You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameSalicylamide
Accession NumberDB08797
TypeSmall Molecule
GroupsApproved
Description

Salicylamide is the common name for the substance o-hydroxybenzamide, or amide of salicyl. Salicylamide is a non-prescription drug with analgesic and antipyretic properties. Its medicinal uses are similar to those of aspirin. Salicylamide is used in combination with both aspirin and caffeine in the over-the-counter pain remedies

Structure
Thumb
Synonyms
2-Carbamoylphenol
2-Carboxamidophenol
2-Hydroxybenzamide
o-hydroxybenzamide
OHB
Salicilamida
Salicylamidum
Salicylic acid amide
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
ExaprinHART Health
Green Guard Pain and Ache ReliefUnifirst First Aid Corporation
Medi First Pain ReliefUnifirst First Aid Corporation
Medi First Plus Pain ZapperUnifirst First Aid Corporation
Pain RelieverAdvanced First Aid, Inc.
Pain Stopper ExtraNorth Safety Products LLC
Pain Stoppers RegularNorth Safety Products LLC
Pain TerminatorProvision Medical Products
Zee Pain AidZee Medical Inc
SaltsNot Available
Categories
UNIIEM8BM710ZC
CAS number65-45-2
WeightAverage: 137.136
Monoisotopic: 137.047678473
Chemical FormulaC7H7NO2
InChI KeyInChIKey=SKZKKFZAGNVIMN-UHFFFAOYSA-N
InChI
InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10)
IUPAC Name
2-hydroxybenzamide
SMILES
NC(=O)C1=CC=CC=C1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylamides
Alternative Parents
Substituents
  • Salicylamide
  • Benzamide
  • Benzoyl
  • Phenol
  • Vinylogous acid
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen 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
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rat LD50: 1890 mg/kg
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9877
Blood Brain Barrier+0.9382
Caco-2 permeable+0.6048
P-glycoprotein substrateNon-substrate0.8565
P-glycoprotein inhibitor INon-inhibitor0.9817
P-glycoprotein inhibitor IINon-inhibitor0.9948
Renal organic cation transporterNon-inhibitor0.9178
CYP450 2C9 substrateNon-substrate0.8207
CYP450 2D6 substrateNon-substrate0.6203
CYP450 3A4 substrateNon-substrate0.7067
CYP450 1A2 substrateNon-inhibitor0.7061
CYP450 2C9 inhibitorNon-inhibitor0.952
CYP450 2D6 inhibitorNon-inhibitor0.9043
CYP450 2C19 inhibitorNon-inhibitor0.8779
CYP450 3A4 inhibitorNon-inhibitor0.8828
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9144
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.864
BiodegradationReady biodegradable0.7192
Rat acute toxicity2.1150 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9867
hERG inhibition (predictor II)Non-inhibitor0.9468
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point142 °CPhysProp
boiling point181.5 °CPhysProp
water solubility2060 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.28HANSCH,C ET AL. (1995)
pKa8.37 (at 20 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility7.82 mg/mLALOGPS
logP0.74ALOGPS
logP1.17ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)8.21ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.12 m3·mol-1ChemAxon
Polarizability13.22 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Elijah J. Gold, Esther Babad, Lydia Peer, Wei K. Chang, “Preparation of (-)-5-(beta)-1-hydroxy-2-((beta)-1-methyl-3-phenylpropyl)aminoethyl) salicylamide.” U.S. Patent US4658060, issued November, 1979.

US4658060
General ReferencesNot Available
External Links
ATC CodesN02BA05N02BA55N02BA75
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (57 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
comments powered by Disqus
Drug created on October 08, 2010 16:10 / Updated on August 17, 2016 12:24