BGC-20-1531

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NCATS

Details

Stereochemistry	ACHIRAL
Molecular Formula	C26H23N2O6S.Na
Molecular Weight	514.525
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of BGC-20-1531

Structure Search

SMILES

[Na+].COC1=CC=C(N=C1)C2=CC=C(OCC3=C(C)OC(=C3)C(=O)[N-]S(=O)(=O)C4=CC=CC=C4C)C=C2

InChI

InChIKey=TVDHMDXPKGMXRT-UHFFFAOYSA-M

InChI=1S/C26H24N2O6S.Na/c1-17-6-4-5-7-25(17)35(30,31)28-26(29)24-14-20(18(2)34-24)16-33-21-10-8-19(9-11-21)23-13-12-22(32-3)15-27-23;/h4-15H,16H2,1-3H3,(H,28,29);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C26H23N2O6S
Molecular Weight	491.536
Charge	-1
Count

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

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

Approval Year

Targets

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid EP4 receptor 12 Target ID: CHEMBL1836 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24703233	Antagonist 2849		3.0 nM [Ki]
Prostaglandin E2 receptor EP4 subtype 3 Target ID: P35408 Gene ID: 5734.0 Gene Symbol: PTGER4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21681585	Antagonist 2849

PubMed

PubMed

Title	Date	PubMed
The pharmacological effect of BGC20-1531, a novel prostanoid EP4 receptor antagonist, in the prostaglandin E2 human model of headache.	2011-10	21681585
BGC20-1531, a novel, potent and selective prostanoid EP receptor antagonist: a putative new treatment for migraine headache.	2009-01	19154437

Substance Class	Chemical Created by `admin` on `Tue Apr 01 16:29:57 GMT 2025` Edited by `admin` on `Tue Apr 01 16:29:57 GMT 2025`
Record UNII	9QV7JG4XYZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BGC-20-1531

Common Name

English

AP-1531

Preferred Name

English

BGC 20-1531

Code

English

4-((4-(5-METHOXY-2-PYRIDYL)PHENOXY)METHYL)-5-METHYL-N-(O-TOLYLSULFONYL)FURAN-2-CARBOXAMIDE; SODIUM HYDRIDE

Systematic Name

English

PGN 1531

Code

English

2-FURANCARBOXAMIDE, 4-((4-(5-METHOXY-2-PYRIDINYL)PHENOXY)METHYL)-5-METHYL-N-((2-METHYLPHENYL)SULFONYL)-, SODIUM SALT (1:1)

Systematic Name

English

BGC20-1531

Code

English

Code System Code Type Description

EPA CompTox

DTXSID301351968

Created by admin on Tue Apr 01 16:29:57 GMT 2025 , Edited by admin on Tue Apr 01 16:29:57 GMT 2025

PRIMARY

SMS_ID

300000042403

Created by admin on Tue Apr 01 16:29:57 GMT 2025 , Edited by admin on Tue Apr 01 16:29:57 GMT 2025

PRIMARY

CAS

1186532-61-5

Created by admin on Tue Apr 01 16:29:57 GMT 2025 , Edited by admin on Tue Apr 01 16:29:57 GMT 2025

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MANUFACTURER PRODUCT INFORMATION

BGC-20-1531

Created by admin on Tue Apr 01 16:29:57 GMT 2025 , Edited by admin on Tue Apr 01 16:29:57 GMT 2025

PRIMARY

Chemical Name: 4-((4-(5-Methoxy-2-pyridinyl)phenoxy)methyl)-5-methyl-N-((2-methylphenyl)sulfonyl)-2-furancarboxamide hydrochloride Biological Activity: High affinity and selective EP4 antagonist (Ki = 3 nM). Exhibits >2500-fold selectivity for EP4 over EP2 and EP3. Also selective over a range of other prostanoid receptors, ion channels, transporters and enzymes. Inhibits PGE2-induced vasodilation of middle cerebral and meningeal arteries in vitro, and carotid blood flow in vivo. Orally bioavailable.

PUBCHEM

25209437

Created by admin on Tue Apr 01 16:29:57 GMT 2025 , Edited by admin on Tue Apr 01 16:29:57 GMT 2025

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FDA UNII

9QV7JG4XYZ

Created by admin on Tue Apr 01 16:29:57 GMT 2025 , Edited by admin on Tue Apr 01 16:29:57 GMT 2025

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Related Record Type Details


					Z49JYU6T3P

BGC-20-1531 free base

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					9QV7JG4XYZ

ACTIVE MOIETY

Comments:

Class: Anti-migraine; Mechanism of Action: Prostaglandin E4 antagonist; Highest Development Phase: Discontinued for Migraine; Most Recent Events: 23 Feb 2016 Discontinued - Phase-I for Migraine in United Kingdom (PO), 12 Jan 2016 BTG withdraw a phase II trial in Migraine in Denmark, Norway and United Kingdom (NCT00888680), 21 Sep 2011 AP 1531 licensed to Ariel Pharmaceuticals


					9QV7JG4XYZ

ACTIVE MOIETY

Comments:

The chemical structure of BGC20-1531 (N-(4-(4-(5-methoxypyridin-2-yl)phenoxymethyl)-5-methylfuran-2-carbonyl)-2-methylbenzenesulphonamide sodium salt). Key results: BGC20-1531 exhibited high affinity at recombinant human EP4 receptors expressed in cell lines (pKB 7.6) and native EP4 receptors in human cerebral and meningeal artery (pKB 7.67.8) but showed no appreciable affinity at a wide range of other receptors (including other prostanoid receptors), channels, transporters and enzymes (pKi < 5). BGC20-1531 competitively antagonized PGE2-induced vasodilatation of human middle cerebral (pKB 7.8) and meningeal (pKB 7.6) arteries in vitro, but had no effect on responses induced by PGE2 on coronary, pulmonary or renal arteries in vitro. BGC20-1531 (110 mgundefinedkg1 i.v.) caused a dose-dependent antagonism of the PGE2-induced increase in canine carotid blood flow in vivo. Conclusions and implications: BGC20-1531 is a potent and selective antagonist at EP4 receptors in vitro and in vivo, with the potential to alleviate the symptoms of migraine that result from cerebral vasodilatation. BGC20-1531 is currently in clinical development for the treatment of migraine headache.