| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-25 18:30:11 UTC |
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| Update Date | 2016-11-09 01:17:28 UTC |
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| Accession Number | CHEM022368 |
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| Identification |
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| Common Name | Plerixafor |
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| Class | Small Molecule |
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| 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 for the purpose of stimulating the immune system. 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. |
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| Contaminant Sources | - HMDB Contaminants - Urine
- STOFF IDENT Compounds
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| Mozobil | Kegg | | AMD3100 | HMDB | | 1,1'-(1,4-Phenylenebis-(methylene))-bis-1,4,8,11-tetraazacyclotetradecane octahydrochloride dihydrate | HMDB | | RPA bicyclam | HMDB | | Bicyclam | HMDB | | Plerixafor hydrochloride | HMDB | | 1,1'-(1,4-Phenylenebis(methylene))bis(1,4,8,11-tetraazacyclotetradecane)octahydrochloride dihydrate | HMDB | | Mezobil | HMDB | | Plerixafor octahydrochloride | MeSH |
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| Chemical Formula | C28H54N8 |
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| Average Molecular Mass | 502.782 g/mol |
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| Monoisotopic Mass | 502.447 g/mol |
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| CAS Registry Number | 110078-46-1 |
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| IUPAC Name | 1-{[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)phenyl]methyl}-1,4,8,11-tetraazacyclotetradecane |
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| Traditional Name | plerixafor |
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| SMILES | C(N1CCCNCCNCCCNCC1)C1=CC=C(CN2CCCNCCNCCCNCC2)C=C1 |
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| InChI Identifier | 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 |
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| InChI Key | YIQPUIGJQJDJOS-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as phenylmethylamines. Phenylmethylamines are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Phenylmethylamines |
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| Direct Parent | Phenylmethylamines |
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| Alternative Parents | |
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| Substituents | - Phenylmethylamine
- Benzylamine
- Aralkylamine
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organoheterocyclic compound
- Secondary amine
- Secondary aliphatic amine
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Amine
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-1697050000-f5d2d801403d4ca1fac2 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-3305690000-8b1839aab22b9234977b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-2119230000-d6684086ac6f6cdefe47 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-6219400000-0f492ce3c99d5723568a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0100190000-61c3b70d31c0660f4c34 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0fk9-0200920000-075cb7149428dfc32da8 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000l-3309400000-dd6ca13528fa27e0cca7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0000090000-f96651fdcc3529f45e1c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0000090000-f96651fdcc3529f45e1c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ot-0950000000-aaf85046f51d6a6ec0b5 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0000090000-bc62744a6284174ba784 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0100090000-717df0f4da7938b8ce9e | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0002-0900000000-6a53e9136e708d1e8f2d | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB06809 |
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| HMDB ID | HMDB0015681 |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Plerixafor |
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| Chemspider ID | 58531 |
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| ChEBI ID | 120346 |
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| PubChem Compound ID | 65015 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | | 1. 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. doi: 10.1517/14712598.8.11.1797 . | | 2. Fricker SP: A novel CXCR4 antagonist for hematopoietic stem cell mobilization. Expert Opin Investig Drugs. 2008 Nov;17(11):1749-60. doi: 10.1517/13543784.17.11.1749 . | | 3. 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. doi: 10.1016/j.bbmt.2008.10.018. | | 4. 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. doi: 10.1182/blood-2008-08-174946. Epub 2009 Apr 10. | | 5. 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. doi: 10.1345/aph.1M380. Epub 2009 Dec 15. | | 6. 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. doi: 10.1159/000315736. Epub 2010 Jun 8. | | 7. Keating GM: Plerixafor: a review of its use in stem-cell mobilization in patients with lymphoma or multiple myeloma. Drugs. 2011 Aug 20;71(12):1623-47. doi: 10.2165/11206040-000000000-00000. |
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