plerixafor   

GtoPdb Ligand ID: 844

Synonyms: AMD 3100 | AMD3100 | bicyclam JM-2987 | JM 3100 | Mozobil®
plerixafor is an approved drug (FDA (2008), EMA (2009))
Compound class: Synthetic organic
Comment: Plerixafor (AMD3100) is an antagonist of the chemokine (C-X-C motif) receptor 4 (CXCR4) [6]. It acts as a stem cell mobiliser.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 6
Rotatable bonds 4
Topological polar surface area 78.66
Molecular weight 502.45
XLogP 0.22
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES C1CNCCN(CCCNCCNC1)Cc1ccc(cc1)CN1CCNCCCNCCNCCC1
Isomeric SMILES C1CNCCN(CCCNCCNC1)Cc1ccc(cc1)CN1CCNCCCNCCNCCC1
InChI InChI=1S/C28H54N8/c1-9-29-15-17-31-13-3-21-35(23-19-33-11-1)25-27-5-7-28(8-6-27)26-36-22-4-14-32-18-16-30-10-2-12-34-20-24-36/h5-8,29-34H,1-4,9-26H2
InChI Key YIQPUIGJQJDJOS-UHFFFAOYSA-N
References
1. Adlere I, Sun S, Zarca A, Roumen L, Gozelle M, Viciano CP, Caspar B, Arimont M, Bebelman JP, Briddon SJ et al.. (2019)
Structure-based exploration and pharmacological evaluation of N-substituted piperidin-4-yl-methanamine CXCR4 chemokine receptor antagonists.
Eur J Med Chem, 162: 631-649. DOI: 10.1016/j.ejmech.2018.10.060 [PMID:30476826]
2. Fricker SP, Anastassov V, Cox J, Darkes MC, Grujic O, Idzan SR, Labrecque J, Lau G, Mosi RM, Nelson KL et al.. (2006)
Characterization of the molecular pharmacology of AMD3100: a specific antagonist of the G-protein coupled chemokine receptor, CXCR4.
Biochem. Pharmacol., 72 (5): 588-96. [PMID:16815309]
3. Gravel S, Malouf C, Boulais PE, Berchiche YA, Oishi S, Fujii N, Leduc R, Sinnett D, Heveker N. (2010)
The peptidomimetic CXCR4 antagonist TC14012 recruits beta-arrestin to CXCR7: roles of receptor domains.
J. Biol. Chem., 285 (49): 37939-43. [PMID:20956518]
4. Hatse S, Princen K, Bridger G, De Clercq E, Schols D. (2002)
Chemokine receptor inhibition by AMD3100 is strictly confined to CXCR4.
FEBS Lett., 527 (1-3): 255-62. [PMID:12220670]
5. Kalatskaya I, Berchiche YA, Gravel S, Limberg BJ, Rosenbaum JS, Heveker N. (2009)
AMD3100 is a CXCR7 ligand with allosteric agonist properties.
Mol. Pharmacol., 75 (5): 1240-7. [PMID:19255243]
6. Zhang WB, Navenot JM, Haribabu B, Tamamura H, Hiramatu K, Omagari A, Pei G, Manfredi JP, Fujii N, Broach JR, Peiper SC. (2002)
A point mutation that confers constitutive activity to CXCR4 reveals that T140 is an inverse agonist and that AMD3100 and ALX40-4C are weak partial agonists.
J Biol Chem, 277: 24515-24521. [PMID:11923301]