Page last updated: 2024-10-15

2,2'-(hydroxynitrosohydrazono)bis-ethanamine

Description

2,2'-(hydroxynitrosohydrazono)bis-ethanamine: a nitric oxide (NO) generating compound [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1,1-bis(2-aminoethyl)-2-hydroxy-3-oxotriazane : A nitroso compound that is triazane in which the the nitrogen at position 1 is substituted by two 2-aminoethyl groups, that at position 2 is substituted by a hydroxy group, and that at position 3 is substituted by an oxo group. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID135402056
CHEMBL ID136200
CHEBI ID50154
SCHEMBL ID448826
SCHEMBL ID960847
MeSH IDM0248242

Synonyms (34)

Synonym
[[bis(2-aminoethyl)amino]-oxo-ammonio]-hydroxy-azanide
1,1-bis(2-aminoethyl)-3-hydroxytriazane 2-oxide
aeed/no
nsc-653048
nsc653048
2,2'-(hydroxynitrosohydrazino)bis-ethanamine
2,2'-(hydroxynitrosohydrazono)bis-ethanamine
146724-94-9
deta-nonoate
detanonoate
diethylenetriamine nonoate
noc-18
deta nonoate
1,1-bis(2-aminoethyl)-2-hydroxy-3-oxotriazane
1-hydroxy-2-oxo-3,3-bis(2-aminoethyl)-1-triazene
CHEMBL136200
chebi:50154 ,
n-[bis(2-aminoethyl)amino]-n-hydroxynitrous amide
unii-lds7zyg72j
lds7zyg72j ,
AKOS006228679
3,3-bis(aminoethyl)-1-hydroxy-2-oxo-1-triazene
SCHEMBL448826
SCHEMBL960847
ethanamine,2,2'-(2-hydroxy-2-nitrosohydrazinylidene)bis-
DTXSID7036795
(z)-[bis(2-aminoethyl)amino]-hydroxyimino-oxidoazanium
J-008253
diethylenetriamine nitric oxide
2,2'-(2-hydroxy-2-nitrosohydrazinylidene)bis(ethanamine)
ethanamine, 2,2'-(2-hydroxy-2-nitrosohydrazinylidene)bis-
ethanamine, 2,2'-(hydroxynitrosohydrazono)bis-
HY-136278
CS-0124043

Toxicity

ExcerptReference
" The remaining animals exhibited no adverse behavioral effects."( Intracranial delivery of the nitric oxide donor diethylenetriamine/nitric oxide from a controlled-release polymer: toxicity in cynomolgus monkeys.
Clatterbuck, RE; Pradilla, G; Tamargo, RJ; Tierney, TS; Wang, PP, 2006
)
" These findings show that continuous intracisternal delivery of DETA/NO is a safe and potentially effective strategy for prophylactic treatment of delayed cerebral vasospasm."( Intracranial delivery of the nitric oxide donor diethylenetriamine/nitric oxide from a controlled-release polymer: toxicity in cynomolgus monkeys.
Clatterbuck, RE; Pradilla, G; Tamargo, RJ; Tierney, TS; Wang, PP, 2006
)

Bioavailability

ExcerptReference
"The overall objective of this study was to assess the contribution of an altered bioavailability of nitric oxide (NO) to the leukocyte adhesion and hypoxic stress elicited in the liver by gut ischemia-reperfusion (I/R)."( Role of nitric oxide in gut ischemia-reperfusion-induced hepatic microvascular dysfunction.
Granger, DN; Horie, Y; Wolf, R, 1997
)
" High glucose inhibits nitric oxide (NO) bioavailability and decreased NO increases TGF-beta activity and extracellular matrix accumulation."( Nitric oxide and cGMP-dependent protein kinase regulation of glucose-mediated thrombospondin 1-dependent transforming growth factor-beta activation in mesangial cells.
Darley-Usmar, V; Murphy-Ullrich, JE; Poczatek, MH; Shiva, S; Wang, S, 2002
)
" If so, systematic proteomic analyses in which redox state and NO bioavailability are carefully controlled will reveal a large array of novel interactions."( Screening for nitric oxide-dependent protein-protein interactions.
Comatas, KE; Liu, L; Matsumoto, A; Stamler, JS, 2003
)
"Nitrite anion is bioactive nitric oxide (NO) species circulating in blood, and represents the NO bioavailability and endothelial function."( Decreased nitrite levels in erythrocytes of children with β-thalassemia/hemoglobin E.
Chuansumrit, A; Fucharoen, S; Sibmooh, N; Sirachainan, N; Srihirun, S; Suvachananonda, T; Tanratana, P; Unchern, S; Wankham, A, 2013
)

Dosage Studied

ExcerptReference
" The death of one animal in the treatment group indicates that the present dosage is at the threshold between therapeutic efficacy and toxicity."( Controlled release of a nitric oxide donor for the prevention of delayed cerebral vasospasm following experimental subarachnoid hemorrhage in nonhuman primates.
Clatterbuck, RE; Clatterbuck, VM; Gailloud, P; Murphy, KJ; Tamargo, RJ; Tierney, T, 2005
)
" Phenylephrine dose-response contraction was obtained after 1, 2, and 3 h in segments pre-incubated with DETA-NONOate or papaverine for 30 min."( Effect of DETA-NONOate and papaverine on vasodilation of human internal mammary artery.
Ansari, M; Dehpour, AR; Javadi-Paydar, M; Rabbani, S; Rahimi, N; Sohanaki, H; Tafti, SH, 2011
)
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID24922Half life of compound for dissociation in DETA and NO1996Journal of medicinal chemistry, Oct-25, Volume: 39, Issue:22
Localizing antithrombotic and vasodilatory activity with a novel, ultrafast nitric oxide donor.
AID362920Antifungal activity against Candida sp. by microdilution assay2008Bioorganic & medicinal chemistry, Sep-01, Volume: 16, Issue:17
NO-donors. Part 17: Synthesis and antimicrobial activity of novel ketoconazole-NO-donor hybrid compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (371)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's40 (10.78)18.2507
2000's229 (61.73)29.6817
2010's97 (26.15)24.3611
2020's5 (1.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials1 (0.27%)5.53%
Reviews3 (0.80%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other372 (98.94%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]