ampiroxicam

Names

[ Name ]:
ampiroxicam

[Synonym ]:
(±)-4-(1-Hydroxyethoxy)-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide ethyl carbonate (ester) 1,1-dioxide
Ethyl 1-{[2-methyl-1,1-dioxido-3-(pyridin-2-ylcarbamoyl)-2H-1,2-benzothiazin-4-yl]oxy}ethyl carbonate
ampiroxicam
4-{1-[(Ethoxycarbonyl)oxy]ethoxy}-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide S,S-dioxide
Ethyl 1-{[2-methyl-1,1-dioxido-3-(2-pyridinylcarbamoyl)-2H-1,2-benzothiazin-4-yl]oxy}ethyl carbonate
4-[1-(Ethoxycarbonyloxy)ethoxy]-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide
Ampiroxicamum [Latin]
MFCD00866079
4-[1-(Ethoxycarbonyloxy)ethoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide
Flucam
Carbonic acid, ethyl 1-[[2-methyl-1,1-dioxido-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl]oxy]ethyl ester
ethyl 1-[[2-methyl-1,1-dioxo-3-(pyridin-2-ylcarbamoyl)-1λ<sup>6</sup>,2-benzothiazin-4-yl]oxy]ethyl carbonate
Ampiroxicamum

Biological Activity

[Description]:

Ampiroxicam(CP65703) is a nonselective cyclooxygenase inhibitor uesd as anti-inflammatory drug.Target: COXAmpiroxicam is a non-steroidal anti-inflammatory drug. It is a prodrug of piroxicam. Ampiroxicam inhibits the stretching response in mice induced by phenylbenzoquinone (PBQ) with maximum protective effect (MPE) of 2 mg/kg. Ampiroxicam inhibits swelling in a dose-responsive manner in the rat foot edema (RFE) assay with ED50 of 28 mg/kg at single oral dose and 7.8 mg/kg at 5 daily oral dose. Ampiroxicam blocks primary and secondary lesion development in rat adjuvant arthritis with ED50 of 2.2 mg/kg and 0.5 mg/kg, respectively. Ampiroxicam (3.2 mg/kg) leads to a plasma concentration of 12 μg/mL at a Tmax of 2 hours for piroxicam derived from ampiroxicam in rats [1]. Ultraviolet-A (UVA)-irradiated 1% Ampiroxicam sensitized in guinea pigs shows positive reaction in the patch testing to UVA-irradiated 1% Ampiroxicam and 1% thiosalicylate (TOS). Concentration of Ampiroxicam is easily reduced by the increase in UVA irradiation doses, as compared with that of piroxicam [2].

[Related Catalog]:

Natural Products >> Alkaloid

Research Areas >> Inflammation/Immunology

[Target]

COX

[References]

[1]. Aoki T, et al. Premedication with cyclooxygenase-2 inhibitor meloxicam reduced postoperative pain in patients after oral surgery. Int J Oral Maxillofac Surg. 2006 Jul;35(7):613-7.

[2]. Sasaki, T., et al., Antigenic characterization in ampiroxicam-induced photosensitivity using an in vivo model of contact hypersensitivity. J Dermatol Sci, 1999. 21(3): p. 170-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Melting Point ]:
159-161?C

[ Molecular Formula ]:
C₂₀H₂₁N₃O₇S

[ Molecular Weight ]:
447.462

[ Exact Mass ]:
447.110016

[ PSA ]:
132.51000

[ LogP ]:
3.12

[ Index of Refraction ]:
1.630

[ Storage condition ]:
-20°C Freezer

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
FG1602400

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

Related Compounds

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