Page last updated: 2024-11-04

iodoacetic acid

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

Description

Iodoacetic Acid: A derivative of ACETIC ACID that contains one IODINE atom attached to its methyl group. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

iodoacetic acid : A haloacetic acid that is acetic acid in which one of the hydrogens of the methyl group is replaced by an iodine atom. [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 CID5240
CHEMBL ID376280
CHEBI ID74571
SCHEMBL ID55098
MeSH IDM0029399

Synonyms (59)

Synonym
iodoaceticacid
64-69-7
monoiodoacetic acid
nsc-2125
nsc2125
acetic acid, iodo-
wln: qv1i
IA ,
iodoacetic acid
2-iodoacetic acid
kyselina jodoctova [czech]
hsdb 4008
monoiodine acetate
acetic acid, iodo- (8ci,9ci)
ccris 667
ai3-52119
einecs 200-590-1
brn 1739079
nsc 2125
monoiodoacetate
IODOACETATE ,
iodoacetic acid, >=98.0% (t)
STK263695
inchi=1/c2h3io2/c3-1-2(4)5/h1h2,(h,4,5)
jdntwhvoxjzdsn-uhfffaoysa-
AKOS000118792
CHEMBL376280
chebi:74571 ,
NCGC00188891-01
wf5188v710 ,
4-02-00-00534 (beilstein handbook reference)
kyselina jodoctova
unii-wf5188v710
acetic acid, 2-iodo-
iodoethanoic acid
LMFA01090135
2-iodo-acetic acid
ch2ico2h
ch2icooh
ich2cooh
ich2co2h
FT-0627257
BRD-K88868628-001-01-0
iodoacetic acid [mi]
iodoacetic acid [hsdb]
SCHEMBL55098
iodo-acetic acid
BP-13415
mfcd00002685
F8880-2820
DTXSID5025445
iodoacetic acid, puriss. p.a., >=99.5% (t)
Q416375
04e ,
STR09520
H11974
A935389
acetic-1-13c acid, 2-iodo- (9ci)
EN300-19476

Research Excerpts

Overview

Iodoacetic acid (IAA) is a water disinfection byproduct that is an ovarian toxicant in vitro. It has been shown to exert cytotoxicity, genot toxicity, tumorigenicity, and reproductive and developmental toxicity.

ExcerptReferenceRelevance
"Iodoacetic acid (IAA) is an unregulated water disinfection byproduct that is an ovarian toxicant. "( Iodoacetic acid exposure alters the transcriptome in mouse ovarian antral follicles.
Drnevich, J; Flaws, JA; Gonsioroski, A; Laws, M; Mourikes, VE; Neff, A; Plewa, MJ, 2022
)
3.61
"Iodoacetic acid (IAA) is an unregulated disinfection byproduct in drinking water and has been shown to exert cytotoxicity, genotoxicity, tumorigenicity, and reproductive and developmental toxicity. "( Effects of iodoacetic acid drinking water disinfection byproduct on the gut microbiota and its metabolism in rats.
Guo, Y; Liu, X; Long, K; Lu, D; Mo, Y; Sha, Y; Su, Z; Wei, S; Wei, X; Wu, H; Xia, Y; Yang, Q; Zheng, W, 2022
)
2.55
"Iodoacetic acid (IAA) is an emerging and the most genotoxic iodinated disinfection byproduct to date. "( Drinking water disinfection byproduct iodoacetic acid affects thyroid hormone synthesis in Nthy-ori 3-1 cells.
Dong, S; Huang, Y; Long, K; Mo, Y; Sha, Y; Wei, X; Wu, H; Xiao, J; Yang, Q; Zeng, Q, 2023
)
2.62
"Iodoacetic acid (IAA) is a water disinfection byproduct that is an ovarian toxicant in vitro. "( Iodoacetic acid affects estrous cyclicity, ovarian gene expression, and hormone levels in mice†.
Flaws, JA; Gao, L; Gonsioroski, A; Meling, DD; Plewa, MJ, 2021
)
3.51
"Iodoacetic acid (IAA) is a water disinfection byproduct (DBP) formed by reactions between oxidizing disinfectants and iodide. "( Iodoacetic Acid, a Water Disinfection Byproduct, Disrupts Hypothalamic, and Pituitary Reproductive Regulatory Factors and Induces Toxicity in the Female Pituitary.
Flaws, JA; Gonsioroski, AV; Gonzalez, RVL; Raetzman, LT; Weis, KE, 2021
)
3.51
"Iodoacetic acid (IAA) is an unregulated drinking-water disinfection byproduct with potent cytotoxicity, genotoxicity, and tumorigenicity in animals. "( Iodoacetic acid activates Nrf2-mediated antioxidant response in vitro and in vivo.
Andersen, ME; He, G; Jiang, S; Liu, X; Lu, D; Pi, J; Qu, W; Tan, H; Wang, S; Xue, P; Zhang, Q; Zheng, W, 2014
)
3.29

Effects

ExcerptReferenceRelevance
"Iodoacetic acid (IAA) has been applied to different species to acutely induce photoreceptor degeneration. "( Functional evaluation of iodoacetic acid induced photoreceptor degeneration in the cat.
Gao, J; Huang, X; Li, X; Nan, Y; Pu, M; Ren, C; Zhang, Q, 2013
)
2.14

Toxicity

ExcerptReferenceRelevance
" Aberrations are formed from DNA double-strand breaks, and DSBs are known to be induced by nonmutagenic (Ames test negative) noncarcinogens at toxic levels [Storer et al."( Chromosome aberrations in vitro related to cytotoxicity of nonmutagenic chemicals and metabolic poisons.
Armstrong, MJ; Bradt, CI; Galloway, SM; Greenwood, SK; Hill, RB; Hilliard, CA, 1998
)
0.3
"Chronic exposure to drinking water disinfection byproducts has been linked to adverse health risks."( Human cell toxicogenomic analysis linking reactive oxygen species to the toxicity of monohaloacetic acid drinking water disinfection byproducts.
Attene-Ramos, MS; Pals, J; Plewa, MJ; Wagner, ED; Xia, M, 2013
)
0.39
" Therefore, the DNA damage-responsive p53 pathway may be an important piece of information to fill in a gap in the adverse outcome pathway framework for the assessment of HBQs."( In Vitro Cytotoxicity and Adaptive Stress Responses to Selected Haloacetic Acid and Halobenzoquinone Water Disinfection Byproducts.
Escher, BI; Leusch, FD; Plewa, MJ; Procházka, E, 2015
)
0.42
" However, little is known about the relationship of catalase (CAT) with the cytotoxicity of IAA and the adverse effects of IAA to CAT."( Drinking water disinfection byproduct iodoacetic acid interacts with catalase and induces cytotoxicity in mouse primary hepatocytes.
Jia, R; Liu, R; Sun, Z; Wang, J; Zheng, X; Zong, W, 2018
)
0.75
"Acute oral toxicity of m-PGA resulted in LD50 values in excess of 2000 mg/kg."( Safety and efficacy of a new micronized formulation of the ALIAmide palmitoylglucosamine in preclinical models of inflammation and osteoarthritis pain.
Cordaro, M; Crupi, R; Cuzzocrea, S; D' Amico, R; Di Paola, R; Fusco, R; Gugliandolo, E; Impellizzeri, D; Peritore, AF; Schievano, C; Siracusa, R, 2019
)
0.51
" IAA also had toxic effects in the pituitary, inducing DNA damage and P21/Cdkn1a expression in vitro (20 μM IAA) and DNA damage and Cdkn1a expression in vivo (500 mg/l)."( Iodoacetic Acid, a Water Disinfection Byproduct, Disrupts Hypothalamic, and Pituitary Reproductive Regulatory Factors and Induces Toxicity in the Female Pituitary.
Flaws, JA; Gonsioroski, AV; Gonzalez, RVL; Raetzman, LT; Weis, KE, 2021
)
2.06

Compound-Compound Interactions

ExcerptReferenceRelevance
" The aim of this study was to evaluate the effect of adelmidrol, a synthetic palmitoylethanolamide analogue, combined with hyaluronic acid on pain severity and modulation of the inflammatory response in a rat model of monosodium iodoacetate (MIA)-induced osteoarthritis."( Adelmidrol, in combination with hyaluronic acid, displays increased anti-inflammatory and analgesic effects against monosodium iodoacetate-induced osteoarthritis in rats.
Britti, D; Cordaro, M; Cuzzocrea, S; Di Paola, R; Evangelista, M; Fusco, R; Impellizzeri, D; Morittu, VM, 2016
)
0.43
" Rats subjected to OA were treated by intra-articular injection of adelmidrol in combination with sodium hyaluronate at different doses and time points after MIA induction."( Adelmidrol, in combination with hyaluronic acid, displays increased anti-inflammatory and analgesic effects against monosodium iodoacetate-induced osteoarthritis in rats.
Britti, D; Cordaro, M; Cuzzocrea, S; Di Paola, R; Evangelista, M; Fusco, R; Impellizzeri, D; Morittu, VM, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" However, the magnitude of the effect varied between animals with the same IAA dose and survival time, suggesting individual differences in the bioavailability of the toxin."( Long-term cellular and regional specificity of the photoreceptor toxin, iodoacetic acid (IAA), in the rabbit retina.
Enzmann, V; Franco, LM; Kaplan, HJ; Katagiri, Y; Liang, L; Sandell, JH; Yamauchi, Y,
)
0.36
" Future work will be required to determine whether α-mangostin may cross the blood-brain barrier and achieve enough bioavailability to elicit a protective response in the brain being an effective nutraceutical compound for preventive therapy of neurodegenerative diseases."( Neuroprotective effect of α-mangostin and curcumin against iodoacetate-induced cell death.
González-Reyes, S; Hernández-Nava, M; Orozco-Ibarra, M; Pedraza-Chaverri, J; Reyes-Fermín, LM; Tarco-Álvarez, NG, 2012
)
0.38

Dosage Studied

ExcerptRelevanceReference
" Monoiodoacetic acid was given to rabbits via an ear vein at a dosage of 40 mg/kg."( [Choroidal blood flow in chronic stage of selective retinal damage after monoiodoacetic acid injection].
Nasu, K, 1990
)
1.02
" Pretreatment of the membranes with trypsin and chymotrypsin abolished the specific binding of both agonist and antagonist, in a dose-response manner, with the former being less affected."( Some characteristics of GnRH receptors in rat-pituitary membranes: differences between an agonist and and antagonist.
Hazum, E, 1981
)
0.26
" Furthermore, in an additional study animals were orally dosed vehicle (5 ml/kg), naproxen (0."( Structural pathology in a rodent model of osteoarthritis is associated with neuropathic pain: increased expression of ATF-3 and pharmacological characterisation.
Ball, AD; Heapy, CG; Ivanavicius, SP; Murray, F; Read, SJ; Westwood, RF, 2007
)
0.34
"4 μM) were spiked to the raw water samples from Yangshupu and Minhang drinking water treatment plant, certain amounts of CHI3 and IAA were found under pH 7 and the concentrations were strongly correlated with ClO2 dosage and water qualities, however, no TIAA was detected."( Formation of iodinated disinfection by-products during oxidation of iodide-containing waters with chlorine dioxide.
Gao, NY; Hu, CY; Lin, L; Lin, YL; Xu, B; Ye, T; Zhang, TY, 2013
)
0.39
"25mg) into rats and orally treated with 2g/ml d-Fuzi at a dosage of 7 ml/kg body weight for 28 days."( Chondroprotective activity of a detoxicated traditional Chinese medicine (Fuzi) of Aconitum carmichaeli Debx against severe-stage osteoarthritis model induced by mono-iodoacetate.
Cao, G; Cheng, Y; Guo, Y; Jin, H; Jin, W; Shan, L; Tong, P; Xiao, L; Xu, S, 2014
)
0.4
" Both 27 and 48 demonstrated robust activity in the acute rat monoiodoacetate-induced osteoarthritis model of pain, and subchronic dosing of 48 showed a shift to a lower EC50 over 7 days."( Substituted Indazoles as Nav1.7 Blockers for the Treatment of Pain.
Daanen, JF; DeGoey, DA; El-Kouhen, OF; Fricano, MM; Frost, JM; Ghoreishi-Haack, N; Gum, RJ; Hsieh, GC; Kort, ME; Lundgaard, GL; Matulenko, MA; Neelands, T; Pai, M; Shi, L; Zhan, C; Zhang, XF, 2016
)
0.43
" Hits from this assay were tested in a plasma assay to assess inhibition of endogenous plasma autotaxin and subsequently tested for their ability to lower plasma LPA levels upon oral dosing of rats."( Identification and pharmacological characterization of a novel inhibitor of autotaxin in rodent models of joint pain.
Bui, HH; Chambers, MG; Jones, SB; Lin, C; Mitchell, PG; Norman, BH; Oskins, JL; Pfeifer, LA; Swearingen, CA; Thirunavukkarasu, K, 2017
)
0.46
" Unexpectedly, vitamin C's effects did not strengthen with the increasing dosage, while the 100 mg/kg dosage was more efficient than the 200 or 300 mg/kg dosages."( Vitamin C Protects Chondrocytes against Monosodium Iodoacetate-Induced Osteoarthritis by Multiple Pathways.
Chang, KL; Cheng, HL; Chiu, PR; Hsieh, BS; Hu, YC; Huang, LW; Huang, TC; Yeh, JP, 2016
)
0.43
" However, it is unknown whether the antalgic gait caused by MIA is associated with severity of degeneration from the high dosage or the whole-joint degeneration associated with glycolysis inhibition."( Quadrupedal rodent gait compensations in a low dose monoiodoacetate model of osteoarthritis.
Allen, KD; Lakes, EH, 2018
)
0.48
" Further fine tuning of alginate formulation and effective dosage for might be required in order to improve therapeutic efficacy depending on the target disease."( MSC encapsulation in alginate microcapsules prolongs survival after intra-articular injection, a longitudinal in vivo cell and bead integrity tracking study.
Bernsen, M; Bos, PK; Haeck, J; Khatab, S; Kops, N; Leijs, MJ; Nieboer, M; van Buul, G; van Osch, GJVM; Verhaar, JAN, 2020
)
0.56
" This study determined the drug dosage and the mechanisms of GMGHT for OA."( Gumiganghwal-tang ameliorates cartilage destruction via inhibition of matrix metalloproteinase.
Ahn, KS; Choi, Y; Hahm, DH; Kim, MH; Lee, SG; Um, JY; Yang, WM, 2020
)
0.56
" Adult CD-1 mice were dosed with water or IAA (0."( Iodoacetic acid affects estrous cyclicity, ovarian gene expression, and hormone levels in mice†.
Flaws, JA; Gao, L; Gonsioroski, A; Meling, DD; Plewa, MJ, 2021
)
2.06
" Adult female CD-1 mice were dosed with water (control) or IAA (10, 100, and 500 mg/L) in the drinking water for 35 days and then mated with unexposed males."( Effects of prenatal and lactational exposure to iodoacetic acid on the F1 generation of mice†.
Flaws, JA; Gonsioroski, A; Plewa, MJ, 2022
)
0.98
" Adult female mice were dosed with water or IAA (10 or 500 mg/L) in the water for 35-40 days."( Iodoacetic acid exposure alters the transcriptome in mouse ovarian antral follicles.
Drnevich, J; Flaws, JA; Gonsioroski, A; Laws, M; Mourikes, VE; Neff, A; Plewa, MJ, 2022
)
2.16
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
alkylating agentHighly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
[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 (2)

ClassDescription
organoiodine compoundAn organoiodine compound is a compound containing at least one carbon-iodine bond.
haloacetic acidA monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a halogen atom.
[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]

Bioassays (8)

Assay IDTitleYearJournalArticle
AID1064582Inhibition of PFKFB3-mediated glycolysis in human MDA-MB-231 cells assessed as extracellular acidification rate at 100 uM after 2 hrs2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).
AID278889Blocking of lactate production in primary human osteoblasts at 100 uM after 1 hr by ELISA2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Influence on mitochondria and cytotoxicity of different antibiotics administered in high concentrations on primary human osteoblasts and cell lines.
AID278891Inhibition of lactate production in primary human osteoblasts after 48 hrs by ELISA2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Influence on mitochondria and cytotoxicity of different antibiotics administered in high concentrations on primary human osteoblasts and cell lines.
AID1064581Induction of mitochondrial respiration in human MDA-MB-231 cells assessed as increase of oxygen consumption rate2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).
AID1064579Cytotoxicity against human MDA-MB-231 cells assessed as cell detachment after 60 mins2014Bioorganic & medicinal chemistry, Feb-01, Volume: 22, Issue:3
Targeting the Warburg Effect in cancer; relationships for 2-arylpyridazinones as inhibitors of the key glycolytic enzyme 6-phosphofructo-2-kinase/2,6-bisphosphatase 3 (PFKFB3).
AID278892Inhibition of lactate production in MG63 cells after 48 hrs by ELISA by ELISA2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Influence on mitochondria and cytotoxicity of different antibiotics administered in high concentrations on primary human osteoblasts and cell lines.
AID278890Blocking of lactate production in MG63 cells at 100 uM after 1 hr by ELISA2007Antimicrobial agents and chemotherapy, Jan, Volume: 51, Issue:1
Influence on mitochondria and cytotoxicity of different antibiotics administered in high concentrations on primary human osteoblasts and cell lines.
AID384212Mutagenic activity in Salmonella Typhimurium TA100 assessed as logarithm of his+ revertant number increasing activity by amens test2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,220)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990435 (35.66)18.7374
1990's363 (29.75)18.2507
2000's88 (7.21)29.6817
2010's203 (16.64)24.3611
2020's131 (10.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.08

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

MetricThis Compound (vs All)
Research Demand Index41.08 (24.57)
Research Supply Index7.14 (2.92)
Research Growth Index4.85 (4.65)
Search Engine Demand Index62.92 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.08)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.16%)5.53%
Reviews6 (0.48%)6.00%
Case Studies2 (0.16%)4.05%
Observational1 (0.08%)0.25%
Other1,245 (99.12%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]