Compounds > tba-354
Page last updated: 2024-11-13

tba-354

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID49836057
CHEMBL ID1630563
SCHEMBL ID508426
MeSH IDM000609325

Synonyms (29)

Synonym
CHEMBL1630563
tba 354
tba-354 ,
(6s)-2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]-3-pyridyl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine
(6s)-2-nitro-6-({6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl}methoxy)-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine
SCHEMBL508426
CS-3576
(s)-2-nitro-6-((6-(4-(trifluoromethoxy)phenyl)pyridin-3-yl)methoxy)-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine
1257426-19-9
AC-35402
tba354
HY-12485
(6s)-2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]methoxy]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine
1403987-02-9
(sn31354((s)-2-nitro-6-((6-(4-trifluoromethoxy)phenyl)pyridine-3-yl)methoxy)-6,7-dihydro-5h-imidazo(2,1-b)(1,3)oxazine))
((6s)-6-((6-(4-(trifluoromethoxy)phenyl)-3-pyridyl)methoxy)-6,7-dihydro-5h-imidazo(2,1-b)(1,3)oxazin-2-yl)azinic acid
911T37M2WY ,
AKOS025404945
EX-A526
unii-911t37m2wy
(6s)-6,7-dihydro-2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]-3-pyridinyl]methoxy]-5h-imidazo[2,1-b][1,3]oxazine
mfcd28009369
NCGC00390647-01
zxsgsfmorailey-hnnxbmfysa-n
Q27896161
A889959
MS-27814
5h-imidazo[2,1-b][1,3]oxazine, 6,7-dihydro-2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]-3-pyridinyl]methoxy]-, (6s)-
5-({[(6s)-2-nitro-5h,6h,7h-imidazo[2,1-b][1,3]oxazin-6-yl]oxy}methyl)-2-[4-(trifluoromethoxy)phenyl]pyridine

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Five such compounds were >100-fold better than the parent drug in a mouse model of acute Mycobacterium tuberculosis infection, and two orally bioavailable pyridine analogues (3-4-fold more soluble than the parent at low pH) were superior to antitubercular drug OPC-67683 in a chronic infection model."( Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
Blaser, A; Denny, WA; Franzblau, SG; Kmentova, I; Ma, Z; Palmer, BD; Sutherland, HS; Thompson, AM; Wan, B; Wang, Y, 2010)		0.36
" Bioisosteric replacement of this biaryl moiety by arylpiperazine resulted in a soluble, orally bioavailable carbamate analogue providing identical activity in the acute model, comparable efficacy to OPC-67683 in a chronic infection model, favorable pharmacokinetic profiles across several species, and enhanced safety."( Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
Blaser, A; Denny, WA; Franzblau, SG; Kmentova, I; Ma, Z; Palmer, BD; Sutherland, HS; Thompson, AM; Wan, B; Wang, Y, 2012)		0.38
" TBA-354 (SN31354[(S)-2-nitro-6-((6-(4-trifluoromethoxy)phenyl)pyridine-3-yl)methoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine]) is a pyridine-containing biaryl compound with exceptional efficacy against chronic murine tuberculosis and favorable bioavailability in preliminary rodent studies."( In vitro and in vivo activities of the nitroimidazole TBA-354 against Mycobacterium tuberculosis.
Cho, S; Franzblau, SG; Kim, Y; Lu, Y; Ma, Z; Mdluli, K; Upton, AM; Wang, B; Wang, Y; Xu, J; Yang, TJ, 2015)		1.58
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51

Dosage Studied

ExcerptRelevanceReference
" Its superior potency and pharmacokinetic profile that predicts suitability for once-daily oral dosing suggest that TBA-354 be studied further for its potential as a next-generation nitroimidazole."( In vitro and in vivo activities of the nitroimidazole TBA-354 against Mycobacterium tuberculosis.
Cho, S; Franzblau, SG; Kim, Y; Lu, Y; Ma, Z; Mdluli, K; Upton, AM; Wang, B; Wang, Y; Xu, J; Yang, TJ, 2015)		0.88
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GVesicular stomatitis virusPotency16.93300.01238.964839.8107AID1645842
Interferon betaHomo sapiens (human)Potency16.93300.00339.158239.8107AID1645842
HLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)Potency16.93300.01238.964839.8107AID1645842
Inositol hexakisphosphate kinase 1Homo sapiens (human)Potency16.93300.01238.964839.8107AID1645842
cytochrome P450 2C9, partialHomo sapiens (human)Potency16.93300.01238.964839.8107AID1645842
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
cell surface receptor signaling pathway via JAK-STATInterferon betaHomo sapiens (human)
response to exogenous dsRNAInterferon betaHomo sapiens (human)
B cell activation involved in immune responseInterferon betaHomo sapiens (human)
cell surface receptor signaling pathwayInterferon betaHomo sapiens (human)
cell surface receptor signaling pathway via JAK-STATInterferon betaHomo sapiens (human)
response to virusInterferon betaHomo sapiens (human)
positive regulation of autophagyInterferon betaHomo sapiens (human)
cytokine-mediated signaling pathwayInterferon betaHomo sapiens (human)
natural killer cell activationInterferon betaHomo sapiens (human)
positive regulation of peptidyl-serine phosphorylation of STAT proteinInterferon betaHomo sapiens (human)
cellular response to interferon-betaInterferon betaHomo sapiens (human)
B cell proliferationInterferon betaHomo sapiens (human)
negative regulation of viral genome replicationInterferon betaHomo sapiens (human)
innate immune responseInterferon betaHomo sapiens (human)
positive regulation of innate immune responseInterferon betaHomo sapiens (human)
regulation of MHC class I biosynthetic processInterferon betaHomo sapiens (human)
negative regulation of T cell differentiationInterferon betaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIInterferon betaHomo sapiens (human)
defense response to virusInterferon betaHomo sapiens (human)
type I interferon-mediated signaling pathwayInterferon betaHomo sapiens (human)
neuron cellular homeostasisInterferon betaHomo sapiens (human)
cellular response to exogenous dsRNAInterferon betaHomo sapiens (human)
cellular response to virusInterferon betaHomo sapiens (human)
negative regulation of Lewy body formationInterferon betaHomo sapiens (human)
negative regulation of T-helper 2 cell cytokine productionInterferon betaHomo sapiens (human)
positive regulation of apoptotic signaling pathwayInterferon betaHomo sapiens (human)
response to exogenous dsRNAInterferon betaHomo sapiens (human)
B cell differentiationInterferon betaHomo sapiens (human)
natural killer cell activation involved in immune responseInterferon betaHomo sapiens (human)
adaptive immune responseInterferon betaHomo sapiens (human)
T cell activation involved in immune responseInterferon betaHomo sapiens (human)
humoral immune responseInterferon betaHomo sapiens (human)
positive regulation of T cell mediated cytotoxicityHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
adaptive immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class I via ER pathway, TAP-independentHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of T cell anergyHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
defense responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
detection of bacteriumHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of interleukin-12 productionHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of interleukin-6 productionHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protection from natural killer cell mediated cytotoxicityHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
innate immune responseHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
regulation of dendritic cell differentiationHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
antigen processing and presentation of endogenous peptide antigen via MHC class IbHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
inositol phosphate metabolic processInositol hexakisphosphate kinase 1Homo sapiens (human)
phosphatidylinositol phosphate biosynthetic processInositol hexakisphosphate kinase 1Homo sapiens (human)
negative regulation of cold-induced thermogenesisInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol phosphate biosynthetic processInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (18)

Processvia Protein(s)Taxonomy
cytokine activityInterferon betaHomo sapiens (human)
cytokine receptor bindingInterferon betaHomo sapiens (human)
type I interferon receptor bindingInterferon betaHomo sapiens (human)
protein bindingInterferon betaHomo sapiens (human)
chloramphenicol O-acetyltransferase activityInterferon betaHomo sapiens (human)
TAP bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
signaling receptor bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protein bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
peptide antigen bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
TAP bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
protein-folding chaperone bindingHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
inositol-1,3,4,5,6-pentakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol heptakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 5-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
protein bindingInositol hexakisphosphate kinase 1Homo sapiens (human)
ATP bindingInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 1-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol hexakisphosphate 3-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol 5-diphosphate pentakisphosphate 5-kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
inositol diphosphate tetrakisphosphate kinase activityInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (22)

Processvia Protein(s)Taxonomy
extracellular spaceInterferon betaHomo sapiens (human)
extracellular regionInterferon betaHomo sapiens (human)
Golgi membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
endoplasmic reticulumHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
Golgi apparatusHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
plasma membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
cell surfaceHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
ER to Golgi transport vesicle membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
secretory granule membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
phagocytic vesicle membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
early endosome membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
recycling endosome membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
extracellular exosomeHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
lumenal side of endoplasmic reticulum membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
MHC class I protein complexHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
extracellular spaceHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
external side of plasma membraneHLA class I histocompatibility antigen, B alpha chain Homo sapiens (human)
fibrillar centerInositol hexakisphosphate kinase 1Homo sapiens (human)
nucleoplasmInositol hexakisphosphate kinase 1Homo sapiens (human)
cytosolInositol hexakisphosphate kinase 1Homo sapiens (human)
nucleusInositol hexakisphosphate kinase 1Homo sapiens (human)
cytoplasmInositol hexakisphosphate kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (41)

Assay IDTitleYearJournalArticle
AID643087Half life in CD-1 mouse plasma at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541702Antitubercular activity against Mycobacterium tuberculosis H37Rv by LORA method2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID643088AUC (0 to infinity) in CD-1 mouse lung at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541920Cmax in CD1 mouse lung at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541929AUClast in Sprague-Dawley rat at 5 mg/kg, iv administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541917Half life in CD1 mouse plasma at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541933AUClast in Sprague-Dawley rat at 20 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541936Antitubercular activity against Mycobacterium tuberculosis infected in BALB/c mouse assessed as reduction in lung microbial load at 100 mg/kg, po qd for 5 days per week for 3 weeks administered 70 days post infection relative to PA-8242010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541921Half life in CD1 mouse lung at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541700Solubility of the compound in water at pH 1.0 by HPLC2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541915AUC (0-infinity) in CD1 mouse plasma at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541925Tmax in Sprague-Dawley rat at 5 mg/kg, iv administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541944Thermodynamic solubility in aqueous buffer at pH 7.4 at 20 degC by HPLC2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541919AUC (0-infinity) in CD1 mouse lung at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541941Metabolic stability in human liver microsomes assessed as compound remaining after 1 hr2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID643091Ratio AUC (0 to infinity) in CD-1 mouse lung to AUC (0 to infinity) in CD-1 mouse plasma at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541916Cmax in CD1 mouse plasma at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541699Solubility of the compound in water at pH 7.0 by HPLC2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541938Antitubercular activity against Mycobacterium tuberculosis infected in BALB/c mouse assessed as reduction in lung microbial load at 30 mg/kg, po qd for 5 days per week for 8 weeks administered 70 days post infection relative to untreated control2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541931Cmax in Sprague-Dawley rat at 20 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541937Antitubercular activity against Mycobacterium tuberculosis infected in BALB/c mouse assessed as reduction in lung microbial load at 100 mg/kg, po qd for 5 days per week for 3 weeks administered 70 days post infection relative to OPC-676832010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID643086Cmax in CD-1 mouse plasma at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID643085AUC (0 to infinity) in CD-1 mouse plasma at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541927Half life in Sprague-Dawley rat at 5 mg/kg, iv administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541942Metabolic stability in CD1 mouse liver microsomes assessed as compound remaining after 1 hr2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541943Thermodynamic solubility in aqueous buffer at pH 1 at 20 degC by HPLC2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541923Cmax in Sprague-Dawley rat at 5 mg/kg, iv administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541935Antitubercular activity against Mycobacterium tuberculosis infected in BALB/c mouse assessed as reduction in lung microbial load at 100 mg/kg, po qd for 5 days per week for 3 weeks administered 70 days post infection relative to untreated control2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID643090Half life in CD-1 mouse lung at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541918Antitubercular activity against Mycobacterium tuberculosis infected in BALB/c mouse assessed as reduction in lung microbial load at 30 mg/kg, po qd for 5 days per week for 8 weeks administered 70 days post infection relative to OPC-676832010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541932Tmax in Sprague-Dawley rat at 20 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541701Antitubercular activity against Mycobacterium tuberculosis H37Rv by MABA method2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541940Antitubercular activity against Mycobacterium tuberculosis infected in BALB/c mouse assessed as reduction in lung microbial load at 100 mg/kg, po qd for 5 days per week for 3 weeks administered 11 days post infection relative to OPC-676832010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541934Oral bioavailability in Sprague-Dawley rat at 20 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID541922Ratio of AUC (0-infinity) in lung to AUC (0-infinity) in plasma of CD1 mouse at 40 mg/kg, po administered as single dose2010Journal of medicinal chemistry, Dec-09, Volume: 53, Issue:23
Synthesis and structure-activity relationships of aza- and diazabiphenyl analogues of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID643089Cmax in CD-1 mouse lung at 40 mg/kg, po2012Journal of medicinal chemistry, Jan-12, Volume: 55, Issue:1
Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's6 (66.67)24.3611
2020's3 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.33

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.33 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index5.45 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.33)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pyrazinamide
pyrazinecarboxamide : A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of pyrazinoic acid (pyrazine-2-carboxylic acid) with ammonia. A prodrug for pyrazinoic acid, pyrazinecarboxamide is used as part of multidrug regimens for the treatment of tuberculosis.		2.1110monocarboxylic acid amide;
N-acylammonia;
pyrazines		antitubercular agent;
prodrug
clofazimine
Clofazimine: A fat-soluble riminophenazine dye used for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients. Clofazimine also has a marked anti-inflammatory effect and is given to control the leprosy reaction, erythema nodosum leprosum. (From AMA Drug Evaluations Annual, 1993, p1619). clofazimine : 3-Isopropylimino-3,5-dihydro-phenazine in which the hydrogen at position 5 is substituted substituted by a 4-chlorophenyl group, and that at position 2 is substituted by a (4-chlorophenyl)amino group. A dark red crystalline solid, clofazimine is an antimycobacterial and is one of the main drugs used for the treatment of multi-bacillary leprosy. However, it can cause red/brown discolouration of the skin, so other treatments are often preferred in light-skinned patients.		2.1110monochlorobenzenes;
phenazines		dye;
leprostatic drug;
non-steroidal anti-inflammatory drug
oxazoles
Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.		2.52201,3-oxazoles;
mancude organic heteromonocyclic parent;
monocyclic heteroarene
azomycin
azomycin: RN given refers to parent cpd with specified locant; structure		3.0240C-nitro compound;
imidazoles		antitubercular agent
moxifloxacin
Moxifloxacin: A fluoroquinolone that acts as an inhibitor of DNA TOPOISOMERASE II and is used as a broad-spectrum antibacterial agent.. moxifloxacin : A quinolone that consists of 4-oxo-1,4-dihydroquinoline-3-carboxylic acid bearing a cyclopropyl substituent at position 1, a fluoro substitiuent at position 6, a (4aS,7aS)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl group at position 7 and a methoxy substituent at position 8. A member of the fluoroquinolone class of antibacterial agents.		2.1110aromatic ether;
cyclopropanes;
fluoroquinolone antibiotic;
pyrrolidinopiperidine;
quinolinemonocarboxylic acid;
quinolone antibiotic;
quinolone		antibacterial drug
pa 824
pretomanid: nitroimidazopyran derived from 5-nitroimidazoles; a prodrug that requires activation by a bacterial F420-depedent glucose-6-phosphate dehydrogenase (Fgd) and nitroreductase to activate components that then inhibit bacterial mycolic acid and protein synthesis; structure in first source		340
bedaquiline
bedaquiline: a diarylquinoline Antitubercular Agent. bedaquiline : A quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria.		2.1110aromatic ether;
naphthalenes;
organobromine compound;
quinolines;
tertiary alcohol;
tertiary amino compound		antitubercular agent;
ATP synthase inhibitor
opc-67683
OPC-67683: an antitubercular agent		340piperidines
ConditionIndicatedRelationship StrengthStudiesTrials
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		03.0340
Koch's Disease
[description not available]		02.7830
Tuberculosis
Any of the infectious diseases of man and other animals caused by species of MYCOBACTERIUM TUBERCULOSIS.		14.7830
Chronic Illness
[description not available]		02.0710
Pulmonary Consumption
[description not available]		02.0710
Acute Disease
Disease having a short and relatively severe course.		02.0710
Chronic Disease
Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).		02.0710
Tuberculosis, Pulmonary
MYCOBACTERIUM infections of the lung.		02.0710
Congenital Zika Syndrome
[description not available]		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Tuberculosis, Drug-Resistant
[description not available]		02.610
Tuberculosis, Multidrug-Resistant
Tuberculosis resistant to chemotherapy with two or more ANTITUBERCULAR AGENTS, including at least ISONIAZID and RIFAMPICIN. The problem of resistance is particularly troublesome in tuberculous OPPORTUNISTIC INFECTIONS associated with HIV INFECTIONS. It requires the use of second line drugs which are more toxic than the first line regimens. TB with isolates that have developed further resistance to at least three of the six classes of second line drugs is defined as EXTENSIVELY DRUG-RESISTANT TUBERCULOSIS.		02.610
Encephalopathy, Toxic
[description not available]		02.1710