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

• ChemBase ID: 4482
• Molecular Formular: C28H54N8
• Molecular Mass: 502.78196
• Monoisotopic Mass: 502.44714377
• SMILES: C1CNCCNCCCN(CCNC1)Cc1ccc(cc1)CN1CCCNCCNCCCNCC1
• Canonical 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
• InChIKey: YIQPUIGJQJDJOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)phenyl]methyl}-1,4,8,11-tetraazacyclotetradecane
• IUPAC Traditional name: plerixafor
• Brand Name: Mozobil
• Synonyms: AMD3100; Plerixafor; JM 3100, AMD3100; 1,4-Bis((1,4,8,11-tetraazacyclotetradecan-1-yl)methyl)benzene; 1,1'-[1,4-Phenylenebis(methylene)]bis-1,4,8,11-tetraazacyclotetradecane

Database IDs

• CAS Number: 155148-31-5; 110078-46-1
• MDL Number: MFCD05662218
• PubChem SID: 99443297; 160967914
• PubChem CID: 65015
• ATC CODE: L03AX16
• CHEMBL: 18442
• Chemspider ID: 58531
• DrugBank ID: DB06809
• IUPHAR ligand ID: 844
• KEGG ID: D08971
• Unique Ingredient Identifier: S915P5499N
• Wikipedia Title: Plerixafor
• Medline Plus: a609018

CALCULATED PROPERTIES

JChem

• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -14.815253
• LogD (pH = 7.4): -9.746932
• Log P: -0.43359208
• Molar Refractivity: 155.0134 cm^3
• Polarizability: 61.66723 Å^3
• Polar Surface Area: 78.66 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.62
• LOG S: -4.03
• Solubility (Water): 4.72e-02 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 123-127°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Target: CXCR
• Admin Routes: Subcutaneous injection
• Excretion: Renal
• Half Life: 3–5 hours
• Metabolism: None
• Protein Bound: Up to 58%
• Legal Status: Rx-only (US)
• Pregnancy Category: D (US)

Product Information

• Purity: 95+%
• Salt Data: Free Base

DETAILS

DrugBank - DB06809

• Drug Groups: approved
• Description: Plerixafor is a hematopoietic stem cell mobilizer. It is used to stimulate the release of stem cells from the bone marrow into the blood in patients with non-Hodgkin lymphoma and multiple myeloma. These stem cells are then collected and used in autologous stem cell transplantation to replace blood-forming cells that were destroyed by chemotherapy. Plerixafor has orphan drug status in the United States and European Union; it was approved by the U.S. Food and Drug Administration on December 15, 2008.
• Indication: Used in combination with granulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin’s lymphoma (NHL) and multiple myeloma (MM).
• Pharmacology: Plerixafor increases circulating CD34+ cells in the peripheral blood, with a peak effect about 6-9 hours.
• Absorption: Plerixafor is rapidly absorbed after subcutaneous injection (Tmax = 30-60 min).
• Half Life: Terminal half-life ranges from 3 to 5 hours.
• Protein Binding: Plerixafor is bound to human plasma proteins up to 58%.
• Elimination: Approximately 70% of the parent drug is excreted in urine during first 24 h.
• Distribution: The apparent volume of distribution of plerixafor is 0.3 L/kg.
• References: Uy GL, Rettig MP, Cashen AF: Plerixafor, a CXCR4 antagonist for the mobilization of hematopoietic stem cells. Expert Opin Biol Ther. 2008 Nov;8(11):1797-804. [Pubmed] ; Fricker SP: A novel CXCR4 antagonist for hematopoietic stem cell mobilization. Expert Opin Investig Drugs. 2008 Nov;17(11):1749-60. [Pubmed] ; DiPersio JF, Stadtmauer EA, Nademanee A, Micallef IN, Stiff PJ, Kaufman JL, Maziarz RT, Hosing C, Fruehauf S, Horwitz M, Cooper D, Bridger G, Calandra G: Plerixafor and G-CSF versus placebo and G-CSF to mobilize hematopoietic stem cells for autologous stem cell transplantation in patients with multiple myeloma. Blood. 2009 Jun 4;113(23):5720-6. Epub 2009 Apr 10. [Pubmed] ; Stewart DA, Smith C, MacFarland R, Calandra G: Pharmacokinetics and pharmacodynamics of plerixafor in patients with non-Hodgkin lymphoma and multiple myeloma. Biol Blood Marrow Transplant. 2009 Jan;15(1):39-46. [Pubmed] ; Brave M, Farrell A, Ching Lin S, Ocheltree T, Pope Miksinski S, Lee SL, Saber H, Fourie J, Tornoe C, Booth B, Yuan W, He K, Justice R, Pazdur R: FDA review summary: Mozobil in combination with granulocyte colony-stimulating factor to mobilize hematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation. Oncology. 2010;78(3-4):282-8. Epub 2010 Jun 8. [Pubmed] ; Choi HY, Yong CS, Yoo BK: Plerixafor for stem cell mobilization in patients with non-Hodgkin's lymphoma and multiple myeloma. Ann Pharmacother. 2010 Jan;44(1):117-26. Epub 2009 Dec 15. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - P580500

Plerixafor is a hematopoietic stem cell (HSC) mobilizer that inhibits the CXCR4 chemokine receptor and blocks binding of its ligand, stromal cell-derived factor-1-α (SDF-1-α). This agent was approved on Dec. 15, 2008, as treatment in combination with gran

REFERENCES

• Uy GL, Rettig MP, Cashen AF: Plerixafor, a CXCR4 antagonist for the mobilization of hematopoietic stem cells. Expert Opin Biol Ther. 2008 Nov;8(11):1797-804. Pubmed
• Fricker SP: A novel CXCR4 antagonist for hematopoietic stem cell mobilization. Expert Opin Investig Drugs. 2008 Nov;17(11):1749-60. Pubmed
• DiPersio JF, Stadtmauer EA, Nademanee A, Micallef IN, Stiff PJ, Kaufman JL, Maziarz RT, Hosing C, Fruehauf S, Horwitz M, Cooper D, Bridger G, Calandra G: Plerixafor and G-CSF versus placebo and G-CSF to mobilize hematopoietic stem cells for autologous stem cell transplantation in patients with multiple myeloma. Blood. 2009 Jun 4;113(23):5720-6. Epub 2009 Apr 10. Pubmed
• Stewart DA, Smith C, MacFarland R, Calandra G: Pharmacokinetics and pharmacodynamics of plerixafor in patients with non-Hodgkin lymphoma and multiple myeloma. Biol Blood Marrow Transplant. 2009 Jan;15(1):39-46. Pubmed
• Brave M, Farrell A, Ching Lin S, Ocheltree T, Pope Miksinski S, Lee SL, Saber H, Fourie J, Tornoe C, Booth B, Yuan W, He K, Justice R, Pazdur R: FDA review summary: Mozobil in combination with granulocyte colony-stimulating factor to mobilize hematopoietic stem cells to the peripheral blood for collection and subsequent autologous transplantation. Oncology. 2010;78(3-4):282-8. Epub 2010 Jun 8. Pubmed
• Choi HY, Yong CS, Yoo BK: Plerixafor for stem cell mobilization in patients with non-Hodgkin's lymphoma and multiple myeloma. Ann Pharmacother. 2010 Jan;44(1):117-26. Epub 2009 Dec 15. Pubmed
• Xie, T., et al.: Science, 290, 328 (2000)
• Leone, D., et al.: J. Pharmacol. Exp. Ther., 305, 1150 (2000)
• Chigaev, A., et al.: J. Immunol. 178, 6828 (2000)
• Kiel, M., et al.: Cell Stem Cell, 1, 204 (2000)