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azides

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Description

Azides: Organic or inorganic compounds that contain the -N3 group. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

azide : Any nitrogen molecular entity containing the group -N3. [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 CID33558
CHEMBL ID79455
CHEBI ID40910
MeSH IDM0002074

Synonyms (37)

Synonym
azide anion
azide, negative ion
BIO1_000953
BIO1_000464
BIO1_001442
azide ion
trinitride (1-)
azide
n3(-)
14343-69-2
trinitride(1-)
CHEBI:40910 ,
chembl79455 ,
2$l^{6}-triaza-1,2-diyne
bdbm26985
n3(-1)
azides
NCGC00090996-03
NCGC00090996-02
azide ion(1-)
azide (n3-)
unii-88bia49l8p
nitrogen ion (n3-)
ccris 1791
azide(1-)
88bia49l8p ,
hydrazoate
hydrazoic acid, ion (1-)
trinitrogen ion (n3-)
C19935
hydrazoic acid, ion(1-)
irbesartan impurity b [ep impurity]
trinitride
IVRMZWNICZWHMI-UHFFFAOYSA-N
DTXSID8074310
azide(1-) ion
Q10853389

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Thus, this commercially important and widely distributed chemical with high acute toxicity is not considered to be teratogenic in hamsters, and it produces embryotoxicity only at dose rates that result in toxic signs in the dams."( Embryotoxic effects of sodium azide infusions in the Syrian hamster.
Ferm, VH; Kruszyna, H; Kruszyna, R; Sana, TR; Smith, RP; Wilcox, DE, 1990
)
0.28
" The toxic effects of the major basic and cationic proteins were inhibited by the polyanions heparin and dextran sulfate, in keeping with the cationic nature of these proteins, or by heat denaturation, suggesting that molecular conformation was also relevant."( Toxic effects produced or mediated by human eosinophil granule components on Trypanosoma cruzi.
Gleich, GJ; Hamann, KJ; Kierszenbaum, F; Molina, HA, 1988
)
0.27
" As target cell lysis is totally or partially inhibited by catalase, sodium azide and potassium cyanide, an involvement of toxic oxygen derivatives as cytolytic mediators was suggested."( Eosinophil-mediated cellular cytotoxicity induced by zymosan-activated serum.
De Simone, C; Ferrarelli, G; Ferrari, M; Pugnaloni, L; Rumi, C; Sorice, F, 1986
)
0.27
" Further characterization of the transport system for uroporphyrin in this model is expected to benefit not only our understanding of the cellular mechanism for disposal of toxic soluble wastes but also potentially the effective management of human uroporphyria and the use of uroporphyric Leishmania for vaccine/drug delivery."( Transgenic Leishmania model for delta-aminolevulinate-inducible monospecific uroporphyria: cytolytic phototoxicity initiated by singlet oxygen-mediated inactivation of proteins and its ablation by endosomal mobilization of cytosolic uroporphyrin.
Chang, KP; Dutta, S; Kolli, BK; Sassa, S; Tang, A, 2008
)
0.35
"Recognition of the occupational hazards from exposure to the propellants hydrazine and monomethylhydrazine (MMH) has led to research into less toxic alternatives."( Genotoxicity assessment of two hypergolic energetic propellant compounds.
Johnson, MS; Mecchi, MS; Reddy, G; Song, J, 2010
)
0.36
"To protect against ricin intoxication, a genetically derived ricin A chain vaccine candidate (RVEc) was developed lacking the toxic N-glycosidase activity (Olson et al."( Evaluation of a ricin vaccine candidate (RVEc) for human toxicity using an in vitro vascular leak assay.
DaSilva, L; Erwin-Cohen, R; Hale, M; Phillips, G; Porter, A; Smith, L; Tammariello, R, 2011
)
0.37
" We have shown that 1 when photoactivated accumulates in tumor cells and binds strongly to nuclear DNA under conditions in which it is toxic to tumor cells."( Interactions of DNA with a new platinum(IV) azide dipyridine complex activated by UVA and visible light: relationship to toxicity in tumor cells.
Brabec, V; Farrer, NJ; Kasparkova, J; Novakova, O; Pracharova, J; Sadler, PJ; Stepankova, J; Zerzankova, L, 2012
)
0.38
" Herein we report on a novel flow process that achieves the safe and effective on-demand synthesis of propargylic amines in a telescoped manner."( Development of a Telescoped Flow Process for the Safe and Effective Generation of Propargylic Amines.
Baumann, M; Donnelly, K; Zhang, H, 2019
)
0.51
" In contrast, the concentrations of PMA tested had no toxic effect on the viability of Vibrio cells studied."( Ethidium and propidium monoazide: comparison of potential toxicity on Vibrio sp. viability.
Bonnin-Jusserand, M; Copin, S; Grard, T; Midelet, G; Mougin, J; Raguenet, V; Robert-Pillot, A, 2021
)
0.62

Pharmacokinetics

ExcerptReferenceRelevance
" In pharmacokinetic studies, HL-60/AR cells exposed to different extracellular concentrations of [14C]DNR consistently accumulated less radioactive drug than the parent HL-60 cells."( Intracellular distribution and pharmacokinetics of daunorubicin in anthracycline-sensitive and -resistant HL-60 cells.
Baker, MA; Bhalla, K; Gervasoni, JE; Hindenburg, AA; Krishna, S; Lutzky, J; Rosado, M; Stewart, VJ; Taub, RN, 1989
)
0.28
" The bioconversion of the prodrug was investigated in vitro and in vivo, and the pharmacokinetic parameters were determined."( Synthesis, biotransformation, and pharmacokinetic studies of 9-(beta-D-arabinofuranosyl)-6-azidopurine: a prodrug for ara-A designed to utilize the azide reduction pathway.
Boudinot, FD; Chu, CK; Cretton-Scott, E; Kotra, LP; Manouilov, KK; Schinazi, RF; Sommadossi, JP, 1996
)
0.29
"The reversal effect of itraconazole on P-glycoprotein (P-gp)-mediated resistance of vinblastine, daunorubicin and doxorubicin was analyzed from a cellular pharmacokinetic point of view, namely by [3H]azidopine photoaffinity labeling, intracellular accumulation and transcellular transport experiments."( Cellular pharmacokinetic aspects of reversal effect of itraconazole on P-glycoprotein-mediated resistance of anticancer drugs.
Komada, F; Nishiguchi, K; Okumura, K; Sakaeda, T; Takara, K; Tanigawara, Y, 1999
)
0.3

Compound-Compound Interactions

ExcerptReferenceRelevance
"0 mg/kg), and Ro15-4513 in combination with Ro15-1788 on the time course of ETOH self-administration."( Ethanol self-administration in deprived rats: effects of Ro15-4513 alone, and in combination with flumazenil (Ro15-1788).
Colker, RE; Domangue, KR; Hicks, LH; June, HL; June, PL; Lewis, MJ; Perry, LE, 1992
)
0.28
"The electrophysiological effects of Ro 15-4513 and FG 7142 alone and in combination with ethanol were investigated."( EEG effects of Ro 15-4513 and FG 7142 alone and in combination with ethanol.
Chaplin, RI; Ehlers, CL; Koob, GF, 1990
)
0.28
" Binding of the 2E9-gold complex is followed by internalization, as judged from Nanovid light microscopy studies in combination with electron microscopic observations."( Dynamics of epidermal growth factor receptor internalization studied by Nanovid light microscopy and electron microscopy in combination with immunogold labeling.
Boonstra, J; de Brabander, M; Defize, LH; Nuijdens, R; van 't Hof, RJ; Verkleij, AJ, 1989
)
0.28
"0 mg/kg) alone and in combination with Ro15-1788, (flumazenil) (8."( Ethanol self-administration in freely feeding and drinking rats: effects of Ro15-4513 alone, and in combination with Ro15-1788 (flumazenil).
Hughes, RW; June, HL; Lewis, MJ; Spurlock, HL, 1994
)
0.29
"Protein chemistry, such as crosslinking and photoaffinity labeling, in combination with modern mass spectrometric techniques, can provide information regarding protein-protein interactions beyond that normally obtained from protein identification and characterization studies."( Photoaffinity labeling combined with mass spectrometric approaches as a tool for structural proteomics.
Borchers, CH; Neamati, N; Robinette, D; Tomer, KB, 2006
)
0.33
" sobrinus, using PMA combined with real-time PCR (PMA-qPCR)."( Monitoring the prevalence of viable and dead cariogenic bacteria in oral specimens and in vitro biofilms by qPCR combined with propidium monoazide.
Ansai, T; Awano, S; Maki, K; Morikawa, K; Nakamura, S; Soh, I; Yasunaga, A; Yoshida, A, 2013
)
0.39
" The aim of this study was to use propidium monoazide (PMA) combined with the quantitative polymerase chain reaction (PMA-qPCR) to selectively detect and quantify viable bacteria cells in full-scale WWTPs in China."( Quantification of viable bacteria in wastewater treatment plants by using propidium monoazide combined with quantitative PCR (PMA-qPCR).
He, M; Li, D; Lin, Y; Tong, T; Wu, S; Zeng, S, 2014
)
0.4
" Here we reported the in vitro activity of azvudine against HIV-1 and HIV-2 when used alone or in combination with other antiretroviral drugs and its drug resistance features."( Azvudine, a novel nucleoside reverse transcriptase inhibitor showed good drug combination features and better inhibition on drug-resistant strains than lamivudine in vitro.
Chang, JB; Chen, H; Cui, XQ; Dai, SX; Huang, JF; Liu, YJ; Luo, RH; Peng, YM; Wang, RR; Yang, QH; Zhang, XJ; Zheng, YT, 2014
)
0.4
"We detected Legionella species in 111 bath water samples and 95 cooling tower water samples by using a combination of conventional plate culture, quantitative polymerase chain reaction (qPCR) and qPCR combined with ethidium monoazide treatment (EMA-qPCR) methods."( Detection of Legionella species in environmental water by the quantitative PCR method in combination with ethidium monoazide treatment.
Agata, K; Inoue, H; Takama, T; Yoshizaki, M, 2015
)
0.42
" Among all the methods for detecting viability, propidium monoazide (PMA) combined with real-time PCR is popular because of its specificity, sensitivity, and speed."( Enumeration of viable non-culturable Vibrio cholerae using propidium monoazide combined with quantitative PCR.
Kan, B; Liang, W; Wu, B, 2015
)
0.42
" Shifts in the bacterial community compositions in secondary effluent samples upon chlorine disinfection, both immediately and after 24 h of storage, were investigated using Illumina MiSeq sequencing combined with propidium monoazide (PMA) treatment."( Shifts of live bacterial community in secondary effluent by chlorine disinfection revealed by Miseq high-throughput sequencing combined with propidium monoazide treatment.
Hu, HY; Huo, ZY; Pang, YC; Xi, JY; Xu, Y, 2016
)
0.43
" paracasei) in fermented milk accurately and quickly, propidium monoazide combined with quantitative loop-mediated isothermal amplification (PMA-qLAMP) was applied."( Detection of viable Lacticaseibacillus paracasei in fermented milk using propidium monoazide combined with quantitative loop-mediated isothermal amplification.
Cui, L; Feng, L; Hu, L; Wang, S; Xue, Y; Zhang, D; Zhang, W, 2021
)
0.62

Bioavailability

ExcerptReferenceRelevance
" The plot of absorption rate vs."( Arachidonic acid intestinal absorption: mechanism of transport and influence of luminal factors of absorption in vitro.
Chow, SL; Hollander, D, 1978
)
0.26
"74 h after intravenous and oral administration, respectively, and the oral bioavailability was about 21 percent."( Antiretroviral activity, biochemistry, and pharmacokinetics of 3'-azido-2',3'-dideoxy-5-methylcytidine.
Boudinot, FD; Chu, CK; Doshi, KJ; Eriksson, BF; McClure, HM; Oswald, B; Schinazi, RF; Sommadossi, JP, 1990
)
0.28
" If these results were extrapolated to humans, they would explain the excellent bioavailability profiles reported for baclofen at normal doses in spite of its physicochemical properties, which do not favour passive diffusion."( Evidence of a specialized transport mechanism for the intestinal absorption of baclofen.
Casabó, VG; García-Carbonell, MC; Martín-Villodre, A; Merino, M; Peris-Ribera, JE; Plá-Delfina, JM; Sánchez-Picó, A; Torres-Molina, F,
)
0.13
"Oral bioavailability for antisense oligonucleotides has recently been reported but the mechanistic details are not known."( Interactions of phosphodiester and phosphorothioate oligonucleotides with intestinal epithelial Caco-2 cells.
Akhtar, S; Beck, GF; Irwin, WJ; Nicklin, PL, 1996
)
0.29
"tert-Azido or amino substituted penciclovir analogs, 1-3 were synthesized for the purpose of improving the efficacy and bioavailability of penciclovir and searching for novel antiviral agents."( Synthesis and biological evaluation of novel tert-azido or tert-amino substituted penciclovir analogs.
Baek, HW; Chun, MW; Jeong, LS; Kim, DK; Kim, HO; Moon, HR, 2004
)
0.32
"The human P-glycoprotein (Pgp, ABCB1) is an ATP-dependent efflux pump for structurally unrelated hydrophobic compounds, conferring simultaneous resistance to and restricting bioavailability of several anticancer and antimicrobial agents."( Modulator-induced interference in functional cross talk between the substrate and the ATP sites of human P-glycoprotein.
Chattopadhyay, A; Dey, S; Ghosh, P; Maki, N; Moitra, K; Silver, C, 2006
)
0.33
"The human ATP-binding cassette transporter, ABCG2, confers resistance to multiple chemotherapeutic agents and also affects the bioavailability of different drugs."( The calcium channel blockers, 1,4-dihydropyridines, are substrates of the multidrug resistance-linked ABC drug transporter, ABCG2.
Ambudkar, SV; Bates, SE; Robey, RW; Shukla, S, 2006
)
0.33
" Based on studies in wild type and abcg2-/- mice, we observed that oral curcumin increased Cmax and relative bioavailability of sulfasalazine by selectively inhibiting ABCG2 function."( Curcumin inhibits the activity of ABCG2/BCRP1, a multidrug resistance-linked ABC drug transporter in mice.
Ambudkar, SV; Bauer, B; Hartz, A; Shukla, S; Ware, JA; Zaher, H, 2009
)
0.35
"Short peptides are important as lead compounds and molecular probes in drug discovery and chemical biology, but their well-known drawbacks, such as high conformational flexibility, protease lability, poor bioavailability and short half-lives in vivo, have prevented their potential from being fully realized."( Stapling of a 3(10)-helix with click chemistry.
Amiry-Moghaddam, M; Ge, NH; Görbitz, CH; Jacobsen, Ø; Klaveness, J; Maekawa, H; Ottersen, OP; Rongved, P, 2011
)
0.37
" Suvorexant (MK-4305) is a potent, selective, and orally bioavailable antagonist of OX(1)R and OX(2)R currently under clinical investigation as a novel therapy for insomnia."( Promotion of sleep by suvorexant-a novel dual orexin receptor antagonist.
Breslin, MJ; Coleman, PJ; Cox, CD; Cui, D; Doran, SM; Fox, SV; Garson, SL; Gotter, AL; Harrell, CM; Reiss, DR; Renger, JJ; Stevens, J; Tannenbaum, PL; Winrow, CJ, 2011
)
0.37
" Increasing PEG size yielded decreasing in vitro antiviral activities along with concomitant increases in elimination half-life, AUC, and bioavailability when administered in rats or monkeys."( Development of copper-catalyzed azide-alkyne cycloaddition for increased in vivo efficacy of interferon β-1b by site-specific PEGylation.
Grabstein, K; Graddis, TJ; Nairn, NW; Shanebeck, KD; Thornton, KC; VanBrunt, MP; Wang, A, 2012
)
0.38
" In vivo bioavailability of micellar nanoparticles was enhanced ~10 fold over free Pt(IV) prodrugs."( Photosensitive Pt(IV)-azide prodrug-loaded nanoparticles exhibit controlled drug release and enhanced efficacy in vivo.
Bilgicer, B; Jing, X; Kiziltepe, T; Noble, GT; Qi, R; Stefanick, JF; Xiao, H, 2014
)
0.4
" However, the limited bioavailability of curcumin prevents its use for modulation of the function of these transporters in the clinical setting."( Synthetic Analogs of Curcumin Modulate the Function of Multidrug Resistance-Linked ATP-Binding Cassette Transporter ABCG2.
Ambudkar, SV; Chufan, EE; Fukuda, M; Ishida, M; Iwabuchi, Y; Kanehara, K; Kudoh, K; Murakami, M; Naitoh, T; Ohnuma, S; Shibata, H; Sugisawa, N; Unno, M, 2017
)
0.46
"In vivo bioavailability and delivery of nucleic acids to the site of action is a severe limitation in oligonucleotide (ON) therapeutics."( Attachment of Peptides to Oligonucleotides on Solid Support Using Copper(I)-Catalyzed Huisgen 1,3-Dipolar Cycloaddition.
Honcharenko, D; Honcharenko, M; Strömberg, R, 2019
)
0.51
"Fabrication of self-delivery drug systems can surmount low drug bioavailability and achieve a precise therapeutic process."( Azide-Locked Prodrug Co-Assembly into Nanoparticles with Indocyanine Green for Chemophotothermal Therapy.
Hou, M; Li, B; Li, Y; Liu, H; Liu, L; Xu, M; Xu, Z; Ye, M; Zhang, H, 2022
)
0.72
" However, there are still many shortcomings that need to be solved urgently, including worse membrane permeability and bioavailability induced by their large molecular weight."( Discovery of intracellular self-assembly protein degraders driven by tumor-specific activatable bioorthogonal reaction.
Hai, P; Li, Y; Pan, X; Si, R; Wang, J; Zhang, J; Zhang, Q; Zheng, Y, 2023
)
0.91

Dosage Studied

ExcerptRelevanceReference
"In rabbits the topical administration of sodium azide (NaNs) or sodium nitroprusside (SNP) increased intraocular pressure in a dose-response manner."( Increased intraocular pressure following topical azide or nitroprusside.
Becker, B; Fritz, C; Holmberg, N; Krupin, T; Weiss, A, 1977
)
0.26
" Comparison of PMN and macrophages from different species showed that the maximal chemiluminescent response seen in the dose-response curve of F-Met- Phe was different in different cell types."( Chemiluminescence of phagocytic cells caused by N-formylmethionyl peptides.
Gardner, DE; Hatch, GE; Menzel, DB, 1978
)
0.26
" Under the time and dosing conditions used in previous reports, Ro 15-4513 did not alter ethanol discrimination whether given prior to or after ethanol exposure."( Effects of Ro 15-4513 on ethanol discrimination in C57BL/6 mice.
Bao, K; Becker, HC; Daniel, SS; Middaugh, LD, 1991
)
0.28
" The latter mutations exhibited dominant traits when gene dosage was increased."( Yeast cAMP-dependent protein kinase regulatory subunit mutations display a variety of phenotypes.
Cannon, JF; Gitan, R; Tatchell, K, 1990
)
0.28
" Although absolute tissue concentrations are not known, dose-response curves constructed using pressure-ejection doses as previously described we found that FG 7142 was more efficacious, but less potent than Ro 15-4513."( GABAergic mechanisms in the electrophysiological actions of ethanol on cerebellar neurons.
Hoffer, BJ; Palmer, MR, 1990
)
0.28
"0% dosage range, a straight-line dose-response relationship occurred between the concentration of SM applied and the number of paranuclear vacuoles seen histologically in the epidermis."( Full-thickness human skin explants for testing the toxicity of topically applied chemicals.
Dannenberg, AM; Moore, KG; Nakamura, M; Pula, PJ; Rikimaru, T; Schofield, BH; Yano, T, 1990
)
0.28
" In mice pre-transplanted with EL-4 cells, T-2-mAb increased the mean survival time (MST) with a direct dosage dependence."( Antitumor activity of T-2 toxin-conjugated monoclonal antibody to murine thymoma.
Chiba, J; Kawamura, O; Murakami, H; Ohi, K; Ohtani, K; Otokawa, M; Shibuya, O; Ueno, Y, 1990
)
0.28
" This study represents the first demonstration, to our knowledge, of the electrophysiologic actions of EtOH on single neurons from human brain, and provides dose-response data collected with known concentrations of EtOH as well as evidence for the blockade of these EtOH effects by the Roche compound."( Electrophysiologic effects of ethanol in human brain xenografts in oculo: antagonism by Ro15-4513.
Bygdeman, M; Eriksdotter-Nilsson, M; Granholm, AC; Hoffer, BJ; Olson, L; Palmer, MR; Seiger, A; Stieg, P; Strömberg, I, 1990
)
0.28
" Five of six chemicals tested yielded statistically significant and generally linear dose-response curves."( Assay of mutagens in aqueous fecal extracts with a modified ames Salmonella test.
Andrews, AW; Riggs, CW; Shaw, R, 1985
)
0.27
" This increase was not due to a shift in the PMA dose-response curve, a change in the time course of the PMA response, or an effect of decreased cell density on the assay system."( Exposure to gamma-irradiation increases phorbol myristate acetate-induced H2O2 production in human macrophages.
Gallin, EK; Green, SW, 1987
)
0.27
" Dose-response and time course studies of Ro 15-4513 against gamma-aminobutyric acid (GABA) antagonists were performed."( Interactions of the imidazodiazepine Ro 15-4513 with chemical convulsants.
Lister, RG; Nutt, DJ, 1988
)
0.27
" Binding and covalent attachment of (125)I-labeled glucagon to the M(r) 53,000 peptide were inhibited by glucagon concentrations that were within the dose-response curve for adenylate cyclase activation, and GTP specifically decreased the photoaffinity crosslinking of (125)I-labeled glucagon to the M(r) 53,000 peptides."( Identification of the glucagon receptor in rat liver membranes by photoaffinity crosslinking.
Johnson, GL; MacAndrew, VI; Pilch, PF, 1981
)
0.26
" The 35,000-Da papain fragment was biologically active as evidenced by an unchanged dose-response curve for peptide-stimulated beta-glucuronidase release and fluorescent peptide uptake."( Formyl peptide chemotactic receptor. Evidence for an active proteolytic fragment.
Dolmatch, B; Niedel, J, 1983
)
0.27
" A clear dose-response relationship to fractional survival was observed for individual tumors tested at multiple dose levels of abrin."( Usefulness of abrin as a positive control for the human tumor clonogenic assay.
Hayes, C; Liu, R; Persaud, J; Roberts, R; Salmon, SE, 1983
)
0.27
" The dose-response curves of the nettle-fed tadpoles when compared with the liver-fed tadpoles were shifted to the right."( Influence of diet on the susceptibility of Xenopus laevis tadpoles to thiopentone and a membrane probe.
Haw, ME, 1981
)
0.26
" MH yielded positive responses in all laboratories but no linear dose-response pattern was observed."( Tradescantia stamen hair mutation bioassay.
Cabrera, GL; Cebulska-Wasilewska, A; Chen, R; Loarca, F; Ma, TH; Salamone, MF; Vandenberg, AL, 1994
)
0.29
" Moreover, the soluble guanylate cyclase inhibitor LY-83583 inhibited in a dose-response manner the effects of the NO donors."( The nitric oxide donors, azide and hydroxylamine, inhibit the programmed cell death of cytokine-deprived human eosinophils.
Beauvais, F; Dubertret, L; Michel, L, 1995
)
0.29
" The ADP dosage was performed by using a spectrophotometric enzymatic assay."( An in vitro method for evaluating vascular endothelial ADPase activity.
Caprino, L; Stella, C; Togna, AR; Togna, G, 1996
)
0.29
" We compared the effects of two dosing paradigms on GABA(A) receptor gene expression and benzodiazepine binding characteristics."( GABA(A) receptor gene expression in rat cortex: differential effects of two chronic diazepam treatment regimes.
Arnot, MI; Bateson, AN; Davies, M; Martin, IL, 2001
)
0.31
" The results obtained in the analysis of dosage forms agreed well with the contents stated on the labels."( Spectrophotometric, difference spectroscopic, and high-performance liquid chromatographic methods for the determination of cefixime in pharmaceutical formulations.
Pundarikakshudu, K; Shah, PB,
)
0.13
", 5-minute pretreatment) shifted the zolpidem dose-response curve to the right in all monkeys showing generalization."( Zolpidem generalization and antagonism in male and female cynomolgus monkeys trained to discriminate 1.0 or 2.0 g/kg ethanol.
Grant, KA; Helms, CM; Rogers, LS; Waters, CA, 2008
)
0.35
", 5-min pretreatment) shifted the ethanol, PB, and midazolam dose-response functions rightward in a vast majority of monkeys tested (15/15, 16/17, and 11/12, respectively)."( Antagonism of the ethanol-like discriminative stimulus effects of ethanol, pentobarbital, and midazolam in cynomolgus monkeys reveals involvement of specific GABA(A) receptor subtypes.
Grant, KA; Helms, CM; Rogers, LS, 2009
)
0.35
" Dosed orally Suvorexant significantly and dose-dependently reduced locomotor activity and promoted sleep in rats (10, 30, and 100 mg/kg), dogs (1 and 3 mg/kg), and rhesus monkeys (10 mg/kg)."( Promotion of sleep by suvorexant-a novel dual orexin receptor antagonist.
Breslin, MJ; Coleman, PJ; Cox, CD; Cui, D; Doran, SM; Fox, SV; Garson, SL; Gotter, AL; Harrell, CM; Reiss, DR; Renger, JJ; Stevens, J; Tannenbaum, PL; Winrow, CJ, 2011
)
0.37
" A Daudi tumor xenograft model provided comparative evaluation of these combined effects, wherein a 40 kDa branched PEG-IFNb was much more effective than conjugates with smaller PEGs or unPEGylated IFNb at preventing tumor growth in spite of dosing with fewer units and lesser frequency."( Development of copper-catalyzed azide-alkyne cycloaddition for increased in vivo efficacy of interferon β-1b by site-specific PEGylation.
Grabstein, K; Graddis, TJ; Nairn, NW; Shanebeck, KD; Thornton, KC; VanBrunt, MP; Wang, A, 2012
)
0.38
" Stage 40-47 tadpoles were also incubated 1 h with microtubule stabilizing agents, epothilone D or discodermolide, followed by dosing with 1-aminoanthracene."( Direct modulation of microtubule stability contributes to anthracene general anesthesia.
Dmochowski, IJ; Eckenhoff, RG; Emerson, DJ; Fiamengo, A; Liao, Z; Psonis, J; Smith, AB; Sugasawa, K; Taratula, O; Wang, X; Weiser, BP, 2013
)
0.39
" Dosage and schedule studies were conducted to evaluate the immunogenicity and protective efficacy of three potential second-generation inactivated EEEV (iEEEV) vaccine candidates in mice: formalin-inactivated CVEV1219 (fCVEV1219), INA-inactivated CVEV1219 (iCVEV1219) and gamma-irradiated CVEV1219 (gCVEV1219)."( Second generation inactivated eastern equine encephalitis virus vaccine candidates protect mice against a lethal aerosol challenge.
Bakken, RR; Cohen, JW; Eccleston, LT; Fisher, D; Glass, PJ; Honnold, SP; Lind, CM; Maheshwari, RK; Spurgers, KB, 2014
)
0.4
" In one prominent example illustrating the importance of incorporating nitrogen-based functionality, the conversion of the ketone of erythromycin to the -N(Me)CH2- group in azithromycin leads to a compound that can be dosed once daily with a shorter treatment time."( Metal-catalysed azidation of tertiary C-H bonds suitable for late-stage functionalization.
Hartwig, JF; Sharma, A, 2015
)
0.42
" The sCAR-T-cell dosing regimen could be tuned to provide efficacy comparable to the corresponding conventional CART-19, but with lower cytokine levels, thereby offering a method of mitigating cytokine release syndrome in clinical translation."( Switch-mediated activation and retargeting of CAR-T cells for B-cell malignancies.
Cao, Y; Du, J; Hampton, EN; Hardy, IR; Kim, CH; Ma, J; Mazagova, M; Nunez, V; Ramadoss, NS; Rodgers, DT; Schulman, A; Schultz, PG; Shen, J; Singer, O; Wang, F; Woods, AK; Wright, TM; Young, TS, 2016
)
0.43
"Our study is the first report evidencing the emergence of VNBC legionella during a long period of continuous MC treatment of a hospital water network, highlighting the importance of keeping an appropriate and uninterrupted MC dosage to ensure the control of legionella colonization in hospital water supplies."( Detection of viable but non-culturable legionella in hospital water network following monochloramine disinfection.
Aquino, F; Baggiani, A; Bruschi, F; Casini, B; Costa, AL; Lopalco, PL; Mansi, A; Miccoli, M; Privitera, G; Totaro, M; Valentini, P, 2018
)
0.48
" These results suggested that hyaluronic acid conjugation could reduce the dosage of antibiotic in treatment of intracellular bacterial infection, and further helping to alleviate the emergence of drug resistance in bacteria due to a long-term, high-dosage treatment."( Synthesis of hyaluronan-amikacin conjugate and its bactericidal activity against intracellular bacteria in vitro and in vivo.
Duan, J; Hou, C; Li, X; Mu, H; Qiu, Y; Sun, F; Wang, D; Wang, F; Wang, Z; Yi, H, 2018
)
0.48
"Liposomal formulations have important therapeutic applications in anti-cancer treatments but current formulations suffer from serious side effects, high dosage requirements and prolonged treatment."( PEGylation and surface functionalization of liposomes containing drug nanocrystals for cell-targeted delivery.
Boyd, BJ; Clulow, AJ; de Campo, L; Gilbert, EP; Hawley, A; Li, T; Liu, Q; Manohar, M; Xiao, Y, 2019
)
0.51
" PEGylation increases the molecular weight of B2036 and considerably extends its circulation time, but also dramatically reduces its bioactivity, contributing to high dosing requirements and increased cost."( Genetic Code Expansion Enables Site-Specific PEGylation of a Human Growth Hormone Receptor Antagonist through Click Chemistry.
Jamieson, SMF; Maynard, HD; Perry, JK; Tamshen, K; Wang, Y, 2020
)
0.56
" Adding antibiotics (sulfamethoxazole and ciprofloxacin), that temporarily inhibited the nitrification process during the dosing period, showed a minor effect in 1,4-dioxane removal (6-8% decline, p < 0."( 1,4-Dioxane removal in nitrifying sand filters treating domestic wastewater: Influence of water matrix and microbial inhibitors.
Brownawell, BJ; Clyde, PM; Lee, CS; Mao, X; Venkatesan, AK; Wang, M, 2023
)
0.91
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mitochondrial respiratory-chain inhibitornull
[role information is derived from 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]

Drug Classes (1)

ClassDescription
pseudohalide anion
[compound class information is derived from 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]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Ki8,326.81250.00001.372610.0000AID1262263; AID1278739; AID1306523; AID1798763; AID1803484
Carbonic anhydrase 2Homo sapiens (human)Ki9,079.96250.00000.72369.9200AID1262264; AID1278740; AID1306524; AID1798763; AID1803485
Carbonic anhydrase 4Homo sapiens (human)Ki16,652.42500.00021.97209.9200AID1798763
Carbonic anhydraseMethanosarcina thermophilaKi8,700.00000.06000.97148.5000AID1803493
Carbonic anhydrase 15Mus musculus (house mouse)Ki16,652.42500.00091.884610.0000AID1798763
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (13)

Processvia Protein(s)Taxonomy
one-carbon metabolic processCarbonic anhydrase 1Homo sapiens (human)
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
bicarbonate transportCarbonic anhydrase 4Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 1Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 1Homo sapiens (human)
protein bindingCarbonic anhydrase 1Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 1Homo sapiens (human)
hydro-lyase activityCarbonic anhydrase 1Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 1Homo sapiens (human)
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 4Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 4Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (19)

Processvia Protein(s)Taxonomy
cytosolCarbonic anhydrase 1Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 1Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
basolateral plasma membraneCarbonic anhydrase 4Homo sapiens (human)
rough endoplasmic reticulumCarbonic anhydrase 4Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentCarbonic anhydrase 4Homo sapiens (human)
Golgi apparatusCarbonic anhydrase 4Homo sapiens (human)
trans-Golgi networkCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
external side of plasma membraneCarbonic anhydrase 4Homo sapiens (human)
cell surfaceCarbonic anhydrase 4Homo sapiens (human)
membraneCarbonic anhydrase 4Homo sapiens (human)
apical plasma membraneCarbonic anhydrase 4Homo sapiens (human)
transport vesicle membraneCarbonic anhydrase 4Homo sapiens (human)
secretory granule membraneCarbonic anhydrase 4Homo sapiens (human)
brush border membraneCarbonic anhydrase 4Homo sapiens (human)
perinuclear region of cytoplasmCarbonic anhydrase 4Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 4Homo sapiens (human)
plasma membraneCarbonic anhydrase 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID1798763CA Inhibition Assay from Article 10.1016/j.bmcl.2008.12.082: \\Carbonic anhydrase inhibitors: the membrane-associated isoform XV is highly inhibited by inorganic anions.\\2009Bioorganic & medicinal chemistry letters, Feb-15, Volume: 19, Issue:4
Carbonic anhydrase inhibitors: the membrane-associated isoform XV is highly inhibited by inorganic anions.
AID1803486ChEMBL_158306 (CHEMBL763191) from Article 10.1016/j.bmc.2016.05.029: \\Anion inhibition profiles of a-, u00DF- and u00BF-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.\\2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1803485ChEMBL_158305 (CHEMBL763190) from Article 10.1016/j.bmc.2016.05.029: \\Anion inhibition profiles of a-, u00DF- and u00BF-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.\\2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1803491ChEMBL_158311 (CHEMBL763368) from Article 10.1016/j.bmc.2016.05.029: \\Anion inhibition profiles of a-, u00DF- and u00BF-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.\\2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1803493ChEMBL_158313 (CHEMBL763370) from Article 10.1016/j.bmc.2016.05.029: \\Anion inhibition profiles of a-, u00DF- and u00BF-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.\\2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1803484ChEMBL_158304 (CHEMBL763189) from Article 10.1016/j.bmc.2016.05.029: \\Anion inhibition profiles of a-, u00DF- and u00BF-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.\\2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1803254CA Inhibition Assay from Article 10.3109/14756366.2011.649268: \\Inhibition of the alpha- and beta-carbonic anhydrases from the gastric pathogen Helycobacter pylori with anions.\\2013Journal of enzyme inhibition and medicinal chemistry, Apr, Volume: 28, Issue:2
Inhibition of the alpha- and beta-carbonic anhydrases from the gastric pathogen Helycobacter pylori with anions.
AID1803487ChEMBL_158307 (CHEMBL763192) from Article 10.1016/j.bmc.2016.05.029: \\Anion inhibition profiles of a-, u00DF- and u00BF-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.\\2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1306530Inhibition of Vibrio cholerae carbonic anhydrase beta preincubated for 15 mins by stopped-flow CO2 hydrase assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1262267Inhibition of Chionodraco hamatus alphaCA incubated for 15 mins prior to testing by stopped flow CO2 hydrase assay2015Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23
Anion and sulfonamide inhibition studies of an α-carbonic anhydrase from the Antarctic hemoglobinless fish Chionodraco hamatus.
AID1306526Inhibition of Vibrio cholerae alpha carbonic anhydrase preincubated for 15 mins by stopped-flow CO2 hydrase assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1306525Inhibition of Helicobacter pylori alpha carbonic anhydrase preincubated for 15 mins by stopped-flow CO2 hydrase assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1306524Inhibition of human carbonic anhydrase 2 preincubated for 15 mins by stopped-flow CO2 hydrase assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1262264Inhibition of human CA2 incubated for 15 mins prior to testing by stopped flow CO2 hydrase assay2015Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23
Anion and sulfonamide inhibition studies of an α-carbonic anhydrase from the Antarctic hemoglobinless fish Chionodraco hamatus.
AID1306523Inhibition of human carbonic anhydrase 1 preincubated for 15 mins by stopped-flow CO2 hydrase assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1278741Inhibition of Vibrio cholerae alpha-carbonic anhydrase preincubated for 15 mins by stopped-flow CO2 hydration assay2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Anion inhibition studies of the β-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.
AID1306532Inhibition of Vibrio cholerae recombinant carbonic anhydrase gamma expressed in Escherichia coli DE3 cells preincubated for 15 mins by stopped-flow CO2 hydrase assay2016Bioorganic & medicinal chemistry, 08-15, Volume: 24, Issue:16
Anion inhibition profiles of α-, β- and γ-carbonic anhydrases from the pathogenic bacterium Vibrio cholerae.
AID1262263Inhibition of human CA1 incubated for 15 mins prior to testing by stopped flow CO2 hydrase assay2015Bioorganic & medicinal chemistry letters, Dec-01, Volume: 25, Issue:23
Anion and sulfonamide inhibition studies of an α-carbonic anhydrase from the Antarctic hemoglobinless fish Chionodraco hamatus.
AID1278742Inhibition of recombinant Vibrio cholerae beta-carbonic anhydrase expressed in competent Escherichia coli BL21(DE3) cells preincubated for 15 mins by stopped-flow CO2 hydration assay2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Anion inhibition studies of the β-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.
AID1278739Inhibition of human carbonic anhydrase 1 preincubated for 15 mins by stopped-flow CO2 hydration assay2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Anion inhibition studies of the β-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.
AID1278740Inhibition of human carbonic anhydrase 2 preincubated for 15 mins by stopped-flow CO2 hydration assay2016Bioorganic & medicinal chemistry letters, Mar-01, Volume: 26, Issue:5
Anion inhibition studies of the β-carbonic anhydrase from the pathogenic bacterium Vibrio cholerae.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11,039)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904202 (38.07)18.7374
1990's1896 (17.18)18.2507
2000's1458 (13.21)29.6817
2010's2786 (25.24)24.3611
2020's697 (6.31)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 89.93

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 very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index89.93 (24.57)
Research Supply Index9.34 (2.92)
Research Growth Index4.61 (4.65)
Search Engine Demand Index168.71 (26.88)
Search Engine Supply Index2.01 (0.95)

This Compound (89.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials18 (0.16%)5.53%
Reviews282 (2.49%)6.00%
Case Studies24 (0.21%)4.05%
Observational3 (0.03%)0.25%
Other11,010 (97.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]