≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
NBI-74330 is a potent antagonist for CXCR3 , and exhibits potent inhibition of ( 125 I)CXCL10 and ( 125 I)CXCL11 specific binding with K i of 1.5 and 3.2 nM, respectively.
In Vitro
BI-74330 demonstrates potent inhibition of [ 125 I]CXCL11 specific binding to membranes prepared from transfected CHO cells expressing CXCR3 (CXCR3-CHO) (K i =3.6 nM). NBI-74330 is 12- and 3.5-fold more potent than CXCL9 (K i =45.2 nM) and CXCL10 (K i =12.5 nM), respectively, at inhibiting [ 125 I]CXCL11 binding to CXCR3-CHO cell membranes. NBI-74330 inhibits calcium mobilization in response to CXCL11 and CXCL10 with an IC 50 value of 7 nM for both ligands used at their EC 80 concentrations (1 nM for CXCL11 and 30 nM for CXCL10). NBI-74330 specifically inhibits CXCR3-mediated calcium mobilization. NBI-74330 also dose-dependently inhibits CXCL11-induced [ 35 S]GTPγS binding in membranes of cells endogenously expressing CXCR3 (H9 cells, IC 50 value 5.5 nM). BI-74330 inhibits CXCL11-induced chemotaxis in these cells with an IC 50 of 3.9 nM. NBI-74330 (30-300 nm, 1-10 μM) produces concentration-dependent, parallel rightward shifts of the CXCL11 E/[A] curve with no significant change in the E/[A] curve maximal response. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
NBI-74330 (100 mg/kg) results in the formation of an N-oxide metabolite, also an antagonist of CXCR3, in mice. Mice treated with 100 mg/kg NBI-74330 (in 1% Na Doc in 0.5% 400Cp Methylcellulose) result in serum concentrations of approximately 1 μM. This concentration is sufficient to fully block the CXCR3 receptor in vivo. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Solid
IC50& Target:[ 125 I]CXCL10-CXCR3 1.5 nM (Ki, in CXCR3-CHO cell membranes) [ 125 I]CXCL11-CXCR3 3.2 nM (Ki, in CXCR3-CHO cell membranes)
| Canonical Smiles | CCOC1=CC=C(C=C1)N2C(=O)C3=C(N=CC=C3)N=C2C(C)N(CC4=CN=CC=C4)C(=O)CC5=CC(=C(C=C5)F)C(F)(F)F |
|---|---|
| IUPAC Name | N-[1-[3-(4-ethoxyphenyl)-4-oxopyrido[2,3-d]pyrimidin-2-yl]ethyl]-2-[4-fluoro-3-(trifluoromethyl)phenyl]-N-(pyridin-3-ylmethyl)acetamide |
| InChIKey | XMRGQUDUVGRCBS-UHFFFAOYSA-N |
| INCHI | 1S/C32H27F4N5O3/c1-3-44-24-11-9-23(10-12-24)41-30(39-29-25(31(41)43)7-5-15-38-29)20(2)40(19-22-6-4-14-37-18-22)28(42)17-21-8-13-27(33)26(16-21)32(34,35)36/h4-16,18,20H,3,17,19H2,1-2H3 |
| Isomeric SMILES | CCOC1=CC=C(C=C1)N2C(=O)C3=C(N=CC=C3)N=C2C(C)N(CC4=CN=CC=C4)C(=O)CC5=CC(=C(C=C5)F)C(F)(F)F |
| MeSH Entry Terms | N-1R-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydropyrido(2,3-d)pyrimidin-2-yl)-ethyl-N-pyridin-3-ylmethyl-2-(4-fluoro-3-trifluoromethylphenyl)acetamide;NBI-74330 |
| Molecular Weight | 605.58 |
| Reaxy-Rn | 11147943 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=11147943&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Trifluoromethylbenzenes |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Trifluoromethylbenzenes |
| Alternative Parents | Pyrido[2,3-d]pyrimidines Phenylacetamides Phenoxy compounds Phenol ethers Pyrimidones Alkyl aryl ethers Fluorobenzenes Pyridines and derivatives Aryl fluorides Tertiary carboxylic acid amides Heteroaromatic compounds Lactams Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organic oxides Organofluorides Alkyl fluorides Organonitrogen compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Pyridopyrimidine - Trifluoromethylbenzene - Pyrido[2,3-d]pyrimidine - Phenylacetamide - Phenol ether - Phenoxy compound - Alkyl aryl ether - Pyrimidone - Halobenzene - Fluorobenzene - Aryl halide - Pyrimidine - Pyridine - Aryl fluoride - Tertiary carboxylic acid amide - Heteroaromatic compound - Lactam - Carboxamide group - Carboxylic acid derivative - Ether - Azacycle - Organoheterocyclic compound - Alkyl halide - Alkyl fluoride - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organooxygen compound - Organohalogen compound - Organofluoride - Organonitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. |
| External Descriptors | Not available |
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Solubility | DMSO : 100 mg/mL (165.13 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 605.600 g/mol |
| XLogP3 | 5.000 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 9 |
| Exact Mass | 605.205 Da |
| Monoisotopic Mass | 605.205 Da |
| Topological Polar Surface Area | 88.000 Ų |
| Heavy Atom Count | 44 |
| Formal Charge | 0 |
| Complexity | 1020.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
