Isoxicam

Names

[ Name ]:
Isoxicam

[Synonym ]:
2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-, 1,1-dioxide
Isoxicam
Isoxicamo [INN-Spanish]
4-Hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
4-hydroxy-2-methyl-N-(5-methylisoxazol-3-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
Isoxicamo
4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide
N-(5-methyl-3-isoxazolyl)-4-hydroxy-2-methyl-2H-1,2-benzthiazine-3-carboxamide 1,1-dioxide
EINECS 252-084-5
4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-1λ<sup>6</sup>,2-benzothiazine-3-carboxamide
Isoxicamum [INN-Latin]
Maxicam
UNII:8XU734C4NG
Pacyl (antiinflammatory)
Isoxicamum
UNII-8XU734C4NG
4-Hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

Biological Activity

[Description]:

Isoxicam is an orally active, long-acting, non-steroidal anti-inflammatory agent for the research of arthritis[1]. Isoxicam is a nonselective inhibitor of COX-1 and COX-2[2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

COX-1

COX-2

[References]

[1]. DiPasquale G, et al. The antiinflammatory properties of isoxicam (4-hydroxy-2methyl-N-(5-methyl-3isoxolyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide). Agents Actions. 1975 Aug;5(3):256-63.

[2]. Xu S, et al. Oxicams bind in a novel mode to the cyclooxygenase active site via a two-water-mediated H-bonding Network. J Biol Chem. 2014 Mar 7;289(10):6799-808.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
518.8ºC at 760mmHg

[ Melting Point ]:
265-271℃

[ Molecular Formula ]:
C₁₄H₁₃N₃O₅S

[ Molecular Weight ]:
335.335

[ Flash Point ]:
267.5ºC

[ Exact Mass ]:
335.057587

[ PSA ]:
121.12000

[ LogP ]:
1.38

[ Index of Refraction ]:
1.686

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DL0703000

CHEMICAL NAME :: 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-, 1,1-dioxide

CAS REGISTRY NUMBER :: 34552-84-6

LAST UPDATED :: 199706

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C14-H13-N3-O5-S

MOLECULAR WEIGHT :: 335.36

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AGACBH Agents and Actions, A Swiss Journal of Pharmacology. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1969/70- Volume(issue)/page/year: 7,481,1977

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DL0703000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Effect of some new prostaglandin synthetase inhibitors on the endotoxin induced mortality and biochemical changes in experimental animals.

Res. Commun. Chem. Pathol. Pharmacol. 60(1) , 19-25, (1988)

The protective effect of some novel nonsteroidal anti-inflammatory agents has been studied on the endotoxin (lipopolysaccharide B) shock induced mortality in mice and biochemical changes in rats. All ...

[The effect of estro-progesterones on the inflammatory episodes of hand arthroses. Apropos of a case].

Rev. Rhum. Mal. Osteoartic. 56(10) , 709-11, (1989)

Controlled-release naproxen compared with isoxicam in patients with osteoarthritis.

Curr. Med. Res. Opin. 11(1) , 28-33, (1988)

The therapeutic efficacy and tolerability of a new controlled-release 1000 mg tablet of naproxen (naproxen CR) were compared with 200 mg isoxicam in 100 out-patients with osteoarthritis. Medications w...