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Merck
CN

SML1433

AMD3465

≥98% (HPLC), CXCR4 antagonist, powder

Synonym(s):

AMD 3465, GENZ-644494, N-[[4-(1,4,8,11-Tetraazacyclotetradec-1-ylmethyl)phenyl]methyl]-2-pyridinemethanamine hexahydrobromide

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About This Item

Empirical Formula (Hill Notation):
C24H38N6 · 6HBr
CAS Number:
185991-07-5
Molecular Weight:
896.07
UNSPSC Code:
51111800
NACRES:
NA.77

Key Documents

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Product Name

AMD3465, ≥98% (HPLC)

SMILES string

N3(CCNCCCNCCNCCC3)Cc1ccc(cc1)CNCc2ncccc2

InChI

1S/C24H38N6/c1-2-13-29-24(5-1)20-28-19-22-6-8-23(9-7-22)21-30-17-4-12-26-15-14-25-10-3-11-27-16-18-30/h1-2,5-9,13,25-28H,3-4,10-12,14-21H2

InChI key

CWJJHESJXJQCJA-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to light brown

solubility

H2O: 25 mg/mL, clear

storage temp.

−20°C

Quality Level

100

Related Categories

Biochem/physiol Actions

AMD3465 is a highly selective chemokine receptor CXCR4 antagonist with antiviral and anticancer activity.
AMD3465 is a highly selective chemokine receptor CXCR4 antagonist with antiviral and anticancer activity. The chemokine receptor CXCR4 is expressed on a wide variety of leukocytes and is the predominant receptor for stromal cell-derived factor-1 (SDF1, CXCL12) in addition to acting as a co-receptor for HIV entry into cells. AMD3465 blocks surface binding of CXCL12 (SDF-1α). AMD3465 is an antagonist of SDF-1 ligand binding (K(i) of 41.7+/-1.2 nM). AMD3465 was found to halt the progression of an agressive childhood blood cancer, T-cell acute lymphoblastic leukemia (T-ALL), within two weeks of starting treatment in an animal model.
AMD3465 is also termed as{N-[1,4,8,11-tetraazacyclotetradecanyl-1,4-phenylenebis(methylene)]-2-(aminomethyl)pyridine}. It controls oncogenic signaling and invasiveness in vitro. It inhibits breast cancer growth and metastasis in vivo. As a chemokine receptor 4 (CXCR4) antagonist, AMD3465 is ten times more efficient than bicyclam AMD3100.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000320851
0000320850
0000320851
0000320850
0000266334

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The CXCR4 Antagonist AMD3465 Regulates Oncogenic Signaling and Invasiveness In Vitro and Prevents Breast Cancer Growth and Metastasis In Vivo
Ling X, et al.
PLoS ONE, 8(3), e58426-e58426 (2013)
Imaging CXCR4 Expression in Human Cancer Xenografts: Evaluation of Monocyclam 64Cu-AMD3465
De Silva RA, et al.
Journal of Nuclear Medicine, 52(6), 986-986 (2011)
Augustus M C Tilley et al.
Cancers, 12(9) (2020-09-03)
The CXCR4-LASP1 axis is an emerging target in the field of breast cancer metastasis. C-X-C chemokine receptor type 4 (CXCR4) mediates directed cell migration when activated by its cognate ligand CXCL12. LIM and SH3 Protein 1 (LASP1) is a critical

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