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Mavorixafor

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Synopsis

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Chemistry

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Also known as: 558447-26-0, Amd-070, Mavorixafor, Amd070, Amd11070, Amd 070

Molecular Formula

C₂₁H₂₇N₅

Molecular Weight

349.5 g/mol

InChI Key

WVLHHLRVNDMIAR-IBGZPJMESA-N

FDA UNII

0G9LGB5O2W

Mavorixafor is an orally bioavailable inhibitor of C-X-C chemokine receptor type 4 (CXCR4), with potential antineoplastic and immune checkpoint inhibitory activities. Upon administration, mavorixafor selectively binds to CXCR4 and prevents the binding of CXCR4 to its ligand, stromal cell-derived factor 1 (SDF-1 or CXCL12). This inhibits receptor activation and results in decreased proliferation and migration of CXCR4-overexpressing tumor cells. In addition, inhibition of CXCR4 prevents the recruitment of regulatory T-cells and myeloid-derived suppressor cells (MDSCs) to the tumor microenvironment, thereby abrogating CXCR4-mediated immunosuppression and enabling the activation of a cytotoxic T-lymphocyte-mediated immune response against cancer cells. The G protein-coupled receptor CXCR4, which is upregulated in several tumor cell types, induces the recruitment of immunosuppressive cells in the tumor microenvironment, suppresses immune surveillance, and promotes tumor angiogenesis and tumor cell proliferation. It is also a co-receptor for HIV entry into T-cells.

1 2D Structure

Mavorixafor

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N'-(1H-benzimidazol-2-ylmethyl)-N'-[(8S)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine

2.1.2 InChI

InChI=1S/C21H27N5/c22-12-3-4-14-26(15-20-24-17-9-1-2-10-18(17)25-20)19-11-5-7-16-8-6-13-23-21(16)19/h1-2,6,8-10,13,19H,3-5,7,11-12,14-15,22H2,(H,24,25)/t19-/m0/s1

2.1.3 InChI Key

WVLHHLRVNDMIAR-IBGZPJMESA-N

2.1.4 Canonical SMILES

C1CC(C2=C(C1)C=CC=N2)N(CCCCN)CC3=NC4=CC=CC=C4N3

2.1.5 Isomeric SMILES

C1C[C@@H](C2=C(C1)C=CC=N2)N(CCCCN)CC3=NC4=CC=CC=C4N3

2.2 Other Identifiers

2.2.1 UNII

0G9LGB5O2W

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amd 070

2. Amd 11070

3. Amd-070

4. Amd-11070

5. Amd070

6. Amd11070

7. Mavorixafor

8. N'-((1h-benzo(d)imidazol-2-yl)methyl)-n'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

9. X 4p-001

10. X4p-001

11. X4p001

2.3.2 Depositor-Supplied Synonyms

1. 558447-26-0

2. Amd-070

3. Mavorixafor

4. Amd070

5. Amd11070

6. Amd 070

7. Amd-11070

8. X4p-001

9. Mavorixafor [usan]

10. X4p001

11. Cxcr4 Inhibitor X4p-001

12. 0g9lgb5o2w

13. X 4p-001

14. Chembl518924

15. Mavorixafor (usan)

16. N'-(1h-benzimidazol-2-ylmethyl)-n'-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine

17. Amd-070 (amd11070)

18. Unii-0g9lgb5o2w

19. Amd 11070

20. Compound 2 [pmid: 20297846]

21. Amd-070; Mavorixafor

22. Mavorixafor [inn]

23. Mavorixafor [who-dd]

24. Gtpl8580

25. Schembl2511950

26. Dtxsid60971247

27. Chebi:138865

28. X4p-001-io

29. X4p-001-ld

30. Bcp07108

31. Ex-a2661

32. Bdbm50315305

33. Mfcd11977316

34. Nsc775637

35. Who 10724

36. Zinc33359232

37. Amd-070 Hcl 75%(w/w%)

38. Cs-0352

39. Cs-1257

40. Db05501

41. Nsc-775637

42. Ncgc00378947-01

43. Ncgc00378947-02

44. Ncgc00378947-03

45. Hy-50101

46. N~1~-[(1h-benzimidazol-2-yl)methyl]-n~1~-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

47. C20266

48. D11510

49. F31237

50. Q27074430

51. (s)-n-((1h-benzo[d]imidazol-2-yl)methyl)-n-(4-aminobutyl)-5,6,7,8-tetrahydroquinolin-8-amine

52. 1,4-butanediamine, N-(1h-benzimidazol-2-ylmethyl)-n-((8s)-5,6,7,8-tetrahydro-8-quinolinyl)-

53. 1,4-butanediamine, N1-(1h-benzimidazol-2-ylmethyl)-n1-((8s)-5,6,7,8-tetrahydro-8-quinolinyl)-

54. 690656-53-2

55. N'-((1h-benzo(d)imidazol-2-yl)methyl)-n'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamine

56. N-(1h-benzimidazol-2-ylmethyl)-n-[(8s)-5,6,7,8-tetrahydroquinolin-8-yl]butane-1,4-diamine

57. N1-(1h-benzimidazol-2-ylmethyl)-n1-((s)-5,6,7,8-tetrahydroquinolin-8-yl)-butane-1,4-diamine

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₇N₅
Molecular Weight	349.5 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	349.22664588 g/mol
Monoisotopic Mass	349.22664588 g/mol
Topological Polar Surface Area	70.8 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	431
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in HIV infection.

5 Pharmacology and Biochemistry

5.1 Pharmacology

AMD-070 is a small molecule drug candidate that belongs to a new investigational class of anti-HIV drugs known as entry (fusion) inhibitors. Approximately 76% of HIV-patients with measurable viral load are infected with a strain of virus that is resistant to one or more classes of antiretroviral agents, thus reducing treatment options. Unlike many existing HIV drugs that target the virus after it has infected a healthy cell, AMD-070 blocks the virus from entering a healthy cell, thus preventing the replication process. AMD-070 targets the CXCR4 receptor on HIV and prevents the virus from entering and infecting healthy cells. * AMD-070 is specific for the CXCR4 receptor and does not interact with any other chemokine receptors in vitro * AMD-070 strongly inhibits viral infection by all CXCR4 using virus (including virus using CXCR4 alone and/or virus using CXCR4 and CCR5) in vitro * AMD-070 is orally bioavailable in animals * Suitable PK and toxicity profile for oral dosing * AMD-070 shows additive or synergistic effects in vitro in combination with other known anti-HIV agents * AMD-070 is active against CXCR4 using HIV strains that are resistant to existing antiretroviral therapies in vitro * Potent anti-HIV activity against CXCR4-using laboratory strains and clinical isolates

5.2 Mechanism of Action

Chemokine receptors expressed on the surface of immune cells are known to play a critical role in virus infection and transmission. CXCR4, and another chemokine receptor CCR5, are involved in HIV infection. The process of HIV entry begins with binding of the viral envelope glycoprotein to both the CD4 receptor and one of only two chemokine receptors, and ends with fusion of viral and cell membranes. Viral entry provides novel therapeutic targets against HIV. To date, at least 3 sub classes of HIV viral entry/fusion inhibitors have emerged: 1. CD4 binding or attachment - targets initial recognition and binding of the viral glycoprotein gp120 to the cell-surface CD4 antigen. 2. Chemokine co-receptor binding - targets binding of virus to the CCR5 or CXCR4 co-receptor. 3. Fusion Inhibition - targets the viral glycoprotein gp41 inhibiting the fusion of virus with the cell. Different strains of HIV prefer one receptor or the other, or may use either receptor to infect cells. * 35% of strains use both CXCR4 and CCR5 * 5% of strains are pure CXCR4 using * 60% of strains are pure CCR5 using * An infected individual may harbor different levels of both CXCR4 and CCR5 using virus * CXCR4 using virus independently predicts CD4 decline and HIV clinical progression and is associated with earlier mortality

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