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Home> Encyclopedia >   /  Pharmaceutical  /  Pharmaceutical Intermediates  /  Antipyretic Analgesics and NSAIDs  /  Organic Intermediate  /  Pharmaceuticals and Biochemicals
Meloxicam structure
Meloxicam structure

Meloxicam

Iupac Name:4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide
CAS No.:71125-38-7
Molecular Weight:351.40072
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
Meloxicam
1.2 Synonyms

2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-, 1,1-dioxide 2H-1,2-Benzothiazine-3-carboximidic acid, 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-, 1,1-dioxide 4-hydroxy-2-méthyl-N-(5-méthyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxyde 4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazin-3-crboxamide 1,1-dioxide 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-carboximidic acid 1,1-dioxide 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-1,1-dioxide-2H-1,2-benzothiazine-3-carboxamide 4-Hydroxy-2-Methyl-N-(5-Methylthiazol-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxaMide 1,1-dioxide Meloxciam Meloxicam (400 mg) MeloxicaM (Mobic) meloxicam (tautomer) MeloxicaM API MeloxicaM, BP MeloxicamUsp27 Metacam MFCD11046047 MOBEC MOBIC Mobicox Movalis Movatec Parocin structure was taken from Chemical Abstracts Index Guide, number

1.3 CAS No.
71125-38-7
1.4 CID
54677470
1.5 EINECS(EC#)
615-253-8
1.6 Molecular Formula
C14H13N3O4S2 (isomer)
1.7 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)
1.8 InChkey
ZRVUJXDFFKFLMG-UHFFFAOYSA-N
1.9 Canonical Smiles
CC1=CN=C(S1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O
1.10 Isomers Smiles
CC1=CN=C(S1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O
2. Properties
3.1 Density
1.613
3.1 Melting point
255 oC
3.1 Boiling point
581.3±60.0
3.1 Refractive index
1.72
3.1 Flash Point
305.4±32.9 °C
3.1 Vapour pressure
1.07X10-15 mm Hg at 25 °C (est)
3.1 Precise Quality
351.03500
3.1 PSA
136.22000
3.1 logP
3.04260
3.1 Solubility
DMSO: soluble
3.2 Appearance
Light Yellow Solid
3.3 Chemical Properties
Light Yellow Solid
3.4 Color/Form
yellow
3.5 pKa
4.08 in water; 4.24 ± 0.01 in water/ethanol (1:1); 4.63 ± 0.03 in water/ethanol (1:4)
3.6 Water Solubility
DMSO: soluble
3.7 Stability
Stable. Incompatible with strong oxidizing agents.
3.8 StorageTemp
0-6°C
3. Use and Manufacturing
4.1 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.
4.2 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.
4.3 Storage
Keep Cold.
4.4 Usage
Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.
4. Safety and Handling
5.1 Symbol
GHS06
5.1 Hazard Codes
Xn
5.1 Signal Word
Danger
5.1 Risk Statements
R22
5.1 Safety Statements
26
5.1 Packing Group
III
5.1 Hazard Class
6.1
5.1 Hazard Declaration
H301
5.1 RIDADR
UN 2811 6.1/PG 3
5.1 Caution Statement
P301 + P310
5.1 WGK Germany
3
5.1 RTECS
DL0702000
5.1 Safety
Hazard Codes:Xn
Risk Statements:22-36/37/38
22:Harmful if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR:UN 2811 6.1/PG 3
WGK Germany:3
5.2 Specification

Light Yellow Solid
usageEng:Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.
Safety Statements:26
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
5.3 Toxicity
LD50 orally in mice: 470 mg/kg (Trummlitz, 1980)
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Reproductive toxicity, Category 1A

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H360 May damage fertility or the unborn child

H412 Harmful to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P273 Avoid release to the environment.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Usage
Meloxicam is developed for the treatment of rheumatoid arthritis and osteoarthritis. It is currently for the treatment of osteoarthritis and rheumatoid arthritis.
9. Computational chemical data
  • Molecular Weight:351.40072g/mol
  • Molecular Formula:C14H13N3O4S2
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:351.03474825
  • Monoisotopic Mass:351.03474825
  • Complexity:628
  • Rotatable Bond Count:2
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:7
  • Topological Polar Surface Area:136
  • Heavy Atom Count:23
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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