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

Details

Stereochemistry ACHIRAL
Molecular Formula C4H6O4
Molecular Weight 118.088
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCCINIC ACID

SMILES

OC(=O)CCC(O)=O

InChI

InChIKey=KDYFGRWQOYBRFD-UHFFFAOYSA-N
InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)

HIDE SMILES / InChI

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Succinic acid is a dicarboxylic acid, which has multiple biological roles as a metabolic intermediate being converted into fumarate by the enzyme succinate dehydrogenase in complex 2 of the electron transport chain which is involved in making ATP, and as a signaling molecule reflecting the cellular metabolic state. Succinate is generated in mitochondria via the tricarboxylic acid cycle (TCA), an energy-yielding process shared by all organisms. Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space, changing gene expression patterns, modulating epigenetic landscape or demonstrating hormone-like signaling. Dysregulation of succinate synthesis, and therefore ATP synthesis, happens in some genetic mitochondrial diseases, such as Leigh's disease, and Mela's disease and degradation can lead to pathological conditions, such as malignant transformation, inflammation and tissue injury. Succinic acid is a precursor to some polyesters and a component of some alkyd resins. Succinic acid also serves as the bases of certain biodegradable polymers, which are of interest in tissue engineering applications. As a food additive and dietary supplement, succinic acid is generally recognized as safe by the U.S. Food and Drug Administration. Succinic acid is used primarily as an acidity regulator in the food and beverage industry. It is also available as a flavoring agent, contributing a somewhat sour and astringent component to umami taste.[11] As an excipient in pharmaceutical products, it is also used to control acidity or as a counter ion. Drugs involving succinate include metoprolol succinate, sumatriptan succinate, Doxylamine succinate or solifenacin succinate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
VESIcare
Inactive ingredient
Metoprolol Succinate ER
Inactive ingredient
Reamberin
PubMed

PubMed

TitleDatePubMed
Charge modification of plasma and milk proteins results in antiviral active compounds.
1999 Dec
Structures and proton-pumping strategies of mitochondrial respiratory enzymes.
2001
Inhibition of spontaneous induction of lambdoid prophages in Escherichia coli cultures: simple procedures with possible biotechnological applications.
2001
[Intermittent hypoxic training with exogenous nitric oxide improves rat liver mitochondrial oxidation and phosphorylation during acute hypoxia].
2001
[Combined treatment of purulent-necrotic lesions of lower extremities in diabetic patients].
2001
Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate.
2001 Apr
N-Acetylaspartate, a marker of both cellular dysfunction and neuronal loss: its relevance to studies of acute brain injury.
2001 Apr
Identification of respiratory complexes I and III as mitochondrial sites of damage following exposure to ionizing radiation and nitric oxide.
2001 Apr
The effects of endurance training and exhaustive exercise on mitochondrial enzymes in tissues of the rat (Rattus norvegicus).
2001 Apr
Glutathione depletion, lipid peroxidation and mitochondrial dysfunction are induced by chronic stress in rat brain.
2001 Apr
Attenuation of malonate toxicity in primary mesencephalic cultures using the GABA transport blocker, NO-711.
2001 Apr 1
Germline SDHD mutation in familial phaeochromocytoma.
2001 Apr 14
Probing the active site of L-aspartate oxidase by site-directed mutagenesis: role of basic residues in fumarate reduction.
2001 Apr 17
Energetic metabolism in mouse cerebral cortex during chronic hypoxia.
2001 Apr 6
Metabolic shifts and myocyte hypertrophy in deflazacort treatment of mdx mouse cardiomyopathy.
2001 Feb
In silico predictions of Escherichia coli metabolic capabilities are consistent with experimental data.
2001 Feb
Establishment and characterization of three new rat renal cell carcinoma cell lines from N-ethyl-N-hydroxyethylnitrosamine-induced basophilic cell tumors.
2001 Feb
Aerobic metabolism of human quadriceps muscle: in vivo data parallel measurements on isolated mitochondria.
2001 Feb
Mitochondrial DNA deletion mutations colocalize with segmental electron transport system abnormalities, muscle fiber atrophy, fiber splitting, and oxidative damage in sarcopenia.
2001 Feb
A novel syndrome affecting multiple mitochondrial functions, located by microcell-mediated transfer to chromosome 2p14-2p13.
2001 Feb
Time-course changes in arteriolar and venular portions of capillary in young treadmill-trained rats.
2001 Jan
Developmental aspects of the rat endolymphatic sac and functional implications.
2001 Jan
Adenine and guanine nucleotide-specific succinyl-CoA synthetases in the clonal beta-cell mitochondria: implications in the beta-cell high-energy phosphate metabolism in relation to physiological insulin secretion.
2001 Jan
Environmental fate and microbial degradation of aminopolycarboxylic acids.
2001 Jan
Cumulative and irreversible cardiac mitochondrial dysfunction induced by doxorubicin.
2001 Jan 15
Characteristics and glycerol metabolism of fumarate-reducing Enterococcus faecalis RKY1.
2001 Jan 5
Expression of a glutamate decarboxylase homologue is required for normal oxidative stress tolerance in Saccharomyces cerevisiae.
2001 Jan 5
Changes in various measures of immune status in mice subject to chronic social conflict.
2001 Jan-Feb
Alloxan-induced mitochondrial permeability transition triggered by calcium, thiol oxidation, and matrix ATP.
2001 Jul 20
Retention of heme in axial ligand mutants of succinate-ubiquinone xxidoreductase (complex II) from Escherichia coli.
2001 Jun 1
Tissue reactions to epoxy-crosslinked porcine heart valves post-treated with detergents or a dicarboxylic acid.
2001 Jun 5
A third crystal form of Wolinella succinogenes quinol:fumarate reductase reveals domain closure at the site of fumarate reduction.
2001 Mar
Depletion of glutathione up-regulates mitochondrial complex I expression in glial cells.
2001 Mar
Variables in human liver microsome preparation: impact on the kinetics of l-alpha-acetylmethadol (LAAM) n-demethylation and dextromethorphan O-demethylation.
2001 Mar
Barth's syndrome-like disorder: a new phenotype with a maternally inherited A3243G substitution of mitochondrial DNA (MELAS mutation).
2001 Mar 1
Conjugative metabolism of 1,2-dibromoethane in mitochondria: disruption of oxidative phosphorylation and alkylation of mitochondrial DNA.
2001 Mar 1
Disruption of mitochondrial respiration by melatonin in MCF-7 cells.
2001 Mar 15
Myxothiazol induces H(2)O(2) production from mitochondrial respiratory chain.
2001 Mar 2
Topology of the Na(+)/dicarboxylate cotransporter: the N-terminus and hydrophilic loop 4 are located intracellularly.
2001 Mar 9
Dynamic responses of Pseudomonas fluorescens DF57 to nitrogen or carbon source addition.
2001 Mar 9
Effects of culture conditions on enhancement of 2,4-dinitrotoluene degradation by Burkholderia engineered with the Vitreoscilla hemoglobin gene.
2001 Mar-Apr
Cytochrome c oxidase deficient cells accumulate in the hippocampus and choroid plexus with age.
2001 Mar-Apr
The Quinone-binding sites of the Saccharomyces cerevisiae succinate-ubiquinone oxidoreductase.
2001 May 18
J-domain protein, Jac1p, of yeast mitochondria required for iron homeostasis and activity of Fe-S cluster proteins.
2001 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Human: 0.20mh/kg/day up tp 12.2mg
Route of Administration: Oral
In Vitro Use Guide
Antiviral activity was measured in a plaque inhibition assay. Confluent Vero cell monolayer in 6-well multidishes were infected with 100 PFU in 1 mL of MEM medium. After adsorption at 37 °C for 2 h, residual inoculum was replaced with 1 mL of MEM medium containing 0.2% gamma-globulin and 1 mL of a dilution of varying concentrations of the Succinic acid. Virus-infected wells without compounds were used as cytopathogenicity controls. Viral cytopathogenicity (CPE) was completed 1-2 days after viral infection
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:36:10 UTC 2019
Edited
by admin
on Mon Oct 21 20:36:10 UTC 2019
Record UNII
AB6MNQ6J6L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUCCINIC ACID
FCC   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
SUCCINIC ACID [MI]
Common Name English
DIHYDROFUMARIC ACID
Common Name English
FEMA NO. 4719
Code English
SUCCINIC ACID [II]
Common Name English
SUCCINIC ACID [USP-RS]
Common Name English
SUCCINIC ACID [INCI]
Common Name English
SUCCINIC ACID [FCC]
Common Name English
SUCCINIC ACID [USP]
Common Name English
1,2-ETHANEDICARBOXYLIC ACID
Systematic Name English
AMBER ACID
Common Name English
SUCCINIC ACID [HSDB]
Common Name English
SUCCINIC ACID [WHO-DD]
Common Name English
SUCCINIC ACID [VANDF]
Common Name English
SUCCINICUM ACIDUM [HPUS]
Common Name English
NSC-106449
Code English
SUCCINIC ACID [MART.]
Common Name English
SUCCINICUM ACIDUM
HPUS  
Common Name English
BUTANEDIOIC ACID
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 172.230
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
NCI_THESAURUS C345
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
CFR 21 CFR 184.1091
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
Code System Code Type Description
MESH
D019802
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
NCI_THESAURUS
C61954
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
CAS
110-15-6
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
EPA CompTox
110-15-6
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
DRUG BANK
DB00139
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
ECHA (EC/EINECS)
203-740-4
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
EVMPD
SUB12599MIG
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
RXCUI
37255
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M10269
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
SUCCINIC ACID
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
PUBCHEM
1110
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL576
Created by admin on Mon Oct 21 20:36:10 UTC 2019 , Edited by admin on Mon Oct 21 20:36:10 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
succinic semialdehyde dehydrogenase converts succinic semialdehyde to succinic acid
PARENT -> METABOLITE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY