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Meloxicam

CAS No.
71125-38-7
Chemical Name:
Meloxicam
Synonyms
MOBIC;oxicam;MELOXICAM SODIUM;Meloxciam;MELEUMYCIN;MeloxicamUsp27;MeloxicaM (Mobic);Meloxicam (400 mg);4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-1,1-dioxide-2H-1,2-benzothiazine-3-carboxamide;4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazin-3-crboxamide 1,1-dioxide
CBNumber:
CB2191355
Molecular Formula:
C14H13N3O4S2
Molecular Weight:
351.4
MDL Number:
MFCD00868752
MOL File:
71125-38-7.mol
Last updated:2024-12-18 14:07:02

Meloxicam Properties

Melting point 255 °C
Density 1.613±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: soluble
form Off-white solid
pka 4.08 in water; 4.24 ± 0.01 in water/ethanol (1:1); 4.63 ± 0.03 in water/ethanol (1:4)
color yellow
Water Solubility practically insoluble in water(0.154 mg/mL), with higher solubility observed in strong acids and bases.
Merck 14,5826
BCS Class 2(CLogP), 4 (LogP)
Stability Stable. Incompatible with strong oxidizing agents.
InChI 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)
InChIKey ZRVUJXDFFKFLMG-UHFFFAOYSA-N
SMILES S1(=O)(=O)C2=CC=CC=C2C(O)=C(C(NC2=NC=C(C)S2)=O)N1C
EWG's Food Scores 1
FDA UNII VG2QF83CGL
NCI Drug Dictionary meloxicam
ATC code M01AC06,M01AC56
EPA Substance Registry System 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-, 1,1-dioxide (71125-38-7)

Pharmacokinetic data

Protein binding 99%
Excreted unchanged in urine 3%
Volume of distribution 11 Litres
Biological half-life 20 / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
Hazard Codes  Xn,T
Risk Statements  22-36/37/38-25
Safety Statements  26-45-60-36/37
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  DL0702000
HazardClass  6.1
PackingGroup  III
HS Code  29349990
Hazardous Substances Data 71125-38-7(Hazardous Substances Data)
Toxicity LD50 orally in mice: 470 mg/kg (Trummlitz, 1980)
NFPA 704
0
2 0

Meloxicam price More Price(48)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 444800 Meloxicam 71125-38-7 100mg $201 2024-03-01 Buy
Sigma-Aldrich 1379401 Meloxicam United States Pharmacopeia (USP) Reference Standard 71125-38-7 400mg $732 2024-03-01 Buy
Sigma-Aldrich BP629 Meloxicam British Pharmacopoeia (BP) Reference Standard 71125-38-7 100MG $252 2023-06-20 Buy
TCI Chemical M1959 Meloxicam >98.0%(HPLC) 71125-38-7 5g $61 2024-03-01 Buy
TCI Chemical M1959 Meloxicam >98.0%(HPLC) 71125-38-7 25g $179 2024-03-01 Buy
Product number Packaging Price Buy
444800 100mg $201 Buy
1379401 400mg $732 Buy
BP629 100MG $252 Buy
M1959 5g $61 Buy
M1959 25g $179 Buy

Meloxicam Chemical Properties,Uses,Production

Description

Known as a nonsteroidal anti-inflammatory drug (NSAID), Meloxicam is commonly used to treat pain or inflammation caused by rheumatoid arthritis and osteoarthritis in adults. It is also used to treat juvenile rheumatoid arthritis in children who are at least 2 years old. It is effective to reduce pain, inflammation, swelling, and stiffness of the joints. Developed by Boehringer-Ingelheim, Meloxicam is a derivative of oxicam that can relieve the symptoms of arthritis, primary dysmenorrhea, fever with analgesic and antipyretic properties. Meloxicam was approved for use in April 2000.
Anti-inflammatory effects of meloxicam function by inhibiting the prostaglandin synthetase (cyclooxygenase 1 and 2) which results in a decrease of the synthesis of prostaglandins. As prostaglandins are chemicals that contribute to inflammation especially within joints, which leads to the common symptoms of pain, tenderness, and swelling associated with arthritis, inhibition of their synthesis can be associated with the analgesic and antipyretic effects of meloxicam. As a result, inflammation and its accompanying symptoms are reduced. Meloxicam starts to relieve pain about 30 to 60 minutes after administration.

Chemical Properties

Meloxicam is a light yellow solid, practically insoluble in water, with higher solubility observed in strong acids and bases. It is very slightly soluble in methanol. Meloxicam has an apparent partition coefficient (log P)app = 0.1 in n-octanol/buffer pH 7.4. It has pKa values of 1.1 and 4.2.

Originator

Boehringer Ingelheim (Germany)

Uses

Meloxicam is a preferential cyclooxygenase (COX-2) inhibitor that used for symptomatic treatment of arthritis and osteoarthritis. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.

Uses

An inhibitor of Cox-1 and Cox-2, selective for Cox-2.

Indications

Meloxicam (Mobic), recently introduced for the treatment of osteoarthritis, is also used for rheumatoid arthritis and certain acute conditions. Although meloxicam is sometimes reported to be a selective COX-2 inhibitor, it is considerably less selective than celecoxib or rofecoxib. Its adverse effects are similar to those of piroxicam and other NSAIDs; however, the frequency of GI side effects is lower for meloxicam than for piroxicam and several other NSAIDs.

Definition

ChEBI: Meloxicam is a benzothiazine that is piroxicam in which the pyridin-2-yl group is replaced by a 5-methyl-1,3-thiazol-2-yl group. A non-steroidal anti-inflammatory drug and selective inhibitor of COX-2, it is used particularly for the management of rheumatoid arthritis. It has a role as a non-steroidal anti-inflammatory drug, an antirheumatic drug, a cyclooxygenase 2 inhibitor and an analgesic. It is a benzothiazine, a monocarboxylic acid amide and a member of 1,3-thiazoles.

Manufacturing Process

A mixture of 26.9 g (0.1 mol) of the 1,1-dioxide of methyl 4-hydroxy-2- methyl-2H-1,2-benzothiazine-3-carboxylate and 12.5 g (0.11 mol) of 2- amino-5-methylthiazole was refluxed in 4 liters of xylene for 24 hours in a nitrogen atmosphere. The methanol formed by the reaction was removed by means of a 4-A-molecular sieve mounted in a Soxhlet-extractor. The hot reaction solution was filtered. Upon cooling and standing overnight, the crude product separated out of the filtrate in the form of crystals (32.0 g, 91% of theory). After recrystallization from ethylene chloride 26.0 g (74% of theory) of 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3- carboxamide-1,1-dioxide were obtained; M.P.: 254°C (decomp.).

brand name

Mobic (Boehringer Ingelheim).

Therapeutic Function

Antiinflammatory

General Description

Meloxicam (Mobic) is a selective COX-2 inhibitor amongoxicams indicated for use in RA and OA. It also has a relativelylong half-life of 15 to 20 hours and has a much lowerrate of serious GI side effects and a lower than average riskof nephropathy when compared with other conventionalNSAIDs.196 The recommended dose is 7.5 mg once dailywith a maximum of 15 mg/d. Meloxicam is metabolized inhumans mainly by CYP2C9 (with a minor contribution viaCYP3A4) to 5'-hydroxymethylmeloxicam and 5 carboxymeloxicam.
In large-scale comparative trials, meloxicam was foundto be at least as effective as most conventional NSAIDs inthe treatment of rheumatic disease or postoperative pain, buthas demonstrated a more favorable GI tolerability profile.

Biological Activity

Meloxicam is a selective inhibitor of COX-2 (IC50s = 11.8 and 143 μM for COX-2 and COX-1, respectively, in an enzyme activity assay) and a non-steroidal anti-inflammatory drug (NSAID). Meloxicam (0.03%) reduces croton oil-induced increases in TNF-α and IL-1β mRNA levels and increases IL-10 mRNA levels in cornea in a rabbit model of acute ocular inflammation. It inhibits pleural plasma exudation in a carrageenan-induced rat model of pleurisy when administered at a dose of 3 mg/kg. In a canine model of unilateral osteoarthritis of the right stifle joint, meloxicam reduces prostaglandin E2 (PGE2) levels in plasma and right stifle joint synovial fluid when administered at a dose of 0.2 mg/kg. Formulations containing meloxicam have been used in the treatment of osteoarthritis and rheumatoid arthritis.

Clinical Use

In April 2000, the U.S. FDA approved meloxicam for the treatment of osteoarthritis. When meloxicam was initially introduced in the United Kingdom, it was promoted as a selective COX-2 inhibitor.

Side effects

Meloxicam may cause stomach upset, nausea, dizziness or diarrhoea, increased blood pressure, headache, easy bruising or bleeding; mental or mood changes; signs of kidney problems (e.g., changes in urine output), unexplained stiffness of the neck, symptoms of heart failure (e.g., swelling of the ankles or feet; unusual tiredness, unusual weight gain).
Meloxicam rarely causes serious (potentially fatal) liver disease. Include: nausea or vomiting, loss of appetite, dark-coloured urine, stomach or abdominal pain, and yellowing of the eyes or skin.
Very serious allergic reactions to Meloxicam are rare. Include: fever, swollen lymph nodes, rash, itching or swelling (especially of the face or tongue or throat), severe dizziness, and difficulty breathing. However, if you notice any symptoms of a severe allergic reaction, seek medical help immediately.

Synthesis

It can be synthesized in four steps from benzisothiazolo-3(2H)-one-1,1-dioxide. Reaction of benzothiazolo-3(2H)-one-1,1-dioxide with methyl chloroacetate gives the methyl 2(3H)-acetate derivative, which is isomerized with sodium methoxide in toluene-tert-butanol yielding methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide. Subsequent methylation with methyl iodide in methanol yields the 2-methyl compound. Finally this compound is treated with 2-amino-5-methylthiazole in xylene.

Veterinary Drugs and Treatments

Meloxicam is principally used for the symptomatic treatment of osteoarthritis in dogs. Short-term (single dose injectable) use is also approved (in the USA) for cats for the control of postoperative pain and inflammation associated with orthopedic surgery, ovariohysterectomy and castration when administered prior to surgery.

Metabolism

Meloxicam, however, is less selective than celecoxib and much less selective than rofecoxib in in vitro studies. Meloxicam is readily absorbed when administered orally and is highly bound to plasma proteins. Meloxicam is extensively metabolized in the liver, primarily by CYP2C9 and, to a lesser extent, by CYP3A4. The advantages of meloxicam over celecoxib and rofecoxib in the treatment of osteoarthritis (or rheumatoid arthritis) are not readily apparent.

Mode of action

Meloxicam, a nonsteroidal anti-inflammatory drug (NSAID), by shutting down prostaglandin synthesis, it has antiinflammatory, antipyretic and analgesic properties. This is accomplished by preferentially inhibiting the COX-2 system relative to the COX-I which also leads to an improved GI safety profile relative to naproxen, diclofenac and prioxicam. It can also interfere with neutrophil function like degranulation. Meloxicam did not inhibit proteoglycan synthesis in osteroarthitic cartilage or chondrocytes and had no effect on platelet aggregation. It is metabolized by the P450 2C9 system into four metabolites which are all inactive.

References

[1] https://en.wikipedia.org/wiki/Meloxicam
[2] https://www.drugbank.ca/drugs/DB00814
[3] https://www.drugs.com/meloxicam.html
[4] http://www.medicinenet.com/meloxicam/article.htm
[5] K OGINO. Evaluation of pharmacological profile of meloxicam as an anti-inflammatory agent, with particular reference to its relative selectivity for cyclooxygenase-2 over cyclooxygenase-1.[J]. Pharmacology, 1997, 55 1: 44-53. DOI:10.1159/000139511.
[6] CHRISTOPHER J JONES. In vivo effects of meloxicam and aspirin on blood, gastric mucosal, and synovial fluid prostanoid synthesis in dogs.[J]. American journal of veterinary research, 2002, 63 11: 1527-1531. DOI:10.2460/ajvr.2002.63.1527.
[7] S NOBLE J A B. Meloxicam.[J]. Drugs, 1996, 51 3: 424-430; discussion 431-32. DOI:10.2165/00003495-199651030-00007.
[8] BANDOO C CHATALE Mariam S D. Synthesis and in-vivo taste assessment of meloxicam pivalate.[J]. Drug Development and Industrial Pharmacy, 2019, 45 10: 1590-1598. DOI:10.1080/03639045.2019.1628250.

892395-40-3
71125-38-7
Synthesis of Meloxicam from 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-, 1,1-dioxide, potassium salt, hydrate (1:1:1)
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View Lastest Price from Meloxicam manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Meloxicam pictures 2024-12-23 Meloxicam
71125-38-7
US $0.00 / kg 25kg 99.0% 10tons Henan Suikang Pharmaceutical Co.,Ltd.
Meloxicam pictures 2024-12-13 Meloxicam
71125-38-7
US $0.00-0.00 / Kg/Drum 1KG 99%-101% 10 tons WUHAN FORTUNA CHEMICAL CO., LTD
Meloxicam pictures 2024-11-20 Meloxicam
71125-38-7
US $1.00 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
  • Meloxicam pictures
  • Meloxicam
    71125-38-7
  • US $0.00 / kg
  • 99.0%
  • Henan Suikang Pharmaceutical Co.,Ltd.
  • Meloxicam pictures
  • Meloxicam
    71125-38-7
  • US $0.00-0.00 / Kg/Drum
  • 99%-101%
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Meloxicam pictures
  • Meloxicam
    71125-38-7
  • US $1.00 / KG
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd

Meloxicam Spectrum

MeloxicaM, BP MeloxicaM API 4-Hydroxy-2-Methyl-N-(5-Methylthiazol-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxaMide 1,1-dioxide Meloxicam Solution, 100ppm 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxid Coxicam MOBEC UH-AC 62XX 4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamidel,1-dioxide METACAM MELOXICAM 4-HYDROXY-2-METHYL-N-(5-METHYL-2-THIAZOLYL)-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE 1,1-DIOXIDE 4-HYDROXY-2-METHYL-N-(5-METHYL-2-THIAZOYL)-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE-1,1-DIOXIDE Meiloxicam MELOXICAM, BP STANDARD MELOXICAM, IMPURITY STANDARD BP(CRM STANDARD) MELOXICAM, IMP. D (BP): METHYL 4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIAZINE-3-CARBOXYLATE 1,1-DIOXIDE MM(CRM STANDARD) MELOXICAM, IMP. B (BP): 2-AMINO-5-METHYLTHIAZOLE MM(CRM STANDARD) MELOXICAM, IMP. A (BP): ETHYL 4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIAZINE-3-CARBOXYLATE 1,1-DIOXIDE MM(CRM STANDARD) MELOXICAM ASSAY STANDARD BP(CRM STANDARD) Meloxicam(SubjectBtoPatentFree) MeloxicamBp2003 CH83850 Metacam, Mobic, 4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1,-dioxide 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-, 1,1-dioxide Mobicox Movalis Movatec Parocin eloxicam Sodium 2-methyl-3-[(5-methyl-1,3-thiazol-2-yl)carbamoyl]-2H-1,2-benzothiazin-4-olate 1,1-dioxide Meloxicam, 99%, a selective COX inhibitor 2H-1,2-benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-, 1,1-dioxide, sodium salt (1:1) 4-hydroxy-2-methyl-N-(5-met 4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-Dioxide Meloxicam - CAS 71125-38-7 - Calbiochem Meloxicam,(S) Meloxicam,Metacam,Parocin Meloxicam Standard Meloxicam CRS Meloxicam> 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide Meloxicam USP/EP/BP MeloxicamQ: What is Meloxicam Q: What is the CAS Number of Meloxicam Q: What is the storage condition of Meloxicam Q: What are the applications of Meloxicam Meloxicam (1379401) 4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazin-3-crboxamide 1,1-dioxide Meloxicam (400 mg) MeloxicaM (Mobic) 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-1,1-dioxide-2H-1,2-benzothiazine-3-carboxamide MELOXICAM SODIUM MOBIC Meloxciam MELEUMYCIN oxicam MeloxicamUsp27 Meloxicam Powder USP Standard Methyl[3-Phenyl-3-[4-(Trifluoromethyl)Phenoxy]Propyl]