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Details

Stereochemistry ACHIRAL
Molecular Formula C15H13ClFNO2
Molecular Weight 293.7211
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LUMIRACOXIB

SMILES

Cc1ccc(c(c1)CC(=O)O)Nc2c(cccc2F)Cl

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 293.7211
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment:: # Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
3.22 µM [IC50]
1.9 µM [IC50]
3.3 µM [IC50]
833.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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

1.08855362E12
Palliative
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

1.08855362E12
PubMed

PubMed

TitleDatePubMed
COX-2 drug may help treat osteoarthritis.
2004 Dec
Novel insights and therapeutical applications in the field of inhibitors of COX-2.
2004 Dec
Chinese herbal recipe versus diclofenac in symptomatic treatment of osteoarthritis of the knee: a randomized controlled trial [ISRCTN70292892].
2004 Dec 13
Gateways to clinical trials.
2004 Nov
Efficacy, safety and tolerability of lumiracoxib in patients with rheumatoid arthritis.
2004 Nov
The future of traditional nonsteroidal antiinflammatory drugs and cyclooxygenase-2 inhibitors in the treatment of inflammation and pain.
2005
Clinical pharmacology of lumiracoxib: a selective cyclo-oxygenase-2 inhibitor.
2005
Cardiovascular and gastrointestinal effects of COX-2 inhibitors and NSAIDs: achieving a balance.
2005
Current state of therapy for pain and inflammation.
2005
Efficacy and tolerability of lumiracoxib 100 mg once daily in knee osteoarthritis: a 13-week, randomized, double-blind study vs. placebo and celecoxib.
2005 Apr
Clinical pharmacology of lumiracoxib, a second-generation cyclooxygenase 2 selective inhibitor.
2005 Apr
Peripheral and spinal mechanisms of antinociceptive action of lumiracoxib.
2005 Apr 18
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 Aug
Monocyte cyclooxygenase-2 activity: a new therapeutic target for atherosclerosis?
2005 Aug
Update on cyclooxygenase inhibitors: has a third COX isoform entered the fray?
2005 Aug
Treatment of osteoarthritis of the knee with a topical diclofenac solution: a randomised controlled, 6-week trial [ISRCTN53366886].
2005 Aug 8
Gateways to clinical trials.
2005 Dec
Oral administration of lumiracoxib reduces choroidal neovascular membrane development in the rat laser-trauma model.
2005 Dec
The safety of lumiracoxib when used in the treatment of arthritis.
2005 Feb
Preclinical pharmacology of lumiracoxib: a novel selective inhibitor of cyclooxygenase-2.
2005 Feb
Safety and efficacy of lumiracoxib compared with NSAIDs.
2005 Jan
Lumiracoxib in the treatment of osteoarthritis, rheumatoid arthritis and acute postoperative dental pain: results of three dose-response studies.
2005 Jan
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 Jan
Gateways to clinical trials.
2005 Jan-Feb
Efficacy of lumiracoxib in osteoarthritis: a review of nine studies.
2005 Jan-Feb
Gateways to clinical trials.
2005 Jul-Aug
Relative thromboembolic risks associated with COX-2 inhibitors.
2005 Jul-Aug
[Lumiracoxib reduces ulcer complications in comparison to NSAR].
2005 Mar-Apr
Lumiracoxib reduced ulcer complications compared with ibuprofen and naproxen in osteoarthritis and did not increase cardiovascular outcomes.
2005 Mar-Apr
Pharmacodynamic behaviour of the selective cyclooxygenase-2 inhibitor lumiracoxib in the lipopolysaccharide-stimulated rat air pouch model.
2005 May
Gateways to clinical trials.
2005 Nov
The post-operative analgesic efficacy and tolerability of lumiracoxib compared with placebo and naproxen after total knee or hip arthroplasty.
2005 Nov
Lumiracoxib is effective in the treatment of episodic tension-type headache.
2005 Oct
Lumiracoxib does not affect the ex vivo antiplatelet aggregation activity of low-dose aspirin in healthy subjects.
2005 Oct
Risk of acute myocardial infarction with nonselective non-steroidal anti-inflammatory drugs: a meta-analysis.
2006
Patients, their doctors, nonsteroidal anti-inflammatory drugs and the perception of risk.
2006
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
Differential direct effects of cyclo-oxygenase-1/2 inhibition on proteoglycan turnover of human osteoarthritic cartilage: an in vitro study.
2006
Systemic inflammation induces COX-2 mediated prostaglandin D2 biosynthesis in mice spinal cord.
2006 Feb
Lumiracoxib is effective in the treatment of osteoarthritis of the knee: a prospective randomized 13-week study versus placebo and celecoxib.
2006 Feb
Gastrointestinal tolerability of lumiracoxib in patients with osteoarthritis and rheumatoid arthritis.
2006 Jan
Systematic review: coxibs, non-steroidal anti-inflammatory drugs or no cyclooxygenase inhibitors in gastroenterological high-risk patients?
2006 Jan 1
Gateways to clinical trials.
2006 Jan-Feb
Gateways to clinical trials.
2006 Jul-Aug
Influence of plasma protein on the potencies of inhibitors of cyclooxygenase-1 and -2.
2006 Mar
[Cyclooxygenase-2: a new therapeutic target in atherosclerosis?].
2006 May 27
COX-2 inhibitors and cardiovascular risk. Inferences based on biology and clinical studies.
2006 Oct
Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials.
2006 Oct 4
Gateways to clinical trials.
2006 Sep
Cardioprotective aspirin users and their excess risk of upper gastrointestinal complications.
2006 Sep 20
Patents

Patents

Sample Use Guides

Oral Osteoarthritis of the knee Adult: 100 mg once daily. Max: 400 mg/day.
Route of Administration: Oral
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 Sat Jun 26 09:44:06 UTC 2021
Edited
by admin
on Sat Jun 26 09:44:06 UTC 2021
Record UNII
V91T9204HU
Record Status Validated (UNII)
Record Version
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Name Type Language
LUMIRACOXIB
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
COX-189
Code English
LUMIRACOXIB [WHO-DD]
Common Name 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 [INN]
Common Name English
BENZENEACETIC ACID, 2-((2-CHLORO-6-FLUOROPHENYL)AMINO)-5-METHYL-
Common Name English
LUMIRACOXIB [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
WHO-VATC QM01AH06
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
WHO-ATC M01AH06
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL404108
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
DRUG CENTRAL
1618
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
MESH
C473384
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
WIKIPEDIA
LUMIRACOXIB
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
PUBCHEM
151166
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
INN
8151
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
EPA CompTox
220991-20-8
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
MERCK INDEX
M6931
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB01283
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
FDA UNII
V91T9204HU
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
EVMPD
SUB21406
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
CAS
220991-20-8
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
IUPHAR
2897
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
NCI_THESAURUS
C66041
Created by admin on Sat Jun 26 09:44:07 UTC 2021 , Edited by admin on Sat Jun 26 09:44:07 UTC 2021
PRIMARY
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ORAL ADMINISTRATION

SINGLE DOSE

Tmax PHARMACOKINETIC SINGLE DOSE

ORAL ADMINISTRATION