Burixafor

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Also known as: Burixafor [inn], 1191448-17-5, Tg-0054, 2g17y0q20g, Phosphonic acid, p-(2-(4-(6-amino-2-(((trans-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)-4-pyrimidinyl)-1-piperazinyl)ethyl)-, (2-(4-(6-amino-2-((((1r,4r)-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl)phosphonic acid

Molecular Formula

C₂₇H₅₁N₈O₃P

Molecular Weight

566.7 g/mol

InChI Key

QLVSJMZJSABWRX-UHFFFAOYSA-N

FDA UNII

2G17Y0Q20G

Burixafor is an orally bioavailable inhibitor of CXC chemokine receptor 4 (CXCR4) with receptor binding and hematopoietic stem cell-mobilization activities. Burixafor binds to the chemokine receptor CXCR4, thereby preventing the binding of stromal derived factor-1 (SDF-1 or CXCL12) to the CXCR4 receptor and subsequent receptor activation; this may induce the mobilization of hematopoietic stem and progenitor cells from the bone marrow into blood. CXCR4, a chemokine receptor belonging to the G protein-coupled receptor (GPCR) gene family, plays an important role in chemotaxis and angiogenesis and is upregulated in several tumor cell types; CXCL12/CXCR4 interaction induces retention of hematopoietic cells in the bone marrow.

1 2D Structure

Burixafor

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-[6-amino-2-[[4-[[3-(cyclohexylamino)propylamino]methyl]cyclohexyl]methylamino]pyrimidin-4-yl]piperazin-1-yl]ethylphosphonic acid

2.1.2 InChI

InChI=1S/C27H51N8O3P/c28-25-19-26(35-15-13-34(14-16-35)17-18-39(36,37)38)33-27(32-25)31-21-23-9-7-22(8-10-23)20-29-11-4-12-30-24-5-2-1-3-6-24/h19,22-24,29-30H,1-18,20-21H2,(H2,36,37,38)(H3,28,31,32,33)

2.1.3 InChI Key

QLVSJMZJSABWRX-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CCC(CC1)NCCCNCC2CCC(CC2)CNC3=NC(=CC(=N3)N4CCN(CC4)CCP(=O)(O)O)N

2.2 Other Identifiers

2.2.1 UNII

2G17Y0Q20G

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Burixafor [inn]

2. 1191448-17-5

3. Tg-0054

4. 2g17y0q20g

5. Phosphonic Acid, P-(2-(4-(6-amino-2-(((trans-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)-4-pyrimidinyl)-1-piperazinyl)ethyl)-

6. (2-(4-(6-amino-2-((((1r,4r)-4-(((3-(cyclohexylamino)propyl)amino)methyl)cyclohexyl)methyl)amino)pyrimidin-4-yl)piperazin-1-yl)ethyl)phosphonic Acid

7. Unii-2g17y0q20g

8. Burixafor [who-dd]

9. Chembl3545224

10. Schembl13332861

11. Schembl13354165

12. Schembl13354172

13. Schembl14693228

14. Schembl14693238

15. Tg0054

16. Db11970

17. Sb17205

18. Tg 0054

19. A857839

20. Q27254687

21. 2-[4-[6-amino-2-[[4-[[3-(cyclohexylamino)propylamino]methyl]cyclohexyl]methylamino]pyrimidin-4-yl]piperazin-1-yl]ethylphosphonic Acid

2.4 Create Date

2009-12-15

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₅₁N₈O₃P
Molecular Weight	566.7 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	14
Exact Mass	566.38217452 g/mol
Monoisotopic Mass	566.38217452 g/mol
Topological Polar Surface Area	152 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	724
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1