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71125-38-7

Basic Information
CAS No.: 71125-38-7
Name: Meloxicam
Article Data: 10
Cas Database
Molecular Structure:
Molecular Structure of 71125-38-7 (Meloxicam)
Formula: C14H13N3O4S2
Molecular Weight: 351.407
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;
EINECS: 615-253-8
Density: 1.614 g/cm3
Melting Point: 255 °C
Boiling Point: N/A
Flash Point: N/A
Solubility: DMSO: soluble
Appearance: light yellow solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-36/37/38
Safety: 26
Transport Information: N/A
PSA: 136.22000
LogP: 3.04260
Synthetic route
892395-40-3

meloxicam potassium salt monohydrate

71125-38-7

meloxicam

Conditions
ConditionsYield
Stage #1: meloxicam potassium salt monohydrate With potassium hydroxide; pyrographite In ethanol; water at 40 - 45℃; for 0.666667h;
Stage #2: With acetic acid In ethanol; water at 10 - 30℃; for 2.5h; pH=3 - 5; Product distribution / selectivity;
98.5%
Stage #1: meloxicam potassium salt monohydrate With potassium hydroxide; pyrographite In ethanol; water at 40 - 45℃; for 0.666667h;
Stage #2: With hydrogenchloride In ethanol; water at 10 - 30℃; for 2.5h; pH=3 - 5; Product distribution / selectivity;
97.1%
Stage #1: meloxicam potassium salt monohydrate With potassium hydroxide In ethanol; water at 50 - 55℃; Large scale reaction;
Stage #2: With hydrogenchloride In ethanol; water at 65 - 70℃; Reflux; Large scale reaction;
91%
7305-71-7

5-methyl-2-thiazol-2-amine

24683-26-9

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

71125-38-7

meloxicam

Conditions
ConditionsYield
In o-xylene for 24h; Product distribution / selectivity; Heating / reflux;95%
In xylene at 139 - 140℃; for 32 - 37h; Product distribution / selectivity; Heating / reflux; Molecular sieve;92.48%
7305-71-7

5-methyl-2-thiazol-2-amine

35511-15-0

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

71125-38-7

meloxicam

Conditions
ConditionsYield
In o-xylene at 25 - 145℃; for 33.5 - 38h; Industry scale;88.8%
In xylene for 48h; Heating;
244241-52-9

N-methylglucamine salt of meloxicam

71125-38-7

meloxicam

Conditions
ConditionsYield
Stage #1: N-methylglucamine salt of meloxicam In water at 70℃; for 0.5h; CN1 carbon;
Stage #2: With water; acetic acid at 70℃; for 0.25h; pH=4.6; Product distribution / selectivity;
87%
7305-71-7

5-methyl-2-thiazol-2-amine

24683-26-9

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

95-50-1

1,2-dichloro-benzene

71125-38-7

meloxicam

Conditions
ConditionsYield
With 1,2-dichloro-ethane76%
7305-71-7

5-methyl-2-thiazol-2-amine

24683-25-8

4-hydroxy-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide

71125-38-7

meloxicam

Conditions
ConditionsYield
With toluene-4-sulfonic acid; 1,2-dichloro-ethane48%
6639-62-9

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

71125-38-7

meloxicam

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 25percent MeONa/MeOH / toluene / 4 h / 80 °C
2: 1M aq.NaOH / ethanol / 24 h / Ambient temperature
3: xylene / 48 h / Heating
View Scheme
35511-14-9

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

71125-38-7

meloxicam

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1M aq.NaOH / ethanol / 24 h / Ambient temperature
2: xylene / 48 h / Heating
View Scheme
81-07-2

saccharin

71125-38-7

meloxicam

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) NaH / 1.) DMF, 50 deg C, 30 min, 2.) DMF, 4 h
2: 25percent MeONa/MeOH / toluene / 4 h / 80 °C
3: 1M aq.NaOH / ethanol / 24 h / Ambient temperature
4: xylene / 48 h / Heating
View Scheme
7305-71-7

5-methyl-2-thiazol-2-amine

24683-26-9

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

A

4-hydroxy-2-methyl-N-ethyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

B

71125-38-7

meloxicam

Conditions
ConditionsYield
In xylene at 139 - 140℃; for 32 - 37h;
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    Name:Meloxicam CAS NO: 71125-38-7 Grade:Medical scientific research and export Molecular formula:C14H13N3O4S2 Molecular weight:351.4007 Product Quality 12 years of chemical raw materials Mature operation of the industry System stability D

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History

In Europe, where the product has been available since the early 1990s, it is also prescribed and licensed for other anti-inflammatory benefits including relief from both acute and chronic pain in dogs and cats. For many years, both injectable and oral (liquid and tablet) formulations of meloxicam have been licensed for use in dogs, and injectable ones for use in cats. In June 2007, a new oral version of Metacam was licensed in Europe for the long-term relief of pain in cats. As of June 2008, Meloxicam is registered for long term use in cats in Australia, New Zealand, and throughout Europe. 'Metacam oral suspension 1.5 is not approved or recommended (according to the manufacture insert) for use in cats in the U.S.

Specification

The IUPAC name of Meloxicam is (3E)-3-[hydroxy-[(5-methyl-1,3-thiazol-2-yl)amino]methylidene]-2-methyl-1,1-dioxo-1λ6,2-benzothiazin-4-one. With the CAS registry number 71125-38-7, it is also named as 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methylthiazolyl)-, 1,1-dioxide. The product's categories are Active Pharmaceutical Ingredients; API; Health & Beauty; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Sulfur & Selenium Compounds; API's; Lipid Signaling, and the other registry number is 133687-22-6. Besides, it is light yellow solid, which should be stored in sealed containers in a cool, dry place away from oxidizing agents at 0-6 °C. In addition, its molecular formula is C14H13N3O4S2 and molecular weight is 351.40.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.66; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 6; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 64; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 136.22 Å2; (13)Index of Refraction: 1.72; (14)Molar Refractivity: 85.956 cm3; (15)Molar Volume: 217.724 cm3; (16)Polarizability: 34.076×10-24cm3; (17)Surface Tension: 85.325 dyne/cm; (18)Density: 1.614 g/cm3; (19)Melting Point: 255 °C; (20)Water Solubility: 7.150 mg/L at 25 °C.

Preparation of Meloxicam: this chemical can be prepared by Methyl 4-hydroxy-2-methyl-(2H)-1,2-benzothiazine-3-carboxylate-1,1-dioxide and 2-Amino-5-methylthiazole. The yield is 74 %.

Uses of Meloxicam: this chemical is a nonsteroidal anti-inflammatory drug with analgesic and fever reducer effects. And it inhibits cyclooxygenase that can be used as an anti-inflammatory. Additionally, it can be used for the treatment of rheumatoid arthritis and osteoarthritis.

When you are using this chemical, please be cautious about it as the following: it irritates to eyes, respiratory system and skin. And it is harmful if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
(1)SMILES: Cc1cnc(s1)NC(=O)C\3=C(/O)c2ccccc2S(=O)(=O)N/3C
(2)InChI: InChI=1/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)
(3)InChIKey: ZRVUJXDFFKFLMG-UHFFFAOYAR

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