Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H24ClFN4O3.ClH |
| Molecular Weight | 471.353 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C[C@@H]1CN(CC2=CC=C(F)C=C2)CCN1C(=O)COC3=C(NC(N)=O)C=C(Cl)C=C3
InChI
InChIKey=FRUCNQBAWUHKLS-PFEQFJNWSA-N
InChI=1S/C21H24ClFN4O3.ClH/c1-14-11-26(12-15-2-5-17(23)6-3-15)8-9-27(14)20(28)13-30-19-7-4-16(22)10-18(19)25-21(24)29;/h2-7,10,14H,8-9,11-13H2,1H3,(H3,24,25,29);1H/t14-;/m1./s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11805137 | https://www.ncbi.nlm.nih.gov/pubmed/11054419 | https://clinicaltrials.gov/ct2/show/NCT00185341
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11805137 | https://www.ncbi.nlm.nih.gov/pubmed/11054419 | https://clinicaltrials.gov/ct2/show/NCT00185341
BX 471 is an oral nonpeptide chemokine receptor1 (CCR1) antagonist that was under clinical development with Bayer Healthcare Pharmaceuticals (formerly Bayer Schering Pharma AG and Berlex) for the treatment of various inflammation-related disorders, including endometriosis. The CCR1 antagonist was also thought to have potential application in diagnostic imaging, particularly as an imaging biomarker for the diagnosis of Alzheimer's disease. Berlex initiated the development of the radiolabelled small molecule CCR1 antagonist, BX 471, for a specific diagnostic test for both early detection and for tracking disease progression following the discovery that the CCR1 protein was found in the brains of patients with Alzheimer's disease, and that increased levels of this protein were correlated with advancement of the disease. However, development of the agent for diagnostic imaging appears to have been discontinued. BX 471 was also in development for the treatment of autoimmune diseases, including multiple sclerosis and psoriasis; however, development in these indications, as well as multiple myeloma and endometriosis, also appears to have been discontinued. A phase II study of BX 471 in endometriosis had been completed.
Originator
Approval Year
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
16 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10748002 |
4 mg/kg single, oral dose: 4 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
BX-471 FREE BASE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
27 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10748002 |
4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
BX-471 FREE BASE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10748002 |
4 mg/kg single, oral dose: 4 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
BX-471 FREE BASE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10748002 |
4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
BX-471 FREE BASE plasma | Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Sample Use Guides
To evaluate efficacy of BX 471 in the treatment of endometriosis associated pelvic pain BX 471 (600 mg) was administrated orally three times daily over 12 weeks.
Route of Administration:
Oral
HEK 293 cells transfected with human or rat CCR1 were incubated with 125I-MIP-1a in the presence of increasing concentrations of BX471. Scatchard analysis of displacement binding studies with BX471 on rat CCR1 revealed that the affinity of the antagonist was 121 +/-60 nM ;100 times less effective for rat CCR1 than for human CCR1.
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SUB193709
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DTXSID50183019
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288262-96-4
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L350B5LO1J
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ACTIVE MOIETY
SUBSTANCE RECORD
