U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C3H4O3
Molecular Weight 88.0621
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRUVIC ACID

SMILES

CC(=O)C(O)=O

InChI

InChIKey=LCTONWCANYUPML-UHFFFAOYSA-N
InChI=1S/C3H4O3/c1-2(4)3(5)6/h1H3,(H,5,6)

HIDE SMILES / InChI

Molecular Formula C3H4O3
Molecular Weight 88.0621
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

CTI-01 (ethyl pyruvate) is an investigational anti-inflammatory agent for the treatment of critical inflammatory conditions. CTI-01 was developed by Critical Therapeutics as a stable prodrug of pyruvate, a potent antioxidant, and a free radical scavenger. The drug showed an anti-inflammatory and tissue protection activity in animal models of pancreatitis, ischemia-reperfusion injury, sepsis, renal injury, and endotoxemia. CTI-01 was investigated in phase 2 clinical trials on patients undergoing cardiac surgery with cardiopulmonary bypass, but despite positive results in animal models, administration of EP does not appear to confer any benefit to cardiac surgical patients undergoing cardiopulmonary bypass. Besides clinical applications, ethyl pyruvate is long used as an additive to pharmaceutical preparations and foods, including candy, beverages, and baked goods. It is generally recognized as safe by the FDA.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
Rejuvesol

Approved Use

Rejuvesol ® Solution is intended only to be used as an in vitro processing solution for the rejuvenation of a unit of RBC.

Launch Date

1997
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Kinetic resolution of chiral amines with omega-transaminase using an enzyme-membrane reactor.
2001-05-05
Chemo-enzymatic D-enantiomerization of DL-lactate.
2001-04-05
Functional complexes of mitochondria with Ca,MgATPases of myofibrils and sarcoplasmic reticulum in muscle cells.
2001-04-02
Glutamine supplementation promotes anaplerosis but not oxidative energy delivery in human skeletal muscle.
2001-04
Dichloroacetate improves cardiac efficiency after ischemia independent of changes in mitochondrial proton leak.
2001-04
Inhibitory effect of sorbitol on sugar metabolism of Streptococcus mutans in vitro and on acid production in dental plaque in vivo.
2001-04
Dysfunctional mitochondrial respiration in the wobbler mouse brain.
2001-03-16
Interdependent effects of inorganic phosphate and creatine phosphate on sarcoplasmic reticulum Ca2+ regulation in mechanically skinned rat skeletal muscle.
2001-03-15
Mitochondria control ampa/kainate receptor-induced cytoplasmic calcium deregulation in rat cerebellar granule cells.
2001-03-15
Snapshots of metabolic phenotypes.
2001-03
Regulation of skeletal muscle amino acid metabolism during exercise.
2001-03
Metabolic characteristics of muscles in the spiny lobster, Jasus edwardsii, and responses to emersion during simulated live transport.
2001-03
Active oligomeric states of pyruvate decarboxylase and their functional characterization.
2001-03
Enzymatic determination of acetylcarnitine for diagnostic applications.
2001-03
The first case of 4-hydroxybutyric aciduria in Japan.
2001-03
Glutamate regulates the viability of retinal cells in culture.
2001-03
Retrobiosynthetic nuclear magnetic resonance analysis of amino acid biosynthesis and intermediary metabolism. Metabolic flux in developing maize kernels.
2001-03
Congenital lactic acidosis: evaluation of the properties of the a199t natural variant of human pyruvate dehydrogenase e1alpha by in vitro mutation.
2001-03
Study of tricarboxylic acid cycle flux changes in human visual cortex during hemifield visual stimulation using (1)H-[(13)C] MRS and fMRI.
2001-03
Caveats when considering ketogenic diets for the treatment of pyruvate dehydrogenase complex deficiency.
2001-03
Molecular characterization, enzyme properties and transcriptional regulation of phosphoenolpyruvate carboxykinase and pyruvate kinase in a ruminal bacterium, Selenomonas ruminantium.
2001-03
Aerobic and anoxic biodegradation of benzoate: stability of biodegradative capability under endogenous conditions.
2001-03
Different sensitivity of rabbit heart and skeletal muscle to endotoxin-induced impairment of mitochondrial function.
2001-03
Formation of Fallopian tubal fluid: role of a neglected epithelium.
2001-03
Crystallization and initial X-ray diffraction analysis of human pyruvate dehydrogenase.
2001-03
IL-4 gene expression up-regulated by mercury in rat mast cells: a role of oxidant stress in IL-4 transcription.
2001-03
The use of biomarkers in Daphnia magna toxicity testing V. In vivo alterations in the carbohydrate metabolism of Daphnia magna exposed to sublethal concentrations of mercury and lindane.
2001-03
Comprehensive messenger ribonucleic acid profiling reveals that peroxisome proliferator-activated receptor gamma activation has coordinate effects on gene expression in multiple insulin-sensitive tissues.
2001-03
Involvement of both phosphatidylinositol 3-kinase and p44/p42 mitogen-activated protein kinase pathways in the short-term regulation of pyruvate kinase L by insulin.
2001-03
Modulation of early [Ca2+]i rise in metabolically inhibited endothelial cells by xestospongin C.
2001-03
Multidrug resistance protein (MRP) activity in normal mature leukocytes and CD34-positive hematopoietic cells from peripheral blood.
2001-02-02
Lactic acidosis update for critical care clinicians.
2001-02
Beneficial effects of low-dose prostacyclin on cat intestinal perfusion during endotoxemia as evaluated with microdialysis and oxygen transport variables.
2001-02
Parasitism enhances the induction of glucogenesis by the insect, Manduca sexta L.
2001-02
The in vitro effects of isometamidium chloride (Samorin) on the piscine hemoflagellate Cryptobia salmositica (Kinetoplastida, Bodonina).
2001-02
Cloning of a pyruvate phosphate dikinase from Trypanosoma cruzi.
2001-02
Aspirin, but not the more selective cyclooxygenase (COX)-2 inhibitors meloxicam and SC 58125, aggravates postischaemic cardiac dysfunction, independent of COX function.
2001-02
Lactate dehydrogenase from the northern krill Meganyctiphanes norvegica: comparison with LDH from the Antarctic krill Euphausia superba.
2001-02
Neuroprotective effects of MK-801 on L-2-chloropropionic acid-induced neurotoxicity.
2001-02
A compactly integrated flow cell with a chemiluminescent FIA system for determining lactate concentration in serum.
2001-01-15
6-Phosphogluconate dehydrogenase deficiency in an Italian family.
2001-01
Intramitochondrial pyruvate attenuates hydrogen peroxide-induced apoptosis in bovine pulmonary artery endothelium.
2001-01
Reclassification of Desulfobacterium phenolicum as Desulfobacula phenolica comb. nov. and description of strain SaxT as Desulfotignum balticum gen. nov., sp. nov.
2001-01
Carboxydobrachium pacificum gen. nov., sp. nov., a new anaerobic, thermophilic, CO-utilizing marine bacterium from Okinawa Trough.
2001-01
Thioflavicoccus mobilis gen. nov., sp. nov., a novel purple sulfur bacterium with bacteriochlorophyll b.
2001-01
Metabolic alterations in cerebrospinal fluid from double hemorrhage model of dogs.
2001-01
Refinements in primary rumen epithelial cell incubation techniques.
2001-01
Severe canine hereditary hemolytic anemia treated by nonmyeloablative marrow transplantation.
2001
Rapid metabolic recovery following vigorous exercise in burrow-dwelling larval sea lampreys (Petromyzon marinus).
2000-10-31
Catabolic capacity of the muscles of shorebird chicks: maturation of function in relation to body size.
2000-10-31
Patents

Sample Use Guides

In a clinical trial, 7,500 mg of ethyl pyruvate was administered intravenously starting after the induction of general anesthesia followed by 5 more doses of 7,500 mg administered every 6 hours. As an additive to pharmaceutical products and foods, ethyl pyruvate is administered orally
Route of Administration: Other
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:33 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:33 GMT 2025
Record UNII
8558G7RUTR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRUVIC ACID
FHFI   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
NSC-179
Preferred Name English
PYRUVATE
Systematic Name English
PYRUVIC ACID [MI]
Common Name English
.ALPHA.-KETOPROPIONIC ACID
Systematic Name English
FEMA NO. 2970
Code English
2-OXOPROPANOIC ACID
Systematic Name English
ACETYLFORMIC ACID
Systematic Name English
PYRUVIC ACID [FHFI]
Common Name English
Pyruvic acid [WHO-DD]
Common Name English
PYRORACEMIC ACID
Common Name English
Classification Tree Code System Code
DSLD 1576 (Number of products:31)
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
CFR 21 CFR 862.1655
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LOINC 14122-6
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LOINC 2550-2
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LOINC 51751-6
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LOINC 59048-9
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LOINC 2908-2
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JECFA EVALUATION PYRUVIC ACID
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LOINC 54309-0
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LOINC 14121-8
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LOINC 2906-6
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LOINC 25132-2
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LOINC 13805-7
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LOINC 32338-6
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FDA ORPHAN DRUG 140900
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LOINC 12247-3
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LOINC 44400-0
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LOINC 2907-4
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CFR 21 CFR 172.515
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LOINC 2905-8
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LOINC 30481-6
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LOINC 51750-8
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Code System Code Type Description
DRUG BANK
DB00119
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
DAILYMED
8558G7RUTR
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
CHEBI
32816
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
RXCUI
72031
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
ALTERNATIVE
JECFA MONOGRAPH
816
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PRIMARY
CHEBI
15361
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
PUBCHEM
1060
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PRIMARY
NSC
179
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PRIMARY
WIKIPEDIA
PYRUVIC ACID
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PRIMARY
MESH
D019289
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PRIMARY
EVMPD
SUB15069MIG
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PRIMARY
RXCUI
35161
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-824-3
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PRIMARY
SMS_ID
100000079122
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PRIMARY
CAS
127-17-3
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
FDA UNII
8558G7RUTR
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID2021650
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY
MERCK INDEX
m9405
Created by admin on Mon Mar 31 17:46:33 GMT 2025 , Edited by admin on Mon Mar 31 17:46:33 GMT 2025
PRIMARY Merck Index
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METABOLIC ENZYME -> SUBSTRATE
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