Details of the Drug

General Information of Drug (ID: DM3WVPJ)

Drug Name
Asacolitin
Synonyms
Apriso; Asacol; Asacol HD; 5-Aminosalicylic acid; Benzoic acid, 5-amino-2-hydroxy-; Canasa; Claversal; Fisalamine; Lialda; Lixacol; Mesalamine [USAN]; Mesalazina; Mesalazina [Spanish]; Mesalazine; Mesalazinum; Mesalazinum [Latin]; Mesasal; Pentasa; Rowasa; Salofalk; m-Aminosalicylic acid; mesalamine; p-Aminosalicylsaeure; p-Aminosalicylsaeure [German]; sfRowasa; 2-Hydroxy-5-aminobenzoic acid; 5-ASA; 5-Amino Salicylic Acid; 5-Amino-2-hydroxybenzoic acid; 5-amino-2-hydroxy-benzoic acid; 89-57-6
Affected Organisms
Humans and other mammals
ATC Code
A07EC02: Asacolitin
A07EC: Aminosalicylic acid and similar agents
A07E: INTESTINAL ANTIINFLAMMATORY AGENTS
A07: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
A: ALIMENTARY TRACT AND METABOLISM
A07EC02: Asacolitin
A07EC: Aminosalicylic acid and similar agents
A07E: INTESTINAL ANTIINFLAMMATORY AGENTS
A07: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
A: ALIMENTARY TRACT AND METABOLISM
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 153.14
Logarithm of the Partition Coefficient (xlogp) 1.3
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Elimination
N-acetylmesalazine was the primary compound excreted in the urine (19% to 30%) following the controlled-release dosing []
Half-life
The concentration or amount of drug in body reduced by one-half in 7 - 12 hours [1]
Vd
The volume of distribution (Vd) of drug is 0.2 L/kg [1]
Chemical Identifiers
Formula
C7H7NO3
IUPAC Name
5-amino-2-hydroxybenzoic acid
Canonical SMILES
C1=CC(=C(C=C1N)C(=O)O)O
InChI
InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
InChIKey
KBOPZPXVLCULAV-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4075
ChEBI ID
CHEMBL704
CAS Number
89-57-6
UNII
4Q81I59GXC
DrugBank ID
DB00244
INTEDE ID
DR1967
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
N-acetyltransferase 1 (NAT1) DE7OAB3 ARY1_HUMAN Substrate [2]
N-acetyltransferase 2 (NAT2) DER7TA0 ARY2_HUMAN Substrate [2]
Arylamine N-acetyltransferase (NAT) DEG7L5K A0A5E5R1G5_PSEAI Substrate [2]
Arylamine N-acetyltransferase (NAT) DE2S6QE A0A1C3HAL9_SERMA Substrate [2]
Arylamine N-acetyltransferase (NAT) DEF5JD3 A0A1C3Q7F5_KLEPN Substrate [2]
Arylamine N-acetyltransferase (NAT) DEJ01UG NHOA_SALTY Substrate [2]
Arylamine N-acetyltransferase (NAT) DEPI0ME A0A0A2RAD0_MORMO Substrate [2]
Arylamine N-acetyltransferase (NAT) DE5DY7B A0A0D7LKP9_CITFR Substrate [2]
Arylamine N-acetyltransferase (NAT) DE97F4R A0A1C3HAL9_SERMA Substrate [2]
Arylamine N-acetyltransferase (NAT) DE14FI7 A0A0H3HB23_KLEOK Substrate [2]
Arylamine N-acetyltransferase (NAT) DEFHZW7 A0A3P8LE58_TSUPA Substrate [2]
Arylamine N-acetyltransferase (NAT) DEKBP7I A0A5E5R1G5_PSEAI Substrate [2]
Arylamine N-acetyltransferase (NAT) DE6C3R7 A0A223JRX2_9ENTR Substrate [2]
Arylamine N-acetyltransferase (NAT) DE8V274 A0A381G6X4_CITAM Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Arylamine N-acetyltransferase 2 (NAT2) OTBPDQOY ARY2_HUMAN Biotransformations [3]
Growth-regulated alpha protein (CXCL1) OT3WCTZV GROA_HUMAN Protein Interaction/Cellular Processes [4]
Heat shock factor protein 1 (HSF1) OTYNJ4KP HSF1_HUMAN Gene/Protein Processing [5]
Metalloproteinase inhibitor 2 (TIMP2) OT8S1RRP TIMP2_HUMAN Gene/Protein Processing [6]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Protein Interaction/Cellular Processes [7]
Solute carrier organic anion transporter family member 1B1 (SLCO1B1) OTNEN8QK SO1B1_HUMAN Regulation of Drug Effects [8]
Solute carrier organic anion transporter family member 1B3 (SLCO1B3) OTOM3BUH SO1B3_HUMAN Regulation of Drug Effects [8]
Solute carrier organic anion transporter family member 2B1 (SLCO2B1) OTERJ4VQ SO2B1_HUMAN Regulation of Drug Effects [8]
Tropomyosin alpha-3 chain (TPM3) OT5RU5G6 TPM3_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 NIH Toxnet: Mesalazine Profile
2 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
3 Eukaryotic arylamine N-acetyltransferase. Investigation of substrate specificity by high-throughput screening. Biochem Pharmacol. 2005 Jan 15;69(2):347-59. doi: 10.1016/j.bcp.2004.09.014. Epub 2004 Nov 24.
4 The effect of sulfasalazine on rheumatoid arthritic synovial tissue chemokine production. Exp Mol Pathol. 2002 Oct;73(2):84-92. doi: 10.1006/exmp.2002.2460.
5 A Gene Expression Biomarker Predicts Heat Shock Factor 1 Activation in a Gene Expression Compendium. Chem Res Toxicol. 2021 Jul 19;34(7):1721-1737. doi: 10.1021/acs.chemrestox.0c00510. Epub 2021 Jun 25.
6 Effects of sulfasalazine and its metabolites on steady state messenger RNA concentrations for inflammatory cytokines, matrix metalloproteinases, and tissue inhibitors of metalloproteinase in rheumatoid synovial fibroblasts. J Rheumatol. 2000 Mar;27(3):653-60.
7 Mesalazine causes a mitotic arrest and induces caspase-dependent apoptosis in colon carcinoma cells. Carcinogenesis. 2003 Mar;24(3):443-51. doi: 10.1093/carcin/24.3.443.
8 Role of organic anion-transporting polypeptides for cellular mesalazine (5-aminosalicylic acid) uptake. Drug Metab Dispos. 2011 Jun;39(6):1097-102.
9 Mesalamine suppresses the expression of TC22, a novel tropomyosin isoform associated with colonic neoplasia. Mol Pharmacol. 2009 Jul;76(1):183-91. doi: 10.1124/mol.109.056028. Epub 2009 Apr 15.