Page last updated: 2024-11-06

n-acetyl-5-aminosalicylic acid

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

N-acetyl-5-aminosalicylic acid (5-ASA) is a prodrug of 5-aminosalicylic acid, which is an anti-inflammatory medication used in the treatment of inflammatory bowel diseases such as ulcerative colitis and Crohn’s disease. 5-ASA is a derivative of salicylic acid and is thought to work by inhibiting the production of prostaglandins, which are chemicals that contribute to inflammation. 5-ASA is available in a variety of formulations, including oral tablets, capsules, suppositories, and enemas. It is often given in combination with other medications, such as corticosteroids, to help control inflammation. 5-ASA is generally well-tolerated, but side effects can include nausea, vomiting, diarrhea, and headache. 5-ASA is an important medication for the treatment of inflammatory bowel diseases. It has been shown to be effective in reducing inflammation and improving symptoms in patients with these conditions. It is a first-line therapy for the treatment of ulcerative colitis and Crohn’s disease. 5-ASA is studied extensively to better understand its mechanism of action, optimize its efficacy, and develop new and improved formulations. Research is also being conducted to identify potential new uses for 5-ASA, such as in the treatment of other inflammatory conditions.'

Cross-References

ID SourceID
PubMed CID65512
CHEMBL ID3410756
CHEBI ID89810
SCHEMBL ID170522
MeSH IDM0092432

Synonyms (52)

Synonym
5-acetylamino-salicylic acid
51-59-2
nsc-54183
5-acetamidosalicylic acid
2-hydroxy-5-acetylaminobenzoic acid
n-acetyl-5-aminosalicylic acid
5-(acetylamino)salicylic acid
nsc54183
salicylic acid, 5-acetamido-
benzoic acid, 5-(acetylamino)-2-hydroxy-
IDI1_014653
OPREA1_150410
OPREA1_590376
MAYBRIDGE3_003266
AKOS000104718
HMS1440E10
5-acetamido-2-hydroxybenzoic acid
FT-0661151
FT-0661152
5-(acetylamino)-2-hydroxybenzoic acid
EN300-52452
einecs 200-107-4
9h126z3pf5 ,
unii-9h126z3pf5
nsc 54183
n-acetyl mesalazine
3-carboxyparacetamol
n-acetyl mesalamine
AB06135
2-hydroxy-5-(acetylamino)benzoic acid
cj-46a
acetylmesalazine
SCHEMBL170522
GEFDRROBUCULOD-UHFFFAOYSA-N
2-hydroxy-5-acetamidobenzoic acid
5-acetamido-2-hydroxy-benzoic acid
CHEMBL3410756
chebi:89810 ,
5-(acetylamino)-2-hydroxybenzoic acid, aldrichcpr
DTXSID80199002
mfcd00463101
5-(acetylamino)-2-hydroxybenzoic acid, analytical standard
5-acetaminosalicylic acid
A935786
Q27161998
AML0004
BCP33382
5-acetamido-2-hydroxybenzoic acid;n-acetyl-5-aminosalicylic acid;5-acetamidosalicylic acid
E78518
AS-77007
CS-0005653
Z239128440

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Adverse events and laboratory changes were monitored throughout the study."( Safety, efficacy, and pharmacokinetics of balsalazide in pediatric patients with mild-to-moderate active ulcerative colitis: results of a randomized, double-blind study.
Attard, TM; Bortey, E; Forbes, WP; Heyman, MB; Pieniaszek, HJ; Pohl, JF; Quiros, JA; Walker, K, 2009
)
0.35
" Adverse events were similar between the treatment groups, the most common being headache and abdominal pain."( Safety, efficacy, and pharmacokinetics of balsalazide in pediatric patients with mild-to-moderate active ulcerative colitis: results of a randomized, double-blind study.
Attard, TM; Bortey, E; Forbes, WP; Heyman, MB; Pieniaszek, HJ; Pohl, JF; Quiros, JA; Walker, K, 2009
)
0.35

Pharmacokinetics

ExcerptReferenceRelevance
" The purpose of this study was to compare the pharmacokinetic profile of this drug between two patient groups, with either inflamed small or large bowel and with volunteers."( Pharmacokinetics of a 5-aminosalicylic acid enteric-coated tablet in patients with Crohn's disease or ulcerative colitis and in healthy volunteers.
Gotthard, R; Norlander, B; Ström, M, 1990
)
0.28
" The purpose of this study was to compare the pharmacokinetic profile of this product to sulphasalazine (SASP; Salazopyrin) and to assess the pharmacokinetics of a suppository 5-ASA dosage form."( Pharmacokinetics of a 5-aminosalicylic acid enteric-coated tablet and suppository dosage form.
Gotthard, R; Norlander, B; Ström, M, 1989
)
0.28
"The pharmacokinetic properties of benzalazine ((2-hydroxy-5-[(4-carboxyphenyl)azo]benzoic acid, CAS 64896-26-0), a new agent for the treatment of ulcerative colitis and Crohn's disease of the large intestine, were investigated."( Pharmacokinetic studies of benzalazine.
Herzog, R; Leuschner, J, 1994
)
0.29
" Pharmacokinetic parameters for balsalazide, 5-aminosalicylic acid, and N-acetyl-5-aminosalicylic acid were determined at 2 weeks."( Safety, efficacy, and pharmacokinetics of balsalazide in pediatric patients with mild-to-moderate active ulcerative colitis: results of a randomized, double-blind study.
Attard, TM; Bortey, E; Forbes, WP; Heyman, MB; Pieniaszek, HJ; Pohl, JF; Quiros, JA; Walker, K, 2009
)
0.59

Bioavailability

ExcerptReferenceRelevance
"The bioavailability of three pure 5-aminosalicylic (5-ASA) preparations (Asacol, Claversal, and Pentasa) was studied in 8 ileostomy patients and 12 normal subjects after 6 days of treatment with 2000 mg 5-ASA."( Topical and systemic availability of 5-aminosalicylate: comparisons of three controlled release preparations in man.
Abildgaard, K; Bondesen, S; Christensen, LA; Fallingborg, J; Hansen, SH; Hvidberg, EF; Jacobsen, BA; Rasmussen, SN; Sanchez, G, 1990
)
0.28
" Food coadministration reduced 5-ASA and acetyl 5-ASA systemic relative bioavailability to 44% and 76%, respectively, compared with the fasting treatment."( Effect of food coadministration on 5-aminosalicylic acid oral suspension bioavailability.
Eichmeier, LS; Elvin, AT; Giesing, DH; Lanman, MB; Lanman, RC; Morrill, B; Yu, DK, 1990
)
0.28

Dosage Studied

ExcerptRelevanceReference
" Incubation with higher concentrations of the drugs revealed a dose-response effect on binding with complete inhibition by 100 mM 4ASA and 10 mM olsalazine, and lesser degrees of inhibition by 100 mM 5ASA, N-acetyl-5ASA, and N-acetyl-4ASA."( Inhibition of binding of interferon-gamma to its receptor by salicylates used in inflammatory bowel disease.
Aronson, JK; Crotty, B; Jewell, DP; Rosenberg, WM, 1992
)
0.28
" For subjects in a fasting state, plasma 5-ASA and acetyl 5-ASA concentrations peaked rapidly 1 hour after dosing to 14."( Effect of food coadministration on 5-aminosalicylic acid oral suspension bioavailability.
Eichmeier, LS; Elvin, AT; Giesing, DH; Lanman, MB; Lanman, RC; Morrill, B; Yu, DK, 1990
)
0.28
" The purpose of this study was to compare the pharmacokinetic profile of this product to sulphasalazine (SASP; Salazopyrin) and to assess the pharmacokinetics of a suppository 5-ASA dosage form."( Pharmacokinetics of a 5-aminosalicylic acid enteric-coated tablet and suppository dosage form.
Gotthard, R; Norlander, B; Ström, M, 1989
)
0.28
"Miniaturised methods have been used to construct dose-response curves for the effects of inhibitory drugs on prostaglandin synthesis using individual rectal biopsies obtained from patients with ulcerative colitis."( Inhibition of prostaglandin synthetase in human rectal mucosa.
Hawkey, CJ; Lo Casto, M, 1983
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aminobenzoic acid
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (10)

Assay IDTitleYearJournalArticle
AID1204222Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 1 hr relative to control2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis and QSAR study of novel anti-inflammatory active mesalazine-metronidazole conjugates.
AID1204226Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 3 hrs relative to control2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis and QSAR study of novel anti-inflammatory active mesalazine-metronidazole conjugates.
AID1282304Inhibition of N-terminal His6-tagged KDM4C (1 to 352 residues) (unknown origin) expressed in Escherichia coli Rosetta 2(DE3)pLysS using biotinylated histone H3 (1 to 21 residues) lysine 9 trimethylated peptide/2 uM alpha-ketoglutarate as substrate/cofacto2016Journal of medicinal chemistry, Feb-25, Volume: 59, Issue:4
Docking and Linking of Fragments To Discover Jumonji Histone Demethylase Inhibitors.
AID1204230Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 24 hrs relative to control2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis and QSAR study of novel anti-inflammatory active mesalazine-metronidazole conjugates.
AID1196811Inhibition of human KLF10 expressed in human HeLa cells assessed as reduction in transcriptional activity at 100 uM after 24 hrs by CACCC-responsive promoter driven TK-luciferase reporter gene assay2015Journal of medicinal chemistry, Feb-12, Volume: 58, Issue:3
Discovery of small molecule inhibitors to Krüppel-like factor 10 (KLF10): implications for modulation of T regulatory cell differentiation.
AID1204228Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 4 hrs relative to control2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis and QSAR study of novel anti-inflammatory active mesalazine-metronidazole conjugates.
AID1204224Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 2 hrs relative to control2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis and QSAR study of novel anti-inflammatory active mesalazine-metronidazole conjugates.
AID1204231Antiinflammatory activity in Wistar rat assessed as inhibition of carrageenan-induced paw edema at 10 mg/kg indomethacin mol equivalent, ip administered 1 hr prior to carrageenan challenge measured at 3 hrs relative to indomethacin2015Bioorganic & medicinal chemistry letters, Jun-01, Volume: 25, Issue:11
Synthesis and QSAR study of novel anti-inflammatory active mesalazine-metronidazole conjugates.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (68)

TimeframeStudies, This Drug (%)All Drugs %
pre-199027 (39.71)18.7374
1990's27 (39.71)18.2507
2000's7 (10.29)29.6817
2010's5 (7.35)24.3611
2020's2 (2.94)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 15.11

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index15.11 (24.57)
Research Supply Index4.44 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (15.11)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (18.31%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other58 (81.69%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]