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Pain	MG30-MG3Z	Withdrawn from market	[1]
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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)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

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: CHEBI:35859
CAS Number: 33369-31-2
DrugBank ID: DB04828
TTD ID: D0SU1G
INTEDE ID: DR1736

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]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)_{Main DME}	DE4LYSA	CP3A4_HUMAN	Substrate	[4]

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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-1 alpha (IL1A)	OTPSGILV	IL1A_HUMAN	Gene/Protein Processing	[8]
Interleukin-6 (IL6)	OTUOSCCU	IL6_HUMAN	Gene/Protein Processing	[8]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 2B7	OT2Q71VQ	UD2B7_HUMAN	Biotransformations	[9]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

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.