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Identification
- Generic Name
- Ethyl pyruvate
- DrugBank Accession Number
- DB05869
- Background
CTI-01 (ethyl pyruvate) is a novel anti-inflammatory agent for the treatment of critical inflammatory conditions. CTI-01 shows a potent anti-inflammatory and tissue protection activity in multiple animal models of disease including pancreatitis, ischemia-reperfusion injury, sepsis, renal injury and endotoxemia.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Ethyl pyruvate (DB05869)
- Weight
- Average: 116.1152
Monoisotopic: 116.047344122 - Chemical Formula
- C5H8O3
- Synonyms
- 2-oxopropanoic acid ethyl ester
- 2-oxopropionic acid ethyl ester
- Ethyl 2-oxopropanoate
- Ethyl 2-oxopropionate
- Ethyl methylglyoxylate
- Pyruvic acid ethyl ester
- Pyruvic acid, ethyl ester
- External IDs
- CTI-01
- FEMA NO. 2457
- NSC-48386
Pharmacology
- Indication
Investigated for use/treatment in burns and burn infections, cardiac surgery, inflammatory disorders (unspecified), ischemic reperfusion injury, and sepsis and septicemia.
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Not Available
- Mechanism of action
CTI-01 inhibits the systemic release of cytokines, such as TNF-alpha and HMGB1, which promote the body's inflammatory response. The over-expression of these cytokines has been linked to diseases that occur in critical care settings, such as severe organ damage following cardiopulmonary bypass (CPB) and post-operative ileus following abdominal surgery.
Target Actions Organism UTumor necrosis factor Not Available Humans UHigh mobility group protein B1 Not Available Humans - 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
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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
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Keto acids and derivatives
- Sub Class
- Alpha-keto acids and derivatives
- Direct Parent
- Alpha-keto acids and derivatives
- Alternative Parents
- Ketones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alpha-keto acid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Ketone / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- a small molecule (CPD0-2053)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 03O98E01OB
- CAS number
- 617-35-6
- InChI Key
- XXRCUYVCPSWGCC-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H8O3/c1-3-8-5(7)4(2)6/h3H2,1-2H3
- IUPAC Name
- ethyl 2-oxopropanoate
- SMILES
- CCOC(=O)C(C)=O
References
- General References
- Kou QY, Guan XD: [Effect of ethyl pyruvate on indices of tissue oxygenation and perfusion in dogs with septic shock]. Zhongguo Wei Zhong Bing Ji Jiu Yi Xue. 2008 Jan;20(1):34-6. [Article]
- Cheng BQ, Liu CT, Li WJ, Fan W, Zhong N, Zhang Y, Jia XQ, Zhang SZ: Ethyl pyruvate improves survival and ameliorates distant organ injury in rats with severe acute pancreatitis. Pancreas. 2007 Oct;35(3):256-61. [Article]
- External Links
- Human Metabolome Database
- HMDB0031643
- PubChem Compound
- 12041
- PubChem Substance
- 175427048
- ChemSpider
- 11544
- 1539968
- ChEMBL
- CHEMBL173373
- ZINC
- ZINC000001679741
- PDBe Ligand
- 9X7
- PDB Entries
- 5w5t
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 data4 Unknown Status Treatment Verruca (Warts) 1 somestatus stop reason just information to hide 2 Terminated Prevention Coronary Heart Disease (CHD) / Valvular Heart Diseases 1 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
- Not Available
- Predicted Properties
Property Value Source Water Solubility 31.3 mg/mL ALOGPS logP 0.24 ALOGPS logP 0.8 Chemaxon logS -0.57 ALOGPS pKa (Strongest Acidic) 16.9 Chemaxon pKa (Strongest Basic) -7.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 43.37 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 27.51 m3·mol-1 Chemaxon Polarizability 11.39 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 + 0.9891 Blood Brain Barrier + 0.9696 Caco-2 permeable + 0.5728 P-glycoprotein substrate Non-substrate 0.7708 P-glycoprotein inhibitor I Non-inhibitor 0.7579 P-glycoprotein inhibitor II Non-inhibitor 0.7139 Renal organic cation transporter Non-inhibitor 0.9187 CYP450 2C9 substrate Non-substrate 0.8866 CYP450 2D6 substrate Non-substrate 0.9172 CYP450 3A4 substrate Non-substrate 0.6648 CYP450 1A2 substrate Non-inhibitor 0.8008 CYP450 2C9 inhibitor Non-inhibitor 0.8727 CYP450 2D6 inhibitor Non-inhibitor 0.95 CYP450 2C19 inhibitor Non-inhibitor 0.9276 CYP450 3A4 inhibitor Non-inhibitor 0.9652 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7997 Ames test Non AMES toxic 0.9132 Carcinogenicity Carcinogens 0.6616 Biodegradation Ready biodegradable 0.9534 Rat acute toxicity 1.0990 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9894 hERG inhibition (predictor II) Non-inhibitor 0.932
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 120.6646615 predictedDarkChem Lite v0.1.0 [M-H]- 120.5883615 predictedDarkChem Lite v0.1.0 [M-H]- 125.02525 predictedDeepCCS 1.0 (2019) [M+H]+ 121.6763615 predictedDarkChem Lite v0.1.0 [M+H]+ 121.6668615 predictedDarkChem Lite v0.1.0 [M+H]+ 127.04318 predictedDeepCCS 1.0 (2019) [M+Na]+ 121.1904615 predictedDarkChem Lite v0.1.0 [M+Na]+ 121.3049615 predictedDarkChem Lite v0.1.0 [M+Na]+ 135.43399 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct action or by stimulation of interleukin-1 secretion and is implicated in the induction of cachexia, Under certain conditions it can stimulate cell proliferation and induce cell differentiation. Impairs regulatory T-cells (Treg) function in individuals with rheumatoid arthritis via FOXP3 dephosphorylation. Up-regulates the expression of protein phosphatase 1 (PP1), which dephosphorylates the key 'Ser-418' residue of FOXP3, thereby inactivating FOXP3 and rendering Treg cells functionally defective (PubMed:23396208). Key mediator of cell death in the anticancer action of BCG-stimulated neutrophils in combination with DIABLO/SMAC mimetic in the RT4v6 bladder cancer cell line (PubMed:16829952, PubMed:22517918, PubMed:23396208). Induces insulin resistance in adipocytes via inhibition of insulin-induced IRS1 tyrosine phosphorylation and insulin-induced glucose uptake. Induces GKAP42 protein degradation in adipocytes which is partially responsible for TNF-induced insulin resistance (By similarity). Plays a role in angiogenesis by inducing VEGF production synergistically with IL1B and IL6 (PubMed:12794819). Promotes osteoclastogenesis and therefore mediates bone resorption (By similarity)
- Specific Function
- Cytokine activity
- Gene Name
- TNF
- Uniprot ID
- P01375
- Uniprot Name
- Tumor necrosis factor
- Molecular Weight
- 25644.15 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Multifunctional redox sensitive protein with various roles in different cellular compartments. In the nucleus is one of the major chromatin-associated non-histone proteins and acts as a DNA chaperone involved in replication, transcription, chromatin remodeling, V(D)J recombination, DNA repair and genome stability (PubMed:33147444). Proposed to be an universal biosensor for nucleic acids. Promotes host inflammatory response to sterile and infectious signals and is involved in the coordination and integration of innate and adaptive immune responses. In the cytoplasm functions as a sensor and/or chaperone for immunogenic nucleic acids implicating the activation of TLR9-mediated immune responses, and mediates autophagy. Acts as a danger-associated molecular pattern (DAMP) molecule that amplifies immune responses during tissue injury (PubMed:27362237). Released to the extracellular environment can bind DNA, nucleosomes, IL-1 beta, CXCL12, AGER isoform 2/sRAGE, lipopolysaccharide (LPS) and lipoteichoic acid (LTA), and activates cells through engagement of multiple surface receptors (PubMed:34743181). In the extracellular compartment fully reduced HMGB1 (released by necrosis) acts as a chemokine, disulfide HMGB1 (actively secreted) as a cytokine, and sulfonyl HMGB1 (released from apoptotic cells) promotes immunological tolerance (PubMed:23446148, PubMed:23519706, PubMed:23994764, PubMed:25048472). Has proangiogdenic activity (By similarity). May be involved in platelet activation (By similarity). Binds to phosphatidylserine and phosphatidylethanolamide (By similarity). Bound to RAGE mediates signaling for neuronal outgrowth (By similarity). May play a role in accumulation of expanded polyglutamine (polyQ) proteins such as huntingtin (HTT) or TBP (PubMed:23303669, PubMed:25549101)
- Specific Function
- Bubble dna binding
- Gene Name
- HMGB1
- Uniprot ID
- P09429
- Uniprot Name
- High mobility group protein B1
- Molecular Weight
- 24893.58 Da
Drug created at November 18, 2007 18:28 / Updated at June 12, 2020 16:52