Identification

Generic Name
L-tartaric acid
Commonly known or available as Tartaric acid
DrugBank Accession Number
DB09459
Background

Tartaric acid is a white crystalline organic acid that occurs naturally in many plants, most notably in grapes.Tartaric is an alpha-hydroxy-carboxylic acid, is diprotic and aldaric in acid characteristics, and is a dihydroxyl derivative of succinic acid.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 150.0868
Monoisotopic: 150.016437924
Chemical Formula
C4H6O6
Synonyms
  • (+)-(R,R)-tartaric acid
  • (+)-L-tartaric acid
  • (+)-Tartaric acid
  • (+)-Weinsäure
  • (2R,3R)-2,3-Dihydroxybernsteinsäure
  • (2R,3R)-2,3-dihydroxysuccinic acid
  • (2R,3R)-Tartaric acid
  • (R,R)-(+)-tartaric acid
  • (R,R)-Tartaric acid
  • ácido tartárico
  • L-threaric acid
  • Rechtsweinsäure
  • Tartaric acid
  • Weinsteinsäure
External IDs
  • E 334
  • E-334
  • FEMA NO. 3044
  • INS NO.334
  • INS-334
  • NSC-62778

Pharmacology

Indication

Tartaric Acid is primarily indicated in conditions like Antiscorbutic, Antiseptic.

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tartaric acid is used to generate carbon dioxide through interaction with sodium bicarbonate following oral administration. Carbon dioxide extends the stomach and provides a negative contrast medium during double contrast radiography. In high doses, this agent acts as a muscle toxin by inhibiting the production of malic acid, which could cause paralysis and maybe death.

Mechanism of action
Not Available
Absorption

Oral or parenteral doses of monosodium 14C-L(+)-tartrate (400 mg/kg) are rapidly excreted by rats and a proportion completely metabolized to CO2. The oral dose was well-absorbed.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract , primarily in the large instestine.

Route of elimination

Only about 15-20% of consumed tartaric acid is secreted in the urine unchanged.

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Routes of Entry: Inhalation. Ingestion.

Toxicity to Animals: Lowest Published Lethal Dose: LDL [Rat - Route: oral; Dose: 7500 mg/kg LDL Rabbit - Route: Oral; Dose: 5000 mg/kg LDL [Dog] - Rout: Oral; Dose: 5000 mg/kg Lethal Dose/Conc 50% kill: LD50 [Mouse] - Route: Intravenous; Dose: 485 mg/kg

Other Toxic Effects on Humans: Acute Potential Health Effects: Skin: Causes skin irritation Eyes: Causes eye irritation Inhalation: Causes respiratory tract irritation Ingestion: Causes gastrointestinal tract irritation with nausea, vomiting and diarrhea. May affect kidneys (kidney damage), blood, and behavior (convulsions, somnolence), and respiration. Chronic Potential Health Effects: Ingestion: Repeated or prolonged ingestion may cause lesions of the mouth, gastric ulcers, gastrointestinal hyperacidity, and symptoms similar to those of metal fume fever - flu-like condition with fever, chills, sweats, nausea, vomiting, muscle aches, pains, and weakness. Skin: Repeated or prolonged skin contact may cause skin ulcerations or lesions.

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.
DrugInteraction
AmphetamineThe excretion of Amphetamine can be decreased when combined with L-tartaric acid.
BenzphetamineThe excretion of Benzphetamine can be decreased when combined with L-tartaric acid.
DemeclocyclineThe therapeutic efficacy of Demeclocycline can be decreased when used in combination with L-tartaric acid.
DextroamphetamineThe excretion of Dextroamphetamine can be decreased when combined with L-tartaric acid.
DiethylpropionThe excretion of Diethylpropion can be decreased when combined with L-tartaric acid.
DoxycyclineThe therapeutic efficacy of Doxycycline can be decreased when used in combination with L-tartaric acid.
EravacyclineThe therapeutic efficacy of Eravacycline can be decreased when used in combination with L-tartaric acid.
Iofetamine I-123The excretion of Iofetamine I-123 can be decreased when combined with L-tartaric acid.
LisdexamfetamineThe excretion of Lisdexamfetamine can be decreased when combined with L-tartaric acid.
LymecyclineThe therapeutic efficacy of Lymecycline can be decreased when used in combination with L-tartaric acid.
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Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AVORAL EFFERVESCENT GRANULESL-tartaric acid (0.89 g) + Citric acid (0.72 g) + Sodium bicarbonate (1.76 g) + Sodium citrate (0.63 g)Granule, for solutionOralXEPA-SOUL PATTINSON (MALAYSIA) SDN BHD2020-09-08Not applicableMalaysia flag
Avosoda Effervescent GranulesL-tartaric acid (0.89 g) + Citric acid (0.72 g) + Sodium bicarbonate (1.76 g) + Sodium citrate (0.63 g)Granule, for solutionOralAbio Marketing Sdn Bhd2020-09-08Not applicableMalaysia flag
Baros Effervescent GranulesL-tartaric acid (420 mg / g) + Sodium bicarbonate (460 mg / g)Granule, effervescentOralTyco Healthcare1988-12-312010-01-07Canada flag
BAROS EFFERVESCENT GRANULESL-tartaric acid (420 mg/g) + Sodium bicarbonate (460 mg/g)GranuleOralEISAI (SINGAPORE) PTE. LTD.1991-05-08Not applicable
BicaruvasL-tartaric acid (2 g/944mL) + Calcium carbonate (1 g/944mL) + Citric acid monohydrate (15 g/944mL) + Sodium bicarbonate (19 g/944mL)Powder, for solutionOralProsana Distribuciones, S.A. De C.V.2013-04-23Not applicableUS flag
BicaruvasL-tartaric acid (220 mg/118mL) + Calcium carbonate (50 mg/118mL) + Citric acid monohydrate (1827 mg/118mL) + Sodium bicarbonate (2452 mg/118mL)Powder, for solutionOralProsana Distribuciones, S.A. De C.V.2013-04-23Not applicableUS flag
BicaruvasL-tartaric acid (2 g/944mL) + Calcium carbonate (1 g/944mL) + Citric acid monohydrate (15 g/944mL) + Sodium bicarbonate (19 g/944mL)Powder, for solutionOralProsana Distribuciones, S.A. De C.V.2013-04-23Not applicableUS flag
Brioschi Childrens Effervescent AntacidL-tartaric acid (1.05 g/4g) + Sodium bicarbonate (1.17 g/4g)Granule, effervescentOralBrioschi, Inc.2011-04-272016-03-25US flag
Brioschi Effervescent AntacidL-tartaric acid (1.63 g/6g) + Sodium bicarbonate (1.8 g/6g)Granule, effervescentOralBrioschi, Inc.2010-09-202016-03-25US flag
CITRAVESCENT GRANULESL-tartaric acid (0.4 g) + Citric acid (1.23 g) + Sodium bicarbonate (1.32 g) + Sodium carbonate (0.08 g)GranuleOralSANOFI-AVENTIS SINGAPORE PTE. LTD.1989-01-07Not applicable

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Sugar acids and derivatives
Alternative Parents
Short-chain hydroxy acids and derivatives / Beta hydroxy acids and derivatives / Monosaccharides / Fatty acids and conjugates / Dicarboxylic acids and derivatives / Alpha hydroxy acids and derivatives / Secondary alcohols / 1,2-diols / Carboxylic acids / Organic oxides
show 2 more
Substituents
1,2-diol / Alcohol / Aliphatic acyclic compound / Alpha-hydroxy acid / Beta-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Fatty acid
show 7 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
tartaric acid (CHEBI:15671)
Affected organisms
Not Available

Chemical Identifiers

UNII
W4888I119H
CAS number
87-69-4
InChI Key
FEWJPZIEWOKRBE-JCYAYHJZSA-N
InChI
InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1
IUPAC Name
(2R,3R)-2,3-dihydroxybutanedioic acid
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O

References

General References
  1. Chasseaud LF, Down WH, Kirkpatrick D: Absorption and biotransformation of L(+)-tartaric acid in rats. Experientia. 1977 Aug 15;33(8):998-9. [Article]
  2. Pubchem [Link]
Human Metabolome Database
HMDB00956
PubChem Compound
444305
PubChem Substance
347827854
ChemSpider
392277
RxNav
37578
ChEBI
15671
ChEMBL
CHEMBL1236315
ZINC
ZINC000000895301
PDBe Ligand
TLA
Wikipedia
Tartaric_acid
PDB Entries
1alu / 1d5r / 1d6j / 1ei6 / 1eks / 1fs5 / 1gu1 / 1h3d / 1j2z / 1k2y
show 508 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Subjects (HS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
GranuleOral460 mg/g
Powder, for solutionOral
Granule, effervescentOral
GranuleOral1.23 g
PowderOral
SolutionOral
TabletOral
Granule, effervescentOral0.72 g
Granule, for solutionOral
Powder
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility161.0 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.8ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)2.72ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.21 m3·mol-1ChemAxon
Polarizability11.33 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-0002-0930000000-19235937e21066a9c484
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-000f-0961000000-559c31b016f4fb3700d2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0007-0961000000-1b17d674621eb9d88c3c
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0002-0930000000-19235937e21066a9c484
GC-MS Spectrum - GC-MSGC-MSsplash10-000f-0961000000-559c31b016f4fb3700d2
MS/MS Spectrum - Quattro_QQQ 10V, NegativeLC-MS/MSsplash10-000b-7900000000-d247ec12b77f427e9a76
MS/MS Spectrum - Quattro_QQQ 25V, NegativeLC-MS/MSsplash10-05fu-9000000000-4bf01ad116d24a453817
MS/MS Spectrum - Quattro_QQQ 40V, NegativeLC-MS/MSsplash10-0006-9000000000-4da65da10f3a34f77688
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-0002-0900000000-ecb902731b9f6eb3764d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-0072-9700000000-1e8e6f410c1d71af856e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-00di-9000000000-f13ad2560d3e6818db9c
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-05fu-9000000000-f46a01eb933ba6fbceac
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-0006-9000000000-08dec35ca6a80add253a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0002-0900000000-ecb902731b9f6eb3764d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0072-9700000000-1e8e6f410c1d71af856e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-f13ad2560d3e6818db9c
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-05fu-9000000000-f46a01eb933ba6fbceac
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-08dec35ca6a80add253a
1H NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Drug created at November 30, 2015 19:10 / Updated at October 07, 2021 12:09