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Merck
CN

B9305

BW 245C

≥98% (HPLC), solid

Synonym(s):

3-(3-Cyclohexyl-3-hydroxypropyl)-2,5-dioxo-(R*,S*)-(±)-4-imidazolineheptanioc acid

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About This Item

Empirical Formula (Hill Notation):
C19H32N2O5
CAS Number:
Molecular Weight:
368.47
PubChem Substance ID:
UNSPSC Code:
12352200
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assay

≥98% (HPLC)

form

solid

color

off-white

solubility

DMSO: soluble 10 mg/mL

originator

GlaxoSmithKline

storage temp.

−20°C

SMILES string

O[C@H](CCN1[C@@H](CCCCCCC(O)=O)C(=O)NC1=O)C2CCCCC2

InChI

1S/C19H32N2O5/c22-16(14-8-4-3-5-9-14)12-13-21-15(18(25)20-19(21)26)10-6-1-2-7-11-17(23)24/h14-16,22H,1-13H2,(H,23,24)(H,20,25,26)/t15-,16+/m0/s1

InChI key

ZIDQIOZJEJFMOH-JKSUJKDBSA-N

Gene Information

human ... PTGDR(5729)

Biochem/physiol Actions

BW 245C was investigated for the affinities potencies, and intrinsic activities in comparison with other natural and synthetic prostanoids using endogenous receptors. The rank order of compound affinities at the DP receptor was SQ27986 (K(i) = 10 +/- 2 nM) > RS93520 = ZK110841 = BW245C (K(i) = 23-26 nM) > ZK118182 (K(i) = 50 +/- 9 nM) > PGD(2) (K(i) = 80 +/- 5 nM). DP receptor agonists produced cAMP in embryonic bovine tracheal fibroblasts with different potencies (EC(50) values in nM): ZK118182 (18 +/- 6), RS93520 (28 +/- 6), SQ27986 (29 +/- 7), ZK110841 (31 +/- 7), BW245C (53 +/- 16), and PGD(2) (98 +/- 10). BW245C was more efficacious and RS93520 was less efficacious.

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

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Alicja Jozkowicz et al.
Antioxidants & redox signaling, 10(12), 2035-2046 (2008-07-31)
15-Deoxy-Delta(12,14)-prostaglandin-J(2) (15d-PGJ(2)) is a cyclopentenone prostaglandin regarded as antiinflammatory mediator, which can act through peroxisome proliferator-activated receptor-gamma (PPARgamma) or through G protein-coupled surface receptors. It has been demonstrated that 15d-PGJ(2) potently increases the generation of interleukin-8 (IL-8) in human microvascular
Xibin Liang et al.
Journal of neurochemistry, 92(3), 477-486 (2005-01-22)
Cyclo-oxygenases (COXs) catalyze the first committed step in the synthesis of the prostaglandins PGE(2), PGD(2), PGF(2alpha), PGI(2) and thomboxane A(2). Expression and enzymatic activity of COX-2, the inducible isoform of COX, are observed in several neurological diseases and result in
N A Sharif et al.
The Journal of pharmacology and experimental therapeutics, 293(2), 321-328 (2000-04-25)
The prostanoid receptor-subtype binding affinities, selectivities, potencies, and intrinsic activities of four natural prostanoids and six synthetic DP class prostanoids were determined using binding and functional assays with endogenous receptors. SQ27986 exhibited the highest affinity for the human platelet DP
Sarah J O'Meara et al.
British journal of pharmacology, 143(2), 292-302 (2004-08-25)
Prostacyclin plays a central role within the vasculature. We have previously established that the prostacyclin receptor (IP) undergoes isoprenylation, a lipid modification obligate for its function. The aim of the current study was to investigate the effect of the hydroxy
Sybille van den Brule et al.
The Journal of pharmacology and experimental therapeutics, 335(2), 472-479 (2010-08-20)
Prostaglandin (PG) D(2) exerts contrasting activities in the inflamed lung via two receptors, the D prostanoid receptor (DP) and the chemoattractant receptor-homologous molecule expressed on T helper 2 lymphocytes. DP activation is known mainly to inhibit proinflammatory cell functions. We

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