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
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)
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 |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10381057
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057 |
36.6 µM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381057 |
4.7 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | MOBIC Approved UseINDICATIONS & 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 Date9.5558402E11 |
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Palliative | MOBIC Approved UseINDICATIONS & 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 Date9.5558402E11 |
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Palliative | MOBIC Approved UseINDICATIONS & 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 Date9.5558402E11 |
Cmax
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 |
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 |
T1/2
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 |
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 |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/19793025/ |
likely | |||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >200 uM] | ||||
no [IC50 >200 uM] | ||||
no [IC50 >200 uM] | ||||
no [IC50 >200 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak [IC50 77.5 uM] | ||||
yes [IC50 1.6 uM] | ||||
yes [IC50 124.3 uM] | ||||
yes [IC50 131.3 uM] | ||||
yes | ||||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2000/20-938_Mobic_biopharmr_P1.pdf#page=8 Page: 8.0 |
yes | |||
yes | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely | ||||
major [Km 9.6 uM] | ||||
minor [Km 475 uM] | ||||
no | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of structural modification of enol-carboxamide-type nonsteroidal antiinflammatory drugs on COX-2/COX-1 selectivity. | 1997 Mar 14 |
|
Role of prostaglandins generated by cyclooxygenase-1 and cyclooxygenase-2 in healing of ischemia-reperfusion-induced gastric lesions. | 1999 Nov 26 |
|
Molecular and pharmacological evidence for modulation of kinin B(1) receptor expression by endogenous glucocorticoids hormones in rats. | 2001 Jan |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
The COX inhibitors indomethacin and meloxicam exhibit anti-emetic activity against cisplatin-induced emesis in piglets. | 2002 Mar |
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Modulation of NSAID-induced antinociceptive and anti-inflammatory effects by alpha2-adrenoceptor agonists with gastroprotective effects. | 2002 May 3 |
|
Selective cyclooxygenase-2 inhibitors show a differential ability to inhibit proliferation and induce apoptosis of colon adenocarcinoma cells. | 2002 Nov 6 |
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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 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Direct binding of Cu(II)-complexes of oxicam NSAIDs with DNA backbone. | 2006 Aug |
|
Protective effects of meloxicam on aluminum overload-induced cerebral damage in mice. | 2006 Oct 10 |
|
The interaction between orally administered non-steroidal anti-inflammatory drugs and prednisolone in healthy dogs. | 2007 Apr |
|
Multichannel liquid chromatography-tandem mass spectrometry cocktail method for comprehensive substrate characterization of multidrug resistance-associated protein 4 transporter. | 2007 Dec |
|
Pharmacodynamic of cyclooxygenase inhibitors in humans. | 2007 Jan |
|
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 |
|
Modulator effects of meloxicam against doxorubicin-induced nephrotoxicity in mice. | 2014 Aug |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23582791
Curator's Comment: In vitro, meloxicam induced a significant (P<0.05) decrease of cell proliferation. A significant (P<0.05) cell cycle arrest on G0/G1 phase was also detected in all the cell lines, with a slight but significant increase of sub-G0/G1 fraction on T24 (P=0.006) and 5637 (P<0.001) cells. Also a significant (P<0.05) increase in DNA damage was found on meloxicam-treated cells.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 18:28:46 UTC 2022
by
admin
on
Fri Dec 16 18:28:46 UTC 2022
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Record UNII |
VG2QF83CGL
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1323
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EMA VETERINARY ASSESSMENT REPORTS |
RECOCAM [AUTHORIZED]
Created by
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDYL [AUTHORIZED]
Created by
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXORAL [AUTHORIZED]
Created by
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EMA VETERINARY ASSESSMENT REPORTS |
RECOCAM [AUTHORIZED]
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FDA ORPHAN DRUG |
160602
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EMA VETERINARY ASSESSMENT REPORTS |
INFLACAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
METACAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
METACAM [AUTHORIZED]
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CFR |
21 CFR 520.1367
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EMA VETERINARY ASSESSMENT REPORTS |
EMDOCAM (AUTHORISED)
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDOLOR [AUTHORIZED]
Created by
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDYL [AUTHORIZED]
Created by
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WHO-VATC |
QM01AC56
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LIVERTOX |
NBK548278
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDYL [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
MELOSUS[AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
RHEUMOCAM [AUTHORIZED]
Created by
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EMA VETERINARY ASSESSMENT REPORTS |
MELOVEM [AUTHORIZED]
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NDF-RT |
N0000175721
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDYL [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS | RHEUMOCAM [AUTHORIZED] | ||
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EMA VETERINARY ASSESSMENT REPORTS |
CONTACERA (AUTHORISED)
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EMA VETERINARY ASSESSMENT REPORTS |
LOXICOM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDOLOR [AUTHORIZED]
Created by
admin on Fri Dec 16 18:28:46 UTC 2022 , Edited by admin on Fri Dec 16 18:28:46 UTC 2022
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXORAL [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
METACAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
METACAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
REVITACAM [WITHDRAWN]
Created by
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EMA VETERINARY ASSESSMENT REPORTS |
MELOVEM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
METACAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
FLEXICAM WITHDRAWN)
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EMA VETERINARY ASSESSMENT REPORTS |
RECOCAM [AUTHORIZED]
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WHO-ATC |
M01AC06
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NDF-RT |
N0000000160
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EMA VETERINARY ASSESSMENT REPORTS |
LOXICOM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
ZELERIS [AUTHORISED]
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WHO-ATC |
M01AC56
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDOLOR [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
FLEXICAM WITHDRAWN)
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admin on Fri Dec 16 18:28:46 UTC 2022 , Edited by admin on Fri Dec 16 18:28:46 UTC 2022
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EMA VETERINARY ASSESSMENT REPORTS |
LOXICOM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
LOXICOM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
CONTACERA (AUTHORISED)
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CFR |
21 CFR 522.1367
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EMA ASSESSMENT REPORTS |
MELOXIDOLOR [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
RHEUMOCAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDYL [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
CONTACERA (AUTHORISED)
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EMA VETERINARY ASSESSMENT REPORTS |
RHEUMOCAM [AUTHORIZED]
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIVET [WITHDRAWM]
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NDF-RT |
N0000175722
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EMA VETERINARY ASSESSMENT REPORTS |
RHEUMOCAM [AUTHORIZED]
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EMA ASSESSMENT REPORTS |
ACTICAM [AUTHORISED]
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WHO-VATC |
QM01AC06
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EMA VETERINARY ASSESSMENT REPORTS |
MELOXIDOLOR [AUTHORIZED]
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41493
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DTXSID1020803
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7741
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VG2QF83CGL
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1676
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C61439
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M7164
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C065757
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6741
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71125-38-7
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JJ-71
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MELOXICAM
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Meloxicam
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5615
Created by
admin on Fri Dec 16 18:28:47 UTC 2022 , Edited by admin on Fri Dec 16 18:28:47 UTC 2022
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VG2QF83CGL
Created by
admin on Fri Dec 16 18:28:46 UTC 2022 , Edited by admin on Fri Dec 16 18:28:46 UTC 2022
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54677470
Created by
admin on Fri Dec 16 18:28:47 UTC 2022 , Edited by admin on Fri Dec 16 18:28:47 UTC 2022
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CHEMBL599
Created by
admin on Fri Dec 16 18:28:46 UTC 2022 , Edited by admin on Fri Dec 16 18:28:46 UTC 2022
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DB00814
Created by
admin on Fri Dec 16 18:28:46 UTC 2022 , Edited by admin on Fri Dec 16 18:28:46 UTC 2022
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7220
Created by
admin on Fri Dec 16 18:28:47 UTC 2022 , Edited by admin on Fri Dec 16 18:28:47 UTC 2022
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1379401
Created by
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SUB08726MIG
Created by
admin on Fri Dec 16 18:28:46 UTC 2022 , Edited by admin on Fri Dec 16 18:28:46 UTC 2022
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE INACTIVE -> PARENT | |||
|
METABOLITE INACTIVE -> PARENT | |||
|
METABOLITE INACTIVE -> PARENT | |||
|
METABOLITE INACTIVE -> PARENT |
In vitro studies indicate that CYP2C9 plays an important role in this metabolic pathway with a minor contribution of the CYP3A4 isozyme.
IN-VITRO
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
Procedure 1 and 2; at 260 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 2.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
Procedure 1; at 350 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
at 260 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
Procedure 2; at 350 nm
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
|
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
|
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Route of Elimination | PHARMACOKINETIC |
|
RENAL |
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MAXIMUM TOLERATED DOSE | TOXICITY |
|
SUSPENSION, TABLET: 15 mg/day |
|
||
BIOAVAILABILITY | PHARMACOKINETIC |
|
|
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Biological Half-life | PHARMACOKINETIC |
|
RENAL FAILURE: 18 HOURS |
|
||
Tmax | PHARMACOKINETIC |
|
EFFECT OF FOOD: INCREASED BY 3 HOURS (ORAL SOLUMATRIX CAPSULE) |
|
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PROTEIN BINDING | PHARMACOKINETIC |
|
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