Salicylamide

Identification

Name
Salicylamide
Accession Number
DB08797
Type
Small Molecule
Groups
Approved
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
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ExaprinSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralHART Health1987-01-20Not applicableUs
Extra Strength Pain RelieverSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralRedicare Llc2017-10-01Not applicableUs
Green Guard Pain and Ache ReliefSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralUnifirst First Aid2008-12-30Not applicableUs
Medi First Pain ReliefSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralUnifirst First Aid Corporation2008-12-30Not applicableUs
Medi First Plus Pain ZapperSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralUnifirst First Aid Corporation2008-12-30Not applicableUs
Pain FreeSalicylamide (152 1/1) + Acetaminophen (110 1/1) + Acetylsalicylic acid (162 1/1) + Caffeine (32.4 1/1)TabletOralAfassco Inc.2016-10-25Not applicableUs
Pain RelieverSalicylamide (152 1/1) + Acetaminophen (110 1/1) + Acetylsalicylic acid (162 1/1)TabletOralAdvanced First Aid, Inc.2015-04-07Not applicableUs
Pain Stopper ExtraSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralNorth Safety Products2012-03-072017-01-01Us
Pain StoppersSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralHoneywell Safety Products USA, Inc2017-01-02Not applicableUs
Pain Stoppers RegularSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralHoneywell Safety Products USA, Inc2013-04-182017-01-01Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Be Flex PlusSalicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)Capsule, gelatin coatedOralLarken Laboratories, Inc2006-04-172010-07-13Us
Be Flex PlusSalicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)Capsule, gelatin coatedOralLarken Laboratories, Inc2006-04-172010-07-13Us
BE-FLEX PlusSalicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)Capsule, gelatin coatedOralLarken Laboratories, Inc.2006-04-172011-10-31Us
Categories
UNII
EM8BM710ZC
CAS number
65-45-2
Weight
Average: 137.136
Monoisotopic: 137.047678473
Chemical Formula
C7H7NO2
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral, rat LD50: 1890 mg/kg

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with 4-hydroxycoumarin.
AbacavirSalicylamide may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with Abciximab.
AcarboseSalicylamide may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololSalicylamide may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Salicylamide.
AcemetacinThe risk or severity of adverse effects can be increased when Salicylamide is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with Acenocoumarol.
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0015687
PubChem Compound
5147
PubChem Substance
99445267
ChemSpider
4963
BindingDB
50056900
ChEBI
32114
ChEMBL
CHEMBL27577
HET
OHB
Wikipedia
Salicylamide
ATC Codes
N02BA75 — Salicylamide, combinations with psycholepticsN02BA05 — SalicylamideN02BA55 — Salicylamide, combinations excl. psycholeptics
PDB Entries
4k17
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Capsule, gelatin coatedOral
TabletOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)142 °CPhysProp
boiling point (°C)181.5 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00du-4900000000-f5a22e5a4fb556796bd9
GC-MS Spectrum - EI-BGC-MSsplash10-00du-8900000000-701c75263149bd35390b
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
MS/MS Spectrum - , negativeLC-MS/MSsplash10-000i-1900000000-132217380eb9a2784eb0

Taxonomy

Description
This compound belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-4-unsubstituted benzenoids
Direct Parent
1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Carboximidic acids / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Carboximidic acid derivative / Carboximidic acid / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, salicylamides (CHEBI:32114) / a small molecule (SALICYLAMIDE)

Drug created on October 08, 2010 16:10 / Updated on November 02, 2018 06:54