NAV

Ethyl pyruvate

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
3D
Similar Structures
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
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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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Contraindications & Blackbox Warnings
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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 AvailableHumans
UHigh mobility group protein B1Not AvailableHumans
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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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

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
  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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0031643
PubChem Compound
12041
PubChem Substance
175427048
ChemSpider
11544
RxNav
1539968
ChEMBL
CHEMBL173373
ZINC
ZINC000001679741
PDBe Ligand
9X7
PDB Entries
5w5t

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Unknown StatusTreatmentVerruca (Warts)1
2TerminatedPreventionCoronary Heart Disease (CHD) / Valvular Heart 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/MSsplash10-0006-9000000000-a4f4ec3b45462153cf03
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-9700000000-6b75a6d2ccd67732aeb8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00r6-9200000000-8bd33e62aee5102d90eb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-9b07ff31ea9c3f1f2a31
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-137d7955aa3322d11b5b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-c8bf9b0f8ef3127f6002
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-120.6646615
predicted
DarkChem Lite v0.1.0
[M-H]-120.5883615
predicted
DarkChem Lite v0.1.0
[M-H]-125.02525
predicted
DeepCCS 1.0 (2019)
[M+H]+121.6763615
predicted
DarkChem Lite v0.1.0
[M+H]+121.6668615
predicted
DarkChem Lite v0.1.0
[M+H]+127.04318
predicted
DeepCCS 1.0 (2019)
[M+Na]+121.1904615
predicted
DarkChem Lite v0.1.0
[M+Na]+121.3049615
predicted
DarkChem Lite v0.1.0
[M+Na]+135.43399
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tumor necrosis factor
Kind
Protein
Organism
Humans
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
Details2. High mobility group protein B1
Kind
Protein
Organism
Humans
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 at November 18, 2007 18:28 / Updated at June 12, 2020 16:52