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

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 8429	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 89 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9fe82229-cc3e-4d79-a448-014fe3d0055b	Primary		Approved 8429	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 1587	inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 110 CYP1A2 1524 CYP1B1 19 CYP2B6 810 UGT 35

Drug as perpetrator

Target	Modality	Activity
UGT 59	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/6425870/ Page: 2.0	likely
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/ Page: 10.0	moderate
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/ Page: 10.0	not significant
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/ Page: 10.0	not significant
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23153057/	yes [IC50 2000 uM]
CYP1A1 218	inhibitor 3277 Sources: https://cancerres.aacrjournals.org/content/64/1/429.long	yes
CYP1B1 67	inhibitor 3277 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
MolPort	MolPort-001-641-072	https://www.molport.com/shop/molecule-link/MolPort-001-641-072
ZINC	ZINC000000002055	http://zinc15.docking.org/substances/ZINC000000002055
eMolecules	476454	https://www.emolecules.com/cgi-bin/more?vid=476454

PubMed

Title	Date	PubMed
Analgesic nephropathy induced by common proprietary mixtures.	1980 May 17	7412682
[Drug induced hemolytic anemia associated with agranulocytosis].	1996 Oct	8952318
Hydrazide-containing inhibitors of HIV-1 integrase.	1997 Mar 14	9083482
Direct determination of salicylamide in serum by matrix isopotential synchronous fluorimetry.	2002 Mar 4	18968528
Matrix-isolation and computational study of salicylhydroxamic acid and its photochemical degradation.	2005 May 7	19787899
Simultaneous spectrophotometric determination of paracetamol and salicylamide in human serum and pharmaceutical formulations by a differential kinetic method.	2005 Nov-Dec	16526453
[Effect of some non-steroidal antiinflammatory drugs and isomeric dihydroxy benzoic acids on the AAPH initiated degradation of crocin].	2006	17094661
Voltammetric analysis of europium at screen-printed electrodes modified with salicylamide self-assembled on mesoporous silica.	2006 Dec	17124543
Towards an understanding of the structurally based potential for mechanically activated disordering of small molecule organic crystals.	2006 Dec	16924685
Protective role of 3-nitro-N-methyl-salicylamide on isolated rat heart during 4 hours of cold storage and reperfusion.	2006 Jun	16797274
Facile synthesis of multivalent nitrilotriacetic acid (NTA) and NTA conjugates for analytical and drug delivery applications.	2006 Nov-Dec	17105240
Synthesis and biological evaluation of benzamides and benzamidines as selective inhibitors of VEGFR tyrosine kinases.	2006 Oct 1	16893647
Response of the bioluminescent bioreporter Pseudomonas fluorescens HK44 to analogs of naphthalene and salicylic acid.	2007	17571789
Development of a multicommuted flow-through optosensor for the determination of a ternary pharmaceutical mixture.	2007 Jan 17	16978822
On the complexation of copper (II) ion with 2-hydroxybenzamide.	2007 Mar-Apr	17822227
Functionalized magnetic nanoparticles for small-molecule isolation, identification, and quantification.	2007 May 1	17402709
[Case of acute generalized exanthematous pustulosis caused by Kerorin].	2007 Oct	17982292
Antiproliferative and cytostatic effects of the natural product eupatorin on MDA-MB-468 human breast cancer cells due to CYP1-mediated metabolism.	2008	18454852
Salicylamide-induced anaphylaxis: increased urinary leukotriene E4 and prostaglandin D2 metabolite.	2008 Apr	18315738
Synthesis, structures, and luminescence properties of lanthanide complexes with structurally related new tetrapodal ligands featuring salicylamide pendant arms.	2008 Dec 15	18998625
DFT and ab initio study of structure of dyes derived from 2-hydroxy and 2,4-dihydroxy benzoic acids.	2008 Feb	17553738
Tuning the self-assembly and luminescence properties of lanthanide coordination polymers by ligand design.	2008 Jul 21	18594707
Design and microwave-assisted synthesis of 5-trifluoromethyl-4,5-dihydro-1H-pyrazoles: novel agents with analgesic and anti-inflammatory properties.	2008 Jun	17889969
Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase.	2008 Jun 1	18479921
Aspirin-exacerbated asthma.	2008 Jun 15	20525128
Novel atomic absorption spectrometric and rapid spectrophotometric methods for the quantitation of paracetamol in saliva: application to pharmacokinetic studies.	2008 May-Jun	20046743
A novel high-throughput screening assay for putative antidiabetic agents through PPARalpha interactions.	2008 Oct	18812576
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 Oct 9	18785698
Development and validation of an MEKC method for determination of nitrogen-containing drugs in pharmaceutical preparations.	2008 Sep	18803214
Tetra-kis[2-(benzyl-amino-carbonyl)phenox-ymeth-yl]methane.	2008 Sep 13	21201120
Influence of conformational flexibility on self-assembly and luminescence properties of lanthanide coordination polymers with flexible exo-bidentate biphenol derivatives.	2009 Apr 20	19290612
QSAR analysis of salicylamide isosteres with the use of quantum chemical molecular descriptors.	2009 Feb	18547684
ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds.	2009 Feb 1	18321716
Biotransformation and cytotoxic effects of hydroxychavicol, an intermediate of safrole metabolism, in isolated rat hepatocytes.	2009 Jun 15	19428348
2-Hydr-oxy-3-nitro-benzamide.	2009 Jun 20	21582897
Size-partitioning of an urban aerosol to identify particle determinants involved in the proinflammatory response induced in airway epithelial cells.	2009 Mar 23	19302717
2-Hydr-oxy-5-nitro-benzamide.	2009 Nov 28	21578956
Contact dermatitis due to topical drugs.	2009 Oct	19834431
Effect of formulation parameters and drug-polymer interactions on drug release from starch acetate matrix tablets.	2009 Oct	19177516
Poly (ethylene glycol) prodrug for anthracyclines via N-Mannich base linker: design, synthesis and biological evaluation.	2009 Sep 8	19540322
Host defense peptides as effector molecules of the innate immune response: a sledgehammer for drug resistance?	2009 Sep 9	19865528
In vivo neutralization of unfractionated heparin and low-molecular-weight heparin by a novel salicylamide derivative.	2010 Aug	20460347
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
Microencapsulation: A promising technique for controlled drug delivery.	2010 Jul	21589795
Synthesis and luminescence properties of lanthanide complexes with a new tripodal ligands featuring salicylamide arms.	2010 Jul-Aug	19743523
Drug-target interaction prediction from chemical, genomic and pharmacological data in an integrated framework.	2010 Jun 15	20529913
JBIR-58, a new salicylamide derivative, isolated from a marine sponge-derived Streptomyces sp. SpD081030ME-02.	2010 May	20339397
N-(3-Chloro-phen-yl)-2-hy-droxy-benzamide.	2010 Nov 6	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 Sep	20822673
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 Apr	24389113

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

Name

Type

Language

SALICYLAMIDE

Official Name

English

SALICYLAMIDE [USP-RS]

Common Name

English

SALICYLAMIDE [MI]

Common Name

English

NSC-3115

Code

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

SALICYLAMIDE [INCI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN02BA75