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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
Camphorated Opium TinctureD.C. Labs Limited
HyophenStar Pharmaceuticals, Llc
Larynsol LozHerbes Universelles Inc.
Mrx LiqMahdeen Mediceuticals, Division of Zeron Inc.
Plax Anti-plaque Dental RinseJohnson & Johnson Inc
Sodium Phenylacetate and Sodium BenzoateTrigen Laboratories, 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
Related Articles
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
Tinctureoral
Tabletoral
Lozengeoral
Liquidtopical
Liquiddental
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 CodesA16AX11V04CG30
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

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Rna polymerase iii regulatory region dna binding
Specific Function:
Reduces hydrogen peroxide and alkyl hydroperoxides with reducing equivalents provided through the thioredoxin system. Involved in intracellular redox signaling.
Gene Name:
PRDX5
Uniprot ID:
P30044
Molecular Weight:
22086.245 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
unknown
General Function:
Not Available
Specific Function:
The biological activity of the toxin is produced by the A chain, which activates intracellular adenyl cyclase.
Gene Name:
eltB
Uniprot ID:
P32890
Molecular Weight:
14133.255 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Rhodococcus sp. (strain MB1 Bresler)
Pharmacological action
unknown
General Function:
Dipeptidyl-peptidase activity
Specific Function:
Hydrolyzes cocaine to benzoate and ecgonine methyl ester, endowing the bacteria with the ability to utilize cocaine as a sole source of carbon and energy for growth, as this bacterium lives in the rhizosphere of coca plants. Also efficiently hydrolyzes cocaethylene, a more potent cocaine metabolite that has been observed in patients who concurrently abuse cocaine and alcohol. Is able to prevent...
Gene Name:
cocE
Uniprot ID:
Q9L9D7
Molecular Weight:
62131.125 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Trisaccharide binding
Specific Function:
Positively regulates the transcription of the maltose regulon whose gene products are responsible for uptake and catabolism of malto-oligosaccharides. Binds and recognizes a DNA motif (called the malT box): 5'-GGA[TG]GA-3'.
Gene Name:
malT
Uniprot ID:
P06993
Molecular Weight:
103117.49 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Intramolecular oxidoreductase activity, interconverting keto- and enol-groups
Specific Function:
Can use enol isomers of phenylpyruvate, 2-hydroxy-2,4-pentadienoate and (p-hydroxyphenyl)pyruvate as substrates.
Gene Name:
pptA
Uniprot ID:
P31992
Molecular Weight:
8672.84 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Receptor binding
Specific Function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act...
Gene Name:
DAO
Uniprot ID:
P14920
Molecular Weight:
39473.75 Da
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:17139284 ]
  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:17016423 ]
  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:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Xenon atom binding
Specific Function:
Endoribonuclease responsible for the inhibition of the translation by cleaving mRNA. Inhibits cell-free protein synthesis. Cleaves phosphodiester bonds only in single-stranded RNA (By similarity).
Gene Name:
HRSP12
Uniprot ID:
P52758
Molecular Weight:
14493.53 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Rhodococcus opacus
Pharmacological action
unknown
General Function:
Ferric iron binding
Specific Function:
Not Available
Gene Name:
clcA
Uniprot ID:
O67987
Molecular Weight:
28952.3 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Gtpase activity
Specific Function:
Involved in the transport of proteins between the endosomes and the trans Golgi network.
Gene Name:
RAB9A
Uniprot ID:
P51151
Molecular Weight:
22837.38 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Transcription factor activity, bacterial-type rna polymerase core promoter proximal region sequence-specific binding
Specific Function:
Hydrogen peroxide sensor. Activates the expression of a regulon of hydrogen peroxide-inducible genes such as katG, gor, ahpC, ahpF, oxyS (a regulatory RNA), dps, fur and grxA. OxyR expression is negatively autoregulated by binding to a 43 bp region upstream of its own coding sequence. OxyR is inactivated by reduction of its essential disulfide bond by the product of GrxA, itself positively regu...
Gene Name:
oxyR
Uniprot ID:
P0ACQ4
Molecular Weight:
34275.59 Da
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:17139284 ]
  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:17016423 ]
Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
unknown
General Function:
Hydrolase activity
Specific Function:
Not Available
Gene Name:
cumD
Uniprot ID:
P96965
Molecular Weight:
31489.385 Da
Kind
Protein
Organism
Streptomyces aureofaciens
Pharmacological action
unknown
General Function:
Chloride peroxidase activity
Specific Function:
Not Available
Gene Name:
cpo
Uniprot ID:
O31168
Molecular Weight:
30354.465 Da
Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
unknown
General Function:
Oxidoreductase activity
Specific Function:
Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred.
Gene Name:
nfsB
Uniprot ID:
Q01234
Molecular Weight:
23949.98 Da
Kind
Protein
Organism
Nocardioides simplex
Pharmacological action
unknown
General Function:
Hydroxyquinol 1,2-dioxygenase activity
Specific Function:
Catalyzes the ortho-cleavage of the aromatic ring of hydroxyquinol.
Gene Name:
chqB
Uniprot ID:
Q5PXQ6
Molecular Weight:
31966.33 Da
Kind
Protein
Organism
Pseudomonas syringae
Pharmacological action
unknown
General Function:
Dna-directed dna polymerase activity
Specific Function:
Not Available
Gene Name:
repA
Uniprot ID:
Q52546
Molecular Weight:
26728.84 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular Weight:
76709.98 Da
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:12724351 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
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:12358729 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Symporter activity
Specific Function:
Proton-coupled monocarboxylate transporter. Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, branched-chain oxo acids derived from leucine, valine and isoleucine, and the ketone bodies acetoacetate, beta-hydroxybutyrate and acetate. Depending on the tissue and on cicumstances, mediates the import or export of lactic acid and ketone bod...
Gene Name:
SLC16A1
Uniprot ID:
P53985
Molecular Weight:
53943.685 Da
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:10714609 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on November 10, 2015 13:11