Meloxicam supplier | CasNO.71125-38-7

Name
Meloxicam
EINECS 615-253-8
CAS No. 71125-38-7
Article Data10
CAS DataBase
Density 1.614 g/cm³
Solubility DMSO: soluble
Melting Point 255 °C
Formula C₁₄H₁₃N₃O₄S₂
Boiling Point
Molecular Weight 351.407
Flash Point
Transport Information
Appearance light yellow solid
Safety 26
Risk Codes 22-36/37/38
Molecular Structure
Hazard Symbols Xn
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;
PSA 136.22000
LogP 3.04260

Synthetic route

: 892395-40-3
meloxicam potassium salt monohydrate

: 71125-38-7
meloxicam

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With 1,2-dichloro-ethane	76%

...Expand

: 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

Conditions	Yield
With toluene-4-sulfonic acid; 1,2-dichloro-ethane	48%

: 6639-62-9
methyl 3-oxo-2,3-dihydrobenzo[d][1,2]thiazol-2-acetate 1,1-dioxide

: 71125-38-7
meloxicam

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In xylene at 139 - 140℃; for 32 - 37h;

...Expand

Reaxys ID: 11649320: Reaxys ID: 11649320

: 71125-38-7
meloxicam

Conditions

Conditions	Yield
Stage #1: With sodium methylate In methanol for 0.166667h; Stage #2: With pyrographite In methanol Stage #3: With hydrogenchloride In methanol; water pH=1.12 - 3.70; Purification / work up;

Reaxys ID: 11649324: Reaxys ID: 11649324

: 71125-38-7
meloxicam

Conditions

Conditions	Yield
Stage #1: With sodium methylate In methanol for 0.166667h; Stage #2: With pyrographite In methanol Stage #3: With hydrogenchloride In methanol; water pH=2.3 - 2.4; Purification / work up;

: 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

A: 67-56-1
methanol

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

C: 71125-38-7
meloxicam

Conditions

Conditions	Yield
pyrographite In xylene at 170 - 180℃; for 24h; Product distribution / selectivity;

...Expand

: 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: 67-56-1
methanol

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

C: 71125-38-7
meloxicam

Conditions

Conditions	Yield
pyrographite In xylene at 170 - 180℃; for 24h; Product distribution / selectivity;

...Expand

: 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

A: 1145656-36-5
N-[3,5-dimethyl-1,3-thiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

B: 71125-38-7
meloxicam

Conditions

Conditions	Yield
With methane In 5,5-dimethyl-1,3-cyclohexadiene at 138 - 142℃; for 24h; Inert atmosphere; Large scale reaction;

...Expand

: 74-85-1
ethene

: 71125-38-7
meloxicam

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene; [(2)H6]acetone

: 97-67-6
(S)-Malic acid

: 71125-38-7
meloxicam

: meloxicam:L-malic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

: 110-94-1
1,5-pentanedioic acid

: 71125-38-7
meloxicam

: 1246227-11-1
meloxicam glutaric acid

Conditions

Conditions	Yield
In chloroform for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

: 71125-38-7
meloxicam

: 110-16-7
maleic acid

: 1174325-93-9
4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide maleic acid (1:1)

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;
In ethyl acetate for 19h; Solvent;
In tetrahydrofuran at 20℃; for 24h;

: 71125-38-7
meloxicam

: 65-85-0
benzoic acid

: 1174325-83-7
meloxicam benzoic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: meloxicam; benzoic acid for 0.25h; Milling; Stage #2: In acetone
In tetrahydrofuran at 20℃; for 0.5h; Solvent; Milling;

: 79-14-1
glycolic Acid

: 71125-38-7
meloxicam

: 1174325-97-3
meloxicam glycolic acid

Conditions

Conditions	Yield
In chloroform for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

: 141-82-2
malonic acid

: 71125-38-7
meloxicam

: 1174325-96-2
meloxicam malonic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

: 110-15-6
succinic acid

: 71125-38-7
meloxicam

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

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: succinic acid; meloxicam for 0.25h; Milling; Stage #2: In acetone Solvent;
In ethyl acetate at 30℃; Solvent;

: 124-04-9
Adipic acid

: 71125-38-7
meloxicam

: meloxicam:adipic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: Adipic acid; meloxicam for 0.25h; Milling; Stage #2: In acetone Solvent;

: 490-79-9
2,5-dihydroxybenzoic acid.

: 71125-38-7
meloxicam

: 1174325-98-4
meloxicam gentisic acid

Conditions

Conditions	Yield
for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

: 71125-38-7
meloxicam

: 99-96-7
4-hydroxy-benzoic acid

: 1174325-95-1
meloxicam 4-hydroxybenzoic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran

: 617-48-1
malic acid

: 71125-38-7
meloxicam

: meloxicam:DL-malic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;

: 71125-38-7
meloxicam

: 69-72-7
salicylic acid

: 1174325-91-7
4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide salicylic acid (1:1)

Conditions

Conditions	Yield
In ethyl acetate for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;
Stage #1: meloxicam; salicylic acid for 0.25h; Milling; Stage #2: In acetone

: 71125-38-7
meloxicam

: 501-52-0
3-Phenylpropionic acid

: 1174326-03-4
meloxicam hydrocinnamic acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran

: 71125-38-7
meloxicam

: 86-48-6
1-hydroxy-2-naphthoic acid

: 1174325-92-8
4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide 1-hydroxy-2-naphthoic acid (1:1)

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%
In tetrahydrofuran Product distribution / selectivity;
In dimethylsulfoxide-d6; water at 25 - 90℃; Solvent;	71 g

: 124-83-4
D-(+)-camphoric acid

: 71125-38-7
meloxicam

: 1246227-13-3
meloxicam (+)-camphoric acid

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%

: 71125-38-7
meloxicam

: 110-17-8
(2E)-but-2-enedioic acid

: C4H4O4*2C14H13N3O4S2

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h;	100%

: 6284-40-8
1-deoxy-1-(methylamino)-D-glucitol

: 71125-38-7
meloxicam

: 244241-52-9
N-methylglucamine salt of meloxicam

Conditions

Conditions	Yield
In ethanol at 60℃; for 0.5h;	93%

: 71125-38-7
meloxicam

: 4-hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, acetic acid solvate

Conditions

Conditions	Yield
With acetic acid	92%

: 124-83-4
D-(+)-camphoric acid

: 71125-38-7
meloxicam

: meloxicam:(+)-camphoric acid

Conditions

Conditions	Yield
In chloroform at 20℃;	91%
In tetrahydrofuran Product distribution / selectivity;

: 35511-15-0
methyl 2-methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

: 71125-38-7
meloxicam

: 7305-71-7
5-methyl-2-thiazol-2-amine

Conditions

Conditions	Yield
With montmorillonite MK10 impregnated with ZnCl2 In o-xylene for 24h; Reagent/catalyst; Reflux; Green chemistry;	90%

: iron(II) acetate tetrahydrate

: 71125-38-7
meloxicam

: [bis(4-oxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide)iron(II)] tetrahydrate

Conditions

Conditions	Yield
In methanol N2, mixed a hot solns., refluxed for 0.5 h; ppt. filtered, washed (hot methanol under N2), dried (vac., room temp.);elem. anal.;	88%

: [osmium(II)dichloride(η6-p-cymene)]2

: 71125-38-7
meloxicam

: dichlorido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)osmium(II)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 12h; Inert atmosphere;	81%

: 64-17-5
ethanol

: 5970-45-6
zinc(II) acetate dihydrate

: 71125-38-7
meloxicam

: trans-[Zn(Hmel)2(EtOH)2]

Conditions

Conditions	Yield
for 2h; Reflux;	80%

...Expand

: 52462-29-0
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2

: 71125-38-7
meloxicam

: dichlorido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)ruthenium(II)

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 12h; Inert atmosphere;	80%

: copper(II) choride dihydrate

: 71125-38-7
meloxicam

: [Cu(meloxicam)2]

Conditions

Conditions	Yield
In ethanol for 24h; Reflux;	79%

: 90591-13-2
di-μ-bromo-bis[bromo(η(6)-para-cymene)ruthenium(II)]

: 71125-38-7
meloxicam

: bromido(4-hydroxy-2-methyl-1,1-dioxo-1,2-dihydro-λ'6-benzo[e][1,2]thiazine-3-carboxylic acid(5-methyl-thiazol-2-yl)amide)(η6-p-cymene)ruthenium(II)

Conditions

Conditions	Yield
Stage #1: meloxicam With sodium methylate In methanol at 20℃; for 0.5h; Stage #2: di-μ-bromo-bis[bromo(η(6)-para-cymene)ruthenium(II)] In methanol at 20℃; for 4h;	79%

Meloxicam 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.

Meloxicam 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

Product Name

Meloxicam

Synthetic route

Meloxicam History

Meloxicam Specification

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