Plerixafor

Base Information

• Chemical Name: Plerixafor
• CAS No.: 110078-46-1
• Molecular Formula: C28H54N8
• Molecular Weight: 502.79
• Hs Code.: 29339900
• European Community (EC) Number: 842-163-8
• UNII: S915P5499N
• DSSTox Substance ID: DTXSID70869520
• Nikkaji Number: J579.015H
• Wikipedia: Plerixafor
• Wikidata: Q905835
• NCI Thesaurus Code: C1777
• RXCUI: 733003
• Pharos Ligand ID: ARBHCJDMDX7U
• Metabolomics Workbench ID: 43709
• ChEMBL ID: CHEMBL18442
• Mol file: 110078-46-1.mol

Synonyms:1,1'-(1,4-phenylenebis(methylene))bis(1,4,8,11-tetraazacyclotetradecane)octahydrochloride dihydrate;1,1'-(1,4-phenylenebis-(methylene))-bis-1,4,8,11-tetraazacyclotetradecane;1,1'-(1,4-phenylenebis-(methylene))-bis-1,4,8,11-tetraazacyclotetradecane octahydrochloride dihydrate;AMD 3100;AMD 3329;AMD-3100;AMD-3329;AMD3100;JM 3100;JM3100;mezobil;mozobil;plerixafor;plerixafor hydrochloride;plerixafor octahydrobromide;plerixafor octahydrochloride;RPA bicyclam

Chemical Property of Plerixafor

Chemical Property:

• Vapor Pressure: 1.06E-34mmHg at 25°C
• Melting Point: 122-125°C
• Boiling Point: 657.5 °C at 760 mmHg
• PKA: 10.60±0.20(Predicted)
• Flash Point: 361.8 °C
• PSA: 78.66000
• Density: 0.962 g/cm³
• LogP: 2.26440
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: 0
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 502.44714376
• Heavy Atom Count: 36
• Complexity: 456

Purity/Quality:

99% ^*data from raw suppliers

Plerixafor ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Transplant Agents
• Canonical SMILES: C1CNCCNCCCN(CCNC1)CC2=CC=C(C=C2)CN3CCCNCCNCCCNCC3
• Recent ClinicalTrials: Scleroderma Treatment With Autologous Transplant (STAT) Study
• Recent EU Clinical Trials: A randomized, double-blind, placebo-controlled, two parallel groups, international multicenter trial to evaluate the effect of Plerixafor in acute respiratory failure related to COVID-19 (LEONARDO)
• Recent NIPH Clinical Trials: A multicenter phase II study to evaluate the efficacy and safety of fixed-duration sequential treatment combined with novel agents and autologous stem cell transplantation for newly diagnosed elderly multiple myeloma. -JSCT EMM21-
• Description: Plerixafor (AMD3100) is a chemokine receptor antagonist for CXCR4 and CXCL12-mediated chemotaxis with IC50 of 44 nM and 5.7 nM in cell-free assays, respectively. Autologous hematopoietic stem cell (HSC) transplantation, a standard treatment for hematological malignancies, such as non-Hodgkin’s lymphoma or multiple myeloma, involves collection of HSCs from the patient, chemo- or radiotherapy of the patient to eliminate malignant cells, and retransplantation of the stored HSCs. Plerixafor is a potent antagonist of the CXCR4 chemokine receptor and a first-in-class drug for stem cell mobilization. CXCR4 is specific for stromal-derived-factor-1 (SDF-1), a molecule endowed with potent chemotactic activity forlymphocytes. Because the interaction between SDF-1 and CXCR4 plays an important role in holding HSCs in the bone marrow, drugs that block the activity of CXCR4 receptor are capable of mobilizing HSCs into the bloodstream. In vitro, plerixafor potently blocks SDF-1 binding of CXCR4 and inhibits SDF-1-induced calcium flux (IC50 = 0.01-0.13 mg/mL) and chemotaxis (IC50 = 0.13 mg/mL) in several different cell types. Plerixafor, in combination with G-CSF, is specifically indicated to mobilize HSCs to the peripheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin’s lymphoma and multiple myeloma.
• Uses: Plerixafor is a chemokine receptor antagonist for CXCR4 and CXCL12-mediated chemotaxis with IC50 of 44 nM and 5.7 nM, respectively 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). on Dec. 15, 2008, as treatment in combination with granulocyte-colony stimulating factor (G-CSF) to mobilize HSCs to the peripheral blood for collection and subsequent autologous transplantation in p atients with non-Hodgkin's lymphoma (NHL) and multiple myeloma (MM). 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 granulocyte-colony stimulating factor (G-CSF) to mobilize HSCs to the peripheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin''s lymphoma (NHL) and multiple myeloma (MM). Selective CXCR4 antagonist.
• Clinical Use: Chemokine receptor antagonist: 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
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Plerixafor

There total 31 articles about Plerixafor which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.3%

C28H40N8(2+)*2Cl(1-) → 1-[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)benzyl]-1,4,8,11-tetraazacyclotetradecane (110078-46-1)

Guidance literature:

With sodium tetrahydroborate; In toluene; at 20 ℃; for 10h; Solvent; Temperature; Reflux; Large scale;

Reference yield: 93.4%

C28H40N8(2+)*2I(1-) → 1-[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)benzyl]-1,4,8,11-tetraazacyclotetradecane (110078-46-1)

Guidance literature:

With sodium tetrahydroborate; In tert-butyl alcohol; at 20 ℃; for 10h; Reflux; Large scale;

Reference yield: 93.0%

C32H52N8(2+)*2Br(1-) → 1-[4-(1,4,8,11-tetraazacyclotetradecan-1-ylmethyl)benzyl]-1,4,8,11-tetraazacyclotetradecane (110078-46-1)

Guidance literature:

With hydroxylamine hydrochloride; sodium ethanolate; In ethanol; for 4h; Heating;

DOI:10.1039/b103995b

upstream raw materials:

1,4-bis(bromomethyl)benzene

1,4,8,11-Tetraazacyclotetradecane

1,1'-p-xylylbis<4,8,11-tris(tert-butyloxycarbonyl)-1,4,8,11-tetraazacyclotetradecane>

1,1'-<1,4-phenylenebis(methylene)>bis<4,8,11-tris(p-tolylsulfonyl)-1,4,8,11-tetraazacyclotetradecane>

Refernces

• 1、 Yang, Wen,Giandomenico, Christen M.,Sartori, Michael,Moore, Dennis A.. "Facile N-1 protection of cyclam, cyclen and 1,4,7-triazacyclononane". . p. 2481 - 2483. Retrieved 2003.
• 2、 -. "Octahydropyrazine bipyrimidine molecular clip compound as well as preparation method and application thereof". Paragraph 0092; 0093; 0102; 0103; 0104; 0105; 0106. . Retrieved 2021/09/26.
• 3、 -. "Preparation method of Plerixafor". . . Retrieved 2017/12/29.