diglycolic acid profile

Diglycolic acid, also known as 2,2'-oxydiacetic acid, is a dicarboxylic acid. It is a white solid that is soluble in water and has a variety of applications. It is commonly used in the synthesis of polymers, resins, and pharmaceuticals. Diglycolic acid is also used as a chelating agent, a sequestering agent, and a buffer. Diglycolic acid can be synthesized by the reaction of chloroacetic acid with sodium hydroxide. It can also be produced by the reaction of formaldehyde with glyoxylic acid. Diglycolic acid is a relatively non-toxic compound, but it can cause skin and eye irritation. It is important to handle it with care. Diglycolic acid is studied for its potential use in a variety of applications, including the production of biodegradable plastics, the removal of heavy metals from wastewater, and the development of new pharmaceuticals.'

diglycolic acid: nephrotoxic metabolite in diethylene glycol poisoning inducing necrosis in human proximal tubule cells [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	8088
CHEMBL ID	1234950
CHEBI ID	169983
SCHEMBL ID	26928
MeSH ID	M0572598

Synonym
3-oxapentanedioic acid
ai3-24216
nsc 8651
bis(carboxymethyl)ether
2,2'-oxybisacetic acid
oxydi(acetic acid)
brn 1072117
oxodiacetic acid
einecs 203-823-5
CHEBI:169983
2-(carboxymethoxy)acetic acid
CHEMBL1234950
110-99-6
2,2'-oxydiacetic acid
nsc8651
nsc-8651
oxydiacetic acid
acetic acid,2'-oxybis-
oxybisacetic acid
oxydiethanolic acid
diglycolic acid
acetic acid, oxydi-
bis(carboxymethyl) ether
acetic acid, 2,2'-oxybis-
inchi=1/c4h6o5/c5-3(6)1-9-2-4(7)8/h1-2h2,(h,5,6)(h,7,8
oeg ,
diglycolic acid, 98%
D0545
diglycolicacid
AKOS000120337
NCGC00248264-01
dtxsid4041575 ,
NCGC00254938-01
dtxcid2021575
cas-110-99-6
tox21_301036
unii-s4651635e0
s4651635e0 ,
FT-0624933
SCHEMBL26928
3-oxapentane-1,5-dioic acid
.alpha.,.alpha.-oxydiacetic acid
anhydroglycolic acid
J-520322
J-002501
mfcd00004309
Z57965384
Q5276305
BS-14418
CCG-351657
EN300-18458
AMY41875
2,2-oxydiacetic acid; diglycollic acid; diglylollic acid
A894817
CS-0158474

Excerpt	Reference	Relevance
"Diglycolic acid (DGA) is a byproduct produced by this condensation which cannot be completely removed."	( Analysis of diglycolic acid in food packaging, over the counter products, direct additive carboxymethyl cellulose, and retail foods. DeJager, L; Young, W, 2018)	1.58

Excerpt	Reference	Relevance
"Diglycolic acid (DGA) has been identified as the metabolite responsible for the nephrotoxicity and hepatotoxicity."	( Diglycolic acid inhibits succinate dehydrogenase activity, depletes mitochondrial membrane potential, and induces inflammation in an SH-SY5Y neuroblastoma model of neurotoxicity in vitro. Landry, GM; Reed, KJ, 2023)	3.07

Excerpt	Reference	Relevance
"Controlling and minimizing the adverse effects of drugs are the key issues in ensuring the safety of drug therapy."	( Identification and analysis of an impurity inducing clinical adverse effect in anti-adhesion carboxymethyl chitosan products. Jiang, TF; Lv, ZH; Wang, DY; Wang, YH; Yu, MM, 2013)	0.39
" A rare case of an accidental direct exposure to extremely high concentrations of DGA in a person revealed that DGA has the potential to be toxic to several organs, with the kidneys and liver being the most affected organs."	( Diglycolic acid induces HepG2/C3A liver cell toxicity in vitro. Belgrave, K; Black, T; Depina, A; Flynn, TJ; Keltner, Z; Mossoba, ME; Olejnik, N; Pugh-Bishop, S; Sprando, J; Sprando, RL; Toomer, H; Topping, V; Vohra, S; Wiesenfeld, PL, 2018)	1.92
" This study identified NaDC-1 as a likely and NaDC-3 as a possible molecular target to reduce uptake of this toxic metabolite by the kidney."	( Role of Plasma Membrane Dicarboxylate Transporters in the Uptake and Toxicity of Diglycolic Acid, a Metabolite of Diethylene Glycol, in Human Proximal Tubule Cells. Dwyer, D; Landry, GM; Luttrell-Williams, ES; McMartin, KE; Robinson, CN; Tobin, JD, 2022)	0.95
"Diethylene glycol is a toxic industrial solvent resulting in a well-defined toxidrome."	( Diglycolic acid inhibits succinate dehydrogenase activity, depletes mitochondrial membrane potential, and induces inflammation in an SH-SY5Y neuroblastoma model of neurotoxicity in vitro. Landry, GM; Reed, KJ, 2023)	2.35

Excerpt	Relevance	Reference
"Adult male Wistar rats were divided into three groups dosed with 0, 100 or 300 mg/kg DGA via single oral gavage."	( In-vivo evidence of nephrotoxicity and altered hepatic function in rats following administration of diglycolic acid, a metabolite of diethylene glycol. Abreo, F; Broussard, K; Latimer, B; McMartin, KE; Robinson, CN, 2017)	0.67
" The steep dose-response threshold for toxicity suggests mechanistically that there is likely a saturable step that results in DGA accumulation in target organs."	( In-vivo evidence of nephrotoxicity and altered hepatic function in rats following administration of diglycolic acid, a metabolite of diethylene glycol. Abreo, F; Broussard, K; Latimer, B; McMartin, KE; Robinson, CN, 2017)	0.67
" Given that DGA is present in our food supply as a chemical byproduct of carboxymethyl starch food additives, we sought to perform in vitro testing of its potential hepatotoxicity to help complement a recent in vivo rat acute dose-response study that also tested for the potential hepatotoxic effects of daily DGA ingestion by oral gavage over a period of 28 days."	( Diglycolic acid induces HepG2/C3A liver cell toxicity in vitro. Belgrave, K; Black, T; Depina, A; Flynn, TJ; Keltner, Z; Mossoba, ME; Olejnik, N; Pugh-Bishop, S; Sprando, J; Sprando, RL; Toomer, H; Topping, V; Vohra, S; Wiesenfeld, PL, 2018)	1.92

Class	Description
dicarboxylic acid	Any carboxylic acid containing two carboxy groups.
[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	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
RAR-related orphan receptor gamma	Mus musculus (house mouse)	Potency	0.0044	0.0060	38.0041	19,952.5996	AID1159521
retinoid X nuclear receptor alpha	Homo sapiens (human)	Potency	6.7860	0.0008	17.5051	59.3239	AID1159527; AID1159531
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (4.76)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	12 (57.14)	24.3611
2020's	8 (38.10)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	22 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
citric acid, anhydrous Citric Acid: A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability.. citric acid : A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms.	2.15	1	tricarboxylic acid	antimicrobial agent; chelator; food acidity regulator; fundamental metabolite
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	2.54	2	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
creatine [no description available]	2.11	1	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	2.08	1	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
succinic acid Succinic Acid: A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawley's Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851). succinic acid : An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle.	2.9	2	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
toluene methylbenzene : Any alkylbenzene that is benzene substituted with one or more methyl groups.	2.07	1	methylbenzene; toluenes; volatile organic compound	cholinergic antagonist; fuel additive; neurotoxin; non-polar solvent
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.07	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.	2.08	1	pyrazoles	antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent
egtazic acid Egtazic Acid: A chelating agent relatively more specific for calcium and less toxic than EDETIC ACID.. ethylene glycol bis(2-aminoethyl)tetraacetic acid : A diether that is ethylene glycol in which the hydrogens of the hydroxy groups have been replaced by 2-[bis(carboxymethyl)amino]ethyl group respectively.	2.13	1	diether; tertiary amino compound; tetracarboxylic acid	chelator
1,4-cyclohexanedimethanol 1,4-cyclohexanedimethanol: used as a monomer in the production of polyester resins; RN given refers to cpd with specified locants for dimethanol groups	2.07	1
tetrahydrofuran oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.	2.07	1	cyclic ether; oxolanes; saturated organic heteromonocyclic parent; volatile organic compound	polar aprotic solvent
diethylene glycol glycol ether : A hydroxyether which contains both an ether and alcohol functional groups. It is one of the most versatile classes of organic solvents which are commonly used in paints, cleaners, adhesives, pharmaceuticals and cosmetics.	3.8	9	hydroxyether
beta-hydroxyethoxyacetic acid beta-hydroxyethoxyacetic acid: metabolite of both dioxane and diethylene glycol	2.8	3
phenyl acetate phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.	2.8	3	benzenes; phenyl acetates
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.13	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
glycidic acid glycidic acid: an inhibitor of glycolate synthesis; structure	2.6	1
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.11	1
chitosan [no description available]	2.08	1
orabase Orabase: used in therapy of oral mucosal ulcers	2.17	1

Condition	Relationship Strength	Studies
Encephalopathy, Toxic [description not available]	2.58	2
Innate Inflammatory Response [description not available]	2.6	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.6	1
Neuroblastoma A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)	7.6	1
Acute Kidney Failure [description not available]	3.07	4
Acute Kidney Injury Abrupt reduction in kidney function. Acute kidney injury encompasses the entire spectrum of the syndrome including acute kidney failure; ACUTE KIDNEY TUBULAR NECROSIS; and other less severe conditions.	3.07	4
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.25	1
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	7.48	2
Poisoning Used with drugs, chemicals, and industrial materials for human or animal poisoning, acute or chronic, whether the poisoning is accidental, occupational, suicidal, by medication error, or by environmental exposure.	2.08	1
Acute Liver Injury, Drug-Induced [description not available]	2.53	2
Metabolic Acidosis [description not available]	2.11	1
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	2.11	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.11	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.53	2

diglycolic acid

Description

Cross-References

Synonyms (55)

Research Excerpts

Overview

Effects

Toxicity

Dosage Studied

Drug Classes (1)

Protein Targets (2)

Potency Measurements

Research

Studies (21)

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Research Demand Index: 34.31

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