dimethyl itaconate profile

Dimethyl itaconate (DMI) is a diester derivative of itaconic acid, a naturally occurring organic compound produced by certain fungi. It has gained significant attention in recent years due to its potential therapeutic applications. DMI exhibits a broad range of pharmacological activities, including antiviral, antibacterial, antifungal, and anti-inflammatory effects. Its synthesis involves the esterification of itaconic acid with methanol. DMI is studied extensively for its potential use in treating various diseases, such as COVID-19, cancer, and autoimmune disorders. Its antiviral properties, particularly against SARS-CoV-2, have led to ongoing clinical trials. The compound's mechanism of action involves interfering with viral replication and host cell signaling pathways. DMI's favorable safety profile and its ability to cross the blood-brain barrier make it an attractive therapeutic candidate.'

dimethyl itaconate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	69240
CHEMBL ID	4750162
SCHEMBL ID	74775
MeSH ID	M0508933

Synonym
itaconic acid dimethyl ester
butanedioic acid, methylene-, dimethyl ester
succinic acid, methylene-, dimethyl ester
dimethyl 2-methylenesuccinate
AC-907/25014187
nsc-9385
methylenesuccinic acid, dimethyl ester
itaconic acid, dimethylester
dimethyl itaconate
617-52-7
itaconic acid, dimethyl ester
nsc9385 ,
inchi=1/c7h10o4/c1-5(7(9)11-3)4-6(8)10-2/h1,4h2,2-3h
dimethyl itaconate, 99%
dimethyl itaconate, 97%
2-methylene-succinic acid dimethyl ester
I0206
dimethyl 2-methylidenebutanedioate
STK801932
A15702
AKOS005622517
ai3-16883
unii-11jib0yi93
ccris 7232
11jib0yi93 ,
nsc 9385
dimethylitaconate
einecs 210-519-6
butanedioic acid, 2-methylene-, 1,4-dimethyl ester
BBL010928
1,4-dimethyl 2-methylidenebutanedioate
FT-0625083
SCHEMBL74775
butanedioic acid, 2-methylene-, dimethyl ester
dimethyl methylenesuccinate
dimethyl 2-methylenesuccinate #
W-105104
STR01598
AC-24615
DTXSID80210701
F0001-1641
mfcd00008446
dimethyl itaconate, (stabilized with hq)
methyl 4-methoxy-2-methylene-4-oxobutanoate
dimethyl-itaconate
CS-W022632
gtpl9939
BCP26657
Q63396620
25587-85-3
EN300-36428
CHEMBL4750162
HY-W041892

Excerpt	Reference	Relevance
"Dimethyl itaconate (DI) is an analog of itaconic acid with anti-inflammatory effects."	( Dimethyl itaconate alleviates the pyroptosis of macrophages through oxidative stress. Cai, GL; Guo, DY; Huang, SS; Jia, BB; Lu, Y; Yan, J; Yang, ZX, 2021)	2.79
"Dimethyl itaconate (DMI) is a surfactant with important anti-inflammatory effects."	( Dimethyl itaconate inhibits LPS-induced inflammatory release and apoptosis in alveolar type II epithelial and bronchial epithelial cells by activating pulmonary surfactant proteins A and D. Shi, Y; Yin, HQ, 2022)	2.89
"Dimethyl itaconate (DI) is an itaconate derivative and has recently attracted extensive interest due to its anti-inflammatory effect."	( Dimethyl itaconate ameliorates cognitive impairment induced by a high-fat diet via the gut-brain axis in mice. Ge, X; Hu, M; Huang, XF; Jiang, P; Meng, X; Nagaratnam, N; Pan, W; Shi, H; Tang, R; Wu, J; Xu, D; Yang, X; Yu, Y; Zhang, P; Zhao, J; Zheng, K, 2023)	3.07
"Dimethyl itaconate (DI) is a membrane-permeable itaconate derivative with anti-inflammatory functions. "	( Dimethyl itaconate protects against fungal keratitis by activating the Nrf2/HO-1 signaling pathway. Fan, Y; Gu, L; Li, C; Lin, H; Lin, J; Lu, C; Niu, Y; Peng, X; Wang, Q; Zhao, G; Zhu, G, 2020)	3.44
"Dimethyl itaconate (DMI) is an analog of dimethyl fumarate (DMF), an approved NF-E2-related Factor 2 (Nrf2) activator for multiple sclerosis. "	( A comparison study between dimethyl itaconate and dimethyl fumarate in electrophilicity, Nrf2 activation, and anti-inflammation Kang, YY; Lan, JQ; Peng, Y; Tang, JS; Wu, L; Zhang, Y; Zhou, YJ, 2022)	2.46
"Dimethyl itaconate is an important raw material for copolymerization, but it is not synthesized from itaconic acid by organisms. "	( Bio-Based Production of Dimethyl Itaconate From Rice Wine Waste-Derived Itaconic Acid. Han, SO; Joo, YC; Jung, KH; Ko, YJ; Shin, SK; Sim, SA; You, SK, 2017)	2.2

Assay ID	Title	Year	Journal	Article
AID1685613	Covalent inhibition of wild type N-terminal polyhis-tagged TEV protease cleavage site fused Mycobacterium tuberculosis ICL1 expressed in Escherichia coli BL21 (DE3) using DL-isocitrate as substrate measured after 1 hr by UV-Vis spectrophotometric analysis	2021	RSC medicinal chemistry, Jan-01, Volume: 12, Issue:1	Itaconate is a covalent inhibitor of the
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	4 (10.00)	29.6817
2010's	9 (22.50)	24.3611
2020's	27 (67.50)	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	2 (5.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	38 (95.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	2.03	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
itaconic acid itaconic acid : A dicarboxylic acid that is methacrylic acid in which one of the methyl hydrogens is substituted by a carboxylic acid group.	8.66	8	dicarboxylic acid; dicarboxylic fatty acid; olefinic compound	fungal metabolite; human metabolite
propylene glycol Propylene Glycol: A clear, colorless, viscous organic solvent and diluent used in pharmaceutical preparations.. propane-1,2-diol : The simplest member of the class of propane-1,2-diols, consisting of propane in which a hydrogen at position 1 and a hydrogen at position 2 are substituted by hydroxy groups. A colourless, viscous, hygroscopic, low-melting (-59degreeC) and high-boiling (188degreeC) liquid with low toxicity, it is used as a solvent, emulsifying agent, and antifreeze.	2.15	1	glycol; propane-1,2-diols	allergen; human xenobiotic metabolite; mouse metabolite; protic solvent
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.	2.15	1	alpha,omega-dicarboxylic acid; C4-dicarboxylic acid	anti-ulcer drug; fundamental metabolite; micronutrient; nutraceutical; radiation protective agent
styrene Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.	2.48	2	styrenes; vinylarene; volatile organic compound	mouse metabolite; mutagen; plant metabolite
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.21	1	dialdehyde	biomarker
rhodium Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.	7.97	4	cobalt group element atom
ruthenium Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.	2.05	1	iron group element atom; platinum group metal atom
phosphine phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.	2.47	2	mononuclear parent hydride; phosphanes; phosphine	carcinogenic agent; fumigant insecticide
ruthenium chloride (rucl3) ruthenium chloride: RN given refers to unlabeled cpd	2.03	1
1,7-phenanthroline [no description available]	2.05	1	phenanthroline
phosphites Phosphites: Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed). phosphite(3-) : A trivalent inorganic anion obtained by removal of all three protons from phosphorous acid.	2.03	1	phosphite ion; trivalent inorganic anion
deoxycholic acid Deoxycholic Acid: A bile acid formed by bacterial action from cholate. It is usually conjugated with glycine or taurine. Deoxycholic acid acts as a detergent to solubilize fats for intestinal absorption, is reabsorbed itself, and is used as a choleretic and detergent.. deoxycholic acid : A bile acid that is 5beta-cholan-24-oic acid substituted by hydroxy groups at positions 3 and 12 respectively.	2.03	1	bile acid; C24-steroid; dihydroxy-5beta-cholanic acid	human blood serum metabolite
aconitic acid trans-aconitic acid : The trans-isomer of aconitic acid.	2.31	1	aconitic acid	fundamental metabolite
benzene-1,3,5-tricarboxamide benzene-1,3,5-tricarboxamide: structure in first source	2.08	1
dimethyl fumarate [no description available]	7.41	1	diester; enoate ester; methyl ester	antipsoriatic; immunomodulator
aconitic acid cis-aconitic acid : The cis-isomer of aconitic acid.	2.31	1	aconitic acid	fundamental metabolite
3-methylitaconate 3-methylitaconate: RN refers to (S)-isomer; structure given in first source	2.31	1
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	2.72	2
leptin Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.	2.41	1

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	5.44	11	1
Insulin Sensitivity [description not available]	2.31	1	0
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.	5.44	11	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	7.31	1	0
Colorectal Cancer [description not available]	2.41	1	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.41	1	0
Pain, Chronic [description not available]	2.41	1	0
Allodynia [description not available]	2.41	1	0
Nerve Pain [description not available]	2.41	1	0
Neuralgia Intense or aching pain that occurs along the course or distribution of a peripheral or cranial nerve.	2.41	1	0
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	7.41	1	0
Hypermelanosis [description not available]	2.41	1	0
B16 Melanoma [description not available]	2.41	1	0
Hyperpigmentation Excessive pigmentation of the skin, usually as a result of increased epidermal or dermal melanin pigmentation, hypermelanosis. Hyperpigmentation can be localized or generalized. The condition may arise from exposure to light, chemicals or other substances, or from a primary metabolic imbalance.	2.41	1	0
Cognitive Decline [description not available]	3.01	2	0
Acute Confusional Senile Dementia [description not available]	2.6	1	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	3.21	4	0
Alzheimer Disease A degenerative disease of the BRAIN characterized by the insidious onset of DEMENTIA. Impairment of MEMORY, judgment, attention span, and problem solving skills are followed by severe APRAXIAS and a global loss of cognitive abilities. The condition primarily occurs after age 60, and is marked pathologically by severe cortical atrophy and the triad of SENILE PLAQUES; NEUROFIBRILLARY TANGLES; and NEUROPIL THREADS. (From Adams et al., Principles of Neurology, 6th ed, pp1049-57)	2.6	1	0
Cognitive Dysfunction Diminished or impaired mental and/or intellectual function.	3.01	2	0
Chronic Lung Injury [description not available]	2.41	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	2.6	1	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.99	1	1
Lipid Metabolism Disorders Pathological conditions resulting from abnormal anabolism or catabolism of lipids in the body.	3.99	1	1
Infection, Toxoplasma gondii [description not available]	2.6	1	0
Toxoplasmosis The acquired form of infection by Toxoplasma gondii in animals and man.	2.6	1	0
B-Cell Chronic Lymphocytic Leukemia [description not available]	2.6	1	0
Leukemia, Lymphocytic, Chronic, B-Cell A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.	2.6	1	0
Cerebral Infarction, Middle Cerebral Artery [description not available]	2.21	1	0
Injury, Ischemia-Reperfusion [description not available]	2.21	1	0
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	7.21	1	0
Infarction, Middle Cerebral Artery NECROSIS occurring in the MIDDLE CEREBRAL ARTERY distribution system which brings blood to the entire lateral aspects of each CEREBRAL HEMISPHERE. Clinical signs include impaired cognition; APHASIA; AGRAPHIA; weak and numbness in the face and arms, contralaterally or bilaterally depending on the infarction.	2.21	1	0
Aspergillus Infection [description not available]	2.25	1	0
Aspergillosis Infections with fungi of the genus ASPERGILLUS.	2.25	1	0
Keratitis Inflammation of the cornea.	7.25	1	0
Allergic Encephalomyelitis [description not available]	2.25	1	0
Infections, Vibrio [description not available]	2.25	1	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	2.25	1	0
Colitis-Associated Cancer [description not available]	2.25	1	0
Colitis Gravis [description not available]	2.25	1	0
Colitis, Ulcerative Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.	2.25	1	0
Blood Poisoning [description not available]	2.31	1	0
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	7.31	1	0
Infarct [description not available]	7.31	1	0
Alveolitis, Fibrosing [description not available]	2.31	1	0
Pulmonary Fibrosis A process in which normal lung tissues are progressively replaced by FIBROBLASTS and COLLAGEN causing an irreversible loss of the ability to transfer oxygen into the bloodstream via PULMONARY ALVEOLI. Patients show progressive DYSPNEA finally resulting in death.	7.31	1	0
Carcinoma, Thymic [description not available]	2.31	1	0
Cancer of the Thymus [description not available]	2.31	1	0
Thymoma A neoplasm originating from thymic tissue, usually benign, and frequently encapsulated. Although it is occasionally invasive, metastases are extremely rare. It consists of any type of thymic epithelial cell as well as lymphocytes that are usually abundant. Malignant lymphomas that involve the thymus, e.g., lymphosarcoma, Hodgkin's disease (previously termed granulomatous thymoma), should not be regarded as thymoma. (From Stedman, 25th ed)	2.31	1	0
Thymus Neoplasms Tumors or cancer of the THYMUS GLAND.	2.31	1	0
Palmoplantaris Pustulosis [description not available]	2.17	1	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	2.17	1	0
Mastitis INFLAMMATION of the BREAST, or MAMMARY GLAND.	7.21	1	0
Cardiac Toxicity [description not available]	2.21	1	0
Acute Disease Disease having a short and relatively severe course.	2.21	1	0
Cardiotoxicity Damage to the HEART or its function secondary to exposure to toxic substances such as drugs used in CHEMOTHERAPY; IMMUNOTHERAPY; or RADIATION.	7.21	1	0

dimethyl itaconate

Description

Cross-References

Synonyms (53)

Research Excerpts

Overview

Bioassays (1)

Research

Studies (40)

Market Indicators

Research Demand Index: 36.56

Study Types