Ethyl pyruvate

Identification

Name
Ethyl pyruvate
Accession Number
DB05869
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
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
Categories
UNII
03O98E01OB
CAS number
617-35-6
Weight
Average: 116.1152
Monoisotopic: 116.047344122
Chemical Formula
C5H8O3
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

Pharmacology

Indication

Investigated for use/treatment in burns and burn infections, cardiac surgery, inflammatory disorders (unspecified), ischemic reperfusion injury, and sepsis and septicemia.

Structured Indications
Not Available
Pharmacodynamics
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.

TargetActionsOrganism
UTumor necrosis factorNot AvailableHuman
UHigh mobility group protein B1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:18199399]
  2. 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. [PubMed:17895847]
External Links
PubChem Compound
12041
PubChem Substance
175427048
ChemSpider
11544
ChEMBL
CHEMBL173373

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedPreventionCoronary Heart Disease (CHD) / Heart Valve Diseases1

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
PropertyValueSource
Water Solubility31.3 mg/mLALOGPS
logP0.24ALOGPS
logP0.8ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)16.9ChemAxon
pKa (Strongest Basic)-7.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.51 m3·mol-1ChemAxon
Polarizability11.39 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9891
Blood Brain Barrier+0.9696
Caco-2 permeable+0.5728
P-glycoprotein substrateNon-substrate0.7708
P-glycoprotein inhibitor INon-inhibitor0.7579
P-glycoprotein inhibitor IINon-inhibitor0.7139
Renal organic cation transporterNon-inhibitor0.9187
CYP450 2C9 substrateNon-substrate0.8866
CYP450 2D6 substrateNon-substrate0.9172
CYP450 3A4 substrateNon-substrate0.6648
CYP450 1A2 substrateNon-inhibitor0.8008
CYP450 2C9 inhibitorNon-inhibitor0.8727
CYP450 2D6 inhibitorNon-inhibitor0.95
CYP450 2C19 inhibitorNon-inhibitor0.9276
CYP450 3A4 inhibitorNon-inhibitor0.9652
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7997
Ames testNon AMES toxic0.9132
CarcinogenicityCarcinogens 0.6616
BiodegradationReady biodegradable0.9534
Rat acute toxicity1.0990 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9894
hERG inhibition (predictor II)Non-inhibitor0.932
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-6b9687c0790faebef406
GC-MS Spectrum - CI-BGC-MSsplash10-014i-4900000000-e148aa184db0bb5b7c16
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-ceddbed69eabcd4ec028
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9000000000-980c9b02bf8c3edc429d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Alpha-keto acid / Ketone / Carboxylic acid ester / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Carbonyl group
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
a small molecule (CPD0-2053)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tumor necrosis factor receptor binding
Specific 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 ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription factor binding
Specific 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 chapero...
Gene Name
HMGB1
Uniprot ID
P09429
Uniprot Name
High mobility group protein B1
Molecular Weight
24893.58 Da

Drug created on November 18, 2007 11:28 / Updated on December 01, 2017 15:37