Details of the Drug

General Information of Drug (ID: DM5ZOX8)

Drug Name
Benoxaprofen
Synonyms
Benoxaprofene; Benoxaprofeno; Benoxaprofenum; Coxigon; Inflamid; Opren; Oraflex; Uniprofen; LRCL3794; Lilly 90459; Benoxaprofene [INN-French]; Benoxaprofeno [INN-Spanish]; Benoxaprofenum [INN-Latin]; Dl-Benoxaprofen; Oraflex (TN); Benoxaprofen (USAN/INN); Benoxaprofen [USAN:INN:BAN]; (+-)-2-(p-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid; (-)-2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid; (-)-Benoxaprofen; (1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acid; 2-(2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl)propanoic acid; 2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid; 2-(p-Chlorophenyl)-.alpha.-methyl-5-benzoxazoleacetic acid; 2-[2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
Indication
Disease Entry ICD 11 Status REF
Inflammation 1A00-CA43.1 Withdrawn from market [1]
Affected Organisms
Humans and other mammals
ATC Code
M01AE06: Benoxaprofen
M01AE: Propionic acid derivatives
M01A: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01: ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M: MUSCULO-SKELETAL SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 301.72
Logarithm of the Partition Coefficient (xlogp) 4.1
Rotatable Bond Count (rotbonds) 3
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Chemical Identifiers
Formula
C16H12ClNO3
IUPAC Name
2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
Canonical SMILES
CC(C1=CC2=C(C=C1)OC(=N2)C3=CC=C(C=C3)Cl)C(=O)O
InChI
InChI=1S/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)
InChIKey
MITFXPHMIHQXPI-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
39941
ChEBI ID
CHEBI:76114
CAS Number
51234-28-7
UNII
17SZX404IM
DrugBank ID
DB04812
TTD ID
D00CCI

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Acetoacetyl-CoA thiolase (ACAT1) TTK3C21 THIL_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Drug Response [4]
Beta-glucuronidase (GUSB) OT9N1DK3 BGLR_HUMAN Protein Interaction/Cellular Processes [5]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [6]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [6]
Polyunsaturated fatty acid 5-lipoxygenase (ALOX5) OT7FOIK2 LOX5_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Drug Response [8]
UDP-glucuronosyltransferase 1A9 OTPCHAFX UD19_HUMAN Drug Response [8]
UDP-glucuronosyltransferase 2B7 OT2Q71VQ UD2B7_HUMAN Biotransformations [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Inflammation
ICD Disease Classification 1A00-CA43.1
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Acetoacetyl-CoA thiolase (ACAT1) DTT ACAT1 4.99E-05 0.73 1.46
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Benoxaprofen: side-effect profile in 300 patients. Br Med J (Clin Res Ed). 1982 May 8;284(6326):1365-8.
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Inhibition of lyso-PAF: acetyl-CoA acetyltransferase by salicylates and other compounds. Prostaglandins. 1988 Jun;35(6):939-44.
4 Benoxaprofen photosensitization of cell membrane disruption. J Invest Dermatol. 1984 Mar;82(3):214-8. doi: 10.1111/1523-1747.ep12260034.
5 Effects of benoxaprofen on human neutrophil function. J Rheumatol. 1984 Jun;11(3):265-71.
6 Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
7 In vitro inhibition of leukotriene B4 formation by exogeneous 5-lipoxygenase inhibitors is associated with enhanced generation of 15-hydroxy-eicosatetraenoic acid (15-HETE) by human neutrophils. Arch Dermatol Res. 1988;280(7):430-6.
8 Carboxylic acid drug-induced DNA nicking in HEK293 cells expressing human UDP-glucuronosyltransferases: role of acyl glucuronide metabolites and glycation pathways. Chem Res Toxicol. 2007 Oct;20(10):1520-7. doi: 10.1021/tx700188x. Epub 2007 Sep 20.
9 Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. J Pharmacol Exp Ther. 1993 Jan;264(1):475-9.