Meloxicam Chemical Properties

Melting point:

255 °C

Density 

1.613±0.06 g/cm3(Predicted)

storage temp. 

0-6°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 

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

Merck 

14,5826

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

ZRVUJXDFFKFLMG-UHFFFAOYSA-N

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)

Safety Information

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

Toxicity

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

MSDS

• Language:English Provider:Meloxicam

Meloxicam Usage And Synthesis

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.

References

https://en.wikipedia.org/wiki/Meloxicam
https://www.drugbank.ca/drugs/DB00814
https://www.drugs.com/meloxicam.html
http://www.medicinenet.com/meloxicam/article.htm

Description

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.

Description

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.

Chemical Properties

Light Yellow Solid

Originator

Boehringer Ingelheim (Germany)

Originator

Boehringer lngelheim (Germany)

Uses

Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.

Uses

angiotensin 2 receptor antagonist

Uses

For symptomatic treatment of arthritis and osteoarthritis.

Uses

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

Uses

Preferential cyclooxygenase (COX-2) inhibitor. Used as an anti-inflammatory.

Definition

ChEBI: 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.

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.

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.

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.

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.

Meloxicam(71125-38-7)Related Product Information

• Piroxicam
• Ampiroxicam
• Tenoxicam
• Lornoxicam
• meloxicam and piroxicam intermediates
• Amido Methyl Meloxicam (Meloxicam Impurity),Meloxicam Impurity
• MELOXICAM RELATED COMPOUND C (30 MG) (ISO-PROPYL 4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIA-ZINE-3-CARBOXYLATE-1,1-DIOXIDE)
• Meloxicam epolamine
• MELOXICAM RELATED COMPOUND C (30 MG) (ISO-PROPYL 4-HYDROXY-2-METHYL-2H-1,2-BENZOTHIA-ZINE-3-CARBOXYLATE-1,1 -DIOXIDE)
• MELOXICAM IMPURITY STANDARD BP STANDARD(CRM STANDARD)
• MELOXICAM BP STANDARD(CRM STANDARD)
• MELOXICAM IMPURITY STANDARD
• 5tert-Butyldimethylsilyloxy Meloxicam
• MELOXICAM IMP. B (BP): 2-AMINO-5-METHYLTHIAZOLE
• MELOXICAM SODIUM SALT HYDRATE,Meloxicam hydrate sodium salt
• 5'-HYDROXY MELOXICAM
• 5'-CARBOXY MELOXICAM
• Meloxicam