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cyanates

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Description

Cyanates: Organic salts of cyanic acid containing the -OCN radical. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N. [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]

isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N). [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 CID105034
CHEBI ID29195
MeSH IDM0005436

Synonyms (30)

Synonym
cyanat
zyanat
cyanate ion
71000-82-3
nitridooxidocarbonate(1-)
CHEBI:29195
[c(n)o](-)
isocyanate
cyanate
hydrogen cyanate
cno(-1)
bdbm26982
isocyanates
unii-yml51wa0fw
cyanates
yml51wa0fw ,
661-20-1
cyanate ion(1-)
isocyanic acid, ion(1-)
isocyanate ion(1-)
un2206
XLJMAIOERFSOGZ-UHFFFAOYSA-M
IQPQWNKOIGAROB-UHFFFAOYSA-N
carbonyl amide
isocynate
bdbm50098562
DTXSID80984596
Q55503523
cyanate anion
DTXSID001015810

Research Excerpts

Overview

Isocyanates are a group of highly reactive cross-linking chemicals that cause airway inflammation and asthma in exposed individuals. Isocyanate is an important class of compounds in occupational hygiene monitoring due mainly to their behaviour as respiratory sensitisers.

ExcerptReferenceRelevance
"Isocyanates are a highly reactive industrial intermediate used widely in manufacturing plastic products, paints, etc."( Isocyanate induces cytotoxicity via activation of phosphorylated alpha synuclein protein, nitrosative stress, and apoptotic pathway in Parkinson's Disease model-SHSY-5Y cells.
Ali, SA; Khan, Z, 2023
)
1.42
"Isocyanates are a well-known and frequent cause of occupational asthma. "( Is the analysis of histamine and/or interleukin-4 release after isocyanate challenge useful in the identification of patients with IgE-mediated isocyanate asthma?
Baur, X; Blindow, S; Budnik, LT; Preisser, AM, 2015
)
1.04
"Diisocyanates are a group of chemically reactive agents, which are used in the production of coatings, adhesives, polyurethane foams, and parts for the automotive industry and as curing agents for cores in the foundry industry. "( Dermal and inhalation exposure to methylene bisphenyl isocyanate (MDI) in iron foundry workers.
Egelrud, L; Eriksson, K; Liljelind, I; Norberg, C; Nylander-French, LA; Westberg, H, 2010
)
0.87
"Diisocyanates are a common cause of occupational asthma, but risk factors are not well defined. "( Genetic variants in antioxidant genes are associated with diisocyanate-induced asthma.
Bernstein, DI; Boulet, LP; Cartier, A; Cruz, MJ; Fluharty, K; Gautrin, D; Germolec, DR; Johnson, VJ; Kissling, GE; Lummus, ZL; Luster, MI; Malo, JL; Munoz, X; Quirce, S; Sastre, J; Tarlo, SM; Yucesoy, B, 2012
)
0.89
"Isocyanates are a common cause of occupational asthma (OA)."( Airway inflammation and functional changes after exposure to different concentrations of isocyanates.
Chaboillez, S; Lemière, C; Malo, JL; Romeo, P; Tremblay, C, 2002
)
1.16
"Isocyanates are an important class of compounds in occupational hygiene monitoring due mainly to their behaviour as respiratory sensitisers. "( Characterisation of derivatised monomeric and prepolymeric isocyanates by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry and structural elucidation by tandem mass spectrometry.
Carolan, VA; Clench, MR; Ford, MJ; Rimmer, DA; Warburton, KE; White, J, 2005
)
1.19
"Isocyanates are a frequent cause of occupational asthma and can also induce hypersensitivity pneumonitis."( Specific IgG response to monomeric and polymeric diphenylmethane diisocyanate conjugates in subjects with respiratory reactions to isocyanates.
Aul, DJ; Bhaumik, A; Brown, WE; Kennedy, AL; Lesage, J; Malo, JL, 1999
)
1.13
"Isocyanates are a group of highly reactive cross-linking chemicals that cause airway inflammation and asthma in exposed individuals. "( Isocyanate-conjugated human lung epithelial cell proteins: A link between exposure and asthma?
Karol, MH; Lemus, R; Redlich, CA; Wisnewski, AV, 1999
)
0.92
"Diisocyanates are a group of low molecular weight aromatic and aliphatic compounds, widely used in the manufacture of polyurethanes. "( Diisocyanates in polyurethane plastics applications.
Klees, JE; Ott, MG,
)
1.16
"Isocyanates are a frequent cause of occupational asthma. "( What is the respiratory retention of inhaled hexamethylene di-isocyanate?
Cloutier, Y; Lesage, J; Malo, JL; Monso, E; Perreault, G, 2000
)
0.93
"Isocyanates are a common cause of occupational lung disease. "( Gene expression profiling in mouse lung following polymeric hexamethylene diisocyanate exposure.
Friedman, M; Hoyle, GW; Lee, CT; Ylostalo, J, 2005
)
0.95
"Isocyanates are an important cause of occupational asthma. "( Evidence that toluene diisocyanate activates the efferent function of capsaicin-sensitive primary afferents.
Chitano, P; Fabbri, LM; Geppetti, P; Maggi, CA; Mapp, CE; Patacchini, R; Santicioli, P, 1990
)
0.9

Effects

Isocyanates have been a leading chemical cause of occupational asthma since their utility for generating polyurethane was first recognized over 60 years ago. The mechanisms of isocyanate asthma pathogenesis remain unclear.

ExcerptReferenceRelevance
"Diisocyanates have been associated with respiratory and dermal sensitization. "( Does diisocyanate exposure result in neurotoxicity?
Carson, M; Collins, MA; Hughes, MA; Jolly, AT; Molenaar, DM; Steffens, W; Swaen, GM, 2014
)
0.92
"Isocyanates have been a leading chemical cause of occupational asthma since their utility for generating polyurethane was first recognized over 60 years ago, yet the mechanisms of isocyanate asthma pathogenesis remain unclear. "( Glutathione reaction products with a chemical allergen, methylene-diphenyl diisocyanate, stimulate alternative macrophage activation and eosinophilic airway inflammation.
Colangelo, CM; Liu, J; Wisnewski, AV, 2015
)
1.04
"Isocyanates have been widely used in the plastic industry as a curing agent. "( [Asthma induced by diphenylmethane diisocyanate].
Wang, SR; Wang, SS, 1983
)
0.89
"Isocyanates have been detected along the airway epithelia of exposed workers and animals, prompting the hypothesis that isocyanates can directly bind to epithelial cell proteins."( Isocyanate-conjugated human lung epithelial cell proteins: A link between exposure and asthma?
Karol, MH; Lemus, R; Redlich, CA; Wisnewski, AV, 1999
)
0.82

Actions

Isocyanates are a common cause of occupational lung disease. Diisocyanate is used to produce a wide variety of polyurethane products. Isocyanating may cause contact dermatitis, sensitization and asthma.

ExcerptReferenceRelevance
"Isocyanates are the main cause of occupational asthma in most countries. "( Specific antibodies to diisocyanate and work-related respiratory symptoms in apprentice car-painters.
Dragos, M; Gautrin, D; Ghezzo, H; Jones, M; Malo, JL, 2009
)
0.97
"Diisocyanates are a common cause of occupational asthma, but risk factors are not well defined. "( Genetic variants in antioxidant genes are associated with diisocyanate-induced asthma.
Bernstein, DI; Boulet, LP; Cartier, A; Cruz, MJ; Fluharty, K; Gautrin, D; Germolec, DR; Johnson, VJ; Kissling, GE; Lummus, ZL; Luster, MI; Malo, JL; Munoz, X; Quirce, S; Sastre, J; Tarlo, SM; Yucesoy, B, 2012
)
0.89
"Isocyanates are a common cause of occupational asthma (OA)."( Airway inflammation and functional changes after exposure to different concentrations of isocyanates.
Chaboillez, S; Lemière, C; Malo, JL; Romeo, P; Tremblay, C, 2002
)
1.16
"Isocyanates, known to cause respiratory sensitization and asthma, are widely used in automotive refinishing where exposures to aliphatic polyisocyanates occur by both inhalation and skin contact. "( Isocyanate exposures in autobody shop work: the SPRAY study.
Bello, D; Cullen, MR; Gore, RJ; Liu, Y; Redlich, CA; Sparer, J; Stowe, MH; Woskie, SR; Youngs, F, 2004
)
0.94
"Isocyanates may cause contact dermatitis and respiratory sensitization leading to asthma. "( A laboratory investigation of the effectiveness of various skin and surface decontaminants for aliphatic polyisocyanates.
Bello, D; Cullen, MR; Liu, Y; Redlich, CA; Sparer, J; Stowe, MH; Streicher, RP; Woskie, SR, 2005
)
1.16
"Isocyanates may cause contact dermatitis, sensitization and asthma. "( An FTIR investigation of isocyanate skin absorption using in vitro guinea pig skin.
Bello, D; Boeniger, MF; Liu, Y; Redlich, CA; Smith, TJ; Streicher, RP; Woskie, SR, 2006
)
0.96
"Diisocyanates are used to produce a wide variety of polyurethane products; they are also recognized as an important cause of occupational asthma. "( Issues in diisocyanate antibody testing.
Brown, WE; Burkert, AL; Jolly, AT; Ott, MG, 2007
)
0.85
"Isocyanates, a leading cause of occupational asthma, are known to induce adaptive immune responses; however, innate immune responses, which generally precede and regulate adaptive immunity, remain largely uncharacterized."( Human innate immune responses to hexamethylene diisocyanate (HDI) and HDI-albumin conjugates.
Liu, J; Liu, Q; Redlich, CA; Wisnewski, AV, 2008
)
0.97
"Isocyanates are a common cause of occupational lung disease. "( Gene expression profiling in mouse lung following polymeric hexamethylene diisocyanate exposure.
Friedman, M; Hoyle, GW; Lee, CT; Ylostalo, J, 2005
)
0.95

Toxicity

ExcerptReferenceRelevance
" Some toxic manifestations are potentially reversible with time after cessation of exposure."( Inhalation toxicity of methyl isocyanate: biochemical and cytological profile of bronchoalveolar lavage fluid in rats.
Dixit, R; Gupta, GS; Kaw, JL; Naqvi, SH; Ray, PK, 1991
)
0.28
" Acute toxic effects of MIC are essentially similar by either route except for the intensity of the effects."( Acute toxicity of methyl isocyanate in mammals. II. Induction of hyperglycemia, lactic acidosis, uraemia, and hypothermia in rats.
Jeevaratnam, K; Kaushik, MP; Vaidyanathan, CS; Vijayaraghavan, R,
)
0.13
"5 LD50 and 1 LD50 doses in female rabbits resulted in significant changes in physiological, clinico-chemical and histological parameters."( Acute toxicity of methyl isocyanate, administered subcutaneously in rabbits: changes in physiological, clinico-chemical and histological parameters.
Jeevarathinam, K; Mukhopadhyay, S; Ray, US; Selvamurthy, W; Thakur, L, 1988
)
0.27
"Acute toxic effects of methyl isocyanate in the rat were determined for two hour exposures to concentrations in the range 11 ppm (very slight effect) to 65 ppm (lethality: pulmonary oedema)."( Acute toxicity of methyl isocyanate: a preliminary study of the dose response for eye and other effects.
Andersson, N; Kerr Muir, M; Salmon, AG, 1985
)
0.27
" There was no adverse effect on general health, survival, body weight, or hematological or clinical chemistry parameters."( Chronic inhalation toxicity and carcinogenicity study of respirable polymeric methylene diphenyl diisocyanate (polymeric MDI) aerosol in rats.
Arts, JH; Feron, VJ; Gembardt, C; Kuijpers, MH; Kuper, CF; Lomax, LG; Löser, E; Reuzel, PG, 1994
)
0.29
" MIC may be the most toxic of all isocyanates because of its very high vapor pressure relative to other isocyanates and because of its ability to exert toxic effects on numerous organ systems."( The Bhopal accident and methyl isocyanate toxicity.
Guest, I; Varma, DR, 1993
)
0.56
"Subcutaneous administration of the LD50 dose of methyl isocyanate (MIC) to rats induced severe hyperglycaemia, lactic acidosis and uraemia in rats."( Influence of methylamine and N,N'-dimethylurea, the hydrolysis products of methyl isocyanate, on its systemic toxicity.
Jeevaratnam, K; Sugendran, K; Vaidyanathan, CS,
)
0.13
" The combination of autoclave sterilization and a PU produced from a larger-molecular-weight polyol is recommended to minimize the production of potentially toxic compounds."( The relative safety of gamma-ray, autoclave, and ethylene oxide gas sterilization of thermosetting polyurethane.
Shintani, H,
)
0.13
" There have been no previous studies on the potential prenatal toxic effects of this compound."( Embryotoxicity study of monomeric 4,4'-methylenediphenyl diisocyanate (MDI) aerosol after inhalation exposure in Wistar rats.
Buschmann, J; Fuhst, R; Heinrich, U; Koch, W, 1996
)
0.29
" The no observed adverse effect concentration for maternal and developmental toxicity was therefore 4 mg/m3."( Prenatal toxicity of inhaled polymeric methylenediphenyl diisocyanate (MDI) aerosols in pregnant wistar rats.
Doe, JE; Gamer, AO; Hellwig, J; Tyl, RW, 2000
)
0.31
" All studies demonstrated that adverse effects were caused by irritation-related responses occurring predominantly in the lower respiratory tract."( Inhalation toxicity of 1,6-hexamethylene diisocyanate homopolymers (HDI-IC and HDI-BT): results of subacute and subchronic repeated inhalation exposure studies.
Mohr, U; Pauluhn, J, 2001
)
0.31
" Of the three toxicants, the most marked perturbations were induced by ANIT exposure, then NI, thereby indicating the effects of ANIT, NI and NA toxicity were distinct, with ANIT being the most, and NA the least, toxic of the three compounds."( Chemometric analysis of biofluids following toxicant induced hepatotoxicity: a metabonomic approach to distinguish the effects of 1-naphthylisothiocyanate from its products.
Azmi, J; Griffin, JL; Holmes, E; Nicholson, JK; Shore, RF, 2005
)
0.33
" The potential for widespread human inhalation exposure to this toxic gas is recognized as a public health concern."( Changes in intracellular pH play a secondary role in hydrogen sulfide-induced nasal cytotoxicity.
Dorman, DC; Lancianese, S; Marshall, MW; McManus, BE; Roberts, ES; Wong, VA, 2006
)
0.33
"We investigated the toxic effects of carbendazim and n-butyl isocyanate (BIC), metabolites of the fungicide benomyl, on development in the African clawed frog, Xenopus laevis."( Toxic effects of carbendazim and n-butyl isocyanate, metabolites of the fungicide benomyl, on early development in the African clawed frog, Xenopus laevis.
Cheong, SW; Hong, SJ; Hwang, YG; Jin, JH; Kim, SJ; Park, JH; Yeo, CY; Yoon, CS, 2008
)
0.35
" Accordingly, a direct toxicity assessment (DTA) based on chronoamperometry was proposed to detect the effect of toxic chemicals on microorganisms."( Direct toxicity assessment of toxic chemicals with electrochemical method.
Dong, S; Liu, C; Sun, T; Xu, X, 2009
)
0.35
" Tellurite was more toxic at all concentrations examined than all three selenium-containing anions, SeO4(2-), SeO3(2-), SeCN(-)."( Biological interactions of selenocyanate: bioprocessing, detection and toxicity.
Burra, R; Chasteen, TG; Fox, JD; Pradenas, GA; Vásquez, CC, 2009
)
0.35
"It is difficult task to measure precisely the toxic effect of beta-amyloid (Aβ 1-42) peptides and also the protective effect of novel drug candidates against Aβ-peptides."( A novel method for the rapid determination of beta-amyloid toxicity on acute hippocampal slices using MTT and LDH assays.
Datki, Z; Hunya, A; Mozes, E; Penke, B; Posa, A, 2012
)
0.38
" PipX is thus deduced to be a toxic protein, but its toxicity has not been clearly defined because of the lack of P(II)-deficient mutants carrying wild-type pipX."( Evaluation of the effects of P(II) deficiency and the toxicity of PipX on growth characteristics of the P(II)-Less mutant of the cyanobacterium Synechococcus elongatus.
Aichi, M; Chang, Y; Maeda, S; Omata, T; Takatani, N, 2013
)
0.39
" The bifunctional electrophiles were capable of cross-linking Trx2 to itself in vitro and to other proteins in cells exposed to toxic concentrations."( Pronounced toxicity differences between homobifunctional protein cross-linkers and analogous monofunctional electrophiles.
Chandran, NN; Chowdhury, S; Daniel, AK; Herrin, RP; Radzinski, NP; Spencer, MK; Tripathi, S; West, JD, 2013
)
0.39
" Toxic exposures had an influence on short-term working memory with fewer correct arm entries (F(2, 19) = 4."( Memory deficits associated with sublethal cyanide poisoning relative to cyanate toxicity in rodents.
Bukachi, F; Kimani, S; Maitai, C; Sinei, K; Tshala-Katumbay, D, 2014
)
0.4
" When the ratio of functional side chain to bis-GMA is increased, the stereo hindrance of resin structure is increased, more toxic resin monomers are trapped in the complicated resin structure, and thus the resin matrix reveals less cytotoxicity."( Biocompatibility and cytotoxicity of two novel low-shrinkage dental resin matrices.
Jan, YD; Lee, BS; Lin, CP; Tseng, WY, 2014
)
0.4
" A medical evaluation can identify hazards as well as lead to improvements in exposure controls and safe return to research."( Isocyanate induced allergic contact dermatitis in a university undergraduate student: An occupational dermatitis case report, review of laboratory safety regulations, and implications for campus research.
Cook-Shimanek, M; McGrath, A; Pacheco, KA, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
"Studies have been made on the bioavailability in blood of sodium cyantate administered orally in gelatin capsules, in gelatin capsules plus antacid, in enteric-coated capsules and in cocoa butter suppositories administered rectally to patients with sickle cell disease."( Bioavailability of sodium cyanate in patients with sickle cell disease and the lack of inhibition in vitro of globin synthesis at in vivo concentrations of cyanate.
Manning, JM; Nigen, AM; Peterson, CM; White, JM, 1975
)
0.25
" The bioavailability data suggest that the selenium from p-XSC is not as efficiently incorporated into glutathione peroxidase as the selenium from selenite or the other selenocyanate analogs."( Comparative effect of inorganic and organic selenocyanate derivatives in mammary cancer chemoprevention.
el-Bayoumy, K; Ganther, H; Ip, C; Thompson, H; Upadhyaya, P; Vadhanavikit, S, 1994
)
0.29
" This suggests that the extent of modification of the protein in vivo may have an important influence on the transport and bioavailability of gold antiarthritic drugs."( A mass spectrometric investigation of the binding of gold antiarthritic agents and the metabolite [Au(CN)2]- to human serum albumin.
Beck, JL; Ralph, SF; Talib, J, 2006
)
0.33
" Some of the antagonists showed good oral bioavailability and/or good brain penetration."( Identification of novel and orally active spiroindoline NPY Y5 receptor antagonists.
Fukami, T; Gao, YD; Gomori, A; Haga, Y; Hidaka, M; Ishihara, A; Iwaasa, H; Kanatani, A; Kitazawa, H; Macneil, DJ; Moriya, M; Nonoshita, K; Okamoto, O; Sakamoto, T; Shibata, T; Takahashi, T; Yang, L, 2009
)
0.35
" Results demonstrated these PU-MIFs hold low water absorption rate and superior biocompatibility, which was highly demanded for maintaining cell viability."( Isolation of viable type I and II methanotrophs using cell-imprinted polyurethane thin films.
Hu, Y; Lu, Y; Ren, X; Xie, L, 2014
)
0.4
" We evaluated the effects of administration route and dose on the bioavailability of nine Se compounds found in biota, the so-called bioselenocompounds, such as selenite, selenate, selenocyanate (SeCN), Se-methylselenocysteine (MeSeCys), selenomethionine (SeMet), selenohomolanthionine (SeHLan), selenocystine (SeCys2), 1β-methylseleno-N-acetyl-d-galactosamine (SeSug1), and trimethylselenonium ion (TMSe)."( Effect of administration route and dose on metabolism of nine bioselenocompounds.
Ogra, Y; Suzuki, N; Takahashi, K, 2018
)
0.48

Dosage Studied

Animal toxicity studies on diisocyanates were evaluated using quantitative weight of evidence (QWoE) to test the hypothesis that the dose-response curve shows a threshold for the induction and/or elicitation of respiratory sensitization. PEITC at either dose resulted in considerable inhibition at 2 or 6 h after NNK administration, while BITC or PITC had little effect.

ExcerptRelevanceReference
" Hypotension was of 30 to 380 minutes duration and mean dosage of 12,44 mg (1,99 mug/kg/min)."( [Plasma level of the thiocyanate ion in sodium nitroprusside perfusion].
Deschodt, J; du Cailar, J; Griffe, O; Mathieu-Daudé, JC, 1976
)
0.26
" In order to establish dose-response relationships and determine host factors, complete biologic monitoring, including pulmonary function and immunologic studies, has been performed concurrently with a comprehensive environmental monitoring program including continuous sampling for atmospheric concentrations of TDI."( Respiratory effects in toluene diisocyanate manufacture: a multidisciplinary approach.
Butcher, B; Neilson, A; Salvaggio, J; Weill, H; Ziskind, M, 1975
)
0.25
" Blood samples obtained prior to and at various times after PIC were used to measure complement and split products of complement and plasma histamine levels and to determine dose-response slopes of lymphocyte cyclic adenosine monophosphate (cAMP) following stimulation with agonists."( Inhalation challenge and pharmacologic studies of toluene diisocyanate (TDI)-sensitive workers.
Butcher, BT; Dharmarajan, V; Karr, RM; O'Neil, CE; Salvaggio, JE; Weill, H; Wilson, MR, 1979
)
0.26
" At low dosage (50 mg."( In vivo hepatic and intestinal toxicity of sodium cyanate in rats: cyanate-induced alterations in hepatic glycogen metabolism.
Conrad, ME; Glader, BE; Haut, MJ; Hildenbrandt, PK; Toskes, PP, 1975
)
0.25
" Safe oral dosage regimens may not be effective, but extra-corporeal treatment of sickle cells with cyanate, or other compounds, might circumvent that problem."( Toxic-therapeutic ratio of sodium cyanate.
Bedine, M; Charache, S; Duffy, TP; Jander, N; Morrell, R; Scott, JC, 1975
)
0.25
" Administration of sodium cyanate in the gelatin capsules, taken with an antacid, improved the dose-response relationship within a given patient."( Bioavailability of sodium cyanate in patients with sickle cell disease and the lack of inhibition in vitro of globin synthesis at in vivo concentrations of cyanate.
Manning, JM; Nigen, AM; Peterson, CM; White, JM, 1975
)
0.25
"S-(N-Methylcarbamoyl)-N-acetylcysteine (AMCC), a chemically labile mercapturic acid conjugate, was identified by liquid chromatography-mass spectrometry (LC-MS) in the urine of rats dosed intraperitoneally with methyl isocyanate (MIC; 45."( Biotransformation of methyl isocyanate in the rat. Evidence for glutathione conjugation as a major pathway of metabolism and implications for isocyanate-mediated toxicities.
Baillie, TA; Han, DH; Pearson, PG; Rashed, MS; Slatter, JG,
)
0.13
" However, phosphoramidon caused a significantly greater leftward shift of the substance P dose-response curve in air-exposed animals than it did in TDI-exposed animals, so that after phosphoramidon, mean values of PD200 in animals exposed to air or TDI did not differ."( Toluene diisocyanate increases airway responsiveness to substance P and decreases airway neutral endopeptidase.
Borson, DB; Dusser, D; Nadel, JA; Scypinski, L; Sheppard, D; Thompson, JE, 1988
)
0.27
" Using an identical dosing regimen, parallel results were observed in the effects of these isothiocyanates on O6-methylguanine formation in the lung, in which PEITC at either dose resulted in considerable inhibition at 2 or 6 h after NNK administration, while BITC or PITC had little effect."( Effects of aromatic isothiocyanates on tumorigenicity, O6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung.
Amin, SG; Chung, FL; Hecht, SS; Morse, MA, 1989
)
0.79
" We measured FEV1 before and at regular intervals after exposure to TDI and performed dose-response curves to methacholine and bronchoalveolar lavage 8 hr after TDI in two subjects with previously documented late asthmatic reaction; then we repeated the same procedure a few weeks after treatment with steroids."( Importance of airway inflammation for late asthmatic reactions induced by toluene diisocyanate in sensitized subjects.
Boschetto, P; Bruchi, O; Cappellazzo, G; Fabbri, LM; Mapp, CE; Milani, GF; Pivirotto, F; Zocca, E, 1987
)
0.27
" We measured FEV1 before and at regular intervals after exposure to TDI, and performed dose-response curves to methacholine and bronchoalveolar lavage at 8 h after TDI in a group of 6 subjects with late asthmatic reactions and in 6 subjects with only early asthmatic reactions."( Bronchoalveolar neutrophilia during late asthmatic reactions induced by toluene diisocyanate.
Boschetto, P; Burlina, A; Fabbri, LM; Licata, B; Mapp, CE; Milani, G; Pivirotto, F; Plebani, M; Zocca, E, 1987
)
0.27
" Similar dose-response relationships are seen for both acute and chronic effects."( Isocyanates and respiratory disease: current status.
Musk, AW; Peters, JM; Wegman, DH, 1988
)
0.9
" Dose-response relationships are not likely to emerge from follow-up studies."( Disaster at Bhopal: the accident, early findings and respiratory health outlook in those injured.
Weill, H,
)
0.13
" Ear thickness increase plotted against the log of the dose of diisocyanate indicated three regions of effects: a no-effect region, a dose-response region, and a region of reduced response at highest dosages."( Contact sensitivity by diisocyanates: potencies and cross-reactivities.
Hillebrand, JA; Karol, MH; Lewis, GR; Thorne, PS, 1987
)
0.57
" In mice, as well as in guinea pigs, a dose-response relationship was apparent between the sensitizing dose and both severity of response and number of animals responding."( Use of dose-response data to compare the skin sensitizing abilities of dicyclohexylmethane-4,4'-diisocyanate and picryl chloride in two animal species.
Karol, MH; Stadler, JC, 1985
)
0.27
" However, it did not occur in guinea pigs after intranasal instillation (instead of inhalation) and only occurred after oral dosage with TDI when the dose was relatively high."( Specific inhibition of contact sensitivity in the guinea pig following tolylene diisocyanate inhalation.
Doe, JE; Hicks, R; Milburn, GM, 1982
)
0.26
"A four-year longitudinal study of ventilatory function in polyurethane-foam production workers exposed to toluene diisocyanate (TDI) revealed a dose-response relationship between average exposure to TDI and change in forced expiratory volume per second (FEV-1)."( Accelerated loss of FEV- in polyurethane production workers: a four-year prospective study.
Main, DM; Musk, AW; Pagnotto, LD; Wegman, DH, 1982
)
0.26
" The dose-response relationships for hemoglobin adducts and urine metabolites were non-linear over this dose range."( Hemoglobin adducts and urine metabolites of 4,4'-methylenedianiline after 4,4'-methylenediphenyl diisocyanate exposure of rats.
Heinrich, U; Henschler, D; Hoymann, HG; Sabbioni, G; Schütze, D; Sepai, O, 1995
)
0.29
" It has been applied to the determination of (+)- and (-)-sotalol in plasma from twelve subjects dosed with racemic sotalol."( Enantioselective analysis of sotalol in plasma by reversed-phase high-performance liquid chromatography using diastereomeric derivatives.
Baker, PV; Hooper, WD, 1995
)
0.29
" At this stage, the ponds were isolated from one another and MDI was added at a dosage of 1 g/liter on top of the sediment of treated part of the first pond, 10 g/liter to the second pond, and 0 g/liter to the third pond (untreated control)."( Fate and biological effects of polymeric MDI (4,4'-diphenylmethane diisocyanate and homologs) in small artificial ponds.
Heimbach, F; Jaeger, K; Sporenberg, W, 1996
)
0.29
" With all other chemicals, the dose-response curves for DNA fragmentation and viability were mirror images."( Investigation of the induction of DNA double-strand breaks by methylenediphenyl-4-4'-diisocyanate in cultured human lung epithelial cells.
Gahlmann, R; Lutz, WK; Vamvakas, S; Vock, EH, 1998
)
0.3
" Basal ACH dose-response curves, measured twice in intervals of 1 h using tracheal preparations of 11 guinea pigs previously not exposed to IC, were reproducible."( Subchronic exposure to diisocyanates increases guinea pig tracheal smooth muscle responses to acetylcholine.
Baur, X; Marczynski, B; Marek, W; Mensing, T; Potthast, J, 1999
)
0.6
" In addition, dose-response curves were analyzed and tested for their linear and quadratic trends."( Occupational asthma caused by isocyanates: patterns of asthmatic reactions to increasing day-to-day doses.
Elie, R; Ghezzo, H; Malo, JL, 1999
)
0.58
" Histopathological findings were then combined with this information to give an overall dose-response curve for both studies as a whole."( Chronic pulmonary effects of respirable methylene diphenyl diisocyanate (MDI) aerosol in rats: combination of findings from two bioassays.
Ernst, H; Feron, VJ; Gamer, A; Hoffmann, HD; Kittel, B; Koch, W; Kuper, CF; Mallett, AK; Muhle, H; Rittinghausen, S, 2001
)
0.31
" This treatment was continued and dosage was tapered until the 10th postoperative day."( Cranial nerve pareses following wrapping of a ruptured dissecting vertebral artery aneurysm: a possible complication of cyanoacrylate glue--case report.
Aoki, K; Aoki, Y; Katsume, M; Kuroki, T; Nemoto, A; Takasu, N; Yamazaki, T, 2003
)
0.32
" However, the increase in CCl(4) dosage significantly worsened survival."( Comparison of murine cirrhosis models induced by hepatotoxin administration and common bile duct ligation.
Chang, ML; Chang, PY; Chen, JC; Yeh, CT, 2005
)
0.33
" Additional groups were dosed by gavage and intraperitoneal injection."( Analysis of biomarkers in rats and dogs exposed to polymeric methylenediphenyl diisocyanate (pMDI) and its glutathione adduct.
Brown, WE; Hext, P; Leibold, E; Leng, G; Pauluhn, J, 2006
)
0.33
" The preliminary bioassay showed that some of the title compounds show excellent insecticidal activity against Mythimna separata at the dosage of 25 mg kg(-1) and moderate insecticidal activity against Nephotettix cincticeps at the dosage of 500 mg kg(-1)."( Synthesis and bioassay evaluation of 1-(4-substitutedideneaminooxymethyl)-phenyl-3-(2,6-difluorobenzoyl)ureas.
Bi, FC; Chen, L; Huang, RQ; Mao, CH; Ou, XM; Shang, J; Wang, QM, 2007
)
0.34
" Clear dose-response relationships were observed between three different measures of exposure and symptoms of the eyes."( Eye and airway symptoms in low occupational exposure to toluene diisocyanate.
Axmon, A; Broberg, K; Littorin, M; Sennbro, CJ; Tinnerberg, H, 2007
)
0.34
" Two types of dose-response relationships are addressed with the following focus: (1) does sensitization dose and surface area influence the subsequent elicitation response and (2) is the elicitation response more dependent on previous elicitation doses or more on skin sensitizing dose? These two aims are investigated in two elaborated experiments, using inflammatory (bronchoalveolar lavage, BAL) and physiologic (Penh) endpoints to characterize asthma-like responses in rats."( Brown Norway rat asthma model of diphenylmethane-4,4'-diisocyanate (MDI): analysis of the elicitation dose-response relationship.
Pauluhn, J, 2008
)
0.35
"Nasal symptoms and signs were associated with exposure, and dose-response relationships between nasal symptoms and exposure to isocyanic acid, methyl isocyanate, and formaldehyde were observed."( Nasal and ocular effects in foundry workers using the hot box method.
Bryngelsson, IL; Löfstedt, H; Ngo, Y; Rudblad, S; Seldén, AI; Svartengren, M; Westberg, H, 2011
)
0.37
" The dose-response curve of HDI-induced pulmonary responses in naïve or dermally sensitized rats after one or several inhalation priming exposures was examined in the Brown Norway (BN) rat asthma model."( Analysis of the interrelationship of the pulmonary irritation and elicitation thresholds in rats sensitized with 1,6-hexamethylene diisocyanate (HDI).
Pauluhn, J, 2015
)
0.42
"Model averaging for dichotomous dose-response estimation is preferred to estimate the benchmark dose (BMD) from a single model, but challenges remain regarding implementing these methods for general analyses before model averaging is feasible to use in many risk assessment applications, and there is little work on Bayesian methods that include informative prior information for both the models and the parameters of the constituent models."( Quantitative Risk Assessment: Developing a Bayesian Approach to Dichotomous Dose-Response Uncertainty.
Allen, BC; Blessinger, T; Davis, JA; Gift, JS; Olszyk, L; Shao, K; Wheeler, MW, 2020
)
0.56
"Animal toxicity studies on diisocyanates were evaluated using quantitative weight of evidence (QWoE) to test the hypothesis that the dose-response curve shows a threshold for the induction and/or elicitation of respiratory sensitization."( Evaluation of animal toxicity studies with diisocyanates regarding presence of thresholds for induction and elicitation of respiratory allergy by quantitative weight of evidence.
Colnot, T; Dekant, W, 2022
)
1.26
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (16)

PathwayProteinsCompounds
Nitrogen Metabolism2622
Cyanate Degradation47
cyanate degradation17
nitrate reduction VI (assimilatory)518
formate oxidation to CO2417
UMP biosynthesis I1234
cyanate degradation417
superpathway of nicotinate degradation1254
histamine biosynthesis421
superpathway of arginine and polyamine biosynthesis18101
thiocyanate degradation I04
nicotinate degradation I833
nicotinate degradation II019
L-arginine biosynthesis I (via L-ornithine)1153
superpathway of pyrimidine ribonucleotides de novo biosynthesis2345
superpathway of pyrimidine deoxyribonucleotides de novo biosynthesis4662
Cysteine degradation619
Cyanate catabolism17

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 1Homo sapiens (human)Ki167.07500.00001.372610.0000AID1798763
Carbonic anhydrase 2Homo sapiens (human)Ki167.07500.00000.72369.9200AID1798763
Carbonic anhydrase 4Homo sapiens (human)Ki167.07500.00021.97209.9200AID1798763
Carbonic anhydrase 15Mus musculus (house mouse)Ki167.07500.00091.884610.0000AID1798763
[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 (1)

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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (3,932)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901693 (43.06)18.7374
1990's523 (13.30)18.2507
2000's735 (18.69)29.6817
2010's795 (20.22)24.3611
2020's186 (4.73)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 75.38

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 Index75.38 (24.57)
Research Supply Index8.35 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index136.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (75.38)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials31 (0.74%)5.53%
Reviews211 (5.03%)6.00%
Case Studies210 (5.01%)4.05%
Observational0 (0.00%)0.25%
Other3,741 (89.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]