Details of the Drug

General Information of Drug (ID: DMENSL5)

Drug Name
Aminosalicylic Acid
Synonyms
4-Aminosalicylic acid; 65-49-6; Aminosalicylic acid; P-AMINOSALICYLIC ACID; Rezipas; Aminopar; Pamisyl; Parasalindon; Ferrosan; Deapasil; Apacil; Parasal; Paser; Paramycin; Gabbropas; Parasalicil; Pasnodia; Osacyl; Aminox; Pasolac; Pasmed; Propasa; Pasalon; Entepas; Pasdium; Pasara; Pamacyl; Pasem; Pasa; 2-Hydroxy-4-aminobenzoic acid; PASK; APAS; Para-Pas; Sanipirol-4; Hellipidyl; Pascorbic; PAS-C; Benzoic acid, 4-amino-2-hydroxy-; PAS (acid); Aminosalicylic Acid Resin Complex; Aminosalicylate Sodium
Indication
Disease Entry ICD 11 Status REF
Crohn disease DD70 Approved [1]
Inflammatory bowel disease DD72 Approved [2]
Pulmonary and extrapulmonary tuberculosis 1B10.Z Approved [2]
Pulmonary tuberculosis 1B10.Z Approved [1]
Ulcerative colitis DD71 Approved [1]
Affected Organisms
Mycobacteria
ATC Code
J04AA01: Aminosalicylic Acid
J04AA: Aminosalicylic acid and derivatives
J04A: DRUGS FOR TREATMENT OF TUBERCULOSIS
J04: ANTIMYCOBACTERIALS
J: ANTIINFECTIVES FOR SYSTEMIC USE
Drug Type
Small molecular drug
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
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Elimination
2% of drug is excreted from urine in the unchanged form [3]
Metabolism
The drug is metabolized via the hepatic []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1306.00525 micromolar/kg/day [4]
Water Solubility
The ability of drug to dissolve in water is measured as 142.85 mg/mL [3]
Chemical Identifiers
Formula
C7H7NO3
IUPAC Name
4-amino-2-hydroxybenzoic acid
Canonical SMILES
C1=CC(=C(C=C1N)O)C(=O)O
InChI
InChI=1S/C7H7NO3/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,9H,8H2,(H,10,11)
InChIKey
WUBBRNOQWQTFEX-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4649
ChEBI ID
CHEMBL1169
CAS Number
65-49-6
UNII
5B2658E0N2
DrugBank ID
DB00233
TTD ID
D01WJL
VARIDT ID
DR01160
INTEDE ID
DR1748
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
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Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dihydrofolate reductase (DHFR) TTYZVDJ DYR_HUMAN Modulator [5]
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Modulator [5]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Modulator [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Sodium-coupled neutral amino acid transporter 3 (SLC38A3) DTKWJH3 S38A3_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
N-acetyltransferase 2 (NAT2)
Main DME 		DER7TA0 ARY2_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Antileukoproteinase (SLPI) OTUNFUU8 SLPI_HUMAN Gene/Protein Processing [8]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [8]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [8]
Proepiregulin (EREG) OTRM4NQY EREG_HUMAN Gene/Protein Processing [8]
PTB-containing, cubilin and LRP1-interacting protein (PID1) OT5YJ7FI PCLI1_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Crohn disease
ICD Disease Classification DD70
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 2.03E-07 1.68 3.86
Prostaglandin G/H synthase 1 (COX-1) DTT PTGS1 4.06E-03 -0.9 -2.26
Sodium-coupled neutral amino acid transporter 3 (SLC38A3) DTP SNAT3 1.97E-01 -1.70E-01 -3.65E-01
N-acetyltransferase 2 (NAT2) DME NAT2 1.27E-04 -1.50E+00 -3.00E+00
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Aminosalicylic Acid (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [9]
Thioguanine DM7NKEV Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Thioguanine. Acute myeloid leukaemia [2A60] [10]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [11]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [12]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Cannabidiol. Epileptic encephalopathy [8A62] [13]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Brentuximab vedotin. Hodgkin lymphoma [2B30] [14]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [15]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Mipomersen. Hyper-lipoproteinaemia [5C80] [16]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Teriflunomide. Hyper-lipoproteinaemia [5C80] [17]
BMS-201038 DMQTAGO Major Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and BMS-201038. Hyper-lipoproteinaemia [5C80] [18]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Methotrexate. Leukaemia [2A60-2B33] [13]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Idelalisib. Mature B-cell leukaemia [2A82] [19]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Clofarabine. Mature B-cell lymphoma [2A85] [20]
Prilocaine DMI7DZ2 Major Increased risk of methemoglobinemia by the combination of Aminosalicylic acid and Prilocaine. Pain [MG30-MG3Z] [21]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Leflunomide. Rheumatoid arthritis [FA20] [17]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [13]
Epirubicin DMPDW6T Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Epirubicin. Solid tumour/cancer [2A00-2F9Z] [9]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Aminosalicylic acid and Naltrexone. Substance abuse [6C40] [22]
⏷ Show the Full List of 18 DDI Information of This Drug

References

1 Aminosalicylic acid FDA Label
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 BDDCS applied to over 900 drugs
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Identification of amino acids imparting acceptor substrate selectivity to human arylamine acetyltransferases NAT1 and NAT2. Biochem J. 2000 May 15;348 Pt 1:159-66.
7 Importance of the evaluation of N-acetyltransferase enzyme activity prior to 5-aminosalicylic acid medication for ulcerative colitis. Inflamm Bowel Dis. 2016 Aug;22(8):1793-802.
8 An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
9 Cerner Multum, Inc. "Australian Product Information.".
10 Product Information. Aubagio (teriflunomide). Genzyme Corporation, Cambridge, MA.
11 Product Information. Sirturo (bedaquiline). Janssen Pharmaceuticals, Titusville, NJ.
12 Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
13 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
14 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
15 Elsharkawy AM, Schwab U, McCarron B, et al. "Efavirenz induced acute liver failure requiring liver transplantation in a slow drug metaboliser." J Clin Virol 58 (2013): 331-3. [PMID: 23763943]
16 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
17 Canadian Pharmacists Association.
18 Product Information. Juxtapid (lomitapide). Aegerion Pharmaceuticals Inc, Cambridge, MA.
19 Product Information. Zydelig (idelalisib). Gilead Sciences, Foster City, CA.
20 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
21 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
22 Product Information. ReVia (naltrexone). DuPont Pharmaceuticals, Wilmington, DE.