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Plerixafor 8HCl (AMD3100 8HCl)

Product Name
Plerixafor 8HCl (AMD3100 8HCl)
CAS No.
155148-31-5
Chemical Name
Plerixafor 8HCl (AMD3100 8HCl)
Synonyms
JM3100;SID791;CS-907;AMD3100;Bicyclam;BISCYCLAM;AMD3100 HCl;SID791 8HCl;JM 3100 8HCl;AMD3100 8HCl
CBNumber
CB9453984
Molecular Formula
C28H54N8
Formula Weight
502.78
MOL File
155148-31-5.mol
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Plerixafor 8HCl (AMD3100 8HCl) Property

Melting point:
188 - 193°C (dec.)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
H2O: ≥10 mg/mL, clear
form 
solid
color 
White
Water Solubility 
Soluble in water (100mM)
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 2 months.
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

H314Causes severe skin burns and eye damage

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
239825
Product name
InSolution? CXCR4 Antagonist I, AMD3100
Packaging
15mg
Price
$225
Updated
2024/03/01
Sigma-Aldrich
Product number
239820
Product name
CXCR4 Antagonist I, AMD3100
Packaging
5mg
Price
$142
Updated
2024/03/01
Cayman Chemical
Product number
10011332
Product name
Plerixafor (hydrochloride hydrate)
Purity
≥98%
Packaging
1mg
Price
$18
Updated
2024/03/01
Cayman Chemical
Product number
10011332
Product name
Plerixafor (hydrochloride hydrate)
Purity
≥98%
Packaging
5mg
Price
$73
Updated
2024/03/01
Sigma-Aldrich
Product number
A5602
Product name
AMD3100 octahydrochloride hydrate
Purity
≥97% (NMR), solid
Packaging
5mg
Price
$123
Updated
2024/03/01
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Plerixafor 8HCl (AMD3100 8HCl) Chemical Properties,Usage,Production

Description

Plerixafor (155148-31-5) is a highly selective CXCR4 antagonist (IC50 = 20-130 nM).1,2 Originally investigated as an HIV replication inhibitor.3 Plerixafor has been investigated for the treatment autoimmune diseases and various cancers.4 Clinically useful for the mobilization of hematopoietic stem cells in the treatment of blood cancers.

Uses

Plerixafor 8HCl (AMD3100 8HCl) is the hydrochloride of Plerixafor, a chemokine receptor antagonist for CXCR4 and CXCL12-mediated chemotaxis with IC50 of 44 nM and 5.7 nM, respectively - See more at: http://www.selleckchem.com/products/plerixafor-8hcl-db06

Uses

A specific CXCR4 antagonist.

Uses

Plerixafor Hydrochloride (1:8), is an immunostimulant used to mobilize hematopoietic stem cells in cancer patients. It 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).

General Description

A symmetrical bicyclam compound that antagonizes CXCL12 (SDF1) binding to CXCR4 (IC50 = 108 and 245 nM using rat and human CXCR4, respectively) and inhibits SDF1-induced Ca2+ flux (by 100% at 100 ng/ml in SUP-T1 and THP-1 cultures) as well as CXCR4-, but not CCR5-, mediated HIV infection (IC50 ≤200 nM), while enhancing the binding of SDF1 to CXCR7 (by ~60% at 1 mM with CXCR7-expressing HEK293T cells) and SDF1-induced β-arrestin recruitment to CXCR7 (EC50 = 6.48 and 11.8 nM, in the presence and absence of 10 μM AMD3100, respectively). Administration AMD3100 via intravenous infusion is also reported to result in hematopoietic stem cell mobilization in humans, dogs, and mice in vivo. Exhibits no inhibitory effects against chemokine-induced signaling via CXCR1/2/3 or CCR1/2/3/4/5/6/7/8/9.

Biological Activity

Highly selective CXCR4 chemokine receptor antagonist (IC 50 values are 0.02 - 0.13 and > 25 μ M for CXCR4 and all other chemokine receptors respectively). Switches inflammatory responses from Th2 to Th1 type and reduces airway hyperresponsiveness in a mouse model of asthma. Potently inhibits HIV-1 and HIV-2 replication in vitro (EC 50 = 4 - 35 nM) and mobilizes hematopoietic stem cells in vivo .

Biochem/physiol Actions

Cell permeable: yes

Clinical Use

Plerixafor hydrochloride, a chemokine CXCR4 (SDF-1) antagonist, was launched by Genzyme for the treatment of enhancing mobilization of hematopoietic stem cells for autologous transplantation in patients with lymphoma and enhancing mobilization of hematopoietic stem cells for transplantation in patients with multiple myeloma. Being a CXCR4 antagonist, a specific cellular chemokine receptor, plerixafor triggers the rapid movement of stem cells out of the bone marrow and into circulating blood where the stem cells can be collected for use in stem cell transplants. Regarding its use for cardiac applications, some clinical data suggests that the presence of stem cells circulating in the bloodstream or directly injected into the hearts of patients who have suffered a heart attack may result in improved cardiac function.

Synthesis

A concise one-pot synthesis was achieved by a rather novel nitrogen protecting strategy. Tetraazacyclotetradecane 88 was protected as its phosphorotriamide 89 by reaction with POCl3 and Et3N in hot DMF. Without isolation, compound 89 was bis-alkylated with dibromide 90 in the presence of sodium carbonate in refluxing DMF overnight to give bis-phosphoramide 91. The crude dimeric bis-phosphoramide was hydrolyzed with 3 M HCl to afford plerixafor hydrochloride (XV) in 62¨C68% yield.

storage

-20°C (desiccate)

References

1) Donzella, et al. (1998), AMD3100, A Small Molecule Inhibitor of HIV-1 Entry via the CXCR4 Co-Receptor; Nat. Med. 4 72 2) Hatse et al. (2002), Chemokine Receptor Inhibition by AMD3100 Is Strictly Confined to CXCR4; FEBS Lett. 527 255 3) Bridger et al. (1995), Synthesis and Structure-Activity Relationships of Phenylenebis(methylene)-linked Bis-Tetraazamacrocycles That Inhibit HIV Replication. Effects of Macrocyclic Ring Size and Substituents on the aromatic Linker; J. Med. Chem. 38 366 4) Wang et al. (2020), CXCR4 antagonist AMD3100 (plerixafor): from an impurity to a therapeutic agent; Pharmacol. Res. 159 105010

Plerixafor 8HCl (AMD3100 8HCl) Preparation Products And Raw materials

Raw materials

Preparation Products

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Plerixafor 8HCl (AMD3100 8HCl) Suppliers

China 162 France 2 India 4 Japan 1 South Korea 1 Switzerland 1 United Kingdom 3 United States 17 Global 191
Hubei Changrun Biomedical Technology Co., Ltd.
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027-63496417; 13667180236
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J & K SCIENTIFIC LTD.
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3B Pharmachem (Wuhan) International Co.,Ltd.
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View Lastest Price from Plerixafor 8HCl (AMD3100 8HCl) manufacturers

Ouhuang Engineering Materials (Hubei) Co., Ltd
Product
Plerixafor 8HCl (AMD3100 8HCl) 155148-31-5
Price
US $100.00-30.00/kg
Min. Order
1kg
Purity
99.93%
Supply Ability
1000kg per week
Release date
2024-04-22
Ouhuang Engineering Materials (Hubei) Co., Ltd
Product
Plerixafor 8HCl (AMD3100 8HCl) 155148-31-5
Price
US $3.00/kg
Min. Order
1kg
Purity
99.92%
Supply Ability
50000tons
Release date
2024-04-22
Henan Fengda Chemical Co., Ltd
Product
Plerixafor 8HCl (AMD3100 8HCl) 155148-31-5
Price
US $3.00-1.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-16

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