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Identification
NameBenzoic Acid
Accession NumberDB03793  (EXPT00675)
TypeSmall Molecule
GroupsApproved
Description

A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid. As the sodium salt form, sodium benzoate is used as a treatment for urea cycle disorders due to its ability to bind amino acids. This leads to excretion of these amino acids and a decrease in ammonia levels. Recent research shows that sodium benzoate may be beneficial as an add-on therapy (1 gram/day) in schizophrenia. Total Positive and Negative Syndrome Scale scores dropped by 21% compared to placebo.

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
AmmonulValeant Pharmaceuticals North America LLC
HyophenStar Pharmaceuticals, Llc
Urophen MbBurel Pharmaceuticals, Inc
Salts
Name/CASStructureProperties
Sodium benzoate
532-32-1
Thumb
  • InChI Key: WXMKPNITSTVMEF-UHFFFAOYSA-M
  • Monoisotopic Mass: 144.018724079
  • Average Mass: 144.1032
DBSALT001289
Categories
UNII8SKN0B0MIM
CAS number65-85-0
WeightAverage: 122.1213
Monoisotopic: 122.036779436
Chemical FormulaC7H6O2
InChI KeyInChIKey=WPYMKLBDIGXBTP-UHFFFAOYSA-N
InChI
InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
IUPAC Name
benzoic acid
SMILES
OC(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Benzoic Acid
Not Available
Benzoyl glucuronide (Benzoic acid)Details
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9886
Blood Brain Barrier+0.9557
Caco-2 permeable+0.9187
P-glycoprotein substrateNon-substrate0.8494
P-glycoprotein inhibitor INon-inhibitor0.9914
P-glycoprotein inhibitor IINon-inhibitor0.9941
Renal organic cation transporterNon-inhibitor0.9136
CYP450 2C9 substrateNon-substrate0.8003
CYP450 2D6 substrateNon-substrate0.9672
CYP450 3A4 substrateNon-substrate0.8374
CYP450 1A2 substrateNon-inhibitor0.8532
CYP450 2C9 inhibitorNon-inhibitor0.9861
CYP450 2D6 inhibitorNon-inhibitor0.957
CYP450 2C19 inhibitorNon-inhibitor0.9878
CYP450 3A4 inhibitorNon-inhibitor0.9822
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9863
Ames testNon AMES toxic0.9923
CarcinogenicityNon-carcinogens0.6024
BiodegradationReady biodegradable0.8983
Rat acute toxicity1.7896 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9708
hERG inhibition (predictor II)Non-inhibitor0.9882
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Injection, solution, concentrateintravenous
Tabletoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point122.4 °CPhysProp
boiling point249.2 °CPhysProp
water solubility3400 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.87HANSCH,C ET AL. (1995)
logS-1.55ADME Research, USCD
pKa4.19 (at 25 °C)LIDE,DR (1996)
Predicted Properties
PropertyValueSource
Water Solubility7.08 mg/mLALOGPS
logP1.72ALOGPS
logP1.63ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.31 m3·mol-1ChemAxon
Polarizability11.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0z00000000-5284a0c1c77a1979e1f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-dz00000000-1c74c32fa650fcd4cb4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-zk00000000-f312a552bef1a2927e64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-z600000000-dafd91c9134bc4143743View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-zi00000000-29ca905567aa5c59d46bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-nz00000000-fa50606b2e84fc4cefe9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-zp00000000-d08dbc757a6de6c3f54eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-zw00000000-2693809ae064e720bf58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-zv00000000-2c6be5ecee1848091a24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-1z00000000-4644ee08861e75d0b808View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-zi00000000-11baabb3c0bb283b1c6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-z500000000-4875643627420279223bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-z000000000-97a21f3206f5c1f0ba7eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-wz00000000-3d79c70c455799ab33e3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Ludovicus A. L. Kleintjens, Hubertus M. J. Grooten, “Process for the preparation of benzoic acid.” U.S. Patent US4539425, issued March, 1932.

US4539425
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
BetamethasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Betamethasone.
CorticotropinThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Corticotropin.
Cortisone acetateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Cortisone acetate.
DexamethasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Dexamethasone.
FludrocortisoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fludrocortisone.
HaloperidolThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Haloperidol.
HydrocortisoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Hydrocortisone.
MethylprednisoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Methylprednisolone.
PrednisoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prednisolone.
PrednisoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prednisone.
ProbenecidThe serum concentration of Benzoic Acid can be increased when it is combined with Probenecid.
Repository corticotropinThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Repository corticotropin.
TriamcinoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Triamcinolone.
Valproic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Valproic Acid.
Food InteractionsNot Available

Targets

1. Peroxiredoxin-5, mitochondrial

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Peroxiredoxin-5, mitochondrial P30044 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Heat-labile enterotoxin B chain

Kind: Protein

Organism: Escherichia coli

Pharmacological action: unknown

Components

Name UniProt ID Details
Heat-labile enterotoxin B chain P32890 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

3. Cocaine esterase

Kind: Protein

Organism: Rhodococcus sp. (strain MB1 Bresler)

Pharmacological action: unknown

Components

Name UniProt ID Details
Cocaine esterase Q9L9D7 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. HTH-type transcriptional regulator MalT

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
HTH-type transcriptional regulator MalT P06993 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. Tautomerase PptA

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Tautomerase PptA P31992 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

6. D-amino-acid oxidase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
D-amino-acid oxidase P14920 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed

7. Ribonuclease UK114

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ribonuclease UK114 P52758 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

8. Chlorocatechol 1,2-dioxygenase

Kind: Protein

Organism: Rhodococcus opacus

Pharmacological action: unknown

Components

Name UniProt ID Details
Chlorocatechol 1,2-dioxygenase O67987 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

9. Ras-related protein Rab-9A

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Ras-related protein Rab-9A P51151 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

10. Hydrogen peroxide-inducible genes activator

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Hydrogen peroxide-inducible genes activator P0ACQ4 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

11. 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase

Kind: Protein

Organism: Pseudomonas fluorescens

Pharmacological action: unknown

Components

Name UniProt ID Details
2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase P96965 Details

12. Non-heme chloroperoxidase

Kind: Protein

Organism: Streptomyces aureofaciens

Pharmacological action: unknown

Components

Name UniProt ID Details
Non-heme chloroperoxidase O31168 Details

13. Oxygen-insensitive NAD(P)H nitroreductase

Kind: Protein

Organism: Enterobacter cloacae

Pharmacological action: unknown

Components

Name UniProt ID Details
Oxygen-insensitive NAD(P)H nitroreductase Q01234 Details

14. Hydroxyquinol 1,2-dioxygenase

Kind: Protein

Organism: Nocardioides simplex

Pharmacological action: unknown

Components

Name UniProt ID Details
Hydroxyquinol 1,2-dioxygenase Q5PXQ6 Details

15. Replication protein

Kind: Protein

Organism: Pseudomonas syringae

Pharmacological action: unknown

Components

Name UniProt ID Details
Replication protein Q52546 Details

Transporters

1. Solute carrier organic anion transporter family member 2B1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 2B1 O94956 Details

References:

  1. Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. Pubmed

2. Solute carrier family 22 member 8

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. Pubmed

3. Monocarboxylate transporter 1

Kind: Protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Monocarboxylate transporter 1 P53985 Details

References:

  1. Kido Y, Tamai I, Okamoto M, Suzuki F, Tsuji A: Functional clarification of MCT1-mediated transport of monocarboxylic acids at the blood-brain barrier using in vitro cultured cells and in vivo BUI studies. Pharm Res. 2000 Jan;17(1):55-62. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on November 10, 2015 13:11