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
Future strategies in the treatment of acute renal failure: growth factors, stem cells, and other novel therapies.
2005 Apr
[Effects of ethyl pyruvate on cell-mediated immune function in rats with delayed resuscitation after burn injury].
2005 Jan
Ethyl pyruvate ameliorates liver ischemia-reperfusion injury by decreasing hepatic necrosis and apoptosis.
2005 Jan 27
Ethyl pyruvate protects PC12 cells from dopamine-induced apoptosis.
2005 Jan 31
[Effects of ethyl pyruvate on splenocyte proliferation and apoptosis in burn rats with delayed resuscitation].
2005 Jul
Dendrimer-enhanced MRI as a diagnostic and prognostic biomarker of sepsis-induced acute renal failure in aged mice.
2005 Jun
The ethyl pyruvate analogues, diethyl oxaloproprionate, 2-acetamidoacrylate, and methyl-2-acetamidoacrylate, exhibit anti-inflammatory properties in vivo and/or in vitro.
2005 Nov 25
The cytokine activity of HMGB1--extracellular escape of the nuclear protein.
2005 Oct
Inhibition of the cerebral ischemic injury by ethyl pyruvate with a wide therapeutic window.
2005 Oct
Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives.
2005 Sep
Ethyl pyruvate improves systemic and hepatosplanchnic hemodynamics and prevents lipid peroxidation in a porcine model of resuscitated hyperdynamic endotoxemia.
2005 Sep
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
Oxidative damage to lens in culture: reversibility by pyruvate and ethyl pyruvate.
2006
Ethyl pyruvate exerts combined anti-inflammatory and anticoagulant effects on human monocytic cells.
2006 Dec
Introduction to serial reviews on redox signaling in immune function and cellular responses in lung injury and diseases.
2006 Jul 1
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
Intrapulmonary delivery of ethyl pyruvate attenuates lipopolysaccharide- and lipoteichoic acid-induced lung inflammation in vivo.
2007 Nov
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
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
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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:06:18 GMT 2023
Edited
by admin
on Fri Dec 15 15:06:18 GMT 2023
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
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
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
RXCUI
72031
Created by admin on Fri Dec 15 15:06:18 GMT 2023 , Edited by admin on Fri Dec 15 15:06:18 GMT 2023
ALTERNATIVE
JECFA MONOGRAPH
816
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
15361
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
PUBCHEM
1060
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
NSC
179
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
WIKIPEDIA
PYRUVIC ACID
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PRIMARY
MESH
D019289
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
EVMPD
SUB15069MIG
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PRIMARY
RXCUI
35161
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
ECHA (EC/EINECS)
204-824-3
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
SMS_ID
100000079122
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
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
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
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LABELED -> NON-LABELED
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METABOLIC ENZYME -> SUBSTRATE
LABELED -> NON-LABELED
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