Salicylamide

Identification

Brand Names
Exaprin
Generic Name
Salicylamide
DrugBank Accession Number
DB08797
Background

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. It has similar medicinal uses to aspirin. Salicylamide is used in combination with both aspirin and caffeine in the over-the-counter pain remedies

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 137.136
Monoisotopic: 137.047678473
Chemical Formula
C7H7NO2
Synonyms
  • 2-Carbamoylphenol
  • 2-Carboxamidophenol
  • 2-Hydroxybenzamide
  • o-hydroxybenzamide
  • OHB
  • Salicilamida
  • Salicylamide
  • Salicylamidum
  • Salicylic Acid amide

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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

Adverse Effects
Adverseeffects
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Toxicity

Oral, rat LD50: 1890 mg/kg

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
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.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Salicylamide.
AclidiniumSalicylamide may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineSalicylamide may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirThe risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Salicylamide.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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dosage, form, labeller, route of administration, and marketing period.
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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4229 First Aid KitSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Caffeine (32.4 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g)KitOral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4248 First Aid KitSalicylamide (152 mg/1) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4346 First Aid KitSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
Aramark Pain FreeSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralWestern First Aid Safety DBA Aramark2021-05-07Not applicableUS flag
Crane Safety XS Pain ReliefSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralCrane Safety LLC2020-01-17Not applicableUS flag
ExaprinSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)TabletOralHART Health1987-01-20Not applicableUS flag
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 flag
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 Aid Corporation2008-12-30Not applicableUS flag
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 flag
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 flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4229 First Aid KitSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Caffeine (32.4 mg/1) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g)KitOral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4248 First Aid KitSalicylamide (152 mg/1) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4346 First Aid KitSalicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
Be Flex PlusSalicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)Capsule, gelatin coatedOralLarken Laboratories, Inc2006-04-172010-07-13US flag
Be Flex PlusSalicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)Capsule, gelatin coatedOralLarken Laboratories, Inc2006-04-172010-07-13US flag
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 flag

Categories

ATC Codes
N02BA75 — Salicylamide, combinations with psycholepticsN02BA55 — Salicylamide, combinations excl. psycholepticsN02BA05 — Salicylamide
Drug Categories
Chemical TaxonomyProvided by Classyfire
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-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Carboximidic acid / Carboximidic acid derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
phenols, salicylamides (CHEBI:32114) / a small molecule (SALICYLAMIDE)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
EM8BM710ZC
CAS number
65-45-2
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

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
Human Metabolome Database
HMDB0015687
KEGG Drug
D01811
PubChem Compound
5147
PubChem Substance
99445267
ChemSpider
4963
BindingDB
50056900
RxNav
9518
ChEBI
32114
ChEMBL
CHEMBL27577
ZINC
ZINC000000002055
PDBe Ligand
OHB
Wikipedia
Salicylamide
PDB Entries
4k17 / 5rsu
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOral; Respiratory (inhalation); Topical
KitOphthalmic; Oral; Respiratory (inhalation); Topical
KitOphthalmic; Oral; Topical
Capsule, gelatin coatedOral
Tablet
TabletOral
EmulsionTopical
Tablet
Capsule
Elixir
Syrup
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

Drug created on October 08, 2010 22:10 / Updated on February 21, 2021 18:52