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Merck
CN

A8227

AH23848 hemicalcium salt

≥90% (HPLC), powder

Synonym(s):

(4Z)-7-[(rel-1S,2S,5R)-5-((1,1′-Biphenyl-4-yl)methoxy)-2-(4-morpholinyl)-3-oxocyclopentyl]- 4-heptenoic acid hemicalcium salt

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About This Item

Empirical Formula (Hill Notation):
C29H34NO5 · 0.5 Ca
CAS Number:
81496-19-7
Molecular Weight:
496.62
NACRES:
NA.77
PubChem Substance ID:
24724400
UNSPSC Code:
12352200
MDL number:
MFCD05665139

Key Documents

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form

powder

InChI key

JDEBIDDIERGZQY-XVFRBOAOSA-L

SMILES string

O=C(C[C@@H](OCC1=CC=C(C2=CC=CC=C2)C=C1)[C@H]3CC/C=C\CCC(O[Ca]OC(CC/C=C\CC[C@@H]4[C@H](OCC5=CC=C(C6=CC=CC=C6)C=C5)CC([C@H]4N7CCOCC7)=O)=O)=O)[C@H]3N8CCOCC8

InChI

1S/2C29H35NO5.Ca/c2*31-26-20-27(35-21-22-12-14-24(15-13-22)23-8-4-3-5-9-23)25(10-6-1-2-7-11-28(32)33)29(26)30-16-18-34-19-17-30;/h2*1-5,8-9,12-15,25,27,29H,6-7,10-11,16-21H2,(H,32,33);/q;;+2/p-2/b2*2-1-;/t2*25-,27-,29+;/m11./s1

assay

≥90% (HPLC)

color

white to beige

solubility

DMSO: 5 mg/mL, clear, H2O: insoluble

originator

GlaxoSmithKline

storage temp.

−20°C

Quality Level

100

Application

AH23848 has been used as an prostaglandin E2 receptor 4 (EP4) receptor antagonist to study its effect on cAMP accumulation in monocrotaline (MCT28d) rat pulmonary arterial smooth muscle cells (PASMCs) and human T cell enriched peripheral blood mononuclear cells (PBMC). It has also been used to study its effect on the expressions of collagen-I, metalloproteinase (MMP-1), MMP-3, and EP4 gene expression in human tendon fibroblasts following interleukin (IL)-1β treatment.

Biochem/physiol Actions

AH23848 regulates nitric oxide (NO) production and reduces endogenous cAMP accumulation. This is carried out by declination of inducible nitric oxide synthase (iNOS) gene expression and acceleration of iNOS protein degradation in glomerular mesangial cells.
EP4 prostanoid receptor antagonist with TP blocking activity.

Features and Benefits

This compound is featured on the Prostanoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000204707
0000204707
0000056594
0000056595
053M4620V

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AH23848 accelerates inducible nitric oxide synthase degradation through attenuation of cAMP signaling in glomerular mesangial cells
Lin YS, et al.
Nitric Oxide, 18(2), 93-104 (2008)
Lipoic acid stimulates cAMP production in T lymphocytes and NK cells
Schillace RV, et al.
Biochemical and biophysical research communications, 354(1), 259-264 (2007)
EP4 receptor regulates collagen type-I, MMP-1, and MMP-3 gene expression in human tendon fibroblasts in response to IL-1$\beta$ treatment
Thampatty BP, et al.
Gene, 386(1-2), 154-161 (2007)
Role of the prostanoid EP4 receptor in iloprost-mediated vasodilatation in pulmonary hypertension
Lai YJ, et al.
American Journal of Respiratory and Critical Care Medicine, 178(2), 188-196 (2008)
Samuel J Taylor et al.
The Journal of pharmacology and experimental therapeutics, 340(2), 377-385 (2011-11-09)
The principal aim of the study was to determine the influence of influenza A virus infection on capsaicin-induced relaxation responses in mouse isolated tracheal segments and clarify the underlying mechanisms. Anesthetized mice were intranasally inoculated with influenza A/PR-8/34 virus (VIRUS)
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