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
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
KBOPZPXVLCULAV-UHFFFAOYSA-N
InChIKey
1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
Cross-matching ID
PubChem CID
4075
ChEBI ID
CHEBI:6775
CAS Number
89-57-6
DrugBank ID
DB00244
INTEDE ID
DR1967

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 1 (NAT1) OTCCNQ3H ARY1_HUMAN Biotransformations [3]
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]
Interleukin-1 beta (IL1B) OT0DWXXB IL1B_HUMAN Gene/Protein Processing [6]
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]
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.