NBD-556, a CD4 mimetic, is a potent HIV-1 entry inhibitor that blocks gp120-CD4 interaction. NBD-556 displays potent cell fusion and virus-cell fusion inhibitory activity at low micromolar levels.

Physicochemical Properties

Molecular Formula	C17H24CLN3O2
Molecular Weight	337.848
Exact Mass	337.156
CAS #	333353-44-9
Related CAS #	333353-44-9;NBD-556 HCl;
PubChem CID	1570601
Appearance	Typically exists as solid at room temperature
LogP	4.073
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Heavy Atom Count	23
Complexity	441
Defined Atom Stereocenter Count	0
SMILES	O=C(C(NC1CC(C)(NC(C)(C1)C)C)=O)NC2=CC=C(C=C2)Cl
InChi Key	ZKXLQCIOURANAD-UHFFFAOYSA-N
InChi Code	InChI=1S/C17H24ClN3O2/c1-16(2)9-13(10-17(3,4)21-16)20-15(23)14(22)19-12-7-5-11(18)6-8-12/h5-8,13,21H,9-10H2,1-4H3,(H,19,22)(H,20,23)
Chemical Name	N'-(4-chlorophenyl)-N-(2,2,6,6-tetramethylpiperidin-4-yl)oxamide
Synonyms	NBD556; NBD 556; NBD-556
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

NBD-556 (1-100 μM) suppresses the fusion of cells and viruses mediated by the HIV-1 envelope [1]. The laboratory-adapted HIV-1 IIIB, MN, and V32 strains are inhibited from infecting MT-2 cells by NBD-556, with IC50 values of 6.5, 15.9, and 5.3 µM, respectively [1]. NBD-556 (1-100 μM) has an IC50 of 22.6 μM and suppresses CD4-dependent viruses in a dose-dependent manner [1].

References

[1]. Zhao Q, Ma L, Jiang S, Lu H, Liu S, He Y, Strick N, Neamati N, Debnath AK. Identification of N-phenyl-N'-(2,2,6,6-tetramethyl-piperidin-4-yl)-oxalamides as a new class of HIV-1 entry inhibitors that prevent gp120 binding to CD4. Virology. 2005 Sep 1;339 [2]. Schon A, et al. Thermodynamics of binding of a low-molecular-weight CD4 mimetic to HIV-1 gp120. Biochemistry. 2006 Sep 12;45(36):10973-10980.

Solubility Data

Solubility (In Vitro)

DMSO : ~33.33 mg/mL (~98.66 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.40 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9599 mL	14.7995 mL	29.5989 mL
	5 mM	0.5920 mL	2.9599 mL	5.9198 mL
	10 mM	0.2960 mL	1.4799 mL	2.9599 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.