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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Salicylamide (DB08797)

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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

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Associated Conditions

• Headache
• Mild pain
• Rhinorrhoea
• Sneezing

Contraindications & Blackbox Warnings

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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

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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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Salicylamide may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with Abciximab.
Acebutolol	Salicylamide may decrease the antihypertensive activities of Acebutolol.
Aceclofenac	The risk or severity of adverse effects can be increased when Aceclofenac is combined with Salicylamide.
Acemetacin	The risk or severity of adverse effects can be increased when Salicylamide is combined with Acemetacin.
Acenocoumarol	The risk or severity of bleeding and hemorrhage can be increased when Salicylamide is combined with Acenocoumarol.
Acetohexamide	The protein binding of Acetohexamide can be decreased when combined with Salicylamide.
Aclidinium	Salicylamide may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Acrivastine	Salicylamide may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Acyclovir	The risk or severity of nephrotoxicity can be increased when Acyclovir is combined with Salicylamide.

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Food Interactions

No interactions found.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
4229 First Aid Kit	Salicylamide (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)	Kit	Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4248 First Aid Kit	Salicylamide (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)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4346 First Aid Kit	Salicylamide (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)	Kit	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
Aramark Pain Free	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Western First Aid Safety DBA Aramark	2021-05-07	Not applicable
Crane Safety XS Pain Relief	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Crane Safety LLC	2020-01-17	Not applicable
Exaprin	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	HART Health	1987-01-20	Not applicable
Extra Strength Pain Reliever	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Redicare Llc	2017-10-01	Not applicable
Green Guard Pain and Ache Relief	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Unifirst First Aid Corporation	2008-12-30	Not applicable
Medi First Pain Relief	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Unifirst First Aid Corporation	2008-12-30	Not applicable
Medi First Plus Pain Zapper	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Unifirst First Aid Corporation	2008-12-30	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
4229 First Aid Kit	Salicylamide (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)	Kit	Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4248 First Aid Kit	Salicylamide (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)	Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
4346 First Aid Kit	Salicylamide (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)	Kit	Ophthalmic; Oral; Topical	Honeywell Safety Products USA, Inc	2018-10-18	Not applicable
Be Flex Plus	Salicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)	Capsule, gelatin coated	Oral	Larken Laboratories, Inc	2006-04-17	2010-07-13
Be Flex Plus	Salicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)	Capsule, gelatin coated	Oral	Larken Laboratories, Inc	2006-04-17	2010-07-13
BE-FLEX Plus	Salicylamide (200 mg/1) + Acetaminophen (300 mg/1) + Phenyltoloxamine citrate (20 mg/1)	Capsule, gelatin coated	Oral	Larken Laboratories, Inc.	2006-04-17	2011-10-31

Categories

ATC Codes

N02BA75 — Salicylamide, combinations with psycholeptics

• N02BA — Salicylic acid and derivatives
• N02B — OTHER ANALGESICS AND ANTIPYRETICS
• N02 — ANALGESICS
• N — NERVOUS SYSTEM

N02BA55 — Salicylamide, combinations excl. psycholeptics

• N02BA — Salicylic acid and derivatives
• N02B — OTHER ANALGESICS AND ANTIPYRETICS
• N02 — ANALGESICS
• N — NERVOUS SYSTEM

N02BA05 — Salicylamide

• N02BA — Salicylic acid and derivatives
• N02B — OTHER ANALGESICS AND ANTIPYRETICS
• N02 — ANALGESICS
• N — NERVOUS SYSTEM

Drug Categories

• Acids, Carbocyclic
• Agents causing hyperkalemia
• Agents that produce hypertension
• Amides
• Analgesics
• Analgesics, Non-Narcotic
• Anti-Inflammatory Agents
• Anti-Inflammatory Agents, Non-Steroidal
• Antirheumatic Agents
• Benzene Derivatives
• Benzoates
• Central Nervous System Agents
• Cyclooxygenase Inhibitors
• Ligands
• Nephrotoxic agents
• Nervous System
• Non COX-2 selective NSAIDS
• Peripheral Nervous System Agents
• Salicylic Acid and Derivatives
• Sensory System Agents

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

External Links

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

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Kit	Oral; Respiratory (inhalation); Topical
Kit	Ophthalmic; Oral; Respiratory (inhalation); Topical
Kit	Ophthalmic; Oral; Topical
Capsule, gelatin coated	Oral
Tablet
Tablet	Oral
Emulsion	Topical
Tablet
Capsule
Elixir
Syrup

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	142 °C	PhysProp
boiling point (°C)	181.5 °C	PhysProp
water solubility	2060 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	1.28	HANSCH,C ET AL. (1995)
pKa	8.37 (at 20 °C)	KORTUM,G ET AL (1961)

Predicted Properties

Property	Value	Source
Water Solubility	7.82 mg/mL	ALOGPS
logP	0.74	ALOGPS
logP	1.17	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.21	ChemAxon
pKa (Strongest Basic)	-1.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å2	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.12 m3·mol-1	ChemAxon
Polarizability	13.22 Å3	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9877
Blood Brain Barrier	+	0.9382
Caco-2 permeable	+	0.6048
P-glycoprotein substrate	Non-substrate	0.8565
P-glycoprotein inhibitor I	Non-inhibitor	0.9817
P-glycoprotein inhibitor II	Non-inhibitor	0.9948
Renal organic cation transporter	Non-inhibitor	0.9178
CYP450 2C9 substrate	Non-substrate	0.8207
CYP450 2D6 substrate	Non-substrate	0.6203
CYP450 3A4 substrate	Non-substrate	0.7067
CYP450 1A2 substrate	Non-inhibitor	0.7061
CYP450 2C9 inhibitor	Non-inhibitor	0.952
CYP450 2D6 inhibitor	Non-inhibitor	0.9043
CYP450 2C19 inhibitor	Non-inhibitor	0.8779
CYP450 3A4 inhibitor	Non-inhibitor	0.8828
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9144
Ames test	Non AMES toxic	0.9133
Carcinogenicity	Non-carcinogens	0.864
Biodegradation	Ready biodegradable	0.7192
Rat acute toxicity	2.1150 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9867
hERG inhibition (predictor II)	Non-inhibitor	0.9468

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-00du-4900000000-f5a22e5a4fb556796bd9
GC-MS Spectrum - EI-B	GC-MS	splash10-00du-8900000000-701c75263149bd35390b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
MS/MS Spectrum - , negative	LC-MS/MS	splash10-000i-1900000000-132217380eb9a2784eb0

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