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
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
The cytokine activity of HMGB1--extracellular escape of the nuclear protein.
2005 Oct
Treatment of severe sepsis: where next? Current and future treatment approaches after the introduction of drotrecogin alfa.
2006
Bench-to-bedside review: critical illness-associated cognitive dysfunction--mechanisms, markers, and emerging therapeutics.
2006
Ethyl pyruvate exerts combined anti-inflammatory and anticoagulant effects on human monocytic cells.
2006 Dec
Highly enantioselective direct reductive coupling of conjugated alkynes and alpha-ketoesters via rhodium-catalyzed asymmetric hydrogenation.
2006 Jan 25
Introduction to serial reviews on redox signaling in immune function and cellular responses in lung injury and diseases.
2006 Jul 1
[Effect of ethyl pyruvate on peroxidation injury of intestinal mucosa in rats with severe abdominal infection].
2006 Mar
[Effect of treatment with ethyl pyruvate on multiple organ dysfunction and mortality following delayed resuscitation after burn injury in rat].
2006 Mar
Determination of geometric orientation of adsorbed cinchonidine on Pt and Fe and quiphos on Pt nanoclusters via DRIFTS.
2006 Mar 21
Pyruvate is an endogenous anti-inflammatory and anti-oxidant molecule.
2006 May
[Relation between level of expression of high mobility group protein B1 in hepatic tissue with the severity and prognosis of sepsis in rat].
2006 Nov
Haemodynamic and metabolic effects of resuscitation with Ringer's ethyl pyruvate in the acute phase of porcine endotoxaemic shock.
2006 Nov
Ethyl pyruvate attenuates kainic acid-induced neuronal cell death in the mouse hippocampus.
2006 Nov 15
Is pyruvate an endogenous anti-inflammatory molecule?
2006 Sep
Bench-to-bedside review: High-mobility group box 1 and critical illness.
2007
Ethyl pyruvate: a novel treatment for sepsis.
2007
HMGB1 as a potential therapeutic target.
2007
Ethyl pyruvate: a novel treatment for sepsis.
2007 Apr
Ethyl pyruvate: a novel anti-inflammatory agent.
2007 Apr
Ethyl pyruvate induces necrosis-to-apoptosis switch and inhibits high mobility group box protein 1 release in A549 lung adenocarcinoma cells.
2007 Aug
Role of guiding groups in cinchona-modified platinum for controlling the sense of enantiodifferentiation in the hydrogenation of ketones.
2007 Aug 29
Oxidative damage in rat erythrocyte membranes following ethanol intake: effect of ethyl pyruvate.
2007 Aug 30
Beneficial effects of ethyl pyruvate in septic shock from peritonitis.
2007 Feb
Enantioselective hydrogenation of ethyl pyruvate over diop modified Pt nanoclusters. Determination of geometry of the ligand adsorption mode via DRIFTS.
2007 Feb 21
Promising therapeutic agents for sepsis.
2007 Jan
Ethyl pyruvate, a potentially effective mitigator of damage after total-body irradiation.
2007 Nov
Intrapulmonary delivery of ethyl pyruvate attenuates lipopolysaccharide- and lipoteichoic acid-induced lung inflammation in vivo.
2007 Nov
Management of sepsis.
2007 Nov 3
A major ingredient of green tea rescues mice from lethal sepsis partly by inhibiting HMGB1.
2007 Nov 7
Protective effect of ethyl pyruvate on msP rat leukocytes damaged by alcohol intake.
2007 Nov-Dec
The protective effect of ethyl pyruvate on lung injury after burn in rats.
2007 Oct
Ethyl pyruvate improves survival and ameliorates distant organ injury in rats with severe acute pancreatitis.
2007 Oct
Exogenous ethyl pyruvate versus pyruvate during metabolic recovery after oxidative stress in neonatal rat cerebrocortical slices.
2007 Oct
Sulfur mustard toxicity following dermal exposure: role of oxidative stress, and antioxidant therapy.
2007 Oct 30
[Effect of ethyl pyruvate on renal high mobility group box-1 protein expression and acute kidney injury in rats with delayed resuscitation after thermal injury].
2007 Sep 1
The first organocatalytic carbonyl-ene reaction: isomerisation-free C-C bond formations catalysed by H-bonding thio-ureas.
2007 Sep 14
Ethyl pyruvate.
2008 Apr
Targeting the lipopolysaccharides: still a matter of debate?
2008 Apr
Ethyl pyruvate reduces germ cell-specific apoptosis and oxidative stress in rat model of testicular torsion/detorsion.
2008 Apr
Bull's eye missed by the magic bullet: preclinical investigations, publication bias, and promising new interventions.
2008 Apr
Ethyl pyruvate decreased early nuclear factor-kappaB levels but worsened survival in lipopolysaccharide-challenged mice.
2008 Apr
Sepsis: from bench to bedside.
2008 Feb
Protective effects of ethyl pyruvate treatment on paraquat-intoxicated rats.
2008 Jan
[Effect of ethyl pyruvate on indices of tissue oxygenation and perfusion in dogs with septic shock].
2008 Jan
The effect of ethyl pyruvate on oxidative stress in intestine and bacterial translocation after thermal injury.
2008 Jan
[Protective effect of ethyl pyruvate on barrier function of intestinal mucosa in dogs with septic shock].
2008 Mar
Ethyl pyruvate inhibits hypoxic pulmonary vasoconstriction and attenuates pulmonary artery cytokine expression.
2008 Mar
Synthesis and biological activity of functionalized indole-2-carboxylates, triazino- and pyridazino-indoles.
2008 May
The role of high mobility group box1 in pulmonary fibrosis.
2008 Oct
Relationship between high-mobility group box 1 protein release and T-cell suppression in rats after thermal injury.
2008 Oct
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
Name Type Language
PYRUVIC ACID
FHFI   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
PYRUVATE
Systematic Name English
NSC-179
Code English
PYRUVIC ACID [MI]
Common Name English
.ALPHA.-KETOPROPIONIC ACID
Systematic Name English
FEMA NO. 2970
Code English
2-OXOPROPANOIC ACID
Systematic Name English
PYRUVIC ACID [INCI]
Common 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 Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
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 Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
DAILYMED
8558G7RUTR
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
CHEBI
32816
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PRIMARY
RXCUI
72031
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ALTERNATIVE
JECFA MONOGRAPH
816
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PRIMARY
CHEBI
15361
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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
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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 Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
FDA UNII
8558G7RUTR
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID2021650
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
PRIMARY
MERCK INDEX
m9405
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PRIMARY Merck Index