MELOXICAM

First approved in 2000

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H13N3O4S2
Molecular Weight	351.401
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(C(=O)NC2=NC=C(C)S2)=C(O)C3=CC=CC=C3S1(=O)=O

InChI

InChIKey=ZRVUJXDFFKFLMG-UHFFFAOYSA-N

InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s026lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/10381057

Meloxicam (brand name Mobic) is an nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Mobic is indicated for the relief of the signs and symptoms of osteoarthritis and rheumatoid arthritis, and has been available in the U.S. since June 2000. The mechanism of action like that of other NSAIDs, is not completely understood but involves inhibition of cyclooxygenase (COX-1 and COX-2). Meloxicam concentrations reached during therapy have produced in vivo effects. Prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain in animal models. Prostaglandins are mediators of inflammation. Because meloxicam is an inhibitor of prostaglandin synthesis, its mode of action may be due to a decrease of prostaglandins in peripheral tissues. MOBIC is contraindicated in patients who have experienced asthma, itching or allergic type reactions after taking aspirin or other NSAIDs. Severe, rarely fatal, anaphylactic-like reactions to NSAIDs have been reported in such patients. As with all NSAIDs, serious GI toxicity such as inflammation, bleeding, ulceration, and perforation of the stomach, small intestine, or large intestine can occur at any time, without symptoms. As with other NSAIDs, meloxicam is not indicated for prevention of thromboembolic events and is not a substitute for aspirin or other drugs indicated for cardiovascular prophylaxis. It was developed by Boehringer Ingelheim and is co-marketed with Abbott Laboratories. Meloxicam is also used in the veterinary field, most commonly in dogs and cats, but also sees off-label use in other animals such as cattle and exotics

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057	Inhibitor 8504		36.6 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057	Inhibitor 8504		4.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Osteoarthritis 157 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s026lbl.pdf	Palliative	Approved 8583	MOBIC Approved Use INDICATIONS & USAGE Meloxicam is a non-steroidal anti-inflammatory drug indicated for: Osteoarthritis (OA) (1.1) Rheumatoid Arthritis (RA) (1.2) Meloxicam is indicated for relief of the signs and symptoms of osteoarthritis [see Clinical Studies (14.1) Launch Date 2000
Rheumatoid arthritis 320 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s026lbl.pdf	Palliative	Approved 8583	MOBIC Approved Use INDICATIONS & USAGE Meloxicam is a non-steroidal anti-inflammatory drug indicated for: Osteoarthritis (OA) (1.1) Rheumatoid Arthritis (RA) (1.2) Meloxicam is indicated for relief of the signs and symptoms of osteoarthritis [see Clinical Studies (14.1) Launch Date 2000
Juvenile rheumatoid arthritis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s026lbl.pdf	Palliative	Approved 8583	MOBIC Approved Use INDICATIONS & USAGE Meloxicam is a non-steroidal anti-inflammatory drug indicated for: Osteoarthritis (OA) (1.1) Rheumatoid Arthritis (RA) (1.2) Meloxicam is indicated for relief of the signs and symptoms of osteoarthritis [see Clinical Studies (14.1) Launch Date 2000

C_max

Value	Dose	Co-administered	Analyte	Population
1.05 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s024s025,021530s014s015lbl.pdf	7.5 mg 1 times / day steady-state, oral dose: 7.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		MELOXICAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1288.8 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26638161	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		MELOXICAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
40875.6 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26638161	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		MELOXICAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
20.1 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s024s025,021530s014s015lbl.pdf	7.5 mg 1 times / day steady-state, oral dose: 7.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		MELOXICAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
23.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26638161	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:		MELOXICAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 150 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 CYP3A 227 CYP2C 20 CYP2B6 926 UGT1A1 246 UGT1A3 89 UGT1A4 98 UGT1A6 136 UGT1A9 148 UGT2B7 197 OATP2B1 157 BSEP 550 MRP3 246 MRP4 290	CYP1A2 1197 MRP4 91 OCT2 434 BCRP 697	P-gp 301

Drug as perpetrator

Target	Modality	Activity
CYP2C 37	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	likely
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/19793025/	likely
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
UGT1A3 99	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
UGT1A4 100	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
UGT1A6 171	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	weak [IC50 77.5 uM]
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/28562037/	yes [IC50 1.6 uM]
UGT1A1 303	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	yes [IC50 124.3 uM]
UGT1A9 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	yes [IC50 131.3 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP3A4 2633	activator 342 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	yes
MRP1 232	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/26600514/	yes
MRP2 625	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes
MRP4 345	binder 7 Sources: https://go.drugbank.com/drugs/DB00814 \| https://pubmed.ncbi.nlm.nih.gov/17939016/	yes
MRP4 345	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/26600514/	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	likely
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 \| https://pubmed.ncbi.nlm.nih.gov/9493314/ Page: 8.0	major [Km 9.6 uM]
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	minor [Km 475 uM]
MRP4 91	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00814 \| https://pubmed.ncbi.nlm.nih.gov/17939016/	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32217099/	yes
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31900711/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6741	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6741
ChemicalBook	CB2191355	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2191355
eMolecules	902094	https://www.emolecules.com/cgi-bin/more?vid=902094
MolPort	MolPort-002-885-839	https://www.molport.com/shop/molecule-link/MolPort-002-885-839
Selleck Chemicals	Meloxicam(Mobic)	http://www.selleckchem.com/products/Meloxicam(Mobic).html
ZINC	ZINC000013129998	http://zinc15.docking.org/substances/ZINC000013129998

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Modulator effects of meloxicam against doxorubicin-induced nephrotoxicity in mice.	2014-08	24799355
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis.	2014	24152722
JNK and p38 MAPK regulate oxidative stress and the inflammatory response in chlorpyrifos-induced apoptosis.	2013-04-26	23416140
Cortisol and interferon tau regulation of endometrial function and conceptus development in female sheep.	2013-02	23264615
The dietary fatty acid 10E12Z-CLA induces epiregulin expression through COX-2 dependent PGF(2α) synthesis in adipocytes.	2012-10	22583689
Endometrial HSD11B1 and cortisol regeneration in the ovine uterus: effects of pregnancy, interferon tau, and prostaglandins.	2012-04	22205698
Eudragit EPO nanoparticles: application in improving therapeutic efficacy and reducing ulcerogenicity of meloxicam on oral administration.	2011-08	21870464
Prostaglandins regulate conceptus elongation and mediate effects of interferon tau on the ovine uterine endometrium.	2011-06	21270428
Paraquat induces cyclooxygenase-2 (COX-2) implicated toxicity in human neuroblastoma SH-SY5Y cells.	2010-12-15	20851755
The COX-2 inhibitors, meloxicam and nimesulide, suppress neurogenesis in the adult mouse brain.	2010-03	20136845
Rapid onset of neurological symptoms and lithium toxicity on starting meloxicam.	2010-01	20073572
Combining kallistatin gene therapy and meloxicam to treat hepatocellular carcinoma in mice.	2009-11	19709125
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).	2009-06	19617648
Differential effects of selective cyclooxygenase-2 inhibitors in inhibiting proliferation and induction of apoptosis in oral squamous cell carcinoma.	2008-02	18202791
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter.	2007-12	17939016
The interaction between orally administered non-steroidal anti-inflammatory drugs and prednisolone in healthy dogs.	2007-04	17485922
Safety of selective cyclooxygenase-2 inhibitors and a basic non-steroidal anti-inflammatory drug (NSAID) in Japanese patients with NSAID-induced urticaria and/or angioedema: Comparison of meloxicam, etodolac and tiaramide.	2007-03	17291297
Pharmacodynamic of cyclooxygenase inhibitors in humans.	2007-01	17164136
Protective effects of meloxicam on aluminum overload-induced cerebral damage in mice.	2006-10-10	16928369
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone.	2006-08	16684565
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Impact of the cyclooxygenase system on doxorubicin-induced functional multidrug resistance 1 overexpression and doxorubicin sensitivity in acute myeloid leukemic HL-60 cells.	2005-01	15501994
Risk of serious upper gastrointestinal and cardiovascular thromboembolic complications with meloxicam.	2004-07-15	15234645
Tolerability of three selective cyclo-oxygenase-2 inhibitors, meloxicam, celecoxib and rofecoxib in NSAID-sensitive patients.	2004-06	15329003
Nonsteroidal anti-inflammatory drug-induced liver injury: a case-control study in primary care.	2004-04	15066135
Therapeutic effect of cyclo-oxygenase inhibitors with different isoform selectivity in lipopolysaccharide-induced preterm birth in mice.	2003-07	12861172
Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells.	2002-11-06	12417326
Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs.	2002-10-11	12147693
Modulation of NSAID-induced antinociceptive and anti-inflammatory effects by alpha2-adrenoceptor agonists with gastroprotective effects.	2002-05-03	12269398
The COX inhibitors indomethacin and meloxicam exhibit anti-emetic activity against cisplatin-induced emesis in piglets.	2002-03	11897121
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001-11	11792017
Postoperative analgesia is not different after local vs systemic administration of meloxicam in patients undergoing inguinal hernia repair.	2001-11	11698316
Cathodic adsorptive stripping square-wave voltammetry of the anti-inflammatory drug meloxicam.	2001-10	11605650
Classic NSAID and selective cyclooxygenase (COX)-1 and COX-2 inhibitors in healing of chronic gastric ulcers.	2001-06-01	11376495
Hyponatraemia associated with the use of a selective serotonin-reuptake inhibitor in an older patient.	2001-01	11322690
Molecular and pharmacological evidence for modulation of kinin B(1) receptor expression by endogenous glucocorticoids hormones in rats.	2001-01	11159707
Non-steroidal anti-inflammatory drugs with different cyclooxygenase inhibitory profiles that prevent aberrant crypt foci formation but vary in acute gastrotoxicity in a rat model.	2000-12	11197048
Expression of cyclooxygenase (COX)-1 and COX-2 in adaptive cytoprotection induced by mild stress.	2000-05-03	10791687
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.	1999-11-26	10594344
Meloxicam-induced liver toxicity.	1999-07-31	10427794
Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity.	1997-03-14	9083488

Patents

Sample Use Guides

In Vivo Use Guide

Osteoarthritis: starting and maintenance oral dose is 7.5 mg once daily. Some patients may receive additional benefit by increasing the dose to 15 mg once daily. Rheumatoid Arthritis: starting and maintenance oral dose is 7.5 mg once daily. Some patients may receive additional benefit by increasing the dose to 15 mg once daily. Juvenile Rheumatoid Arthritis (JRA) Pauciarticular and Polyarticular Course: is 7.5 mg once daily in children who weigh ≥60 kg. There was no additional benefit demonstrated by increasing the dose above 7.5 mg in clinical trials.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Name

Type

Language

MELOXICAM

Official Name

English

ACTICAM

Preferred Name

English

RECOCAM

Brand Name

English

MELOXIDOLOR

Common Name

English

Meloxicam [WHO-DD]

Common Name

English

COXICAM

Brand Name

English

MELOXIVET

Brand Name

English

UH-AC-62 XX

Code

English

MELOXICAM [HSDB]

Common Name

English

VIVLODEX

Brand Name

English

meloxicam [INN]

Common Name

English

MELOXICAM [ORANGE BOOK]

Common Name

English

MELOXORAL

Brand Name

English

REVITACAM

Brand Name

English

N1539

Code

English

FLEXICAM

Brand Name

English

MOVATEC

Brand Name

English

MELOXICAM [GREEN BOOK]

Common Name

English

ZELERIS COMPONENT MELOXICAM

Brand Name

English

4-HYDROXY-2-METHYL-N-(5-METHYL-2-THIAZOLYL)-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE-1,1-DIOXIDE

Systematic Name

English

MELFAX

Brand Name

English

UH-AC 62XX

Code

English

QMIIZ ODT

Brand Name

English

MELOXICAM [MI]

Common Name

English

MELOXICAM [MART.]

Common Name

English

ANJESO

Brand Name

English

N-1539

Code

English

MELOXICAM [JAN]

Common Name

English

MELOXICAM [EMA EPAR VETERINARY]

Common Name

English

ZYNRELEF COMPONENT MELOXICAM

Brand Name

English

INFLACAM

Brand Name

English

MELOVEM

Brand Name

English

METACAM

Brand Name

English

MELOXICAM [VANDF]

Common Name

English

MELOXICAM [USP-RS]

Common Name

English

RHEUMOCAM

Brand Name

English

MELOXIDYL

Brand Name

English

SYMBRAVO COMPONENT MELOXICAM

Brand Name

English

MELOXICAM [USAN]

Common Name

English

MELOXICAM [USP MONOGRAPH]

Common Name

English

MOBIC

Brand Name

English

LOXICOM

Common Name

English

MELOXICAM [EP MONOGRAPH]

Common Name

English

CONTACERA

Brand Name

English

EMDOCAM

Brand Name

English

MELOSUS

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323