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Merck
CN

SML3116

BMS-378806

≥98% (HPLC)

Synonym(s):

1-[(2R )-4-Benzoyl-2-methyl-1-piperazinyl]-2-(4-methoxy-1H -pyrrolo[2,3-b ]pyridin-3-yl)-1,2-ethanedione, 4-Benzoyl-1-[(4-methoxy-1H- pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2-(R)-methylpiperazine, BMS 378806, BMS 806, BMS-806, BMS378806, BMS806

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About This Item

Empirical Formula (Hill Notation):
C22H22N4O4
CAS Number:
357263-13-9
Molecular Weight:
406.43
UNSPSC Code:
12352107
NACRES:
NA.77
MDL number:
MFCD09026945

Key Documents

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InChI

1S/C22H22N4O4/c1-14-13-25(21(28)15-6-4-3-5-7-15)10-11-26(14)22(29)19(27)16-12-24-20-18(16)17(30-2)8-9-23-20/h3-9,12,14H,10-11,13H2,1-2H3,(H,23,24)/t14-/m1/s1

SMILES string

O=C(N1[C@@H](CN(CC1)C(C2=CC=CC=C2)=O)C)C(C3=CNC4=NC=CC(OC)=C34)=O

InChI key

OKGPFTLYBPQBIX-CQSZACIVSA-N

assay

≥98% (HPLC)

form

powder

color

white to gray

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

General description

BMS-378806 is an indole-based compound that exhibits improved antiviral potency, and pharmaceutical and pharmacokinetic activities. BMS-378806 is inactive against HIV-2 and Simian immunodeficiency virus (SIV) and a few other viruses.

Biochem/physiol Actions

BMS-378806 (BMS-806) is a potent and selective HIV-1 attachment inhibitor that blocks HIV glycoprotein 120 (gp120) from interacting with host T-cell surface glycoprotein CD4 (IC50 = 100 nM against CD4 for binding gp120; CYP1A2/2C9/2C19/2D6/3A4 IC50 >23 μM) without affecting HIV integrase, protease, or reverse transcriptase activity. BMS-806 effectively prevents various HIV-1 isolates from replication (EC50 from 0.85 to 26.5 nM in MT-2 and PM1 cultures; host cytotoxicity IC50 >300 μM) without affecting HIV-2, SIV, MuLV, RSV, HCMV, BVDV, VSV, or influenza virus.
Potent and selective HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions and protects against HIV-1 infection in host cultures.

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
0000152534
0000152535
0000152535
0000152534
0000141352

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A small molecule HIV-1 inhibitor that targets the HIV-1 envelope and inhibits CD4 receptor binding
Pin-Fang Lin, et al.
Proceedings of the National Science Council, Republic of China / Applied Science, 100(19), 11013-11018 (2003)
Shitao Zou et al.
Journal of virology, 94(10) (2020-03-13)
During human immunodeficiency virus type 1 (HIV-1) entry into cells, the viral envelope glycoprotein (Env) trimer [(gp120/gp41)3] binds the receptors CD4 and CCR5 and fuses the viral and cell membranes. CD4 binding changes Env from a pretriggered (state-1) conformation to
Quantitative determination of BMS-378806 in human plasma and urine by high-performance liquid chromatography/tandem mass spectrometry
Y.-J. Xue, et al.
Journal of Separation Science (2007)
Tao Wang et al.
Journal of medicinal chemistry, 46(20), 4236-4239 (2003-09-19)
Indole derivative 1 interferes with the interaction of the HIV surface protein gp120 with the host cell receptor CD4. The 4-fluoro derivative 2 exhibited markedly enhanced potency and was bioavailable in the rat, dog, and cynomolgus monkey when administered orally
Yuta Hikichi et al.
mBio, 12(1) (2021-01-14)
Despite the effectiveness of antiretroviral (ARV) therapy, virological failure can occur in some HIV-1-infected patients in the absence of mutations in drug target genes. We previously reported that, in vitro, the lab-adapted HIV-1 NL4-3 strain can acquire resistance to the
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