Lornoxicam

Base Information

• Chemical Name: Lornoxicam
• CAS No.: 70374-39-9
• Molecular Formula: C13H10ClN3O4S2
• Molecular Weight: 371.825
• Hs Code.: 29349990
• Mol file: 70374-39-9.mol

Synonyms:Chlortenoxicam;Lornoxicamum;6-Chloro-4-hydroxy-2-methyl-N-2-pyridinyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide;2H-Thieno(2,3-e)-1,2-thiazine-3-carboxamide, 6-chloro-4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide;

Chemical Property of Lornoxicam

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 225-230 °C (dec.)
• Refractive Index: 1.741
• PKA: pKa2 4.7(at 25℃)
• PSA: 136.22000
• Density: 1.742 g/cm³
• LogP: 3.38760
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >5mg/mL (warmed)

Purity/Quality:

99% ^*data from raw suppliers

Lornoxicam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T+
• Statements: 36/37/38-28
• Safety Statements: 26-36-45-36/37-28

MSDS Files:

SDS file from LookChem

Useful:

• Description: Lornoxicam (Trade name: “Xefo”) belongs to a non-steroidal anti-inflammatory drug. As a kind of oxicam class drug, it has analgesic, anti-inflammatory and antipyretic properties. It can be used for the treatment of various type of acute mild to moderate pain which results from inflammatory diseases of the joints, osteoarthritis, surgery, sciatica and rheumatic diseases. Lornoxicam is capable of potently inhibiting the prostaglandin biosynthesis process, making it have highly pronounced efficacy. The exact mechanism of Lornoxicam is not exactly understood. However, it is indicated that Lornoxicam can inhibit the prostaglandin and thromboxane synthesis by inhibiting both COX-1 and COX-2, leading to reduction of inflammation, pain, fever, and swelling. Lornoxicam is a COX inhibitor and non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory and analgesic properties. It inhibits production of thromboxane B2 (TXB2; ) from arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in HEL human erythroleukemic cells (IC50 = 3 nM), which endogenously express COX-1, as well as inhibits LPS-induced formation of prostaglandin F1α (PGF1α; ) from arachidonic acid in Mono-Mac-6 cells (IC50 = 8 nM), which endogenously express COX-2. Lornoxicam reduces LPS-induced production of nitric oxide and IL-6 in cell-based assays with IC50 values of 65 and 54 μM, respectively. It reduces carrageenan-induced paw edema in rats when administered intravenously at doses ranging from 0.1 to 9 mg/kg. Formulations containing lornoxicam have been used in the management of postoperative pain. Lornoxicam is a nonselective NSAID for oral and intravenous administration. It has been available for human use since two decades and there is a growing body of evidence supporting its efficacy and tolerability for management of acute pain.Xefo, a member of the oxicam family of nonsteroidal antiinflammatory agents, was launched in Denmark for mild to moderate pain and inflammation. A seven step synthesis, beginning with 2,5-dichlorothiophene, provides access to this compound. It inhibits prostaglandin synthesis at the level of cyclooxygenase (Cox1 :Cox2 = 0.6) but does not inhibit 5-lipoxygenase. Xefo did not increase serum levels of pepsinogen I (an indicator of gastric mucosal status) and readily penetrates perivascular interstitial spaces including synovial fluid. It is as effective as morphine, meperidine and tramadol in relieving post operative pain and as efficient as other NSAlDs in relieving the symptoms of osteoarthritis and rheumatoid arthritis. It is 100 times more potent than Tenoxicam in inhibiting PGD2 and more active than indomethacin (6x) or piroxicam (10x) in preventing arachadonic acid influenced lethality in mice. Xefo has inhibitor effects on spinal nocicceptive processing presumably via release of endogenous opiods and evidence suggests it is good for migraine.
• Uses: Lornoxicam belongs to the oxicam class. It has anti-inflammatory and antipyretic properties. Lornoxicam prevents the synthesis of prostaglandin (PG) by inhibiting cyclo-oxygenase. It is used to relieve various types of symptoms associated with osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute sciatica and low back pain.Lornoxicam is approved for use in Japan.Lornoxicam has been used as a drug in melanin binding study with cassette dosing and rapid equilibrium dialysis inserts. Lornoxicam differs from other oxicam compounds in its potent inhibition of prostaglandin biosynthesis, a property that explains the particularly pronounced efficacy of the drug. For the treatment of acute mild to moderate pain, as well as pain and inflammation of the joints caused by certain types of rheumatic diseases. Cyclooxygenase inhibitor; structurally similar to tenoxicam. Anti-inflammatory; analgesic
• Indications: Lornoxicam is a non-steroidal anti-inflammatory drug (NSAID) that is used as a painkiller (analgesic). A high level of pain relief is experienced by about 45% of those with moderate to severe postoperative dental pain after a single dose of lornoxicam 8 mg, compared to about 10% with placebo. This is comparable to the proportion experiencing the same level of pain relief with ibuprofen 200 to 400 mg. Adverse events were generally mild and did not differ from placebo in these singe dose studies. There were insufficient data to assess duration of action, but it is likely to be similar to ibuprofen 200 mg.

Technology Process of Lornoxicam

There total 4 articles about Lornoxicam 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: 98.4%

methyl 6-chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylate 1,1-dioxide (70415-50-8) + 2-aminopyridine (504-29-0) → lornoxicam (70374-39-9)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; at 160 ℃; Temperature; Inert atmosphere;

Reference yield: 87.0%

C14H14ClN3O5S2 → lornoxicam (70374-39-9)

Guidance literature:

With sodium methylate; for 2h; Reflux;

Reference yield:

2-aminopyridine (504-29-0) → lornoxicam (70374-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: benzotriazol-1-ol; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 2 h / Large scale

1.2: 1 h / 20 °C / Large scale

2.1: triethylamine / ethyl acetate / 0 - 20 °C / Large scale

3.1: sodium methylate / 2 h / Reflux

With sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; ethyl acetate;

upstream raw materials:

2-aminopyridine

methyl 6-chloro-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxylate 1,1-dioxide

Downstream raw materials:

methyl 5-chloro-2-thiophenecarboxylate

methyl (pyridin-2-ylcarbamoyl)formate

Refernces

• 1、 -. "Preparation method of non-steroidal anti-inflammatory analgesic lornoxicam". . . Retrieved 2017/07/20.