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Meloxicam

Product Name
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
Formula Weight
351.4
MOL File
71125-38-7.mol
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Meloxicam Property

Melting point:
255 °C
Density 
1.613±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: soluble
pka
4.08 in water; 4.24 ± 0.01 in water/ethanol (1:1); 4.63 ± 0.03 in water/ethanol (1:4)
form 
Off-white solid
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
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)
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
444800
Product name
Meloxicam
Packaging
100mg
Price
$201
Updated
2024/03/01
Sigma-Aldrich
Product number
1379401
Product name
Meloxicam
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
400mg
Price
$732
Updated
2024/03/01
Sigma-Aldrich
Product number
BP629
Product name
Meloxicam
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$252
Updated
2023/06/20
TCI Chemical
Product number
M1959
Product name
Meloxicam
Purity
>98.0%(HPLC)
Packaging
5g
Price
$61
Updated
2024/03/01
TCI Chemical
Product number
M1959
Product name
Meloxicam
Purity
>98.0%(HPLC)
Packaging
25g
Price
$179
Updated
2024/03/01
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Meloxicam Chemical Properties,Usage,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.

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.

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.

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.

Meloxicam Preparation Products And Raw materials

Raw materials

Preparation Products

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Meloxicam Suppliers

Jinan Hongda Trading Co., Ltd.
Tel
182-6550-6873 18265506873
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439706954@qq.com
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China
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Shandong Mingfeng Pharmaceutical and Technology Co. Ltd
Tel
-1345456643 15315114555
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QQ:1345456643
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1345456643@qq.com
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China
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Wuhan Huajiu Pharmaceutical Technology Co.,Ltd.
Tel
027-59225746 18062681621
Fax
027-59225746
Email
730880265@qq.com
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China
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4895
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Wuhan Xinru Chemical Industry Co., Ltd
Tel
15927387915
Email
2162228368@qq.com
Country
China
ProdList
3410
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58
Jinan Hongkangda Chemical Co., Ltd
Tel
0531-88901705 18753193522
Email
810353473@qq.com
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China
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Nanjing Paite Meisheng Technology Co., Ltd
Tel
133-27728092 13327728092
Email
xu_meiqin@petmedtech.com
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China
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30
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Hubei Yangyi Xinsheng Biological Medicine Co., LTD
Tel
15927387915
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2162228368@qq.com
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China
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J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
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jkinfo@jkchemical.com
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China
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96815
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
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86-21-61259102
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market03@meryer.com
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3B Pharmachem (Wuhan) International Co.,Ltd.
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View Lastest Price from Meloxicam manufacturers

Sigma Audley
Product
Meloxicam 71125-38-7
Price
US $35.00-25.00/kg
Min. Order
1kg
Purity
99.8%
Supply Ability
200tons/year
Release date
2024-03-15
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Meloxicam 71125-38-7
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-10-12
shandong perfect biotechnology co.ltd
Product
Meloxicam 71125-38-7
Price
US $0.00/KG
Min. Order
1KG
Purity
75% HPLC
Supply Ability
1000kgs
Release date
2023-07-19

71125-38-7, MeloxicamRelated Search:


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