Salicylamide

US Previously Marketed

First approved in 1943

Details

Stereochemistry	ACHIRAL
Molecular Formula	C7H7NO2
Molecular Weight	137.136
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=C(O)C=CC=C1

InChI

InChIKey=SKZKKFZAGNVIMN-UHFFFAOYSA-N

InChI=1S/C7H7NO2/c8-7(10)5-3-1-2-4-6(5)9/h1-4,9H,(H2,8,10)

HIDE SMILES / InChI

Molecular Formula	C7H7NO2
Molecular Weight	137.136
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9fe82229-cc3e-4d79-a448-014fe3d0055b
Curator's Comment: Description was created using several sources including: http://www.drugbank.ca/drugs/DB08797; https://www.ncbi.nlm.nih.gov/pubmed/7606337; http://www.chemicalbook.com/ProductChemicalPropertiesCB4854078_EN.htm; https://www.ncbi.nlm.nih.gov/pubmed/4020644

Salicylamide is a non-prescription drug with analgesic and antipyretic properties (NSAID). It is used in combination with aspirin and caffeine in the over-the-counter pain remedies (such as EXAPRIN). Salicylamide can produce sedation and sleep in humans and animals. Has been used as model drug in pharmacokinetic and metabolic studies as a dophamine 2 receptor ligand. Salicylamide is a white or light pink crystals or powder. Organic compound it is a carboxamide derivative of salicylic acid.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Common cold 58 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9fe82229-cc3e-4d79-a448-014fe3d0055b	Primary		Approved 8583	EXAPRIN Approved Use Pain Reliever / Fever Reducer. Temporarily relieves minor aches and pains due to headache, backache, muscular aches, minor arthritis pain, the common cold, toothache, menstrual cramps. Temporarily reduces fever
Arthritis 87 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9fe82229-cc3e-4d79-a448-014fe3d0055b	Primary		Approved 8583	EXAPRIN Approved Use Pain Reliever / Fever Reducer. Temporarily relieves minor aches and pains due to headache, backache, muscular aches, minor arthritis pain, the common cold, toothache, menstrual cramps. Temporarily reduces fever

C_max

Value	Dose	Co-administered	Analyte	Population
30.9 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6689276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		SALICYLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
76 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6689276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		SALICYLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
12 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6689276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		SALICYLAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 CYP1A2 2153 CYP1B1 32 CYP2B6 926 UGT 45

Drug as perpetrator

Target	Modality	Activity
UGT 70	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/6425870/ Page: 2.0	likely
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/ Page: 10.0	moderate
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/ Page: 10.0	not significant
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/ Page: 10.0	not significant
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/	yes [IC50 2000 uM]
CYP1A1 272	inhibitor 4027 Sources: https://cancerres.aacrjournals.org/content/64/1/429.long	yes
CYP1B1 93	inhibitor 4027 Sources: https://cancerres.aacrjournals.org/content/64/1/429.long	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:32114	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32114
ChemicalBook	CB4854078	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4854078
eMolecules	476454	https://www.emolecules.com/cgi-bin/more?vid=476454
MolPort	MolPort-001-641-072	https://www.molport.com/shop/molecule-link/MolPort-001-641-072
ZINC	ZINC000000002055	http://zinc15.docking.org/substances/ZINC000000002055

PubMed

Title	Date	PubMed
A novel MDCKII in vitro model for assessing ABCG2-drug interactions and regulation of ABCG2 transport activity in the caprine mammary gland by environmental pollutants and pesticides.	2014-04	24389113
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
N-(3-Chloro-phen-yl)-2-hy-droxy-benzamide.	2010-11-06	21589406
Screening and quantitative determination of twelve acidic and neutral pharmaceuticals in whole blood by liquid-liquid extraction and liquid chromatography-tandem mass spectrometry.	2010-09	20822673
In vivo neutralization of unfractionated heparin and low-molecular-weight heparin by a novel salicylamide derivative.	2010-08	20460347
Microencapsulation: A promising technique for controlled drug delivery.	2010-07	21589795
Drug-target interaction prediction from chemical, genomic and pharmacological data in an integrated framework.	2010-06-15	20529913
JBIR-58, a new salicylamide derivative, isolated from a marine sponge-derived Streptomyces sp. SpD081030ME-02.	2010-05	20339397
2-Hydr-oxy-5-nitro-benzamide.	2009-11-28	21578956
Contact dermatitis due to topical drugs.	2009-10	19834431
Effect of formulation parameters and drug-polymer interactions on drug release from starch acetate matrix tablets.	2009-10	19177516
Synthesis and luminescence properties of lanthanide complexes with a new tripodal ligands featuring salicylamide arms.	2009-09-11	19743523
Host defense peptides as effector molecules of the innate immune response: a sledgehammer for drug resistance?	2009-09-09	19865528
Poly (ethylene glycol) prodrug for anthracyclines via N-Mannich base linker: design, synthesis and biological evaluation.	2009-09-08	19540322
2-Hydr-oxy-3-nitro-benzamide.	2009-06-20	21582897
Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes.	2009-06-15	19428348
Influence of conformational flexibility on self-assembly and luminescence properties of lanthanide coordination polymers with flexible exo-bidentate biphenol derivatives.	2009-04-20	19290612
Size-partitioning of an urban aerosol to identify particle determinants involved in the proinflammatory response induced in airway epithelial cells.	2009-03-23	19302717
ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds.	2009-02-01	18321716
QSAR analysis of salicylamide isosteres with the use of quantum chemical molecular descriptors.	2009-02	18547684
Synthesis, structures, and luminescence properties of lanthanide complexes with structurally related new tetrapodal ligands featuring salicylamide pendant arms.	2008-12-15	18998625
Energetics of the O-H bond and of intramolecular hydrogen bonding in HOC6H4C(O)Y (Y = H, CH3, CH2CH=CH2, C[triple bond]CH, CH2F, NH2, NHCH3, NO2, OH, OCH3, OCN, CN, F, Cl, SH, and SCH3) compounds.	2008-10-09	18785698
A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions.	2008-10	18812576
Tetra-kis[2-(benzyl-amino-carbonyl)phenox-ymeth-yl]methane.	2008-09-13	21201120
Development and validation of an MEKC method for determination of nitrogen-containing drugs in pharmaceutical preparations.	2008-09	18803214
Tuning the self-assembly and luminescence properties of lanthanide coordination polymers by ligand design.	2008-07-21	18594707
Aspirin-exacerbated asthma.	2008-06-15	20525128
Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase.	2008-06-01	18479921
Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties.	2008-06	17889969
Salicylamide-induced anaphylaxis: increased urinary leukotriene E4 and prostaglandin D2 metabolite.	2008-04	18315738
DFT and ab initio study of structure of dyes derived from 2-hydroxy and 2,4-dihydroxy benzoic acids.	2008-02	17553738
Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism.	2008	18454852
[Case of acute generalized exanthematous pustulosis caused by Kerorin].	2007-10	17982292
On the complexation of copper (II) ion with 2-hydroxybenzamide.	2007-09-08	17822227
Novel atomic absorption spectrometric and rapid spectrophotometric methods for the quantitation of paracetamol in saliva: application to pharmacokinetic studies.	2007-06-25	20046743
Functionalized magnetic nanoparticles for small-molecule isolation, identification, and quantification.	2007-05-01	17402709
Development of a multicommuted flow-through optosensor for the determination of a ternary pharmaceutical mixture.	2007-01-17	16978822
Response of the bioluminescent bioreporter Pseudomonas fluorescens HK44 to analogs of naphthalene and salicylic acid.	2007	17571789
Voltammetric analysis of europium at screen-printed electrodes modified with salicylamide self-assembled on mesoporous silica.	2006-12	17124543
Towards an understanding of the structurally based potential for mechanically activated disordering of small molecule organic crystals.	2006-12	16924685
Facile synthesis of multivalent nitrilotriacetic acid (NTA) and NTA conjugates for analytical and drug delivery applications.	2006-11-16	17105240
Synthesis and biological evaluation of benzamides and benzamidines as selective inhibitors of VEGFR tyrosine kinases.	2006-10-01	16893647
Protective role of 3-nitro-N-methyl-salicylamide on isolated rat heart during 4 hours of cold storage and reperfusion.	2006-06	16797274
Simultaneous spectrophotometric determination of paracetamol and salicylamide in human serum and pharmaceutical formulations by a differential kinetic method.	2006-03-11	16526453
[Effect of some non-steroidal antiinflammatory drugs and isomeric dihydroxy benzoic acids on the AAPH initiated degradation of crocin].	2006	17094661
Matrix-isolation and computational study of salicylhydroxamic acid and its photochemical degradation.	2005-05-07	19787899
Direct determination of salicylamide in serum by matrix isopotential synchronous fluorimetry.	2002-03-04	18968528
Hydrazide-containing inhibitors of HIV-1 integrase.	1997-03-14	9083482
[Drug induced hemolytic anemia associated with agranulocytosis].	1996-10	8952318
Analgesic nephropathy induced by common proprietary mixtures.	1980-05-17	7412682

Patents

Sample Use Guides

In Vivo Use Guide

152 mg salicylamide/tablet: 1 - 2 tablets every 4 hours while sympotms persist (adults and children 12 years of age and over); no more than 8 tablets in 24 hours unless directed by a doctor. Not for use by children under 12 years.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:01:29 GMT 2025` Edited by `admin` on `Mon Mar 31 18:01:29 GMT 2025`
Record UNII	EM8BM710ZC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-3115

Preferred Name

English

Salicylamide

Official Name

English

SALICYLAMIDE [USP-RS]

Common Name

English

SALICYLAMIDE [MI]

Common Name

English

Salicylamide [WHO-DD]

Common Name

English

SALICYLAMIDE [JAN]

Common Name

English

SALICYLAMIDE [MART.]

Common Name

English

SALICYLAMIDE [VANDF]

Common Name

English

salicylamide [INN]

Common Name

English

SALICYLAMIDE [HSDB]

Common Name

English

BENZAMIDE, 2-HYDROXY-

Systematic Name

English

SALICYLAMIDE [USP MONOGRAPH]

Common Name

English

2-Hydroxybenzamide

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QN02BA75