ZOMEPIRAC SODIUM

First approved in 1980

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H13ClNO3.Na.2H2O
Molecular Weight	349.742
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.[Na+].CN1C(CC([O-])=O)=CC(C)=C1C(=O)C2=CC=C(Cl)C=C2

InChI

InChIKey=ZJXLSCXDGPDZOL-UHFFFAOYSA-M

InChI=1S/C15H14ClNO3.Na.2H2O/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);;2*1H2/q;+1;;/p-1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7018870 | https://www.ncbi.nlm.nih.gov/pubmed/7241789 | https://www.drugbank.ca/drugs/DB04828 | https://www.ncbi.nlm.nih.gov/pubmed/7044754

Zomepirac Sodium (Zomax) is a pyrrole-acetic acid structurally related to tolmetin sodium. Zomepirac is a prostaglandin synthetase inhibitor and is not an opioid, an opioid antagonist, or a salicylate. Zomepirac was approved by the Food and Drug Administration for marketing in the United States as an analgesic. It was indicated for all forms of mild to moderately severe pain, and was being promoted as a "comprehensive, non-addicting analgesic." Later Zomepirac was found to be associated with fatal and near-fatal anaphylactoid reactions. The manufacturer voluntarily removed Zomax tablets from the Canadian, US, and UK markets in March 1983.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2096674 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7018870	Inhibitor 8504		15.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7018870 https://www.ncbi.nlm.nih.gov/pubmed/6776300	Primary		Withdrawn	ZOMAX Approved Use ZOMAX is indicated for all forms of mild to moderately severe pain. Launch Date 1979

C_max

Value	Dose	Analyte	Population
2.47 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOMEPIRAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.42 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOMEPIRAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
7.94 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOMEPIRAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
232.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOMEPIRAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
494.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOMEPIRAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1102.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7357796	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	ZOMEPIRAC plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
100 mg 6 times / day multiple, oral Dose: 100 mg, 6 times / day Route: oral Route: multiple Dose: 100 mg, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6222714	unhealthy, 28 years Health Status: unhealthy Age Group: 28 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6222714	Disc. AE: Renal insufficiency... AEs leading to discontinuation/dose reduction: Renal insufficiency (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6222714
300 mg 1 times / day multiple, oral Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6222714	unhealthy, 36-72 years Health Status: unhealthy Age Group: 36-72 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6222714	Disc. AE: Renal insufficiency... AEs leading to discontinuation/dose reduction: Renal insufficiency (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6222714
800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6883915	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6883915	Other AEs: Backache, Nausea... Other AEs: Backache (2 patients) Nausea (2 patients) Churning of stomach (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/6883915

AEs

AE	Significance	Dose	Population
Renal insufficiency	1 patient Disc. AE	100 mg 6 times / day multiple, oral Dose: 100 mg, 6 times / day Route: oral Route: multiple Dose: 100 mg, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6222714	unhealthy, 28 years Health Status: unhealthy Age Group: 28 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6222714
Renal insufficiency	2 patients Disc. AE	300 mg 1 times / day multiple, oral Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6222714	unhealthy, 36-72 years Health Status: unhealthy Age Group: 36-72 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/6222714
Backache	2 patients	800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6883915	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6883915
Churning of stomach	2 patients	800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6883915	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6883915
Nausea	2 patients	800 mg 1 times / day single, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: single Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6883915	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/6883915

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252		substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP1A2 1197 CYP2C8 810 CYP2E1 729

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 6.0	no

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0	no
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 3.0	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16251255/ Page: 6.0	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-044091	http://www.3bsc.com/index/pro_info.php?id=76290
AA Blocks	AA003VCA	https://www.aablocks.com/goods/Goods/detail?id=AA003VCA
AbMole Bioscience	M6067	http://www.abmole.com/products/zomepirac-sodium-salt.html
AHH Chemical co.,ltd	MT-60607	http://www.ahhchemical.com/product/MT-60607.html
Ambinter	Amb10843649	http://www.ambinter.com/reference/10843649
Ambinter	Amb22352686	http://www.ambinter.com/reference/22352686
Angel Pharmatech	AG302903	http://www.angelpharmatech.com/64092-48-4.html
Aurora Fine Chemicals LLC	A06.999.444	http://online.aurorafinechemicals.com/info?ID=A06.999.444
Aurora Fine Chemicals LLC	A17.913.073	http://online.aurorafinechemicals.com/info?ID=A17.913.073
BOC Sciences	33369-31-2	https://www.bocsci.com/zomepirac-cas-33369-31-2-item-109159.html
BOC Sciences	64092-48-4	https://www.bocsci.com/zomepirac-sodium-cas-64092-48-4-item-74212.html
Chem Scene	CS-4353	http://www.chemscene.com/64092-48-4.html
ChemMol	30106032	http://www.chemmol.com/chemmol/30106032.html
ChemMol	99071483	http://www.chemmol.com/chemmol/99071483.html
ChemMol	99123860	http://www.chemmol.com/chemmol/99123860.html
Chemspace	CSSB00000078942	https://chem-space.com/CSSB00000078942
Debye Scientific	DA-06775	http://www.debyesci.com/cas_33369-31-2.html
Finetech	FT-0675929	http://www.finetechnology-ind.com/prod/detail/pub/64092-48-4.html
Finetech	FT-0708860	http://www.finetechnology-ind.com/prod/detail/pub/33369-31-2.html
Glentham Life Sciences	GP8300	http://www.glentham.com/products/product/GP8300/
mcule	MCULE-3654355863	https://mcule.com/MCULE-3654355863/
MedChem Express	HY-B0890	https://www.medchemexpress.com/Zomepirac-sodium-salt.html
Molcore	MC549251	https://www.molcore.com/product/33369-31-2
Molcore	MC565048	https://www.molcore.com/product/64092-48-4
MolPort	MolPort-005-936-008	https://www.molport.com/shop/molecule-link/MolPort-005-936-008
MuseChem	I004423	https://www.musechem.com/product/I004423.html
Sigma-Aldrich	Z2625_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/z2625?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S573360	https://www.smolecule.com/products/s573360
Yuhao Chemical	RT2519	http://www.chemyuhao.com/64092-48-4.html

PubMed

Title	Date	PubMed
Downstream gene activation of the receptor ALX by the agonist annexin A1.	2010-09-17	20862244
The pharmacokinetic profile of a novel fixed-dose combination tablet of ibuprofen and paracetamol.	2010-07-05	20602760
Neuroprotective effects of zonisamide target astrocyte.	2010-02	20225289
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009-12-02	19956587
Entrapment of ketorolac tromethamine in polymeric vehicle for controlled drug delivery.	2009-11	20376226
Type 5 17beta-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs.	2009-03-16	19010312
The effects of etodolac, nimesulid and naproxen sodium on the frequency of sister chromatid exchange after enclused third molars surgery.	2008-10-31	18972594
Faecal blood loss with aspirin, nonsteroidal anti-inflammatory drugs and cyclo-oxygenase-2 selective inhibitors: systematic review of randomized trials using autologous chromium-labelled erythrocytes.	2008	18201374
Determination of degradation pathways and kinetics of acyl glucuronides by NMR spectroscopy.	2007-06	17536843
Clinical management of adult patients with a history of nonsteroidal anti-inflammatory drug-induced urticaria/angioedema: update.	2007-03-15	20525150
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin.	2007-01-31	17243824
Angioedema: clinical and etiological aspects.	2007	18317527
A simple in vitro model to study the stability of acylglucuronides.	2006-03-23	16713308
Effect of drug utilization reviews on the quality of in-hospital prescribing: a quasi-experimental study.	2006-03-14	16536865
Predicting the pharmacokinetics of acyl glucuronides and their parent compounds in disease states.	2006-02	16472105
Pharmaceutical quality control of acid and neutral drugs based on competitive self-assembly in amphiphilic systems.	2006-01	16365667
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.	2006-01	16251255
In vitro and in vivo studies on acyl-coenzyme A-dependent bioactivation of zomepirac in rats.	2005-11	16300382
ABC transporters as multidrug resistance mechanisms and the development of chemosensitizers for their reversal.	2005-10-04	16202168
I almost crossed over.	2005-10	17094512
Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2.	2005-03	15563582
Evaluation of a lymph node proliferation assay for its ability to detect pharmaceuticals with potential to cause immune-mediated drug reactions.	2005-01-01	18958655
Photolysis of NSAIDs. IV. Photoproducts of zomepirac determined by LC-ESI-MS.	2004-12	15386573
Identification of zomepirac-S-acyl-glutathione in vitro in incubations with rat hepatocytes and in vivo in rat bile.	2003-11	14570776
Investigating the TNP-OVA and direct popliteal lymph node assays for the detection of immunostimulation by drugs associated with anaphylaxis in humans.	2002-05-17	12015798
Hepatic covalent adduct formation with zomepirac in the CD26-deficient mouse.	2002-01	11895555
Reversible binding of tolmetin, zomepirac, and their glucuronide conjugates to human serum albumin and plasma.	1994-02	8027947
Reinduction of the hypnotic effects of thiopental with NSAIDs by decreasing thiopental plasma protein binding in humans.	1993-04	8517101
Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs.	1993-01	8423545
Zomepirac-induced anaphylactic shock: an under-reported phenomenon.	1985-10	4073114
Reversible renal failure and nephrotic syndrome without interstitial nephritis from zomepirac.	1985-10	3901736
Nephrotoxicity from nonsteroidal anti-inflammatory drugs.	1985-03	3975749
Severe coronary spasm during zomepirac-induced allergic reaction.	1984-07	6610944
A zomepirac reaction mimicking ectopic pregnancy.	1984-06	6734436
Focal renal cortical necrosis associated with zomepirac.	1984-06	6731466
Interstitial nephritis, proteinuria, and renal failure caused by nonsteroidal anti-inflammatory drugs. Immunologic characterization of the inflammatory infiltrate.	1984-06	6375363
Interstitial nephritis and proteinuria associated with zomepirac.	1984-03-01	6723230
Long-term therapy for the pain of osteoarthritis: a comparison of zomepirac sodium and aspirin.	1983-11-01	6363464
Influence of uremia, hemodialysis, and nonesterified fatty acids on zomepirac plasma protein binding.	1983-11	6627828
Zomepirac-induced renal failure.	1983-06	6222714
Nonoliguric renal failure associated with zomepirac.	1983-04-01	6827751
Effect of zomepirac on experimental coronary artery thrombosis and ischemic myocardial injury in the conscious dog.	1983-03-01	6188907
Renal failure and tubular dysfunction due to zomepirac therapy.	1983-01-21	6848832
Zomepirac-related acute renal failure.	1983-01	6825559
Zomepirac, interstitial nephritis, and renal failure.	1982-09	7114649
Reversible nonoliguric acute renal failure associated with zomepirac therapy.	1982-06	7078269
Anaphylactic shock, acute renal failure, and disseminated intravascular coagulation. Suspected complications of zomepirac.	1982-02-26	7057609
Orally administered zomepirac and parenterally administered morphine. Comparison for the treatment of postoperative pain.	1980-11-21	6776300
Long-term safety of zomepirac: a double-blind comparison with aspirin in patients with osteoarthritis.	1980-05-01	6995502
Clinical analgesic assay of oral zomepirac and intramuscular morphine.	1979	121342

Patents

Sample Use Guides

In Vivo Use Guide

The oral dose of zomepirac for mild to moderately severe pain is 50-100 mg every four to six hours. In acute moderate to severe pain in adults, a 100-mg dose would be reasonable initial therapy. In chronic pain situations, the 50-mg dose may be as effective in some patients as the 100-mg dose. Doses of more than 100 mg are not recommended.

Route of Administration: Oral

In Vitro Use Guide

Zomepirac failed to displace tritiated etorphine significantly at concentrations up to 200 umol/l. It was active (3-7 X 10(-5) mol/l) on both the electrically stimulated guinea pig ileum and mouse vas deferens but was less efficacious than morphine; these effects were not reversed by narcotic antagonists.

Name

Type

Language

ZOMEPIRAC SODIUM SALT DIHYDRATE

Preferred Name

English

ZOMEPIRAC SODIUM

Official Name

English

ZOMEPIRAC SODIUM SALT DIHYDRATE [MI]

Common Name

English

ZOMEPIRAC SODIUM [MART.]

Common Name

English

ZOMEPIRAC SODIUM [USAN]

Common Name

English

1H-PYRROLE-2-ACETIC ACID, 5-(4-CHLOROBENZOYL)-1,4-DIMETHYL-, SODIUM SALT, HYDRATE (1:1:2)

Common Name

English

SODIUM 5-(P-CHLOROBENZOYL)-1,4-DIMETHYLPYRROLE-2-ACETATE DIHYDRATE

Common Name

English

ZOMAXIN

Brand Name

English

MCN-2783-21-98

Code

English

ZOMAX

Common Name

English

1H-PYRROLE-2-ACETIC ACID, 5-(4-CHLOROBENZOYL)-1,4-DIMETHYL-, SODIUM SALT, DIHYDRATE

Common Name

English

NSC-757379

Code

English

ZOPIRAC

Brand Name

English

Classification Tree Code System Code

CFR

21 CFR 216.24