Sudoxicam

Modify Date: 2024-01-09 15:04:15

Sudoxicam Structure
Sudoxicam structure
Common Name Sudoxicam
CAS Number 34042-85-8 Molecular Weight 337.37400
Density 1.675g/cm3 Boiling Point N/A
Molecular Formula C13H11N3O4S2 Melting Point 240-243 °C (dec.)
MSDS N/A Flash Point N/A

 Use of Sudoxicam


Sudoxicam is a reversible and orally active COX antagonist and a non-steroidal anti-inflammatory drug (NSAID) from the enol-carboxamide class. Sudoxicam has potent anti-inflammatory, anti-edema and antipyretic activity[1][2][3].

 Names

Name 4-hydroxy-2-methyl-1,1-dioxo-N-(1,3-thiazol-2-yl)-1λ6,2-benzothiazine-3-carboxamide
Synonym More Synonyms

 Sudoxicam Biological Activity

Description Sudoxicam is a reversible and orally active COX antagonist and a non-steroidal anti-inflammatory drug (NSAID) from the enol-carboxamide class. Sudoxicam has potent anti-inflammatory, anti-edema and antipyretic activity[1][2][3].
Related Catalog
Target

COX[3]

In Vitro Sudoxicam demonstrates NADPH-dependent covalent binding to human liver microsomes. With addition of glutathione (GSH) in microsomal incubations, about half of the covalent incorporation of Sudoxicam is blocked by addition of GSH[1]. Metabolite identification studies on [14C]-Sudoxicam in NADPH-supplemented human liver microsomes indicated that the primary route of metabolism involved a P450-mediated thiazole ring scission to the corresponding acylthiourea metabolite (S3), a well-established pro-toxin[1]. In vitro, Sudoxicam underwent the oxidative thiazole-open biotransformation, resulting in the formation of an acylthiourea and the subsequent hydroxylated metabolite[3].
In Vivo Sudoxicam (1-10 mg/kg; oral administration; daily; for 7 days; rats) treatment effective reduces plasma inflammation units, reduces the swelling of inflamed hind-paws and restores toward normal the daily gain in body weight[2]. In the intact rat, Sudoxicam significantly inhibited edema formation at doses as low as 0.1 mg/kg, p.o[2]. Sudoxicam inhibits the erythema caused by ultraviolet irradiation in the guinea pig. Sudoxicam (3.3 mg/kg, i.p.) is capable of counteracting the pyrexia induced by the intraperitoneal injection of typhoid/paratyphoid vaccine in rats, maintaining body temperature about that of uninjected control rats[2]. The plasma half-life of Sudoxicam ranged between 8 hours (monkey), 13 hours (rat), and 60 hours (dog)[2]. Animal Model: Rats injected with ,i>M. butyrieum[2] Dosage: 1 mg/kg, 3.3 mg/kg, 10 mg/kg Administration: Oral administration; daily; for 7 days Result: Were both effective in reducing plasma inflammation units, in reducing the swelling of inflamed hind-paws.
References

[1]. Obach RS, et al. In vitro metabolism and covalent binding of enol-carboxamide derivatives and anti-inflammatory agents sudoxicam and meloxicam: insights into the hepatotoxicity of sudoxicam. Chem Res Toxicol. 2008 Sep;21(9):1890-9.

[2]. Wiseman EH, et al. Anti-inflammatory and pharmacokinetic properties of sudoxicam N-(2-thiazolyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide. Biochem Pharmacol. 1972 Sep 1;21(17):2323-34.

[3]. Zhi-Yi Zhang. Sudoxicam. Handbook of Metabolic Pathways of Xenobiotics. September 2014.

 Chemical & Physical Properties

Density 1.675g/cm3
Melting Point 240-243 °C (dec.)
Molecular Formula C13H11N3O4S2
Molecular Weight 337.37400
Exact Mass 337.01900
PSA 136.22000
LogP 2.73420
Index of Refraction 1.741
Storage condition 2-8°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DL0710500
CHEMICAL NAME :
2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-thiazolyl-, 1,1-dioxide
CAS REGISTRY NUMBER :
34042-85-8
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C13-H11-N3-O4-S2
MOLECULAR WEIGHT :
337.39

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 :
136 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 28,1714,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
260 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 15,848,1972

 Synonyms

Sudoxicamum
4-hydroxy-2-methyl-N-(2-thiazole)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
N-(2-thiazolyl)-4-hydroxy-2-methyl-2H,1,2-benzothiazine-3-carboxamide 1,1-dioxide
Sudoxicamum [INN-Latin]
2H-1,2-Benzothiazine-3-carboxamide,4-hydroxy-2-methyl-N-2-thiazolyl-,1,1-dioxide
4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
EINECS 251-808-7
SUDOXICAM
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