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Technical details about Plerixafor, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: 110078-46-1, Mozobil, 1,4-bis((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzene, Amd3100, Amd 3100, Bicyclam jm-2987
Molecular Formula
C28H54N8
Molecular Weight
502.8  g/mol
InChI Key
YIQPUIGJQJDJOS-UHFFFAOYSA-N
FDA UNII
S915P5499N

Plerixafor is a bicyclam with hematopoietic stem cell-mobilizing activity. Plerixafor blocks the binding of stromal cell-derived factor (SDF-1alpha) to the cellular receptor CXCR4, resulting in hematopoietic stem cell (HSC) release from bone marrow and HSC movement into the peripheral circulation.
Plerixafor is a Hematopoietic Stem Cell Mobilizer. The physiologic effect of plerixafor is by means of Increased Hematopoietic Stem Cell Mobilization.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane
2.1.2 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
2.1.3 InChI Key
YIQPUIGJQJDJOS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CNCCNCCCN(CCNC1)CC2=CC=C(C=C2)CN3CCCNCCNCCCNCC3
2.2 Other Identifiers
2.2.1 UNII
S915P5499N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,1'-(1,4-phenylenebis(methylene))bis(1,4,8,11-tetraazacyclotetradecane)octahydrochloride Dihydrate

2. 1,1'-(1,4-phenylenebis-(methylene))-bis-1,4,8,11-tetraazacyclotetradecane

3. 1,1'-(1,4-phenylenebis-(methylene))-bis-1,4,8,11-tetraazacyclotetradecane Octahydrochloride Dihydrate

4. Amd 3100

5. Amd 3329

6. Amd-3100

7. Amd-3329

8. Amd3100

9. Jm 3100

10. Jm3100

11. Mezobil

12. Mozobil

13. Plerixafor Hydrochloride

14. Plerixafor Octahydrobromide

15. Plerixafor Octahydrochloride

16. Rpa Bicyclam

2.3.2 Depositor-Supplied Synonyms

1. 110078-46-1

2. Mozobil

3. 1,4-bis((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzene

4. Amd3100

5. Amd 3100

6. Bicyclam Jm-2987

7. Plerixafor Hydrochloride

8. Sdz Sid 791

9. Plerixafor (amd3100)

10. Amd-3100

11. Jm3100

12. Jm 3100

13. 1-[[4-(1,4,8,11-tetrazacyclotetradec-1-ylmethyl)phenyl]methyl]-1,4,8,11-tetrazacyclotetradecane

14. Jkl 169

15. Jm-3100

16. Chembl18442

17. 1,1'-[1,4-phenylenebis(methylene)]bis-1,4,8,11-tetraazacyclotetradecane

18. S915p5499n

19. 1,1'-[1,4-phenylenebis(methylene)]bis[1,4,8,11-tetraazacyclotetradecane]

20. 1-{[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)phenyl]methyl}-1,4,8,11-tetraazacyclotetradecane

21. 1,4,8,11-tetraazacyclotetradecane, 1,1'-(1,4-phenylenebis(methylene))bis-

22. Mozobil (tn)

23. Plerixafor [usan]

24. Plerixaforum

25. Plerixafor [usan:inn:ban]

26. Sid791

27. 1,1'-[1,4-phenylenebis(methylene)]bis(1,4,8,11-tetraazacyclotetradecane)

28. Unii-s915p5499n

29. 1,1'-(1,4-phenylenebis(methylene))bis-1,4,8,11-tetraazacyclotetradecane

30. Gna & Amd-3100

31. Hha & Amd-3100

32. Jm 2987

33. Plerixafor [mi]

34. Plerixafor [inn]

35. Plerixafor [jan]

36. Plerixafor [vandf]

37. Plerixafor [mart.]

38. Plerixafor-d4 (deuterated)

39. Plerixafor [who-dd]

40. Schembl19038

41. Gtpl844

42. Plerixafor (jan/usan/inn)

43. Plerixafor [ema Epar]

44. Plerixafor [orange Book]

45. Dtxsid70869520

46. Amd-3100 (cxcr4)

47. Chebi:125354

48. Bcpp000104

49. Bcp02337

50. Ex-a1762

51. Bdbm50035696

52. Mfcd05662218

53. Nsc754363

54. Nsc761388

55. S8030

56. Zinc22443609

57. 1,1'-{1,4-phenylenebis(methylene)}-bis{1,4,8,11-tetraaza-cyclotetradecane}

58. Akos005266706

59. Ccg-269710

60. Cs-0451

61. Db06809

62. Nsc-754363

63. Nsc-761388

64. Ncgc00165722-01

65. Ncgc00165722-02

66. Ncgc00165722-03

67. 1,1'-[1,4-phenylenebis(methylene)]bis[1,4,8,11-tetraazacyclotetradecane] & Galanthus Nivalis Agglutinin (gna)

68. Ac-26837

69. As-42504

70. Hy-10046

71. Ft-0660392

72. Ft-0673966

73. P2678

74. A25446

75. D08971

76. Ab01566900_01

77. 078p461

78. A809618

79. L000104

80. Q905835

81. Sr-01000941593

82. J-503718

83. Sr-01000941593-1

84. 11''''-xylyl Bis-1,4,8,11-tetraazacyclotetradecane

85. Brd-k33240821-367-01-8

86. Z2196779619

87. 1,1''''-{1,4-phenylenebis(methylene)}-bis{1,4,8,11-tetraaza-cyclotetradecane}

88. 1,1'-(benzene-1,4-diyldimethanediyl)bis(1,4,8,11-tetraazacyclotetradecane)

89. 1,1'[1,4-phenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclotetradecane

90. 1,1'-[1,4-phenylenebis(methylene)]bis[1,4,8,11-tetraazacyclotetradecane] & Hippeastrum Hybrid Agglutinin( Hha)

91. 1,4,8,11-tetraazacyclotetradecanyl[4-(1,4,8,11-tetraazacyclotetradecanylmethyl)phenyl]methane

92. 1,4,8,11-tetraazacyclotetradecanyl[4-(1,4,8,11-tetraazacyclotetradecanylmethyl)phenyl]methane(8hbr.2h2o)

93. 1,4-bis((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzene Octahydrochloride;plerixafor Octahydrochloride

94. 1-({4-[(1,4,8,11-tetraazacyclotetradecan-1-yl)methyl]phenyl}methyl)-1,4,8,11-tetraazacyclotetradecane

95. 11-{4-[4,8, 11-1,4,8,11tetraaza-cyclotetradec-1-ylmethyl]-benzyl}-1,4,8,11tetraaza-cyclotetradecane-1,4,8-tricarboxylic Acid Tri-tert-butyl Ester

2.4 Create Date
2005-08-01
3 Chemical and Physical Properties
Molecular Weight 502.8 g/mol
Molecular Formula C28H54N8
XLogP30
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass502.44714376 g/mol
Monoisotopic Mass502.44714376 g/mol
Topological Polar Surface Area78.7 Ų
Heavy Atom Count36
Formal Charge0
Complexity456
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameMozobil
PubMed HealthPlerixafor (Injection)
Drug ClassesHematopoietic
Drug LabelMozobil (plerixafor injection) is a sterile, preservative-free, clear, colorless to pale yellow, isotonic solution for subcutaneous injection. Each mL of the sterile solution contains 20 mg of plerixafor. Each single-use vial is filled to deliver 1...
Active IngredientPlerixafor
Dosage FormSolution
RouteSubcutaneous
Strength24mg/1.2ml (20mg/ml)
Market StatusPrescription
CompanyGenzyme

2 of 2  
Drug NameMozobil
PubMed HealthPlerixafor (Injection)
Drug ClassesHematopoietic
Drug LabelMozobil (plerixafor injection) is a sterile, preservative-free, clear, colorless to pale yellow, isotonic solution for subcutaneous injection. Each mL of the sterile solution contains 20 mg of plerixafor. Each single-use vial is filled to deliver 1...
Active IngredientPlerixafor
Dosage FormSolution
RouteSubcutaneous
Strength24mg/1.2ml (20mg/ml)
Market StatusPrescription
CompanyGenzyme

4.2 Drug Indication

Used in combination with granulocyte-colony stimulating factor (G-CSF, filgrastim) to mobilize hematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkins lymphoma (NHL) and multiple myeloma (MM).


FDA Label


Mozobil is indicated in combination with granulocyte-colony-stimulating factor to enhance mobilisation of haematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation in patients with lymphoma and multiple myeloma whose cells mobilise poorly.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Plerixafor is a bicyclam derivative that antagonizes CXCR4 by binding to three acidic residues in the ligand-binding pocket: Asp171, Asp262, and Glu288. Blood levels of CD34+ cells peaked at 9 hours after administration of 0.24 mg/kg plerixafor in healthy subjects. In patients that have non-Hodgkins lymphoma or multiple myeloma, blood levels of CD34+ peaked at 6 hours. In combination with a G-CSF, circulating CD34+ cells in the peripheral blood peaked at 9-14 hours.


5.2 MeSH Pharmacological Classification

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
PLERIXAFOR
5.3.2 FDA UNII
S915P5499N
5.3.3 Pharmacological Classes
Increased Hematopoietic Stem Cell Mobilization [PE]; Hematopoietic Stem Cell Mobilizer [EPC]
5.4 ATC Code

L03AX16


L03AX16

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


L - Antineoplastic and immunomodulating agents

L03 - Immunostimulants

L03A - Immunostimulants

L03AX - Other immunostimulants

L03AX16 - Plerixafor


5.5 Absorption, Distribution and Excretion

Absorption

Pharmacokinetic profile follows a two-compartment model with first-order absorption. A median peak plasma concentration of 0.24 mg/kg of plerixafor occurred 30-60 minutes after subcutaneous dose.


Route of Elimination

0.24 mg/kg, healthy subjects: ~70% of the parent drug is excreted in urine in the first 24 hours.


Volume of Distribution

0.3 L/kg


Clearance

Total plasma clearance: 4.38 L/h; Renal clearance: 3.15 L/h


5.6 Metabolism/Metabolites

Metabolism does not involved CYP isoenzymes


5.7 Biological Half-Life

Terminal elimination half-life, NHL patients: 4.4 hours; Terminal elimination half-life, MM patients: 5.6 hours; Terminal elimination half-life, Hodgkin's lymphoma patients: 3.5 hours; Distribution half-life: 0.3 hours


5.8 Mechanism of Action

Plerixafor inhibits the CXCR4 chemokine receptors on CD34+ cells and reversibly blocks binding of the ligand, stromal cell-derived factor-1-alpha (SDF-1). By blocking the interaction between SDF-1 and CXCR4 with plerixafor, mobilization of progenitor cells is triggered. Filgrastim, a granulocyte-colony stimulating factor, is added to enhance CD34+ cell mobilization, thus increasing the yield of stem cells- an important determinant of graft adequacy.


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