SML1981

NIBR189

≥98% (HPLC)

• Synonym(s): (2E)-3-(4-Bromophenyl)-1-(4-(4-methoxybenzoyl)-1-piperazinyl)-2-propen-1-one, (E)-3-(4-Bromophenyl)-1-(4-(4-methoxybenzoyl)piperazin-1-yl)prop-2-en-1-one, NIBR 189
• Empirical Formula (Hill Notation): C₂₁H₂₁BrN₂O₃
• CAS Number: 1599432-08-2
• Molecular Weight: 429.31
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 10 mg/mL, clear (warmed)
• storage temp.: room temp
• SMILES string: Brc1ccc(cc1)\C=C\C(=O)N2CCN(CC2)C(=O)c3ccc(cc3)OC
• InChI: 1S/C21H21BrN2O3/c1-27-19-9-5-17(6-10-19)21(26)24-14-12-23(13-15-24)20(25)11-4-16-2-7-18(22)8-3-16/h2-11H,12-15H2,1H3/b11-4+
• InChI key: OFHXXBRBGWUOHR-NYYWCZLTSA-N

Description

Biochem/physiol Actions

High-affinity, potent and selective EBI2 (GPR183) antagonist with good pharmacokinetic properties and oral availability in mice in vivo.

NBIR189 is a high-affinity, potent and selective EBI2 (GPR183) antagonist (IC50 = 16 nM against 10 nM 7α,25-OHC for binding human EBI2) that inhibits 7α,25-OHC-induced GTPγS binding (IC50 = 8.5 and 7.0 nM, respectively, against 0.33 and 0.1 nM OHC; human EBI2-expressing CHO membrane), calcium mobilization (IC50 = 11 and 15 nM using human or mouse EBI2-transfected cells, respectively), and chemotaxis (IC50 = 0.3 nM against 20 nM OHC-induced U937 migration). NBIR189 displays no inhibitory potency against 5HT2A, muscarinic acetylcholine receptor M2, adrenoreceptor α1A, nor significant affintiy toward 18 other GPCRs/transporters/enzymes, and exhibits good pharmacokinetic properties and oral availability in mice (AUC = 3608 nmol h/L, Cmax = 835 nM, tmax = 1 h, F = 49%; 3 mg/kg p.o.). A useful tool for probing EBI2-mediated physiological functions and autoimmune disorders.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable