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1144035-53-9

1144035-53-9 Structure

1144035-53-9 Structure
IdentificationBack Directory
[Name]

4-[3-Oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylic acid 3,5-dichlorobenzyl ester
[CAS]

1144035-53-9
[Synonyms]

CS-894
PF 8380
PF-8380 HCL
PF 8380; PF8380
PF-8380;PF 8380;PF8380
PF-8380, ATX Inhibitor
Autotaxin Inhibitor III, PF-8380
Autotaxin Inhibitor III, PF-8380 - CAS 1144035-53-9 - Calbiochem
3,5-Dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)propyl)piperazine-1-ca.
3,5-Dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo-[d]oxazol-6-yl)propyl)piperazine-1-carbo
3,5-dichlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-2-carboxylate
3,5-dichlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylate
3,5-Dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo-[d]oxazol-6-yl)propyl)piperazine-1-carboxyl
3,5-dichlorobenzyl 4-(3-oxo-3-(2-oxo-2,3-dihydrobenzo[d]oxazol-6-yl)propyl)piperazine-1-carboxylate
3,5-Dichlorobenzyl 4-[3-oxo-3-(2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)propyl]-1-piperazinecarboxylate
4-[3-Oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylic acid 3,5-dichlorobenzyl ester
4-[3-(2,3-Dihydro-2-oxo-6-benzoxazolyl)-3-oxopropyl]-1-piperazinecarboxylic acid (3,5-dichlorophenyl)methyl ester
1-Piperazinecarboxylic acid, 4-[3-(2,3-dihydro-2-oxo-6-benzoxazolyl)-3-oxopropyl]-, (3,5-dichlorophenyl)methyl ester
[Molecular Formula]

C22H21Cl2N3O5
[MDL Number]

MFCD20527274
[MOL File]

1144035-53-9.mol
[Molecular Weight]

478.33
Chemical PropertiesBack Directory
[Melting point ]

149-150 °C
[density ]

1.419
[storage temp. ]

-20°C
[solubility ]

DMSO: soluble5mg/mL, clear (warmed)
[form ]

Tan powder
[pka]

8.74±0.70(Predicted)
[color ]

white to beige
[InChI]

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)
[InChIKey]

JMSUDQYHPSNBSN-UHFFFAOYSA-N
[SMILES]

N1(C(OCC2=CC(Cl)=CC(Cl)=C2)=O)CCN(CCC(C2C=C3OC(=O)NC3=CC=2)=O)CC1
Safety DataBack Directory
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

PF8380 is a novel autotaxin inhibitor which reduces lysophosphatidic acid levels in plasma and at the site of inflammation.
[General Description]

An orally bioavailable piperazinylbenzoxazolone compound that acts as a substrate competitive and tight-binding inhibitor of autotaxin activity {IC50 = 2.8 and 1.7 nM for recombinant human enzyme-β isoform employing FS-3 and LPC (lysophosphatidylcholine) as substrates, respectively; 1.16 and 1.15 nM for rat/murine enzyme-FS-3 and fetal fibroblast cell-LPC; 101 nM for human whole blood}. Displays desirable pharmacokinetics properties and efficiently blocks inflammation-induced LPA (lysophosphatidic acid) production both in plasma and at the site of inflammation by 95% in rat adjuvant-induced arthritis model (30 mg/kg, p.o.).
[Biological Activity]

pf-8380 is a specific and potent inhibitor of autotaxin (atx) with an ic50 value of 2.8 nm [1].autotaxin (atx) is a secreted enzyme having lysophospholipase d activity
[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.
[in vivo]

The pharmacokinetic profile of PF-8380 is evaluated at an intravenous dose of 1 mg/kg and oral doses of 1 to 100 mg/kg out to 24 h. PF-8380 has mean clearance of 31 mL/min/kg, volume of distribution at steady state of 3.2 L/kg, and effective t1/2 of 1.2 h. Oral bioavailability is moderate, ranging from 43 to 83%. Plasma concentrations increased with single oral escalating doses, but Cmax increased at a rate that is approximately proportional to dose from 1 to 10 mg/kg and less than proportional to dose from 10 to 100 mg/kg. PF-8380 exposures estimated by area under the curve are approximately proportional to dose and linear up to 100 mg/kg. Plasma C16:0, C18:0, and C20:0 LPA levels are measured immediately after collection. Maximal reduction of LPA levels is observed by the 3 mg/kg dose at 0.5 h with all LPA returning at or above baseline at 24 h[1]. Treatment with 10 mg/kg PF-8380 increases tumor-associated vascularity modestly by 20% (P=0.497). When compared to control, treatment of PF-8380 45 min before 4 Gy irradiation decreases vascularity by nearly 48% when compared to control (P=0.031) and by 65% when compared to mice that received radiation alone (P=0.011)[2].

[IC 50]

Autotaxin: 2.8 nM (IC50, In isolated enzyme assay)
Spectrum DetailBack Directory
[Spectrum Detail]

4-[3-Oxo-3-(2-oxo-2,3-dihydrobenzoxazol-6-yl)propyl]piperazine-1-carboxylic acid 3,5-dichlorobenzyl ester(1144035-53-9)1HNMR
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