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

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Pharmacology

Indication

Not Available

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination for symptomatic treatment of	Headache	Combination Product in combination with: Chlorpheniramine (DB01114)	••••••••••••			••••••
Treatment of	Mild pain		••• •••
Used in combination for symptomatic treatment of	Rhinorrhoea	Combination Product in combination with: Chlorpheniramine (DB01114)	••••••••••••			••••••
Used in combination for symptomatic treatment of	Sneezing	Combination Product in combination with: Chlorpheniramine (DB01114)	••••••••••••			••••••

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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Food Interactions

No interactions found.

Products

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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) + Lidocaine hydrochloride (20 mg/1mL) + Menthol (0.33 g/100g) + 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; Liquid; Ointment; Spray; Tablet	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
CON-Z-LIN TABLET	Salicylamide (250 mg) + Caffeine (15 mg)	Tablet, sugar coated	Oral	CENTRAL CHEMICAL & ENTERPRISES PTE. LTD.	1991-04-22	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) + Lidocaine hydrochloride (20 mg/1mL) + Menthol (0.33 g/100g) + 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; Liquid; Ointment; Spray; Tablet	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

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
• Cyclooxygenase Inhibitors
• 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 / 7dqh

MSDS

Download (57 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

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; liquid; ointment; spray; tablet	Ophthalmic; Oral; Topical
Capsule, gelatin coated	Oral
Tablet, sugar coated	Oral	15 mg
Capsule	Oral	30 mg
Tablet	Oral
Emulsion	Topical
Tablet		500 MG
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)	-0.97	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	splash10-00dr-5900000000-34487b27347166b47c91
GC-MS Spectrum - EI-B	GC-MS	splash10-00du-4900000000-f5a22e5a4fb556796bd9
GC-MS Spectrum - EI-B	GC-MS	splash10-00du-8900000000-701c75263149bd35390b
MS/MS Spectrum - , negative	LC-MS/MS	splash10-000i-1900000000-132217380eb9a2784eb0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00di-1900000000-44f47541fedafcd8e76d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000l-7900000000-aa62e3be7a6f71e43059
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9000000000-19db7c819c68901e7edc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00dl-9800000000-6424dce9850d6a781079
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-9000000000-63ed04f886ceb14e859d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f6x-9000000000-613b83c918e21b465b3c
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	126.073412	predicted	DarkChem Lite v0.1.0
[M-H]-	126.043212	predicted	DarkChem Lite v0.1.0
[M-H]-	125.834412	predicted	DarkChem Lite v0.1.0
[M-H]-	127.046	predicted	DeepCCS 1.0 (2019)
[M+H]+	126.983912	predicted	DarkChem Lite v0.1.0
[M+H]+	126.740812	predicted	DarkChem Lite v0.1.0
[M+H]+	126.922612	predicted	DarkChem Lite v0.1.0
[M+H]+	129.43472	predicted	DeepCCS 1.0 (2019)
[M+Na]+	126.091812	predicted	DarkChem Lite v0.1.0
[M+Na]+	126.096612	predicted	DarkChem Lite v0.1.0
[M+Na]+	126.179012	predicted	DarkChem Lite v0.1.0
[M+Na]+	137.93105	predicted	DeepCCS 1.0 (2019)

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