LUMIRACOXIB

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H13ClFNO2
Molecular Weight	293.721
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(NC2=C(F)C=CC=C2Cl)C(CC(O)=O)=C1

InChI

InChIKey=KHPKQFYUPIUARC-UHFFFAOYSA-N

InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)

HIDE SMILES / InChI

Molecular Formula	C15H13ClFNO2
Molecular Weight	293.721
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugbank.ca/drugs/DB01283
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15311562

Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug. It has never been approved for use in the United States. Lumiracoxib has a different structure from the standard COX-2 inhibitors (e.g. celecoxib). It more closely resembles the structure of diclofenac (one chlorine substituted by fluorine, the phenylacetic acid has another methyl group in meta position), making it a member of the arylalkanoic acid family of NSAIDs. It binds to a different site on the COX-2 receptor than the standard COX-2 inhibitors. It displays extremely high COX-2 selectivity. The mechanism of action of lumiracoxib is due to inhibition of prostaglandin synthesis via inhibition of cyclooygenase-2 (COX-2). Lumiracoxib does not inhibit COX-1 at therapeutic concentrations. Lumiracoxib is used for the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.drugbank.ca/drugs/DB01283	Inhibitor 8504	3.5 nM [IC50]
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.drugbank.ca/drugs/DB01283	Inhibitor 8504	3.22 µM [IC50]
Solute carrier family 22 member 8 17 Target ID: CHEMBL1641348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877132	Inhibitor 8504	1.9 µM [IC50]
Solute carrier family 22 member 6 19 Target ID: CHEMBL1641347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877132	Inhibitor 8504	3.3 µM [IC50]
NCI-H460 5 Target ID: CHEMBL396 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18466679	Inhibitor 8504	833.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteoarthritis 157 Sources: https://www.tga.gov.au/alert/lumiracoxib-prexige-urgent-advice-regarding-management-patients	Palliative		Approved 8583	Prexige Approved Use Lumiracoxib (tradename Prexige) was approved for the indications: Symptomatic relief in the treatment of osteoarthritis. Relief of acute pain, including post-operative pain and pain related to dental procedures. Relief of pain due to primary dysmenorrhoea. Launch Date 2004
Pain 619 Sources: https://www.tga.gov.au/alert/lumiracoxib-prexige-urgent-advice-regarding-management-patients	Palliative		Approved 8583	Prexige Approved Use Lumiracoxib (tradename Prexige) was approved for the indications: Symptomatic relief in the treatment of osteoarthritis. Relief of acute pain, including post-operative pain and pain related to dental procedures. Relief of pain due to primary dysmenorrhoea. Launch Date 2004

C_max

Value	Dose	Analyte	Population
2550.4 ng/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/10.1046/j.1365-2036.2003.01691.x	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status:
7.28 μg × eq/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15100180/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6635 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15139795/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6689 ng/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7486 ng/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3165 ng/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3039 ng/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4719 ng/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
12502 ng × h/mL EXPERIMENT https://onlinelibrary.wiley.com/doi/10.1046/j.1365-2036.2003.01691.x	200 mg 2 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status:
48.4 μg × eq × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15100180/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
31942 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15139795/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
29036 ng × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
28654 ng × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11074 ng × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
10644 ng × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
14231 ng × h/mL OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=91	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15100180/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:		LUMIRACOXIB plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15139795/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15139795/	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		LUMIRACOXIB plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1% OTHER GOV'T https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=43 \| https://mhraproducts4853.blob.core.windows.net/docs/57920ad7838765ea88ca7e6139bfb364771a77d2#page=95			LUMIRACOXIB plasma	Homo sapiens

Doses

Dose	Population	Adverse events
800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15017615/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15017615/	Sources: https://pubmed.ncbi.nlm.nih.gov/15017615/
800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	Other AEs: Abdominal pain NOS, Abdominal pain upper... Other AEs: Abdominal pain NOS (1.8%) Abdominal pain upper (10.6%) Diarrhoea NOS (7.9%) Dyspepsia (27.8%) GI upset (4.4%) Nausea (8.8%) Headache (16.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/

AEs

AE	Significance	Dose	Population
Abdominal pain NOS	1.8%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/
Abdominal pain upper	10.6%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/
Headache	16.3%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/
Dyspepsia	27.8%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/
GI upset	4.4%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/
Diarrhoea NOS	7.9%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/
Nausea	8.8%	800 mg 1 times / day multiple, oral Highest studied dose Dose: 800 mg, 1 times / day Route: oral Route: multiple Dose: 800 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15153172/

PubMed

Title	Date	PubMed
Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials.	2006-10-04	16968832
Selective COX-2 inhibitors and risk of thromboembolic events - regulatory aspects.	2006-10	17003918
COX-2 inhibitors and cardiovascular risk. Inferences based on biology and clinical studies.	2006-10	17003914
A validated high-performance liquid chromatographic assay for determination of lumiracoxib in human plasma.	2006-10	16602135
Cardioprotective aspirin users and their excess risk of upper gastrointestinal complications.	2006-09-20	16987411
Gateways to clinical trials.	2006-09	17003851
Gateways to clinical trials.	2006-08-09	16894408
Accounting for the increase in NSAID expenditure: substitution or leakage?	2006-05-31	16737538
[Cyclooxygenase-2: a new therapeutic target in atherosclerosis?].	2006-05-27	16792983
Different COX-independent effects of the COX-2 inhibitors etoricoxib and lumiracoxib.	2006-04-14	16598848
Gateways to clinical trials.	2006-03-17	16541195
Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2.	2006-03	16403783
Systemic inflammation induces COX-2 mediated prostaglandin D2 biosynthesis in mice spinal cord.	2006-02	16182321
Lumiracoxib is effective in the treatment of osteoarthritis of the knee: a prospective randomized 13-week study versus placebo and celecoxib.	2006-02	16132165
Systematic review: coxibs, non-steroidal anti-inflammatory drugs or no cyclooxygenase inhibitors in gastroenterological high-risk patients?	2006-01-01	16393277
Gastrointestinal tolerability of lumiracoxib in patients with osteoarthritis and rheumatoid arthritis.	2006-01	16431306
Risk of acute myocardial infarction with nonselective non-steroidal anti-inflammatory drugs: a meta-analysis.	2006	16995929
Patients, their doctors, nonsteroidal anti-inflammatory drugs and the perception of risk.	2006	16542490
First-dose analgesic effect of the cyclo-oxygenase-2 selective inhibitor lumiracoxib in osteoarthritis of the knee: a randomized, double-blind, placebo-controlled comparison with celecoxib [NCT00267215].	2006	16469112
Differential direct effects of cyclo-oxygenase-1/2 inhibition on proteoglycan turnover of human osteoarthritic cartilage: an in vitro study.	2006	16356188
Gateways to clinical trials.	2005-12	16395422
Oral administration of lumiracoxib reduces choroidal neovascular membrane development in the rat laser-trauma model.	2005-12	16340537
Gateways to clinical trials.	2005-11	16357953
The post-operative analgesic efficacy and tolerability of lumiracoxib compared with placebo and naproxen after total knee or hip arthroplasty.	2005-11	16223396
Lumiracoxib is effective in the treatment of episodic tension-type headache.	2005-10	16178946
Lumiracoxib does not affect the ex vivo antiplatelet aggregation activity of low-dose aspirin in healthy subjects.	2005-10	16172182
Gateways to clinical trials.	2005-09-24	16179960
Treatment of osteoarthritis of the knee with a topical diclofenac solution: a randomised controlled, 6-week trial [ISRCTN53366886].	2005-08-08	16086839
Cardiovascular safety of lumiracoxib: a meta-analysis of all randomized controlled trials > or =1 week and up to 1 year in duration of patients with osteoarthritis and rheumatoid arthritis.	2005-08	16199245
Monocyte cyclooxygenase-2 activity: a new therapeutic target for atherosclerosis?	2005-08	16101563
Update on cyclooxygenase inhibitors: has a third COX isoform entered the fray?	2005-08	16083531
Relative thromboembolic risks associated with COX-2 inhibitors.	2005-06-16	15956235
Pharmacodynamic behaviour of the selective cyclooxygenase-2 inhibitor lumiracoxib in the lipopolysaccharide-stimulated rat air pouch model.	2005-05	15854797
[Lumiracoxib reduces ulcer complications in comparison to NSAR].	2005-04-26	15849631
Gateways to clinical trials.	2005-04-19	15834459
Peripheral and spinal mechanisms of antinociceptive action of lumiracoxib.	2005-04-18	15878712
Efficacy and tolerability of lumiracoxib 100 mg once daily in knee osteoarthritis: a 13-week, randomized, double-blind study vs. placebo and celecoxib.	2005-04	15899100
Clinical pharmacology of lumiracoxib, a second-generation cyclooxygenase 2 selective inhibitor.	2005-04	15882125
Lumiracoxib reduced ulcer complications compared with ibuprofen and naproxen in osteoarthritis and did not increase cardiovascular outcomes.	2005-03-03	15739993
The safety of lumiracoxib when used in the treatment of arthritis.	2005-02	15757430
Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2.	2005-02	15655513
Efficacy of lumiracoxib in osteoarthritis: a review of nine studies.	2005-01-18	15651713
Safety and efficacy of lumiracoxib compared with NSAIDs.	2005-01	16265092
Lumiracoxib in the treatment of osteoarthritis, rheumatoid arthritis and acute postoperative dental pain: results of three dose-response studies.	2005-01	15881487
Efficacy and tolerability of lumiracoxib in the treatment of osteoarthritis of the knee: a 13-week, randomized, double-blind comparison with celecoxib and placebo.	2005-01	15763607
The future of traditional nonsteroidal antiinflammatory drugs and cyclooxygenase-2 inhibitors in the treatment of inflammation and pain.	2005	16415488
Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor.	2005	16372823
Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance.	2005	16168077
Current state of therapy for pain and inflammation.	2005	16168076
COX-2 drug may help treat osteoarthritis.	2004-12	15645573

Patents

Sample Use Guides

In Vivo Use Guide

Oral Osteoarthritis of the knee Adult: 100 mg once daily. Max: 400 mg/day.

Route of Administration: Oral

In Vitro Use Guide

Lumiracoxib (15 - 240 umol/L) has an inhibitory effect on the proliferation of A549 and NCI-H460 cell lines in concentration- and time-dependent manners with the IC50 values of 2597 umol/L and 833 umol/L, respectively.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 07:45:53 GMT 2025` Edited by `admin` on `Wed Apr 02 07:45:53 GMT 2025`
Record UNII	V91T9204HU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LUMIRACOXIB

Official Name

English

LUMIRACOXIB [MI]

Preferred Name

English

COX-189

Code

English

2-[(2-Chloro-6-fluorophenyl)amino]-5-methylphenyl]acetic acid

Common Name

English

LUMIRACOXIB [MART.]

Common Name

English

PREXIGE

Brand Name

English

LUMIRACOXIB [USAN]

Common Name

English

Lumiracoxib [WHO-DD]

Common Name

English

lumiracoxib [INN]

Common Name

English

BENZENEACETIC ACID, 2-((2-CHLORO-6-FLUOROPHENYL)AMINO)-5-METHYL-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323