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Merck
CN

SML0715

PF-8380

≥98% (HPLC)

Synonym(s):

4-[3-(2,3-Dihydro-2-oxo-6-benzoxazolyl)-3-oxopropyl]-1-piperazinecarboxylic acid (3,5-dichlorophenyl)methyl ester, 4-[3-Oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylic acid 3,5-dichlorobenzyl ester

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About This Item

Empirical Formula (Hill Notation):
C22H21Cl2N3O5
CAS Number:
1144035-53-9
Molecular Weight:
478.33
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−20°C

SMILES string

Clc1cc(cc(c1)COC(=O)N2CCN(CC2)CCC(=O)c3cc4[o][c]([nH]c4cc3)=O)Cl

InChI

1S/C22H21Cl2N3O5/c23-16-9-14(10-17(24)12-16)13-31-22(30)27-7-5-26(6-8-27)4-3-19(28)15-1-2-18-20(11-15)32-21(29)25-18/h1-2,9-12H,3-8,13H2,(H,25,29)

InChI key

JMSUDQYHPSNBSN-UHFFFAOYSA-N

Application

PF-8380 has been used in biological assays. It has also been used to estimate the role of intestinally-derived lysophosphatidic acid in dyslipidemia and atherosclerosis.

Biochem/physiol Actions

PF-8380 [6-(3-(piperazin-1-yl)propanoyl)benzo[d]oxazol-2(3H)-one] has the ability to change the resistant and invasive features of glioblastoma and helps to improve the response to radiation therapy.
PF-8380 is a potent orally bioavailable inhibitor of autotaxin (ATX), the enzyme that synthesize lysophosphatidic acid (LPA) from lysophosphatidyl choline, and is an emerging target for treatment of inflammatory conditions, including cancer, arthritis and multiple sclerosis. PF-8380 blocks inflammation-induced LPA synthesis. PF-8380 works both in vitro and in vivo through direct inhibition of autotaxin. In human whole blood PF-8380 inhibited autotaxin with an IC50 of 101 nM.
PF-8380 is a potent orally bioavailable inhibitor of autotaxin (ATX).

Storage Class Code

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
0000198549
0000165024
0000198549
0000165024
0000134743

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Source and role of intestinally-derived lysophosphatidic acid in dyslipidemia and atherosclerosis.
Navab M, et al.
Journal of Lipid Research, 59(11) (2015)
Design, synthesis, and biological evaluation of 2, 4-dihydropyrano [2, 3-c] pyrazole derivatives as autotaxin inhibitors.
Pantsar T, et al.
European Journal of Pharmaceutical Sciences, 107, 97-111 (2017)
Sandeep R Bhave et al.
Frontiers in oncology, 3, 236-236 (2013-09-26)
Glioblastoma multiforme (GBM) is an aggressive primary brain tumor that is radio-resistant and recurs despite aggressive surgery, chemo, and radiotherapy. Autotaxin (ATX) is over expressed in various cancers including GBM and is implicated in tumor progression, invasion, and angiogenesis. Using
Tatu Pantsar et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 107, 97-111 (2017-07-09)
Inhibition of Autotaxin (ATX) is a potential treatment strategy for several diseases, including tumors with elevated ATX-lysophosphatidic acid (LPA) signaling. Combining structure-based virtual screening together with hen egg-white Autotaxin (ewATX) activity assays enabled the discovery of novel small-molecule ATX inhibitors

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