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Details

Stereochemistry ACHIRAL
Molecular Formula C7H7NO2
Molecular Weight 137.1362
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALICYLAMIDE

SMILES

c1ccc(c(c1)C(=N)O)O

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 137.1362
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment:: Known to be CNS penetrant in rats. Human data not available.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
30.9 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
76 μg × min/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
12 min
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​
PubMed

PubMed

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

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: EXAPRIN- acetaminophen, aspirin, caffeine and salicylamide
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 Fri Jun 25 20:58:00 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:00 UTC 2021
Record UNII
EM8BM710ZC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SALICYLAMIDE
HSDB   INCI   INN   JAN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN   INCI  
Official Name English
SALICYLAMIDE [USP-RS]
Common Name English
SALICYLAMIDE [MI]
Common Name English
NSC-3115
Code English
SALICYLAMIDE [JAN]
Common Name English
SALICYLAMIDE [MART.]
Common Name English
SALICYLAMIDE [WHO-DD]
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
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
WHO-VATC QN02BA05
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
WHO-ATC N02BA05
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
NCI_THESAURUS C257
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
Food Contact Sustance Notif, (FCN No.) FCN NO. 46
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
WHO-ATC N02BA55
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
WHO-VATC QN02BA55
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
WHO-ATC N02BA75
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
LIVERTOX 868
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
200-609-3
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL27577
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
HSDB
227
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
INN
1861
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
FDA UNII
EM8BM710ZC
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
CAS
65-45-2
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
EPA CompTox
65-45-2
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
MERCK INDEX
M9735
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY Merck Index
PUBCHEM
5147
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
NCI_THESAURUS
C80566
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
RXCUI
9518
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB08797
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
DRUG CENTRAL
2415
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
USP_CATALOG
1608000
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
SALICYLAMIDE
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
EVMPD
SUB10426MIG
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
MESH
C031060
Created by admin on Fri Jun 25 20:58:01 UTC 2021 , Edited by admin on Fri Jun 25 20:58:01 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY