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
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
| 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 | C26H23N2O6S |
| Molecular Weight | 491.536 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:31:13 UTC 2023
by
admin
on
Sat Dec 16 11:31:13 UTC 2023
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| Record UNII |
9QV7JG4XYZ
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| Record Status |
Validated (UNII)
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| Record Version |
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300000042403
Created by
admin on Sat Dec 16 11:31:13 UTC 2023 , Edited by admin on Sat Dec 16 11:31:13 UTC 2023
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1186532-61-5
Created by
admin on Sat Dec 16 11:31:13 UTC 2023 , Edited by admin on Sat Dec 16 11:31:13 UTC 2023
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BGC-20-1531
Created by
admin on Sat Dec 16 11:31:13 UTC 2023 , Edited by admin on Sat Dec 16 11:31:13 UTC 2023
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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. | ||
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25209437
Created by
admin on Sat Dec 16 11:31:13 UTC 2023 , Edited by admin on Sat Dec 16 11:31:13 UTC 2023
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9QV7JG4XYZ
Created by
admin on Sat Dec 16 11:31:13 UTC 2023 , Edited by admin on Sat Dec 16 11:31:13 UTC 2023
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
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
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ACTIVE MOIETY |
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.
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