Meloxicam

Base Information

• Chemical Name: Meloxicam
• CAS No.: 71125-38-7
• Molecular Formula: C14H13N3O4S2
• Molecular Weight: 351.407
• Hs Code.: 29349990
• Mol file: 71125-38-7.mol

Synonyms:Mobic;Meloxicam [USAN:BAN:INN];Meloxicam (JAN/USAN);(8E)-8-[hydroxy-[(5-methyl-1,3-thiazol-2-yl)amino]methylidene]-9-methyl-10,10-dioxo-10$l^{6}-thia-9-azabicyclo[4.4.0]deca-1,3,5-trien-7-one;4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide;133687-22-6;Mobec;Mobic (TN);2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methylthiazolyl)-, 1,1-dioxide;UH-AC 62XX;Meloxicam BP2000;Meloxican;

Chemical Property of Meloxicam

Chemical Property:

• Appearance/Colour: light yellow solid
• Melting Point: 255 °C
• Refractive Index: 1.72
• PKA: 4.08 in water; 4.24 ± 0.01 in water/ethanol (1:1); 4.63 ± 0.03 in water/ethanol (1:4)
• PSA: 136.22000
• Density: 1.614 g/cm³
• LogP: 3.04260
• Storage Temp.: 0-6°C
• Solubility.: DMSO: soluble
• Water Solubility.: Soluble in water (22 mg/ml), DMSO (25 mg/ml), DMF, acetone(slightly soluble), ethanol(slightly soluble), and methanol(slightly soluble).

Purity/Quality:

99% ^*data from raw suppliers

Meloxicam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T
• Statements: 22-36/37/38-25
• Safety Statements: 26-45-60-36/37

MSDS Files:

SDS file from LookChem

Useful:

• 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. Mobec was launched in Columbia, Denmark, France, Germany, Ireland, Italy, Netherlands, S. Africa, Sweden, and the UK for osteo- and rheumatoid arthritis as an NSAID. It can be synthesized in four steps from benzisothiazolo-3(2H)-one- 1,1-dioxide. 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. Viramune was launched in the US for use in combination with nucleoside analogs to treat HIV-infected adults who have experienced clinical and/or immulogic deterioration. It can be prepared in four steps from 2chloro-4-methyl-3-nitropyridine. It is a potent inhibitor of HIV-1 reverse transcriptase with no rnuscarinic or benzodiazepine activity. Mechanistically, it is a non-competitive non-nucleoside inhibitor. It has a low toxicity for uninfected cells most likely due to its specificity, i.e., it does not inhibit eukaryotic DNA polymerase α, β, γ and δ. HIV-2, SIV and FeLV are not affected by nevirapine and monotherapy is limited by the rapid onset of resistance. 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.
• Uses: Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class. angiotensin 2 receptor antagonist For symptomatic treatment of arthritis and osteoarthritis. An inhibitor of Cox-1 and Cox-2, selective for Cox-2. Preferential cyclooxygenase (COX-2) inhibitor. Used as an anti-inflammatory.
• 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.
• Therapeutic Function: Antiinflammatory
• 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.

Technology Process of Meloxicam

There total 20 articles about Meloxicam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

meloxicam potassium salt monohydrate (892395-40-3) → meloxicam (71125-38-7)

Guidance literature:

meloxicam potassium salt monohydrate; With potassium hydroxide; pyrographite; In ethanol; water; at 40 - 45 ℃; for 0.666667h;

With acetic acid; In ethanol; water; at 10 - 30 ℃; for 2.5h; pH=3 - 5; Product distribution / selectivity;

Reference yield: 95.0%

5-methyl-2-thiazol-2-amine (7305-71-7) + ethyl 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (24683-26-9) → meloxicam (71125-38-7)

Guidance literature:

In o-xylene; for 24h; Product distribution / selectivity; Heating / reflux;

Reference yield: 88.8%

5-methyl-2-thiazol-2-amine (7305-71-7) + methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide (35511-15-0) → meloxicam (71125-38-7)

Guidance literature:

In o-xylene; at 25 - 145 ℃; for 33.5 - 38h; Industry scale;

upstream raw materials:

5-methyl-2-thiazol-2-amine

methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide

methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Downstream raw materials:

N-[3,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

meloxicam benzoic acid

meloxicam gentisic acid

meloxicam 4-hydroxybenzoic acid

Refernces

• 1、 -. "USE OF NON-STEROIDAL ANTI-INFLAMMATORY DRUGS MELOXICAM AND PIROXICAM, ADMINISTERED INTRAVAGINALLY, FOR INTERRUPTION OF A WOMAN'S OVULATION PROCESS". Page/Page column. . Retrieved 2014/07/09.
• 2、 -. "Process for the preparation of crystalline form-1 of 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide". Page/Page column 2-3. . Retrieved 2010/02/15.