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Key Documents

A8227

Sigma-Aldrich

AH23848 hemicalcium salt

≥90% (HPLC), powder

Synonyme(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

Formule empirique (notation de Hill):
C29H34NO5 · 0.5 Ca
Numéro CAS:
Poids moléculaire :
496.62
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Pureté

≥90% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 5 mg/mL, clear
H2O: insoluble

Auteur

GlaxoSmithKline

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

JDEBIDDIERGZQY-XVFRBOAOSA-L

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.

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
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)
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)
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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