Details of the Drug

General Information of Drug (ID: DM7APNJ)

Drug Name
Zomepirac
Synonyms
ZOMEPIRAC SODIUM; Zomepirac sodium [USAN:USP]; UNII-Y0185WZ209; McN-2783-21-98; Y0185WZ209; 64092-49-5; Zomepirac sodium dihydrate; 1H-Pyrrole-2-acetic acid, 5-(4-chlorobenzoyl)-1,4-dimethyl-, sodium salt, dihydrate; Zomepirac sodium (USAN); CHEMBL3989403; DTXSID60214282; ZJXLSCXDGPDZOL-UHFFFAOYSA-M; D06382; Sodium 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetate dihydrate; Sodium 5-(4-chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetate Dihydrate
Indication
Disease Entry ICD 11 Status REF
Pain MG30-MG3Z Withdrawn from market [1]
Affected Organisms
Humans and other mammals
ATC Code
M01AB04: Zomepirac
M01AB: Acetic acid derivatives and related substances
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) 291.73
Logarithm of the Partition Coefficient (xlogp) 2.8
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Chemical Identifiers
Formula
C15H14ClNO3
IUPAC Name
2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
Canonical SMILES
CC1=C(N(C(=C1)CC(=O)O)C)C(=O)C2=CC=C(C=C2)Cl
InChI
InChI=1S/C15H14ClNO3/c1-9-7-12(8-13(18)19)17(2)14(9)15(20)10-3-5-11(16)6-4-10/h3-7H,8H2,1-2H3,(H,18,19)
InChIKey
ZXVNMYWKKDOREA-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5733
ChEBI ID
CHEMBL19490
CAS Number
33369-31-2
UNII
822G987U9J
DrugBank ID
DB04828
TTD ID
D0SU1G
INTEDE ID
DR1736
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Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase (COX) TTK0943 PGH1_HUMAN ; PGH2_HUMAN Modulator [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4)
Main DME 		DE4LYSA CP3A4_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [5]
Aldo-keto reductase family 1 member C1 (AKR1C1) OTQKR4CM AK1C1_HUMAN Gene/Protein Processing [6]
Aldo-keto reductase family 1 member C2 (AKR1C2) OTQ2XMO3 AK1C2_HUMAN Gene/Protein Processing [6]
Aldo-keto reductase family 1 member C3 (AKR1C3) OTU2SXBA AK1C3_HUMAN Gene/Protein Processing [6]
Dehydrogenase/reductase SDR family member 11 (DHRS11) OTU3J0ZL DHR11_HUMAN Gene/Protein Processing [7]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [8]
UDP-glucuronosyltransferase 2B7 OT2Q71VQ UD2B7_HUMAN Biotransformations [9]
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References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3 Effect of preischemia cyclooxygenase inhibition by zomepirac sodium on reflow, cerebral autoregulation, and EEG recovery in the cat after global ischemia. J Cereb Blood Flow Metab. 1986 Dec;6(6):691-702.
4 Evidence for the bioactivation of zomepirac and tolmetin by an oxidative pathway: identification of glutathione adducts in vitro in human liver microsomes and in vivo in rats. Drug Metab Dispos. 2006 Jan;34(1):145-51.
5 Influence of uremia, hemodialysis, and nonesterified fatty acids on zomepirac plasma protein binding. Clin Pharmacol Ther. 1983 Nov;34(5):681-8. doi: 10.1038/clpt.1983.232.
6 Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs. Chem Biol Interact. 2009 Mar 16;178(1-3):221-7.
7 Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chem Biol Interact. 2019 May 25;305:12-20. doi: 10.1016/j.cbi.2019.03.026. Epub 2019 Mar 26.
8 Neutrophil depletion protects against zomepirac-induced acute kidney injury in mice. Chem Biol Interact. 2018 Jan 5;279:102-110. doi: 10.1016/j.cbi.2017.11.011. Epub 2017 Nov 14.
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.