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

3D

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Salicylamide (DB08797)

×

Close

Synonyms

• 2-Carbamoylphenol
• 2-Carboxamidophenol
• 2-Hydroxybenzamide
• o-hydroxybenzamide
• OHB
• Salicilamida
• Salicylamidum
• Salicylic acid amide

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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	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	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	2008-12-30	Not applicable
Pain Free	Salicylamide (152 1/1) + Acetaminophen (110 1/1) + Acetylsalicylic acid (162 1/1) + Caffeine (32.4 1/1)	Tablet	Oral	Afassco Inc.	2016-10-25	Not applicable
Pain Reliever	Salicylamide (152 1/1) + Acetaminophen (110 1/1) + Acetylsalicylic acid (162 1/1)	Tablet	Oral	Advanced First Aid, Inc.	2015-04-07	Not applicable
Pain Stopper Extra	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	North Safety Products	2012-03-07	2017-01-01
Pain Stoppers	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Honeywell Safety Products USA, Inc	2017-01-02	Not applicable
Pain Stoppers Regular	Salicylamide (152 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Caffeine (32.4 mg/1)	Tablet	Oral	Honeywell Safety Products USA, Inc	2013-04-18	2017-01-01

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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

• Acids, Carbocyclic
• Agents causing hyperkalemia
• Amides
• Analgesics
• Analgesics, Non-Narcotic
• Anti-Inflammatory Agents
• Anti-Inflammatory Agents, Non-Steroidal
• Benzene Derivatives
• Benzoates
• Central Nervous System Agents
• Cyclooxygenase Inhibitors
• Ligands
• Nephrotoxic agents
• Nervous System
• Peripheral Nervous System Agents
• Salicylic Acid and Derivatives
• Sensory System Agents

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

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• Withdrawn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

Drug	Interaction
(4R)-limonene	The risk or severity of adverse effects can be increased when Salicylamide is combined with (4R)-limonene.
16-Bromoepiandrosterone	The risk or severity of adverse effects can be increased when Salicylamide is combined with 16-Bromoepiandrosterone.
19-norandrostenedione	The risk or severity of adverse effects can be increased when Salicylamide is combined with 19-norandrostenedione.
5-androstenedione	The risk or severity of adverse effects can be increased when Salicylamide is combined with 5-androstenedione.
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 Salicylamide is combined with Aceclofenac.
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.
Acetaminophen	Salicylamide may decrease the excretion rate of Acetaminophen which could result in a higher serum level.

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 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

N02BA55 — Salicylamide, combinations excl. psycholeptics

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

PDB Entries

4k17

MSDS

Download (57 KB)

Clinical Trials

Clinical Trials

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Capsule, gelatin coated	Oral
Tablet	Oral

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

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 October 01, 2018 14:42