Tenoxicam

Base Information

• Chemical Name: Tenoxicam
• CAS No.: 59804-37-4
• Molecular Formula: C13H11N3O4S2
• Molecular Weight: 337.38
• Hs Code.: 2934999090
• Mol file: 59804-37-4.mol

Synonyms:Tenoxicam (JAN/USAN);Ro 12-0068/000;Tilcotil (TN);Tenoxicam [USAN:BAN:INN:JAN];2H-Thieno(2,3-e)-1,2-thiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide;Tenoxicamum [INN-Latin];(3Z)-3-[hydroxy-(pyridin-2-ylamino)methylidene]-4-methyl-5,5-dioxo-5$l^{6},9-dithia-4-azabicyclo[4.3.0]nona-7,10-dien-2-one;Ro 12-0068;Prestwick_849;4-Hydroxy-2-methyl-N-2-pyridinyl-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide;Tilcotil;Tenoxicam CP EP;4-Hydroxy-2-methyl-N-pyridin-2-yl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide-1,1-dioxide;

Chemical Property of Tenoxicam

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Melting Point: 209-213 °C
• Refractive Index: 1.741
• PKA: pKa1 5.3, pKa2 1.1(at 25℃)
• PSA: 136.22000
• Density: 1.675 g/cm³
• LogP: 2.73420
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, sparingly soluble in methylene chloride, very slightly soluble in anhydrous ethanol. It dissolves in solutions of acids and alkalis.
• Water Solubility.: 61.9mg/L(32 oC)

Purity/Quality:

99% ^*data from raw suppliers

Tenoxicam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 23/24/25-36/37/38
• Safety Statements: 36/37/39-45-36-26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Tenoxicam is a non-steroidal antiinflammatory agent with a profile similar to related piroxicam and now withdrawn isoxicam (55). It is useful in the treatment of rheumatoid arthritis, osteoarthritis and related disorders.
• Uses: Tenoxicam has been used:as a non-steroidal anti-inflammatory agent (NSAID) to study its effects on root gravitropism in Arabidopsis thalianaas a standard in microanalysis of NSAIDs by spectrophotometryto test its effect on surface potential andmembrane fluidity modification in phosphoglyceride monolayers antipsychotic Nonsteroidal anti-inflamatory agent
• Clinical Use: NSAID and analgesic
• Drug interactions: Potentially hazardous interactions with other drugs ACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemia. Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage). Antibacterials: possibly increased risk of convulsions with quinolones. Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban. Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine. Antidiabetic agents: effects of sulphonylureas enhanced. Antiepileptics: possibly increased phenytoin concentration. Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavir. Ciclosporin: may potentiate nephrotoxicity. Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib. Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics. Lithium: excretion decreased. Pentoxifylline: increased risk of bleeding. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Tenoxicam

There total 13 articles about Tenoxicam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

4-hydroxy-N-2-pyridyl-2H-thieno<2,3-e>-1,2-thiazine-3-carboxamide 1,1-dioxide (106820-67-1) + carbonic acid dimethyl ester (616-38-6) → tenoxicam (59804-37-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 7h; Large scale;

Reference yield: 83.0%

2-aminopyridine (504-29-0) + methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide (98827-44-2) + carbonic acid dimethyl ester (616-38-6) → tenoxicam (59804-37-4)

Guidance literature:

methyl 4-hydroxy-2H-thieno<2,3-e>-1,2-thiazine-3-carboxylate 1,1-dioxide; carbonic acid dimethyl ester; With potassium carbonate; In N,N-dimethyl-formamide; at 140 ℃; for 5h; Large scale;

2-aminopyridine; With potassium carbonate; In N,N-dimethyl-formamide; for 7h; Large scale;

Reference yield: 76.9%

2-aminopyridine (504-29-0) + 4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine,1,1-dioxide (59804-25-0) → tenoxicam (59804-37-4)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; for 6h; Concentration; Reflux;

upstream raw materials:

2-aminopyridine

4-hydroxy-3-methoxycarbonyl-2-methyl-2H-thieno[2,3-e]-1,2-thiazine,1,1-dioxide

3-chlorothiophene-2-carboxylic acid

2-(carbomethoxy)thiophene-3-sulfonyl chloride

Downstream raw materials:

4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxylic acid 2-phenylhydrazide 1,1-dioxide

4-hydroxy-2-methyl-N-phenyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

4-hydroxy-N-(3-methylphenyl)-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

N-(3-chlorophenyl)-4-hydroxy-2-methyl-2H-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

Refernces

• 1、 -. "Tenoxicam preparation method". Paragraph 0042-0045. . Retrieved 2017/08/31.
• 2、 Demertzis, Mavroudis A.,Hadjikakou, Sotiris K.,Kovala-Demertzi, Dimitra,Koutsodimou, Aglaia,Kubicki, Maciej. "Organotin-drug interactions. Organotin adducts of tenoxicam: Synthesis and characterization of the first organotin complex of tenoxicam". . p. 2787 - 2801. Retrieved 2007/10/03.