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Merck
CN

SML1913

ASB14780

≥98% (HPLC)

Synonym(s):

3-(3-Phenethyl-1-(4-phenoxyphenyl)-1H-indol-5-yl)propanoic acid, 2-amino-2-(hydroxymethyl)-1,3-propanediol, 3-[1-(4-Phenoxyphenyl)-3-(2-phenylethyl)-1H-indol-5-yl]propanoic acid, 2-amino-2-(hydroxymethyl)-1,3-propanediol

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About This Item

Empirical Formula (Hill Notation):
C31H27NO3 · C4H11NO3
CAS Number:
1069046-00-9
Molecular Weight:
582.69
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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InChI

1S/C31H27NO3.C4H11NO3/c33-31(34)20-13-24-12-19-30-29(21-24)25(14-11-23-7-3-1-4-8-23)22-32(30)26-15-17-28(18-16-26)35-27-9-5-2-6-10-27;5-4(1-6,2-7)3-8/h1-10,12,15-19,21-22H,11,13-14,20H2,(H,33,34);6-8H,1-3,5H2

InChI key

MBPXGBINIINSEU-UHFFFAOYSA-N

SMILES string

O=C(O)CCC1=CC2=C(N(C3=CC=C(OC4=CC=CC=C4)C=C3)C=C2CCC5=CC=CC=C5)C=C1.NC(CO)(CO)CO

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

ASB14780 can be a potential therapeutic for the treatment of asthma and other pulmonary diseases. In addition, its inhibitory function on group IVA phospholipase A2 (IVA-PLA2) qualifies this drug to be a potential candidate for the treatment of non-alcoholic fatty liver diseases.
ASB14780 is an indole-based selective and potent cytosolic phospholipase A2α inhibitor (IC50 = 20 nM/cPLA2α and >10 μM/sPLA2α). ASB14780 inhibits cPLA2α-dependent inflammatory responses both in cultures and in animals in vivo, including LPS-induced PGE2 production (IC50 = 0.5 μM; mouse peritoneal exudate cells), A23187-induced TXB2 production (IC50 = 0.54 and 0.64 μM using guinea pig and human whole blood, respectively), TPA-induced ear edema (50 mg/kg, p.o.; mice), OVA-induced asthma (5 - 20 mg/kg/d, p.o.; guinea pig), CCl4-induced hepatic fibrosis and high-fat cholesterol diet-induced fatty liver (0.1-0.3 g/kg/d, p.o.; mouse). SB14780 bioavailability is also demonstrated in dog and monkey, albeit at a lower value (F = 34.3%/dog and 30.9%/monkey vs. 89.6%/mouse).
ASB14780 is an indole-based selective and potent cytosolic phospholipase A2α inhibitor.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
037M4710V

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Toshiyuki Tomoo et al.
Journal of medicinal chemistry, 57(17), 7244-7262 (2014-08-08)
This article describes the design, synthesis, and biological evaluation of new indole-based cytosolic phospholipase A2α (cPLA2α, a group IVA phospholipase A2) inhibitors. A screening-hit compound from our library, (E)-3-{4-[(4-chlorophenyl)thio]-3-nitrophenyl}acrylic acid (5), was used to design a class of 3-(1-aryl-1H-indol-5-yl)propanoic acids
Shiho Kanai et al.
The Journal of pharmacology and experimental therapeutics, 356(3), 604-614 (2015-12-25)
We have previously shown that high-fat cholesterol diet (HFCD)-induced fatty liver and carbon tetrachloride (CCl4)-induced hepatic fibrosis are reduced in mice deficient in group IVA phospholipase A2 (IVA-PLA2), which plays a role in inflammation. We herein demonstrate the beneficial effects

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