Page last updated: 2024-11-05

aminoacetonitrile

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

Description

Aminoacetonitrile is a simple organic compound with the formula CH2(NH2)CN. It is a colorless liquid with a pungent odor. It is a precursor to the amino acid glycine and is also used in the synthesis of other organic compounds. Aminoacetonitrile has been detected in interstellar space, suggesting that it may play a role in the formation of organic molecules in the universe. Aminoacetonitrile is also of interest to astrochemists as it is a potential precursor to prebiotic molecules. It has been suggested that aminoacetonitrile could have been involved in the early stages of life on Earth. The compound has also been studied for its potential use in the development of new drugs and materials.'

Aminoacetonitrile: Cyanomethylamine. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID10901
CHEMBL ID1193997
MeSH IDM0000933

Synonyms (31)

Synonym
cyanomethylamine
einecs 208-751-8
2-aminoacetonitrile
aminoacetonitrile
brn 0773694
glycinonitrile
glycinenitrile
h2nch2cn
acetonitrile, amino-
540-61-4
aminoacetonitrile, >=98%
AKOS000201450
CHEMBL1193997
BBL009721
STL141086
unii-3739oq10ij
3739oq10ij ,
FT-0622280
amino acetonitrile
amino-acetonitrile
ami-noacetonitrile
aminoacetonitrile [mi]
.alpha.-aminoacetonitrile
ncch2nh2
DTXSID90202314
540-61-4hcl
F1905-7133
Q48819
3-hydroxy-n,n-dimethyl-propanamide
CS-0498388
EN300-40750

Research Excerpts

Overview

Aminoacetonitrile is a potent repressor of DMN-demethylase I.

ExcerptReferenceRelevance
"Aminoacetonitrile is a potent repressor of DMN-demethylase I."( Comparative effects of indole and aminoacetonitrile derivatives on dimethylnitrosamine-demethylase and aryl hydrocarbon hydroxylase activities.
Arcos, JC; Argus, MF; Myers, SC; Neuburger, BJ, 1980
)
1.26

Effects

ExcerptReferenceRelevance
"Aminoacetonitrile (AAN) has been reported to be a dimethylnitrosamine (DMN) demethylase inhibitor which prevents the metabolic activation of DMN to a hepatotoxin. "( Differential effects of coadministration of aminoacetonitrile on immunosuppression and hepatotoxicity produced by dimethylnitrosamine.
Boise, LH; Haggerty, HG; Holsapple, MP; Jordan, SD, 1988
)
1.98

Toxicity

ExcerptReferenceRelevance
" In late pregnancy AAN induces nonspecific toxic effects resulting in hemorrhages, edema, disturbance of weight development, and severe interaction with viability."( [Aminoacetonitrile and fetogenesis of the rat. I. Fetal toxicity and gross malformations (author's transl)].
Gabler, W; Schmidt, W; Wendler, D, 1980
)
1.17
" All sheep were inspected at least daily, to check for any adverse effects of treatment."( A large-scale clinical field study to evaluate the efficacy and safety of an oral formulation of the amino-acetonitrile derivative ( AAD ), monepantel , in sheep in New Zealand.
Chamberlain, B; Cole, DJ; Griffiths, TM; Hosking, BC; Kaye-Smith, BG; Mason, PC; McKay, CH; Nottingham, RM; Seewald, W, 2009
)
0.35
" The monepantel solution used in this study was well tolerated by the sheep, and no adverse events could be attributed to its use."( A large-scale clinical field study to evaluate the efficacy and safety of an oral formulation of the amino-acetonitrile derivative ( AAD ), monepantel , in sheep in New Zealand.
Chamberlain, B; Cole, DJ; Griffiths, TM; Hosking, BC; Kaye-Smith, BG; Mason, PC; McKay, CH; Nottingham, RM; Seewald, W, 2009
)
0.35
" Detailed recording at multiple time points were made of veterinary examinations, observations for adverse events, bodyweight measurements, faecal scores, and haematology, clinical chemistry and coagulation variables."( Safety of an amino-acetonitrile derivative ( AAD ), monepantel, in weaned lambs following repeated oral administration.
Alexander, A; Helbig, R; Hosking, BC; Malikides, N; Roth, DR; Strehlau, GA, 2009
)
0.35
" No treatment-related, toxicologically relevant adverse events, clinical observations or macroscopic or microscopic changes were observed."( Safety of an amino-acetonitrile derivative ( AAD ), monepantel, in weaned lambs following repeated oral administration.
Alexander, A; Helbig, R; Hosking, BC; Malikides, N; Roth, DR; Strehlau, GA, 2009
)
0.35
"Repeated oral administration of monepantel at the MRD and three and five times the MRD every 3 weeks for eight treatments was not associated with any treatment-related adverse effects and was systemically very well tolerated in weaned, growing lambs."( Safety of an amino-acetonitrile derivative ( AAD ), monepantel, in weaned lambs following repeated oral administration.
Alexander, A; Helbig, R; Hosking, BC; Malikides, N; Roth, DR; Strehlau, GA, 2009
)
0.35
" Detailed recording at multiple time points were made of veterinary examinations; observations for adverse events; bodyweight measurements; faecal scores; haematology, clinical chemistry and coagulation variables; semen indices; evaluation of serving capacity; and gross pathology (including measurement of organ weights) performed on 10 rams from each group at the completion of the study."( Reproductive safety of an amino-acetonitrile derivative (AAD), monepantel, in rams following repeated oral administration.
Baker, K; Debenedetti, R; George, B; Hall, C; Helbig, R; Mahoney, R; Malikides, N; Spencer, K; Strehlau, GA; Vanhoff, K, 2009
)
0.35
" No treatment-related, toxicologically relevant adverse events, clinical observations or macroscopic changes were observed."( Reproductive safety of an amino-acetonitrile derivative (AAD), monepantel, in rams following repeated oral administration.
Baker, K; Debenedetti, R; George, B; Hall, C; Helbig, R; Mahoney, R; Malikides, N; Spencer, K; Strehlau, GA; Vanhoff, K, 2009
)
0.35
"Repeated oral administration of monepantel at three times the MRD every 5 days over an entire spermatogenic cycle and during mating was not associated with any treatment-related adverse effects on the reproductive performance of rams and was systemically very well tolerated."( Reproductive safety of an amino-acetonitrile derivative (AAD), monepantel, in rams following repeated oral administration.
Baker, K; Debenedetti, R; George, B; Hall, C; Helbig, R; Mahoney, R; Malikides, N; Spencer, K; Strehlau, GA; Vanhoff, K, 2009
)
0.35
" Fasting or feeding had no statistically significant effects on the efficacy of the monepantel solution against the nematodes, and the period of fasting had no adverse effects."( Effect of fasting sheep for a short period on the efficacy and safety of monepantel.
Hosking, BC; Stein, PA, 2009
)
0.35
" Detailed recording at multiple time points were made of veterinary examinations; observations for adverse events; bodyweight measurements; faecal scores; and haematology, clinical chemistry and coagulation variables."( Safety of an amino-acetonitrile derivative (AAD), monepantel, in ewes and their offspring following repeated oral administration.
Baker, K; Debenedetti, R; Hall, C; Mahoney, R; Malikides, N; Spencer, K; Strehlau, GA; Vanhoff, K, 2009
)
0.35
" No treatment-related, toxicologically relevant adverse events, clinical observations or gross post-mortem changes were observed."( Safety of an amino-acetonitrile derivative (AAD), monepantel, in ewes and their offspring following repeated oral administration.
Baker, K; Debenedetti, R; Hall, C; Mahoney, R; Malikides, N; Spencer, K; Strehlau, GA; Vanhoff, K, 2009
)
0.35
"Repeated oral administration of monepantel at three times the MRD every 5 days over an entire reproductive cycle was not associated with any treatment-related adverse effects on the reproductive performance of ewes nor on the viability of their offspring, and was systemically very well tolerated."( Safety of an amino-acetonitrile derivative (AAD), monepantel, in ewes and their offspring following repeated oral administration.
Baker, K; Debenedetti, R; Hall, C; Mahoney, R; Malikides, N; Spencer, K; Strehlau, GA; Vanhoff, K, 2009
)
0.35
" Monepantel was safe for the target animals and human operators when used in a field situation."( Clinical field study to evaluate the efficacy and safety of the amino-acetonitrile derivative, monepantel, compared with registered anthelmintics against gastrointestinal nematodes of sheep in Australia.
Besier, RB; Griffiths, TM; Hosking, BC; Kaye-Smith, BG; Le Feuvre, AS; Nilon, P; Seewald, W; Trengove, C; Vanhoff, KJ; Woodgate, RG, 2009
)
0.35
" There were no treatment-related adverse events during the study, which included the use of a range of concomitant treatments."( European field study of the efficacy and safety of the novel anthelmintic monepantel in sheep.
Dobson, DP; Hunter, RP; Jones, MD; Kubacki, P; Reymond, N; Strehlau, GA; Tranchard, ES; Walters, ME, 2010
)
0.36
" These results, considered in the light of an earlier series of studies demonstrating the efficacy of monepantel in older animals, and an absence of any adverse events, provides strong support for the use of monepantel as a safe and effective anthelmintic in lambs from six weeks of age."( Safety and efficacy against fourth-stage gastrointestinal nematode larvae, of monepantel in 6-week old lambs.
George, SD; Hosking, BC; Rolfe, PF; Stein, PA, 2012
)
0.38

Pharmacokinetics

ExcerptReferenceRelevance
"The pharmacokinetic properties of the developmental Amino-Acetonitrile Derivative (AAD), monepantel and its sulfone metabolite, monepantel sulfone were investigated in sheep following intravenous (i."( Pharmacokinetics of monepantel and its sulfone metabolite, monepantel sulfone, after intravenous and oral administration in sheep.
Bouvier, J; Browning, A; Giraudel, JM; Karadzovska, D; Seewald, W; Smal, M, 2009
)
0.35
" In a comparison of pharmacokinetic profiles from two studies, Merino lambs had significantly greater maximum concentrations of monepantel and monepantel sulfone, and faster times to reach these concentrations than Dorset cross lambs."( The effect of sheep breed, age, and gender on the pharmacokinetics and efficacy of monepantel, an amino-acetonitrile derivative.
Giraudel, JM; Hosking, BC; Kaminsky, R; Karadzovska, D; Sager, H; Seewald, W; Vercruysse, J, 2010
)
0.36
" The same pattern was observed in the pharmacokinetic analysis, with lambs treated orally having more favourable exposure to monepantel and its sulfone metabolite (albeit in all but one instance not significantly different) than the lambs treated by the other routes of administration, which were very similar for most parameters."( Effect of route of administration on the efficacy and pharmacokinetics of an experimental formulation of the amino-acetonitrile derivative monepantel in sheep.
Giraudel, JM; Hosking, BC; House, JK; Karadzovska, D; Seewald, W; Stein, PA, 2010
)
0.36
" The aim of the current review article was to provide an overview of the relationship between the pharmacokinetic features of different anthelmintic drugs, their availability in host tissues, accumulation within target helminths and resulting therapeutic efficacy."( Host pharmacokinetics and drug accumulation of anthelmintics within target helminth parasites of ruminants.
Alvarez, L; Lanusse, C; Lifschitz, A, 2017
)
0.46

Compound-Compound Interactions

ExcerptReferenceRelevance
" The in vivo effects of single drug (CCI-779), and drug combination of CCI-779 with SL327 (a brain penetrant MEK inhibitor) to eliminate the unfavorable activation of MAPK pathway were evaluated in MDA-MB231-BR brain metastases xenograft mice."( The effect of mTOR inhibition alone or combined with MEK inhibitors on brain metastasis: an in vivo analysis in triple-negative breast cancer models.
Brandl, MB; Chang, J; Cui, K; Jin, G; Li, F; Mao, Y; Nie, F; Rodriguez, A; Wang, L; Wong, ST; Xue, Z; Zhao, H, 2012
)
0.38

Bioavailability

ExcerptReferenceRelevance
"28 nM; >800-fold selectivity vs Cat B, L, and S; PK data in dogs: F 55%, t(1/2) = 15 h) exhibit great potential for development as an orally bioavailable therapeutic for treatment of diseases that involve bone loss."( Beta-substituted cyclohexanecarboxamide: a nonpeptidic framework for the design of potent inhibitors of cathepsin K.
Bayly, CI; Black, WC; Chauret, N; Crane, SN; Davis, DE; Desmarais, S; Massé, F; McKay, DJ; Oballa, RM; Ouellet, M; Palmer, JT; Paquet, J; Robichaud, J; Scheigetz, J; Seto, C; Setti, E; Somoza, JR; Wesolowski, G, 2006
)
0.33

Dosage Studied

ExcerptRelevanceReference
" All of the cytochrome P450 parameters that were measured, following CCl4 treatment, demonstrated very flat dose-response curves which appeared to parallel the effects of CCl4 on antibody responses."( The role of metabolism in carbon tetrachloride-mediated immunosuppression: in vivo studies.
Barnes, DW; Holsapple, MP; Jordan, SD; Kaminski, NE, 1990
)
0.28
" Although not present in neonate-lesioned rats treated with saline, these morphological changes persisted at least 21 days after repeated dosing with SKF-38393, and were not accompanied by markers of neurodegenerative change."( Changes in apical dendritic structure correlate with sustained ERK1/2 phosphorylation in medial prefrontal cortex of a rat model of dopamine D1 receptor agonist sensitization.
Blake, BL; Breese, GR; Halloran, C; McCown, TJ; Papadeas, ST, 2008
)
0.35
"5 mg sulfone per kg dung observed under an exaggerated dosing regime in sheep indicates that monepantel poses no risk to insect dung fauna when used as recommended."( Assessment of risk of monepantel faecal residues to dung fauna.
Hoffmann, S; Skripsky, T, 2010
)
0.36
" The resistant isolate showed the presence of two distinct subpopulations, separated by a plateau in the dose-response curve."( Larval development assays reveal the presence of sub-populations showing high- and low-level resistance in a monepantel (Zolvix®)-resistant isolate of Haemonchus contortus.
Chambers, M; Hunt, PW; Kotze, AC; Lamb, J; Raza, A, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (300)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990104 (34.67)18.7374
1990's10 (3.33)18.2507
2000's67 (22.33)29.6817
2010's109 (36.33)24.3611
2020's10 (3.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 30.15

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 Index30.15 (24.57)
Research Supply Index5.79 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index38.01 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (30.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials16 (5.16%)5.53%
Reviews7 (2.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other287 (92.58%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]