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=C(C=CC=C3)S1(=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

Molecular Formula	C14H13N3O4S2
Molecular Weight	351.401
Charge	0
Count

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

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-1 127 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057	Inhibitor 8297		36.6 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057	Inhibitor 8297		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 8429	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 9.5558402E11
Rheumatoid arthritis 316 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s026lbl.pdf	Palliative	Approved 8429	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 9.5558402E11
Juvenile rheumatoid arthritis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020938s026lbl.pdf	Palliative	Approved 8429	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 9.5558402E11

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

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
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
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

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 80 substrate 1737	inhibitor 1767 substrate 1037	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2E1 882 CYP3A 214 CYP2C 19 CYP2B6 810 UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A9 116 UGT2B7 146 OATP2B1 123 BSEP 402 MRP3 157 MRP4 204	CYP1A2 1054 MRP4 77 OCT2 355 BCRP 561	P-gp 257

Drug as perpetrator

Target	Modality	Activity
CYP2C 34	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	likely
P-gp 1650	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/19793025/	likely
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
UGT1A4 80	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	no [IC50 >200 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
CYP3A 298	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	no
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	weak [IC50 77.5 uM]
OATP2B1 126	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28562037/	yes [IC50 1.6 uM]
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	yes [IC50 124.3 uM]
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25522350/	yes [IC50 131.3 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
CYP3A4 1925	activator 214 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	yes
MRP1 172	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/26600514/	yes
MRP2 475	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	yes
MRP4 238	binder 7 Sources: https://go.drugbank.com/drugs/DB00814 \| https://pubmed.ncbi.nlm.nih.gov/17939016/	yes
MRP4 238	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/26600514/	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0	likely
CYP2C9 1037	substrate 3367 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 1737	substrate 3367 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 77	substrate 3367 Sources: https://go.drugbank.com/drugs/DB00814 \| https://pubmed.ncbi.nlm.nih.gov/17939016/	no
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/32217099/	yes
OCT2 355	substrate 3367 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
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
eMolecules	902094	https://www.emolecules.com/cgi-bin/more?vid=902094

PubMed

Title	Date	PubMed
Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity.	1997 Mar 14	9083488
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions.	1999 Nov 26	10594344
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 Dec	11197048
Hyponatraemia associated with the use of a selective serotonin-reuptake inhibitor in an older patient.	2001 Jan	11322690
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Postoperative analgesia is not different after local vs systemic administration of meloxicam in patients undergoing inguinal hernia repair.	2001 Nov	11698316
Cathodic adsorptive stripping square-wave voltammetry of the anti-inflammatory drug meloxicam.	2001 Oct	11605650
The COX inhibitors indomethacin and meloxicam exhibit anti-emetic activity against cisplatin-induced emesis in piglets.	2002 Mar	11897121
Modulation of NSAID-induced antinociceptive and anti-inflammatory effects by alpha2-adrenoceptor agonists with gastroprotective effects.	2002 May 3	12269398
Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells.	2002 Nov 6	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 Oct 11	12147693
Therapeutic effect of cyclo-oxygenase inhibitors with different isoform selectivity in lipopolysaccharide-induced preterm birth in mice.	2003 Jul	12861172
Nonsteroidal anti-inflammatory drug-induced liver injury: a case-control study in primary care.	2004 Apr	15066135
Risk of serious upper gastrointestinal and cardiovascular thromboembolic complications with meloxicam.	2004 Jul 15	15234645
Tolerability of three selective cyclo-oxygenase-2 inhibitors, meloxicam, celecoxib and rofecoxib in NSAID-sensitive patients.	2004 Jun	15329003
Impact of the cyclooxygenase system on doxorubicin-induced functional multidrug resistance 1 overexpression and doxorubicin sensitivity in acute myeloid leukemic HL-60 cells.	2005 Jan	15501994
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone.	2006 Aug	16684565
Protective effects of meloxicam on aluminum overload-induced cerebral damage in mice.	2006 Oct 10	16928369
The interaction between orally administered non-steroidal anti-inflammatory drugs and prednisolone in healthy dogs.	2007 Apr	17485922
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter.	2007 Dec	17939016
Pharmacodynamic of cyclooxygenase inhibitors in humans.	2007 Jan	17164136
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 Mar	17291297
Differential effects of selective cyclooxygenase-2 inhibitors in inhibiting proliferation and induction of apoptosis in oral squamous cell carcinoma.	2008 Feb	18202791
Lack of effect of naltrindole on the spinal synergism of morphine and non-steroidal anti-inflammatory drugs (NSAIDS).	2009 Jun	19617648
Combining kallistatin gene therapy and meloxicam to treat hepatocellular carcinoma in mice.	2009 Nov	19709125
Paraquat induces cyclooxygenase-2 (COX-2) implicated toxicity in human neuroblastoma SH-SY5Y cells.	2010 Dec 15	20851755
Rapid onset of neurological symptoms and lithium toxicity on starting meloxicam.	2010 Jan	20073572
The COX-2 inhibitors, meloxicam and nimesulide, suppress neurogenesis in the adult mouse brain.	2010 Mar	20136845
Eudragit EPO nanoparticles: application in improving therapeutic efficacy and reducing ulcerogenicity of meloxicam on oral administration.	2011 Aug	21870464
Prostaglandins regulate conceptus elongation and mediate effects of interferon tau on the ovine uterine endometrium.	2011 Jun	21270428
Endometrial HSD11B1 and cortisol regeneration in the ovine uterus: effects of pregnancy, interferon tau, and prostaglandins.	2012 Apr	22205698
The dietary fatty acid 10E12Z-CLA induces epiregulin expression through COX-2 dependent PGF(2α) synthesis in adipocytes.	2012 Oct	22583689
JNK and p38 MAPK regulate oxidative stress and the inflammatory response in chlorpyrifos-induced apoptosis.	2013 Apr 26	23416140
Cortisol and interferon tau regulation of endometrial function and conceptus development in female sheep.	2013 Feb	23264615
Assessing the cardiovascular risk between celecoxib and nonselective nonsteroidal antiinflammatory drugs in patients with rheumatoid arthritis and osteoarthritis.	2014	24152722
Modulator effects of meloxicam against doxorubicin-induced nephrotoxicity in mice.	2014 Aug	24799355
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:52:40 UTC 2023` Edited by `admin` on `Fri Dec 15 15:52:40 UTC 2023`
Record UNII	VG2QF83CGL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MELOXICAM

Official 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

MELOXICAM COMPONENT OF ZYNRELEF

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

MELOXICAM COMPONENT OF ZELERIS

Brand Name

English

ACTICAM

Brand Name

English

EMDOCAM

Brand Name

English

MELOSUS

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323