Details of the Drug

General Information of Drug (ID: DMR1NMD)

Drug Name
Nimesulide
Synonyms
nimesulide; 51803-78-2; N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide; Mesulid; Flogovital; Sulidene; Nimed; R-805; 4-NITRO-2-PHENOXYMETHANESULFONANILIDE; Nisulid; Nimesulidum [INN-Latin]; Nimesulida [INN-Spanish]; R 805; UNII-V4TKW1454M; 4-Nitro-2-phenoxy-methanesulfonanilide; 4'-Nitro-2'-phenoxymethanesulfonanilide; Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)-; EINECS 257-431-4; 4'-Nitro-2'-phenoxymethansulfonanilid; BRN 2421175; CHEMBL56367; MLS000069680; V4TKW1454M; Methanesulfonanilide, 4'-nitro-2'-phenoxy-; CHEBI:44445; Dulanermin
Indication
Disease Entry ICD 11 Status REF
Metastatic colorectal cancer 2B91 Terminated [1]
Non-hodgkin lymphoma 2B33.5 Terminated [1]
Non-small-cell lung cancer 2C25.Y Terminated [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 308.31
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption
The drug is rapidly absorbed following oral administration []
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination
2% of drug is excreted from urine in the unchanged form [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.8C4.7 hours [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 9.2671 micromolar/kg/day [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.014 mg/mL [2]
Chemical Identifiers
Formula
C13H12N2O5S
IUPAC Name
N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
Canonical SMILES
CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2=CC=CC=C2
InChI
InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3
InChIKey
HYWYRSMBCFDLJT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4495
ChEBI ID
CHEBI:44445
CAS Number
51803-78-2
DrugBank ID
DB04743
TTD ID
D0C0JT
INTEDE ID
DR1160
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
Lactotransferrin (LTF) TTSZDQU TRFL_HUMAN Inhibitor [5]
Prostaglandin G/H synthase 2 (COX-2) TTVKILB PGH2_HUMAN Inhibitor [5]
TNF related apoptosis inducing ligand (TNFSF10) TTA5MS9 TNF10_HUMAN Modulator [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [7]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Angiopoietin-related protein 4 (ANGPTL4) OTQL5SPX ANGL4_HUMAN Gene/Protein Processing [8]
Angiotensin-converting enzyme 2 (ACE2) OTTRZGU7 ACE2_HUMAN Gene/Protein Processing [9]
Antileukoproteinase (SLPI) OTUNFUU8 SLPI_HUMAN Gene/Protein Processing [10]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [11]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [12]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [13]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Gene/Protein Processing [14]
Bone morphogenetic protein 6 (BMP6) OT9WN536 BMP6_HUMAN Gene/Protein Processing [10]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [15]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Metastatic colorectal cancer
ICD Disease Classification 2B91
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Prostaglandin G/H synthase 2 (COX-2) DTT PTGS2 7.93E-04 -0.29 -0.34
Cytochrome P450 3A4 (CYP3A4) DME CYP3A4 1.04E-02 6.29E-02 3.54E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of Genentech (2011).
2 BDDCS applied to over 900 drugs
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
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 Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
6 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
7 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
8 Regulation of peroxisome proliferator-activated receptor-beta/delta by the APC/beta-CATENIN pathway and nonsteroidal antiinflammatory drugs. Mol Carcinog. 2009 Oct;48(10):942-52. doi: 10.1002/mc.20546.
9 Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Arch Toxicol. 2020 Dec;94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. Epub 2020 Aug 17.
10 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.
11 Effects of cyclooxygenase-2 non-selective and selective inhibitors on proliferation inhibition and apoptosis induction of esophageal squamous carcinoma cells. Dis Esophagus. 2009;22(1):21-31. doi: 10.1111/j.1442-2050.2008.00836.x. Epub 2008 Jun 17.
12 COX-2 inhibitor nimesulide analogs are aromatase suppressors in breast cancer cells. J Steroid Biochem Mol Biol. 2010 Oct;122(4):232-8. doi: 10.1016/j.jsbmb.2010.06.004. Epub 2010 Jun 11.
13 COX-2 inhibitors block chemotherapeutic agent-induced apoptosis prior to commitment in hematopoietic cancer cells. Biochem Pharmacol. 2011 Nov 15;82(10):1277-90. doi: 10.1016/j.bcp.2011.06.028. Epub 2011 Jun 24.
14 Cyclooxygenase-2 inhibitor, nimesulide, improves radiation treatment against non-small cell lung cancer both in vitro and in vivo. Oncol Rep. 2006 Oct;16(4):771-6.
15 Cyclooxygenase inhibitors down regulate P-glycoprotein in human colorectal Caco-2 cell line. Pharm Res. 2008 Sep;25(9):1991-2001. doi: 10.1007/s11095-008-9596-1. Epub 2008 Jun 26.
16 The effect of COX-2 inhibitor, nimesulide, on angiogenetic factors in primary endometrial carcinoma cell culture. Clin Exp Med. 2007 Mar;7(1):6-10. doi: 10.1007/s10238-007-0119-x.