99464-64-9 Usage
Uses
Used in Pharmaceutical Industry:
Ampiroxicam is used as a prodrug for piroxicam, a widely used anti-inflammatory agent. It is employed for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis. Ampiroxicam is used for its potent anti-inflammatory properties and its ability to have fewer side effects on the gastric mucosa compared to piroxicam.
Used in Anti-inflammatory Applications:
Ampiroxicam is used as an anti-inflammatory agent for suppressing various inflammation-related conditions in animals, such as carrageenan edema, ultraviolet erythema, traumatic edema, capillary permeability, acetic acid writhing, yeast algesia, and yeast hyperthermia. Its potency is similar or greater than that of piroxicam, making it a valuable alternative for managing inflammation.
Brand Names:
Ampiroxicam is marketed under the brand names Nacycl and Flucam.
Originator
Pflzer (Japan)
Manufacturing Process
To a round bottomed flask equipped with a reflux condenser and stirring bar
were added 2-methyl-N-(2-pyridyl)-4-hydroxy-2H-1,2-benzodiazine-3-
carboxamide 1,1-dioxide (piroxicam, 10.0 g, 30.2 mmol), potassium
carbonate (8.35 g, 60.4 mmol), α-chloroethyl ethyl carbonate (12.35 mL,
13.81 g, 90.6 mmol) and acetone (350 mL). The heterogenous reaction
mixture was heated to reflux under a nitrogen atmosphere. After 19 hours,
anhydrous sodium iodide (22.6 g, 150.7 mmol) was added and reflux
continued for an additional 5 hours. The acetone was removed in vacuum
leaving a brown residue which was treated with water (250 mL) and
methylene chloride (250 mL). The organic layer was separated and the
aqueous layer extracted with additional methylene chloride (250 mL). The
combined organic extracts were washed with water (250 mL), brine (250 mL),
dried (Na2SO4) and concentrated in vacuum to a brown oil. Column
chromatography on silica gel (1:9 ethyl acetate:methylene chloride) afforded
a pale yellow foam (10.67 g, 79.0%). The 4-[1-(ethoxycarbonyloxy)ethoxy]-
2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide was
recrystallized from toluene to give 9.50 g of pure white crystals; melting point
159-161°C.
Check Digit Verification of cas no
The CAS Registry Mumber 99464-64-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,9,4,6 and 4 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 99464-64:
(7*9)+(6*9)+(5*4)+(4*6)+(3*4)+(2*6)+(1*4)=189
189 % 10 = 9
So 99464-64-9 is a valid CAS Registry Number.
InChI:InChI=1/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)
99464-64-9Relevant articles and documents
Deuterium Isotope Effects on Carbon-13 NMR Shifts and the Tautomeric Equilibrium in N-Substituted Pyridyl Derivatives of Piroxicam
Bordner, Jon,Hammen, Philip D.,Whipple, Earl B.
, p. 6572 - 6578 (1989)
N-Alkylated pyridyl derivatives of piroxicam are formally zwitterionic but can, at the expense of aromaticity in the pyridyl ring, revert to neutral structures by means of fast internal proton transfers.The large change in dipole moment accompanying these tautomeric shifts makes the equilibrium unusually sensitive to changes in chemical substitution, solvent, and temperature.This property is used to formulate, test, and verify a new type of deuterium isotope effect on carbon-13 NMR shifts recently proposed by Hansen and, in the process, establish close correspondencewith the general theory of isotope effects on proton transfer equilibria.
Anti-inflammatory 2-methyl-2H-1,2-benzo-(or -thieno-)thiazine-3-carboxamide 1,1-dioxide derivatives, compositions, and method of use therefor
-
, (2008/06/13)
Certain enol ether derivatives of oxicams (1,1-dioxides of N-heteroaryl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamides and N-heteroaryl-4-hydroxy-2-methyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamides) are useful as prodrugs of these antiinflammatory compounds.
