Identification

Name
Benzoic Acid
Accession Number
DB03793  (EXPT00675)
Type
Small Molecule
Groups
Approved
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
Synonyms
Not Available
External IDs
E-210 / FEMA NO. 2131 / INS NO.210 / INS-210 / NSC-149
Product Ingredients
IngredientUNIICASInChI Key
Sodium benzoateOJ245FE5EU532-32-1WXMKPNITSTVMEF-UHFFFAOYSA-M
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AmmonulSodium benzoate (100 mg/mL) + Sodium phenylacetate (100 mg/mL)Injection, solution, concentrateIntravenousUcyclyd Pharma Inc.2005-02-17Not applicableUs
AmmonulSodium benzoate (100 mg/mL) + Sodium phenylacetate (100 mg/mL)Injection, solution, concentrateIntravenousValeant Pharmaceuticals North America2005-02-17Not applicableUs
Camphorated Opium TinctureBenzoic Acid (500 mg) + Camphor (300 mg) + Opium (5 ml)TinctureOralD.C. Labs Limited1951-12-312003-07-11Canada
GlycothymolineSodium benzoate (20 mg) + Sodium borate (20 mg)LiquidTopicalGlendale Agencies1951-12-311996-11-29Canada
HyophenBenzoic Acid (9 mg/1) + Hyoscyamine sulfate (.12 mg/1) + Methenamine (81.6 mg/1) + Methylene blue (10.8 mg/1) + Phenyl salicylate (36.2 mg/1)TabletOralStar Pharmaceuticals, Llc2010-09-21Not applicableUs00076 0901 01 nlmimage10 cc15e64f
Larynsol LozBenzoic Acid (5 mg) + Chlorobutanol (.6 mg) + Eucalyptol (3.2 mg)LozengeOralHerbes Universelles Inc.1979-12-312009-07-15Canada
Mrx LiqBenzoic Acid (0.2 %) + Benzethonium chloride (0.13 %) + Camphor (0.7 %) + Ethanol (40 %)LiquidTopicalMahdeen Mediceuticals, Division of Zeron Inc.1972-12-312002-02-12Canada
Plax Anti-plaque Dental RinseSodium benzoate (2 %) + Sodium salicylate (0.2 %) + Sodium lauryl sulfate (0.25 %)LiquidDentalJohnson & Johnson1988-12-312010-08-04Canada
Sodium Phenylacetate and Sodium BenzoateSodium benzoate (100 mg/mL) + Sodium phenylacetate (100 mg/mL)Injection, solution, concentrateIntravenousMylan Institutional2017-05-23Not applicableUs
Sodium Phenylacetate and Sodium BenzoateSodium benzoate (100 mg/mL) + Sodium phenylacetate (100 mg/mL)Injection, solution, concentrateIntravenousMaia Pharmaceuticals, Inc2017-05-22Not applicableUs
Categories
UNII
8SKN0B0MIM
CAS number
65-85-0
Weight
Average: 122.1213
Monoisotopic: 122.036779436
Chemical Formula
C7H6O2
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPeroxiredoxin-5, mitochondrialNot AvailableHuman
UHeat-labile enterotoxin B chainNot AvailableEscherichia coli
UCocaine esteraseNot AvailableRhodococcus sp. (strain MB1 Bresler)
UHTH-type transcriptional regulator MalTNot AvailableEscherichia coli (strain K12)
UTautomerase PptANot AvailableEscherichia coli (strain K12)
UD-amino-acid oxidaseNot AvailableHuman
URibonuclease UK114Not AvailableHuman
UChlorocatechol 1,2-dioxygenaseNot AvailableRhodococcus opacus
URas-related protein Rab-9ANot AvailableHuman
UHydrogen peroxide-inducible genes activatorNot AvailableEscherichia coli (strain K12)
U2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolaseNot AvailablePseudomonas fluorescens
UNon-heme chloroperoxidaseNot AvailableStreptomyces aureofaciens
UOxygen-insensitive NAD(P)H nitroreductaseNot AvailableEnterobacter cloacae
UHydroxyquinol 1,2-dioxygenaseNot AvailableNocardioides simplex
UReplication proteinNot AvailablePseudomonas syringae
USolute carrier family 15 member 1Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-BromoepiandrosteroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with 16-Bromoepiandrosterone.Investigational
19-norandrostenedioneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with 19-norandrostenedione.Experimental, Illicit
5-androstenedioneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with 5-androstenedione.Experimental, Illicit
AlclometasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Alclometasone.Approved
AldosteroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Aldosterone.Experimental
AmcinonideThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Amcinonide.Approved
AmlodipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Benzoic Acid.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Amrinone.Approved
AndrostenedioneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Androstenedione.Experimental, Illicit
AnecortaveThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Anecortave.Investigational
anecortave acetateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with anecortave acetate.Investigational
AtamestaneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Atamestane.Investigational
AzelnidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Azelnidipine.Approved
AzimilideThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Barnidipine.Approved
Beclomethasone dipropionateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Beclomethasone dipropionate.Approved, Investigational
BencyclaneThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Benidipine.Approved
BepridilThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Bepridil.Approved, Withdrawn
BetamethasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Betamethasone.Approved, Vet Approved
BudesonideThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Budesonide.Approved
BuspironeThe metabolism of Buspirone can be decreased when combined with Benzoic Acid.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Benzoic Acid.Approved, Investigational
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Caroverine.Experimental
CiclesonideThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Ciclesonide.Approved, Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Cinnarizine.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Benzoic Acid.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Clevidipine.Approved
ClobetasolThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Clobetasol.Investigational
Clobetasol propionateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Clobetasol propionate.Approved
ClobetasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Clobetasone.Approved
ClocortoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Clocortolone.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Benzoic Acid.Approved, Investigational
Cortexolone 17α-propionateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Cortexolone 17α-propionate.Investigational
CorticosteroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Corticosterone.Experimental
Cortisone acetateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Cortisone acetate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Benzoic Acid.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Darodipine.Experimental
DesoximetasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Desoximetasone.Approved
Desoxycorticosterone acetateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Desoxycorticosterone acetate.Approved
Desoxycorticosterone PivalateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Desoxycorticosterone Pivalate.Experimental, Vet Approved
DexamethasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Dexamethasone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Dexamethasone isonicotinate.Vet Approved
DidanosineDidanosine can cause a decrease in the absorption of Benzoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiflorasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Diflorasone.Approved
DifluocortoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Difluocortolone.Approved
DifluprednateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Difluprednate.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Benzoic Acid.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Benzoic Acid.Approved
DotarizineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Eperisone.Approved, Investigational
EquileninThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Equilenin.Experimental
EquilinThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Equilin.Approved
EstroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Estrone.Approved
Estrone sulfateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Estrone sulfate.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Benzoic Acid.Approved
FelodipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Fendiline.Withdrawn
fluasteroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with fluasterone.Investigational
FludrocortisoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fludrocortisone.Approved
FlumethasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Flumethasone.Approved, Vet Approved
FlunarizineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Flunarizine.Approved
Fluocinolone AcetonideThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fluocinolone Acetonide.Approved, Investigational, Vet Approved
FluocinonideThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fluocinonide.Approved, Investigational
FluocortoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fluocortolone.Approved, Withdrawn
FluorometholoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fluorometholone.Approved
FluprednideneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fluprednidene.Approved, Withdrawn
FluprednisoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Fluprednisolone.Approved
FlurandrenolideThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Flurandrenolide.Approved
FormestaneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Formestane.Approved, Investigational, Withdrawn
FosphenytoinThe serum concentration of Benzoic Acid can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Gallopamil.Investigational
HaloperidolThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Haloperidol.Approved
HE3286The therapeutic efficacy of Benzoic Acid can be decreased when used in combination with HE3286.Investigational
HydrocortisoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Hydrocortisone.Approved, Vet Approved
IsradipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Isradipine.Approved
IstaroximeThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Istaroxime.Investigational
LacidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Lacidipine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Lercanidipine.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Lidoflazine.Experimental
LosartanThe metabolism of Losartan can be decreased when combined with Benzoic Acid.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Manidipine.Approved
ME-609The therapeutic efficacy of Benzoic Acid can be decreased when used in combination with ME-609.Investigational
MedrysoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Medrysone.Approved
MelengestrolThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Melengestrol.Vet Approved
MethylprednisoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Methylprednisolone.Approved, Vet Approved
MibefradilThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Mibefradil.Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Naftopidil.Investigational
NCX 1022The therapeutic efficacy of Benzoic Acid can be decreased when used in combination with NCX 1022.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nilvadipine.Approved
NimesulideThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nimesulide.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Nitrendipine.Approved
Oleoyl-estroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Oleoyl-estrone.Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Otilonium.Experimental
ParamethasoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Paramethasone.Approved
PerhexilineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Benzoic Acid.Approved, Vet Approved
PimozideBenzoic Acid may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Pinaverium.Approved
PrasteroneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prasterone.Approved, Nutraceutical
Prasterone sulfateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prasterone sulfate.Investigational
PrednicarbateThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prednicarbate.Approved
PrednisoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prednisolone.Approved, Vet Approved
PrednisoneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Prednisone.Approved, Vet Approved
PregabalinThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Pregabalin.Approved, Illicit, Investigational
PregnenoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Pregnenolone.Experimental
PrenylamineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Prenylamine.Withdrawn
ProbenecidThe serum concentration of Benzoic Acid can be increased when it is combined with Probenecid.Approved
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Benzoic Acid.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Benzoic Acid.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Benzoic Acid.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Benzoic Acid.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Benzoic Acid.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Benzoic Acid.Approved
RimexoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Rimexolone.Approved
RisedronateThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Risedronate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Benzoic Acid.Approved
SucralfateSucralfate can cause a decrease in the absorption of Benzoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Benzoic Acid.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Benzoic Acid.Approved, Investigational
TerodilineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Tetrahydropalmatine.Investigational
TixocortolThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Tixocortol.Approved
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Tranilast.Approved, Investigational
TriamcinoloneThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Triamcinolone.Approved, Vet Approved
Valproic AcidThe therapeutic efficacy of Benzoic Acid can be decreased when used in combination with Valproic Acid.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Benzoic Acid.Approved
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB01870
KEGG Drug
D00038
KEGG Compound
C00539
PubChem Compound
243
PubChem Substance
46504911
ChemSpider
238
BindingDB
197302
ChEBI
30746
ChEMBL
CHEMBL541
PharmGKB
PA448578
HET
BEZ
Wikipedia
Benzoic_acid
ATC Codes
V04CG30 — Caffeine and sodium benzoateA16AX11 — Sodium benzoate
PDB Entries
1a8u / 1djr / 1gxs / 1gyx / 1h4o / 1hd2 / 1hkq / 1hz4 / 1i69 / 1i7q
show 121 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentAmino Acid Metabolism, Inborn Errors1
2TerminatedTreatmentHepatic Encephalopathy1
2WithdrawnTreatmentAttenuated or Transient Psychosis1
4RecruitingPreventionAnaesthesia therapy1
Not AvailableCompletedOtherUCDs (The Data May be Helpful in the Treatment of UCDs.) / Urea Cycle Disorders, Inborn1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Injection, solution, concentrateIntravenous
TinctureOral
LozengeOral
LiquidTopical
LiquidDental
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)122.4 °CPhysProp
boiling point (°C)249.2 °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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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)

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-MSsplash10-0a70-0900000000-5284a0c1c77a1979e1f4
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-056r-3900000000-1c74c32fa650fcd4cb4d
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-05i0-6900000000-fa50606b2e84fc4cefe9
GC-MS Spectrum - EI-BGC-MSsplash10-0a6r-9600000000-d08dbc757a6de6c3f54e
GC-MS Spectrum - EI-BGC-MSsplash10-0adi-9800000000-40f904bf20072c72a08b
GC-MS Spectrum - EI-BGC-MSsplash10-0pk9-9800000000-b93fc1120a1c74b88fa3
GC-MS Spectrum - EI-BGC-MSsplash10-05i0-5900000000-1b6bbf98557af374f3a5
GC-MS Spectrum - EI-BGC-MSsplash10-0570-0900000000-ecd208f1e7b4d5ad85f2
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a70-0900000000-5284a0c1c77a1979e1f4
GC-MS Spectrum - GC-MSGC-MSsplash10-056r-3900000000-1c74c32fa650fcd4cb4d
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0a70-0900000000-cec9e1ab69521049d1e4
Mass Spectrum (Electron Ionization)MSsplash10-0pk9-8900000000-3d79c70c455799ab33e3
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00b9-9500000000-f312a552bef1a2927e64
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-004i-9100000000-dafd91c9134bc4143743
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00b9-9400000000-29ca905567aa5c59d46b
MS/MS Spectrum - EI-B (HITACHI RMU-7) , PositiveLC-MS/MSsplash10-05i0-6900000000-fa50606b2e84fc4cefe9
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , PositiveLC-MS/MSsplash10-0a6r-9600000000-d08dbc757a6de6c3f54e
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-0adi-9800000000-2693809ae064e720bf58
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-0pk9-9800000000-2c6be5ecee1848091a24
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-00di-0900000000-4644ee08861e75d0b808
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-00b9-9400000000-11baabb3c0bb283b1c6e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-004l-9100000000-4875643627420279223b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0006-9000000000-97a21f3206f5c1f0ba7e
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/MSsplash10-00di-0900000000-4644ee08861e75d0b808
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00b9-9400000000-11baabb3c0bb283b1c6e
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004l-9100000000-4875643627420279223b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-9000000000-97a21f3206f5c1f0ba7e
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acids
Alternative Parents
Benzoyl derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Benzoic acid / Benzoyl / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoic acids (CHEBI:30746)

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
Uniprot Name
Peroxiredoxin-5, mitochondrial
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
Uniprot Name
Heat-labile enterotoxin B chain
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 ...
Gene Name
cocE
Uniprot ID
Q9L9D7
Uniprot Name
Cocaine esterase
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 m...
Gene Name
malT
Uniprot ID
P06993
Uniprot Name
HTH-type transcriptional regulator MalT
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
Uniprot Name
Tautomerase PptA
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]
Details
6. D-amino-acid oxidase
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...
Gene Name
DAO
Uniprot ID
P14920
Uniprot Name
D-amino-acid oxidase
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
Uniprot Name
Ribonuclease UK114
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
Uniprot Name
Chlorocatechol 1,2-dioxygenase
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
Uniprot Name
Ras-related protein Rab-9A
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 ne...
Gene Name
oxyR
Uniprot ID
P0ACQ4
Uniprot Name
Hydrogen peroxide-inducible genes activator
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
Uniprot Name
2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase
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
Uniprot Name
Non-heme chloroperoxidase
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
Uniprot Name
Oxygen-insensitive NAD(P)H nitroreductase
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
Uniprot Name
Hydroxyquinol 1,2-dioxygenase
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
Uniprot Name
Replication protein
Molecular Weight
26728.84 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Omkvist DH, Trangbaek DJ, Mildon J, Paine JS, Brodin B, Begtrup M, Nielsen CU: Affinity and translocation relationships via hPEPT1 of H-X aa-Ser-OH dipeptides: evaluation of H-Phe-Ser-OH as a pro-moiety for ibuprofen and benzoic acid prodrugs. Eur J Pharm Biopharm. 2011 Feb;77(2):327-31. doi: 10.1016/j.ejpb.2010.12.009. Epub 2010 Dec 13. [PubMed:21147219]

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
Uniprot Name
Solute carrier organic anion transporter family member 2B1
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, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
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 leucin...
Gene Name
SLC16A1
Uniprot ID
P53985
Uniprot Name
Monocarboxylate transporter 1
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]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 05:26