Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H22N4O4 |
| Molecular Weight | 406.4345 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2C(NC=C2C(=O)C(=O)N3CCN(C[C@H]3C)C(=O)C4=CC=CC=C4)=NC=C1
InChI
InChIKey=OKGPFTLYBPQBIX-CQSZACIVSA-N
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
| Molecular Formula | C22H22N4O4 |
| Molecular Weight | 406.4345 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12930892
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12930892
BMS-378806 is a recently discovered small molecule HIV-1 inhibitor that blocks viral entrance to cells. The compound exhibits potent inhibitory activity against a panel of R5-(virus using the CCR5 coreceptor), X4-(virus using the CXCR4 coreceptor), and R5/X4 HIV-1 laboratory and clinical isolates of the B subtype (median EC50 of 0.04 microM) in culture assays. BMS-378806 is selective for HIV-1 and inactive against HIV-2, SIV and a panel of other viruses, and exhibits no significant cytotoxicity in the 14 cell types tested (concentration for 50% reduction of cell growth, >225 microM). BMS-378806 was proved to be specific for HIV-1, with no activity against HIV-2 or simian immunodeficiency virus. BMS-378806 is active against HIV-1 isolates irrespective of chemokine receptor preference. Mechanism of action studies demonstrated that BMS-378806 binds to gp120 and inhibits the interactions of the HIV-1 envelope protein to cellular CD4 receptors. BMS-378806 potently inhibited HIV-1 infection regardless of the particular chemokine receptor used.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibitors of HIV-1 attachment. Part 11: the discovery and structure-activity relationships associated with 4,6-diazaindole cores. | 2013-01-01 |
|
| Inhibitors of HIV-1 attachment. Part 10. The discovery and structure-activity relationships of 4-azaindole cores. | 2013-01-01 |
|
| Synthesis and biological evaluation of coumarin derivatives as inhibitors of Mycobacterium bovis (BCG). | 2012-12 |
|
| Development of the next generation of HIV-1 integrase inhibitors: pyrazolone as a novel inhibitor scaffold. | 2010-11-15 |
|
| Protection against HIV-envelope-induced neuronal cell destruction by HIV attachment inhibitors. | 2010-05 |
|
| An antibody-recruiting small molecule that targets HIV gp120. | 2009-11-18 |
|
| Heterobiaryl human immunodeficiency virus entry inhibitors. | 2009-07-23 |
|
| Variation in HIV-1 R5 macrophage-tropism correlates with sensitivity to reagents that block envelope: CD4 interactions but not with sensitivity to other entry inhibitors. | 2008-01-18 |
|
| Betulinic acid derivatives that target gp120 and inhibit multiple genetic subtypes of human immunodeficiency virus type 1. | 2008-01 |
|
| Potent antiviral synergy between monoclonal antibody and small-molecule CCR5 inhibitors of human immunodeficiency virus type 1. | 2006-10 |
|
| Modification and structure-activity relationship of a small molecule HIV-1 inhibitor targeting the viral envelope glycoprotein gp120. | 2005-05-07 |
|
| Small-molecule inhibitors of HIV-1 entry block receptor-induced conformational changes in the viral envelope glycoproteins. | 2004-04-06 |
|
| Biochemical and genetic characterizations of a novel human immunodeficiency virus type 1 inhibitor that blocks gp120-CD4 interactions. | 2003-10 |
|
| Discovery of 4-benzoyl-1-[(4-methoxy-1H- pyrrolo[2,3-b]pyridin-3-yl)oxoacetyl]-2- (R)-methylpiperazine (BMS-378806): a novel HIV-1 attachment inhibitor that interferes with CD4-gp120 interactions. | 2003-09-25 |
|
| A small molecule HIV-1 inhibitor that targets the HIV-1 envelope and inhibits CD4 receptor binding. | 2003-09-16 |
Patents
Sample Use Guides
In rats, linear pharmacokinetics was observed between i.v. doses of 1 and 5 mg/kg and between p.o. doses of 5 and 25 mg/kg.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:40:53 GMT 2025
by
admin
on
Mon Mar 31 22:40:53 GMT 2025
|
| Record UNII |
IMN5E6PLUK
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
IMN5E6PLUK
Created by
admin on Mon Mar 31 22:40:53 GMT 2025 , Edited by admin on Mon Mar 31 22:40:53 GMT 2025
|
PRIMARY | |||
|
5495818
Created by
admin on Mon Mar 31 22:40:53 GMT 2025 , Edited by admin on Mon Mar 31 22:40:53 GMT 2025
|
PRIMARY | |||
|
DTXSID401351335
Created by
admin on Mon Mar 31 22:40:53 GMT 2025 , Edited by admin on Mon Mar 31 22:40:53 GMT 2025
|
PRIMARY | |||
|
357263-13-9
Created by
admin on Mon Mar 31 22:40:53 GMT 2025 , Edited by admin on Mon Mar 31 22:40:53 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
