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Meloxicam

pharmaceutical raw materials
Meloxicam structure

Meloxicam 

structure
  • CAS No:

    71125-38-7

  • Formula:

    C14H13N3O4S2

  • Chemical Name:

    Meloxicam

  • Synonyms:

    2H-1,2-Benzothiazine-3-carboxamide,4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-,1,1-dioxide;Meloxicam;UH-AC 62XX;Mobec;Metacam;Mobic;Mobicox;Movalis;Melonex;Coxflam;Revmoksikam;Movatec;Maxicam;Melfax;Melfax (NSAID);Coxicam;Novem 5;Rheumocam;Recocam;RevitaCAM;Novaquin;Novem;Meloxivet;Meloxoral;Emdocam;Contacera;Meloxidyl;Acticam;Melosus;Loxicom;Inflacam;Flexicam;Meloxidolor;Melovem;133687-22-6

  • Categories:

    Active Pharmaceutical Ingredients  >  Antipyretic Analgesics

Description

Meloxicam is a non-steroidal antiinflammatory agent, inhibits COX activity, with IC50s of 0.49 µM and 36.6 µM for COX-2 and COX-1, respectively.

Meloxicam Basic Attributes

351.40100

351.40

615-253-8

2934999090

Characteristics

136.22000

3

Light Yellow Solid

1.613 g/cm3

254 °C (decomp)

305.4±32.9 °C

1.72

Soluble in water (22 mg/ml), DMSO (25 mg/ml), DMF, acetone(slightly soluble), ethanol(slightly soluble), and methanol(slightly soluble).

0-6ºC

1.07X10-15 mm Hg at 25 deg C (est)

LD50 orally in mice: 470 mg/kg (Trummlitz, 1980)

Safety Information

III

UN 2811 6.1/PG 3

3

R22

S26

DL0702000

Xn

Stable. Incompatible with strong oxidizing agents.

P301 + P310

H301

Meloxicam Use and Manufacturing

Methods of Manufacturing

One proceeds according to with the only difference that the solution of the potassium salt is treated with 6.0 ml 96percent acetic acid instead of hydrochloric acid.34.1 g (83.7 mmol) meloxicam potassium salt monohydrate are dissolved in the mixture of 1500 ml of 0.5 percent aqueous potassium hydroxide solution and 25 ml of ethanol at the temperature of 40-45 C by stirring for 30 minutes. The yellow solution are added 2.0 g of activated carbon and after stirring for ten minutes, the carbon is filtered off. The filtrate are added 100 ml aqueous hydrochloric acid solution prepared by diluting 20 ml (23.6 g) concentrated hydrochloric acid to 100 ml final volume, at 30 C in 30 minutes (pH 3-5). The suspension is stirred for two hours at 10 C temperature, filtered and the product is washed on the filter with water.Ortho xylene (1800 L), 18 kg of methyl 4-hydroxy-2-methyl-2H-1, 2-benzothiazine-3-carboxalate1, 1-dioxide (IV) and 8.6 kg of 2-amino-5-methyl-thiazole were added into a reactor. This salt is then dried in vacuo and taken up in 450 ml of deionised water. EXAMPLE 1- Process for preparing crude meloxicam In a 6 litre round-bottom flask, in a nitrogen flow, are placed respectively 226.64g (0.80 mol) of 4-hydroxy-2-methyl-2H-1, 2-benzothiazine-3-carboxylate of ethyl-1, 1-dioxide and 91.36g (0.80 mol) of 2-amino-5-methyl-thiazole and 3.6 l of xylene. The suspension is heated under reflux (139-140°C), passing the condensate on a bed of molecular sieves 4Å. Initially a dark brown solution is obtained and then, as the reaction proceeds, the reaction product is crystallised in the form of a yellow-green solid. It is kept under reflux until completion of the reaction (32-37 hours). When the reaction is completed it is cooled to a temperature comprised between 20 and 25°C in at least 2 hours. The crude product is filtered and washed with xylol and acetone. 279.34g of wet yellow-greenish crude product are obtained, the equivalent of 260.0 g of dry product. Theoretical yield 281.12 g RDT =92.48percent. The crude meloxicam thus obtained has a content of the impurity composed of ethylamide amounting to 0.707percent assessed with HPLC using the 'Related substances' method given in the monographic report of the British Pharmacopoeia 2002. Repeating example 1, products are obtained that contain the above-mentioned impurity in variable quantities between 0.230 and 0.782percent.1 g of compound 1 was dissolved in 50 ml of methanol solution, and stirred at 157 C. for the night after adding 157 mg MeONa, and then the compound 1 was gotten. 1.20 g of compound 2 was dissolved 30 ml DMF, and added 1.20 mg Ethyl 4-bromobutyrate stir at 80 C. for the night, and then the mixture 2 was gotten. The step 4 is to concentrate the obtained mixture 2 and then purify it with a silica gel column to obtain compound 3. The 800 mg compound 3 was dissolved into 3 mL tetrahydrofuran and 1 mL water, adding 180 mg 1-hydrated lithium hydroxide, adjusting pH to 4-6, and stirring at room temperature overnight to get mixture 4. The aqueous solution layer with ethylamine from mixture 4 was extracted, and the organic layer was combined, washing with salt water, drying with anhydrous sodium sulfate and being concentrated to obtain The fluorescence measurements were performed as follows:1.0mL Tris-HCl buffer solution (pH7.40), 2.0mL trypsin(2.0105 mol/L), and different volumes of General procedure: The cocrystals were synthesized by liquid-assisted grinding(LAG).

Uses

1. Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.
2. Angiotensin 2 receptor antagonist.
3. For symptomatic treatment of arthritis and osteoarthritis.
4. Preferential cyclooxygenase (COX-2) inhibitor. Used as an anti-inflammatory.
5. An inhibitor of Cox-1 and Cox-2, selective for Cox-2.

Computed Properties

Molecular Weight:351.4
XLogP3:3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:351.03474825
Monoisotopic Mass:351.03474825
Topological Polar Surface Area:136
Heavy Atom Count:23
Complexity:628
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Drug Function and Efficacy

Meloxicam is a nonsteroidal anti-inflammatory analgesic (NSAID) of the enolic acid class, which has anti-inflammatory, analgesic and antipyretic effects. It exerts the above effects by inhibiting the biosynthesis of inflammatory mediators prostaglandins, and its selective inhibition of COX-2 is stronger than that of COX-1, thereby reducing gastrointestinal and renal side effects. Clinical studies have shown that the incidence of gastrointestinal adverse reactions is low when the recommended dose is used.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • APEX HEALTHCARE LTD

    United States United States
    Active
  • SWATI SPENTOSE PRIVATE LTD

    United States United States
    Active
  • UNIMARK REMEDIES LTD

    United States United States
    Active

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