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	22.98976928
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 2849		1.2 nM [IC50]

PubMed

Title	Date	PubMed
Celecoxib, but not indomethacin, ameliorates the hypertensive and perivascular fibrotic actions of cyclosporine in rats: role of endothelin signaling.	2015-04-01	25656942
Celecoxib offsets the negative renal influences of cyclosporine via modulation of the TGF-β1/IL-2/COX-2/endothelin ET(B) receptor cascade.	2014-03-01	24462674
Endothelins decrease the expression of aquaporins and plasma membrane water permeability in cultured rat astrocytes.	2011-03	21259319
Antiviral effect of Bosentan and Valsartan during coxsackievirus B3 infection of human endothelial cells.	2010-08	20392896
Simvastatin stimulates production of the antiapoptotic protein Bcl-2 via endothelin-1 and NFATc3 in SH-SY5Y cells.	2010-06	20369390
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.	2009-07-03	19429182
Endothelin receptor B antagonists decrease glioma cell viability independently of their cognate receptor.	2008-11-28	19040731
Aldosterone induces interleukin-18 through endothelin-1, angiotensin II, Rho/Rho-kinase, and PPARs in cardiomyocytes.	2008-09	18660453
Mechanisms of direct peritoneal resuscitation-mediated splanchnic hyperperfusion following hemorrhagic shock.	2007-04	17414428
Endothelin-1 stimulates NO production and inhibits cAMP accumulation in rat inner medullary collecting duct through independent pathways.	2006-06	16380457
Contribution of endothelin receptors and cyclooxygenase-derivatives to the altered response of the rabbit renal artery to endothelin-1 in diabetes.	2006-03-18	16612843
Leptin regulates cardiomyocyte contractile function through endothelin-1 receptor-NADPH oxidase pathway.	2006-02	16380530
Role of endothelin-1-dependent up-regulation of leptin in oral mucosal repair.	2005-12	16391412
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.	2005-11	16151434
Involvement of nitric oxide pathways in short term modulation of tyrosine hydroxylase activity by endothelins 1 and 3 in the rat anterior hypothalamus.	2005-09-02	16023617
Endothelin receptors in lower esophageal sphincter circular smooth muscle.	2005-04-15	15680467
Chronic endothelin exposure inhibits connexin43 expression in cultured cortical astroglia.	2005-02-01	15605384
Effects of an endothelin B receptor agonist on secretory phospholipase A2-IIA-induced apoptosis in cortical neurons.	2005-02	15695168
Endothelin-1-dependent up-regulation of leptin production in gastric mucosal injury by indomethacin.	2005	16280098
Endothelins induce ETB receptor-mediated mechanical hypernociception in rat hindpaw: roles of cAMP and protein kinase C.	2004-10-06	15464066
The endothelin/sarafotoxin-induced increase of the proliferation of undifferentiated and DMSO-differentiated GEM-81 goldfish erythrophoroma cells is mediated by ETB receptors.	2004-10	15357834
Endothelin upregulates the expression of vasopressin V2 mRNA in the inner medullary collecting duct of the rat.	2004-09	15334381
Endothelin 1 and 3 enhance neuronal nitric oxide synthase activity through ETB receptors involving multiple signaling pathways in the rat anterior hypothalamus.	2004-07	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.	2004-07	15007106
Endothelin-3 induced mesenteric vasoconstriction and PMN infiltration in the rat small intestine: role of endothelin receptors.	2004-06-15	15093706
Ventricular nonmyocytes inhibit doxorubicin-induced myocyte apoptosis: involvement of endogenous endothelin-1 as a paracrine factor.	2004-05	14736733
Modulatory effect of endothelin-1 and -3 on neuronal norepinephrine release in the rat posterior hypothalamus.	2004-04-15	14759557
Actions of endothelin and corticotropin releasing factor in the guinea-pig ileum: no evidence for an interaction with capsaicin-sensitive neurons.	2003-08	12906840
Endothelin receptor blockade inhibits molecular effectors of Kaposi's sarcoma cell invasion and tumor growth in vivo.	2003-08	12875994
Endothelin ET(A) but not ET(B) receptors mediate contraction of common bile duct.	2003-05-15	12686472
High glucose-induced, endothelin-dependent fibronectin synthesis is mediated via NF-kappa B and AP-1.	2003-02	12388107
Endothelin-1 and -3 diminish neuronal NE release through an NO mechanism in rat anterior hypothalamus.	2002-09	12184995
Endothelin-1 binding to endothelin receptors in the rat anterior pituitary gland: possible formation of an ETA-ETB receptor heterodimer.	2002-04	12363203
Endothelin-1 as a protective factor against beta-adrenergic agonist-induced apoptosis in cardiac myocytes.	2000-10	11028503

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 `Mon Mar 31 19:01:59 GMT 2025` Edited by `admin` on `Mon Mar 31 19:01:59 GMT 2025`
Record UNII	44OLL8XEJ4
Record Status	`Validated (UNII)`
Record Version

Download

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)

Preferred Name

English

ENB-001

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

506215