Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Fumaric acid
- DrugBank Accession Number
- DB01677
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Fumaric acid (DB01677)
- Weight
- Average: 116.0722
Monoisotopic: 116.010958616 - Chemical Formula
- C4H4O4
- Synonyms
- (2E)-2-butenedioic acid
- (E)-2-butenedioic acid
- Fumaric acid
- Fumaricum acidum
- Fumarsäure
- trans-1,2-ethylenedicarboxylic acid
- trans-but-2-enedioic acid
- trans-Butenedioic acid
- External IDs
- E-297
- FEMA NO. 2488
- INS NO.297
- INS-297
- NSC-2752
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AInterferon gamma binderHumans UMalate dehydrogenase Not Available Chloroflexus aurantiacus (strain ATCC 29366 / DSM 635 / J-10-fl) UFumarate reductase flavoprotein subunit Not Available Shewanella oneidensis (strain MR-1) UNAD-dependent malic enzyme, mitochondrial Not Available Humans UFumarylacetoacetase Not Available Humans UFumarate reductase flavoprotein subunit Not Available Shewanella frigidimarina - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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- Fumaderm (Biogen Idec)
Categories
- ATC Codes
- D05AX01 — Fumaric acid
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Dicarboxylic acids and derivatives
- Direct Parent
- Dicarboxylic acids and derivatives
- Alternative Parents
- Unsaturated fatty acids / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Dicarboxylic acid or derivatives / Fatty acid / Fatty acyl / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- butenedioic acid (CHEBI:18012)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 88XHZ13131
- CAS number
- 110-17-8
- InChI Key
- VZCYOOQTPOCHFL-OWOJBTEDSA-N
- InChI
- InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+
- IUPAC Name
- (2E)-but-2-enedioic acid
- SMILES
- OC(=O)\C=C\C(O)=O
References
- Synthesis Reference
Chung Kun Shih, Craig W. Gleason, Edmund H. Braun, II, "Solventless process for producing dialkyl fumarate-vinyl acetate copolymers." U.S. Patent US4772674, issued September, 1980.
US4772674- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000134
- KEGG Drug
- D02308
- KEGG Compound
- C00122
- PubChem Compound
- 444972
- PubChem Substance
- 46508303
- ChemSpider
- 10197150
- BindingDB
- 26122
- 25389
- ChEBI
- 18012
- ChEMBL
- CHEMBL503160
- ZINC
- ZINC000003860193
- PDBe Ligand
- FUM
- RxList
- RxList Drug Page
- Wikipedia
- Fumaric_acid
- PDB Entries
- 1d4e / 1e39 / 1gz3 / 1gz4 / 1jrx / 1jry / 1jrz / 1kss / 1ksu / 1lj1 … show 53 more
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Inflammatory Bowel Diseases (IBD) / Psoriasis 1 somestatus stop reason just information to hide Not Available Completed Not Available Psoriasis 2 somestatus stop reason just information to hide 4 Completed Treatment Psoriasis Vulgaris (Plaque Psoriasis) 1 somestatus stop reason just information to hide 4 Unknown Status Prevention Cardiovascular Disease (CVD) / Psoriasis / Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 3 Completed Treatment Psoriasis 3 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 287 dec °C PhysProp boiling point (°C) 522 °C PhysProp water solubility 7000 mg/L (at 25 °C) US EPA (1981) logP 0.46 HANSCH,C ET AL. (1995) pKa 3.03 (at 18 °C) LIDE,DR (1996) - Predicted Properties
Property Value Source Water Solubility 24.1 mg/mL ALOGPS logP 0.21 ALOGPS logP -0.041 Chemaxon logS -0.68 ALOGPS pKa (Strongest Acidic) 3.35 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 24.61 m3·mol-1 Chemaxon Polarizability 9.35 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7887 Blood Brain Barrier + 0.9647 Caco-2 permeable - 0.5173 P-glycoprotein substrate Non-substrate 0.8606 P-glycoprotein inhibitor I Non-inhibitor 0.981 P-glycoprotein inhibitor II Non-inhibitor 0.9857 Renal organic cation transporter Non-inhibitor 0.9554 CYP450 2C9 substrate Non-substrate 0.8341 CYP450 2D6 substrate Non-substrate 0.9298 CYP450 3A4 substrate Non-substrate 0.7844 CYP450 1A2 substrate Non-inhibitor 0.9137 CYP450 2C9 inhibitor Non-inhibitor 0.9264 CYP450 2D6 inhibitor Non-inhibitor 0.9486 CYP450 2C19 inhibitor Non-inhibitor 0.9485 CYP450 3A4 inhibitor Non-inhibitor 0.9524 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.977 Ames test Non AMES toxic 0.7926 Carcinogenicity Non-carcinogens 0.5114 Biodegradation Ready biodegradable 0.9713 Rat acute toxicity 2.1231 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9714 hERG inhibition (predictor II) Non-inhibitor 0.9929
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 120.8230784 predictedDarkChem Lite v0.1.0 [M-H]- 120.8847784 predictedDarkChem Lite v0.1.0 [M-H]- 120.7865784 predictedDarkChem Lite v0.1.0 [M-H]- 117.78497 predictedDeepCCS 1.0 (2019) [M+H]+ 121.09091 predictedDeepCCS 1.0 (2019) [M+Na]+ 129.69632 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Type II interferon produced by immune cells such as T-cells and NK cells that plays crucial roles in antimicrobial, antiviral, and antitumor responses by activating effector immune cells and enhancing antigen presentation (PubMed:16914093, PubMed:8666937). Primarily signals through the JAK-STAT pathway after interaction with its receptor IFNGR1 to affect gene regulation (PubMed:8349687). Upon IFNG binding, IFNGR1 intracellular domain opens out to allow association of downstream signaling components JAK2, JAK1 and STAT1, leading to STAT1 activation, nuclear translocation and transcription of IFNG-regulated genes. Many of the induced genes are transcription factors such as IRF1 that are able to further drive regulation of a next wave of transcription (PubMed:16914093). Plays a role in class I antigen presentation pathway by inducing a replacement of catalytic proteasome subunits with immunoproteasome subunits (PubMed:8666937). In turn, increases the quantity, quality, and repertoire of peptides for class I MHC loading (PubMed:8163024). Increases the efficiency of peptide generation also by inducing the expression of activator PA28 that associates with the proteasome and alters its proteolytic cleavage preference (PubMed:11112687). Up-regulates as well MHC II complexes on the cell surface by promoting expression of several key molecules such as cathepsins B/CTSB, H/CTSH, and L/CTSL (PubMed:7729559). Participates in the regulation of hematopoietic stem cells during development and under homeostatic conditions by affecting their development, quiescence, and differentiation (By similarity)
- Specific Function
- cytokine activity
- Gene Name
- IFNG
- Uniprot ID
- P01579
- Uniprot Name
- Interferon gamma
- Molecular Weight
- 19348.165 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Chloroflexus aurantiacus (strain ATCC 29366 / DSM 635 / J-10-fl)
- Pharmacological action
- Unknown
- General Function
- Catalyzes the reversible oxidation of malate to oxaloacetate.
- Specific Function
- L-malate dehydrogenase activity
- Gene Name
- mdh
- Uniprot ID
- P80040
- Uniprot Name
- Malate dehydrogenase
- Molecular Weight
- 32750.54 Da
References
- Kind
- Protein
- Organism
- Shewanella oneidensis (strain MR-1)
- Pharmacological action
- Unknown
- General Function
- Flavocytochrome that catalyzes the reduction of fumarate to succinate (PubMed:12196158, PubMed:12899636, PubMed:22458729). Is essential for fumarate respiration during anaerobic growth, acting as the terminal reductase (By similarity). Receives electrons from the membrane-bound tetraheme c-type cytochrome CymA (PubMed:12196158, PubMed:12899636, PubMed:19837833, PubMed:22458729). Under ferric iron-reducing conditions, can be part of an electron transport chain to ferric iron, by accepting electrons from CymA and transfering them to the c-type cytochrome MtrA (PubMed:19837833). Also plays an important role in the reduction of selenite to elemental selenium (PubMed:24435070). May act as a transient electron storage protein (PubMed:19837833).
- Specific Function
- FMN binding
- Gene Name
- Not Available
- Uniprot ID
- P83223
- Uniprot Name
- Fumarate reductase flavoprotein subunit
- Molecular Weight
- 62447.475 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- NAD-dependent mitochondrial malic enzyme that catalyzes the oxidative decarboxylation of malate to pyruvate
- Specific Function
- electron transfer activity
- Gene Name
- ME2
- Uniprot ID
- P23368
- Uniprot Name
- NAD-dependent malic enzyme, mitochondrial
- Molecular Weight
- 65442.945 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- fumarylacetoacetase activity
- Gene Name
- FAH
- Uniprot ID
- P16930
- Uniprot Name
- Fumarylacetoacetase
- Molecular Weight
- 46373.97 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Shewanella frigidimarina
- Pharmacological action
- Unknown
- General Function
- Flavocytochrome that catalyzes the reduction of fumarate to succinate (PubMed:10978153). Is essential for fumarate respiration during anaerobic growth, acting as the terminal reductase (By similarity). Receives electrons from the membrane-bound tetraheme c-type cytochrome CymA (By similarity). In vitro, can use the artificial electron donor methyl viologen (PubMed:10978153).
- Specific Function
- electron transfer activity
- Gene Name
- fccA
- Uniprot ID
- P0C278
- Uniprot Name
- Fumarate reductase flavoprotein subunit
- Molecular Weight
- 60620.95 Da
References
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:23