Identification
NameEthyl pyruvate
Accession NumberDB05869
TypeSmall Molecule
GroupsInvestigational
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
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNII03O98E01OB
CAS number617-35-6
WeightAverage: 116.1152
Monoisotopic: 116.047344122
Chemical FormulaC5H8O3
InChI KeyXXRCUYVCPSWGCC-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
PharmacodynamicsNot 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Tumor necrosis factorProteinunknownNot AvailableHumanP01375 details
High mobility group protein B1ProteinunknownNot AvailableHumanP09429 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedPreventionCoronary Heart Disease (CHD) / Heart Valve Diseases1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassAlpha-keto acids and derivatives
Direct ParentAlpha-keto acids and derivatives
Alternative ParentsKetones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
SubstituentsAlpha-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 FrameworkAliphatic acyclic compounds
External Descriptorsa 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 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 ...
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 chaperone involved in replication, transcription, chromatin remodeling, V(D)J recombination, DNA repair and genome stability. Proposed to be an universal biosensor for nucleic acids. Promotes host inflammato...
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 June 30, 2017 00:49