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AMD 3465 hexahydrobromide
- Parent CAS: 185991-24-6
- Soluble in water and DMSO
- MF: C24H38N6.6HBr
- MW: 896.07
Description
Potent and selective CXCR4 antagonist; Potent anti-HIV agent that specifically blocks the interaction of HIV gp120 with CXCR4. Compared to AMD 3100 (Axon 1738), AMD3465 was even 10-fold more effective as a CXCR4 antagonist, while showing no interaction whatsoever with CCR5; AMD3465 has the potential to mobilize hematopoietic stem cells
More Information
| Parent CAS No. | 185991-24-6 |
|---|---|
| Chemical Name | N-(4-((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzyl)-1-(pyridin-2-yl)methanamine hexahydrobromide |
| SMILES | C1(CNCC2=CC=C(CN3CCCNCCNCCCNCC3)C=C2)=NC=CC=C1.Br.Br.Br.Br.Br.Br |
| MFCD | N.A. |
| InChi | InChI=1S/C24H38N6.6BrH/c1-2-13-29-24(5-1)20-28-19-22-6-8-23(9-7-22)21-30-17-4-12-26-15-14-25-10-3-11-27-16-18-30;;;;;;/h1-2,5-9,13,25-28H,3-4,10-12,14-21H2;6*1H |
| InChiKey | ARHBIBDGWDRBJH-UHFFFAOYSA-N |
| CID | 9897616 |
| Short Description | CXCR4 antgonist |
References
- S Hatse et al. AMD3465, a monomacrocyclic CXCR4 antagonist and potent HIV entry inhibitor. Biochem. Pharmacol. 2005, 70(5), 752-761.
- MM Rosenkilde et al. Molecular mechanism of action of monocyclam versus bicyclam non-peptide antagonists of the CXCR4 chemokine receptor. J. Biol. Chem. 2007, 282, 27354.
- V Bodart et al. Pharmacology of AMD3465: a small molecule antagonist of the chemokine receptor CXCR4. Biochem. Pharmacol. 2009, 78(8), 993-1000.
- GJ Bridger et al. Synthesis and structure-activity relationships of azamacrocyclic C-X-C chemokine receptor 4 antagonists: analogues containing a single azamacrocyclic ring are potent inhibitors of (...). J. Med. Chem. 2010, 53(3), 1250-1260.
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