](CC1=CN(C(=O)OC)C2=C1C=CC=C2)NC(=O)[C@H](CC(C)(C)C)NC(=O)N3[C@@H](C)CCC[C@H]3C)C([O-])=O

InChI

InChIKey=QCVIFBRTTLMEOV-FUKQNADPSA-M

InChI=1S/C34H51N5O7.Na/c1-8-9-16-25(31(42)43)35-29(40)26(18-23-20-38(33(45)46-7)28-17-11-10-15-24(23)28)36-30(41)27(19-34(4,5)6)37-32(44)39-21(2)13-12-14-22(39)3;/h10-11,15,17,20-22,25-27H,8-9,12-14,16,18-19H2,1-7H3,(H,35,40)(H,36,41)(H,37,44)(H,42,43);/q;+1/p-1/t21-,22+,25-,26-,27+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C34H50N5O7
Molecular Weight	640.7901
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12070534 | https://www.ncbi.nlm.nih.gov/pubmed/28966265 | https://adisinsight.springer.com/drugs/800013322 | https://www.ncbi.nlm.nih.gov/pubmed/26330458

BQ-788, a selective endothelin (ET) B-receptor antagonist, was developed by Banyu. This compound is widely used to demonstrate the role of ET-1 and ET(B) receptor subtypes in physiological and/or pathophysiological conditions. BQ-788 was studied against hypertension. However, this study was discontinued. Besides, was shown that BQ788 could protect against brain edema by inhibiting vascular endothelial growth factor-A-mediated decrease in claudin-5. The intralesional applications of BQ788 were well tolerated and showed signs of directly and indirectly reducing the viability of melanoma cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Endothelin receptor ET-B 11 Target ID: CHEMBL1785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12070534	Antagonist 2778		1.2 nM [IC50]

PubMed

Title	Date	PubMed
Endothelin-1 as a protective factor against beta-adrenergic agonist-induced apoptosis in cardiac myocytes.	2000 Oct	11028503
Endothelin-1 binding to endothelin receptors in the rat anterior pituitary gland: possible formation of an ETA-ETB receptor heterodimer.	2002 Apr	12363203
Endothelin-1 and -3 diminish neuronal NE release through an NO mechanism in rat anterior hypothalamus.	2002 Sep	12184995
Actions of endothelin and corticotropin releasing factor in the guinea-pig ileum: no evidence for an interaction with capsaicin-sensitive neurons.	2003 Aug	12906840
Endothelin receptor blockade inhibits molecular effectors of Kaposi's sarcoma cell invasion and tumor growth in vivo.	2003 Aug	12875994
High glucose-induced, endothelin-dependent fibronectin synthesis is mediated via NF-kappa B and AP-1.	2003 Feb	12388107
Endothelin ET(A) but not ET(B) receptors mediate contraction of common bile duct.	2003 May 15	12686472
Modulatory effect of endothelin-1 and -3 on neuronal norepinephrine release in the rat posterior hypothalamus.	2004 Apr 15	14759557
Endothelin 1 and 3 enhance neuronal nitric oxide synthase activity through ETB receptors involving multiple signaling pathways in the rat anterior hypothalamus.	2004 Jul	15245872
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	15007106
Endothelin-3 induced mesenteric vasoconstriction and PMN infiltration in the rat small intestine: role of endothelin receptors.	2004 Jun 15	15093706
Ventricular nonmyocytes inhibit doxorubicin-induced myocyte apoptosis: involvement of endogenous endothelin-1 as a paracrine factor.	2004 May	14736733
The endothelin/sarafotoxin-induced increase of the proliferation of undifferentiated and DMSO-differentiated GEM-81 goldfish erythrophoroma cells is mediated by ETB receptors.	2004 Oct	15357834
Endothelins induce ETB receptor-mediated mechanical hypernociception in rat hindpaw: roles of cAMP and protein kinase C.	2004 Oct 6	15464066
Endothelin upregulates the expression of vasopressin V2 mRNA in the inner medullary collecting duct of the rat.	2004 Sep	15334381
Endothelin-1-dependent up-regulation of leptin production in gastric mucosal injury by indomethacin.	2005	16280098
Endothelin receptors in lower esophageal sphincter circular smooth muscle.	2005 Apr 15	15680467
Role of endothelin-1-dependent up-regulation of leptin in oral mucosal repair.	2005 Dec	16391412
Effects of an endothelin B receptor agonist on secretory phospholipase A2-IIA-induced apoptosis in cortical neurons.	2005 Feb	15695168
Chronic endothelin exposure inhibits connexin43 expression in cultured cortical astroglia.	2005 Feb 1	15605384
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	16151434
Involvement of nitric oxide pathways in short term modulation of tyrosine hydroxylase activity by endothelins 1 and 3 in the rat anterior hypothalamus.	2005 Sep 2	16023617
Leptin regulates cardiomyocyte contractile function through endothelin-1 receptor-NADPH oxidase pathway.	2006 Feb	16380530
Endothelin-1 stimulates NO production and inhibits cAMP accumulation in rat inner medullary collecting duct through independent pathways.	2006 Jun	16380457
Contribution of endothelin receptors and cyclooxygenase-derivatives to the altered response of the rabbit renal artery to endothelin-1 in diabetes.	2006 Mar 18	16612843
Mechanisms of direct peritoneal resuscitation-mediated splanchnic hyperperfusion following hemorrhagic shock.	2007 Apr	17414428
Endothelin receptor B antagonists decrease glioma cell viability independently of their cognate receptor.	2008 Nov 28	19040731
Aldosterone induces interleukin-18 through endothelin-1, angiotensin II, Rho/Rho-kinase, and PPARs in cardiomyocytes.	2008 Sep	18660453
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	19429182
Antiviral effect of Bosentan and Valsartan during coxsackievirus B3 infection of human endothelial cells.	2010 Aug	20392896
Simvastatin stimulates production of the antiapoptotic protein Bcl-2 via endothelin-1 and NFATc3 in SH-SY5Y cells.	2010 Jun	20369390
Endothelins decrease the expression of aquaporins and plasma membrane water permeability in cultured rat astrocytes.	2011 Mar	21259319
Celecoxib offsets the negative renal influences of cyclosporine via modulation of the TGF-β1/IL-2/COX-2/endothelin ET(B) receptor cascade.	2014 Mar 1	24462674
Celecoxib, but not indomethacin, ameliorates the hypertensive and perivascular fibrotic actions of cyclosporine in rats: role of endothelin signaling.	2015 Apr 1	25656942

Patents

Sample Use Guides

In Vivo Use Guide

Three patients received a single intralesional BQ788 application of 3 mg

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:04:58 UTC 2023` Edited by `admin` on `Fri Dec 15 18:04:58 UTC 2023`
Record UNII	44OLL8XEJ4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BQ-788

Code

English

D-NORLEUCINE, N-(((2R,6S)-2,6-DIMETHYL-1-PIPERIDINYL)CARBONYL)-4-METHYL-L-LEUCYL-1-(METHOXYCARBONYL)-D-TRYPTOPHYL-, SODIUM SALT (1:1)

Systematic Name

English

ENB-001

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

506215