Sulfamonomethoxine

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Sulfamonomethoxine
Category Enzyme inhibitors
Catalog number BBF-04518
CAS 1220-83-3
Molecular Weight 280.30
Molecular Formula C11H12N4O3S
Purity ≥93%

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Description

Sulfamonomethoxine, a sulfonamide derivative, is an antibacterial agent commonly used as a veterinary drug. It is also an enzyme inhibitor used to address hyperpyrexia.

Specification

Synonyms Sulfamonomethoxin; Daimeton; Sulfamonomethoxinum; 4-Methoxy-6-sulfanilamidopyrimidine; 4-Sulfanilamido-6-methoxypyrimidine; 6-Methoxy-4-sulfanilamidopyrimidine; N1-(6-Methoxy-4-pyrimidinyl)sulfanilamide; Ro 4-3476
Shelf Life As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage Store at 2-8°C
IUPAC Name 4-amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide
Canonical SMILES COC1=NC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI InChI=1S/C11H12N4O3S/c1-18-11-6-10(13-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,14,15)
InChI Key WMPXPUYPYQKQCX-UHFFFAOYSA-N
Source Semi-synthetic

Properties

Appearance White to Off-white Solid
Application Anti-Infective Agents
Antibiotic Activity Spectrum Bacteria
Boiling Point 513.2°C at 760 mmHg
Melting Point 203-206°C
Density 1.465 g/cm3
Solubility Slightly soluble in DMSO, Methanol

Reference Reading

1.[Sulfanilamide absorption and acetylation in rats with experimental hyperlipidemia and cellular regulation of the process of acetylation].
Makarov VA;Vasilenko IuK;Suetina IV;Vaskanian VL;Lubiankina SV Farmakol Toksikol. 1981 Jan-Feb;44(1):109-15.
Experiments on an isolated ileum of the rat with experimental hyperlipidemia have shown the decreased acetylation rate of sulfalen, sulfamonomethoxin and sulfapyridazine. The absorption rate of the free forms of sulfanilamides was increased (significantly for sulfalen and sulfapyridazine). Isadrin (1 . 10(-8) M) and cAMP (1 . 10(-5) M) introduced into the liquid exposed to the mucosa of the rat ileum raised the acetylation rate of sulfamonomethoxin by the ileic wall while anaprilin (1 . 10(-6) M) led to the reduction of both absorption and acetylation of this sulfanilamide. Addition of cAMP to the incubation mixture of mitochondria and microsomes increased the acetylation rate of sulfamonomethoxin.
2.Determination of sulfonamide residues in eggs by liquid chromatography.
Furusawa N J AOAC Int. 2002 Jul-Aug;85(4):848-52.
A method was developed for determining residual sulfonamide antibacterials such as sulfamethazine (SMZ), sulfamonomethoxine (SMM), sulfadimethoxine (SDM), and sulfaquinoxaline (SQ) in eggs using liquid chromatography with a photodiode array detector. The spiked and blank samples were cleaned up by using an Ultrafree-MC/PL centrifugal ultrafiltration unit. A Mightysil RP-4 GP column and a mobile phase of 28% (v/v) ethanol-H2O with a photodiode array detector were used for the determination. Average recoveries from eggs spiked with each drug at 0.1, 0.2, 0.4, and 1.0 ppm were > or = 80.9%, with relative standard deviations between 1.3 and 4.7%. The limits of quantitation were 0.060 ppm for SMZ, 0.045 for SMM, 0.044 for SDM, and 0.093 for SQ. The analysis of one sample required < 30 min and < 5 mL ethanol as solvent.
3.Liquid chromatographic determination of multiple sulfonamides, nitrofurans, and chloramphenicol residues in pasteurized milk.
Perez N;Gutierrez R;Noa M;Diaz G;Luna H;Escobar I;Munive Z J AOAC Int. 2002 Jan-Feb;85(1):20-4.
A rapid and selective liquid chromatographic method was developed to detect 6 sulfonamides, 3 nitrofurans, and chloramphenicol residues in pasteurized milk. The 10 drugs were extracted with chloroform-acetone and the organic phase was evaporated; the residues were dissolved in an aqueous sodium acetate buffer solution 0.02M (pH = 4.8), and the fat was removed by washing with hexane. The aqueous layer was collected, filtered, and injected. The 6 sulfonamides and chloramphenicol were detected at 275 nm ultraviolet (UV) using a gradient system starting with sodium acetate buffer solution-acetonitrile (95 + 5) and finishing with sodium acetate buffer solution-acetonitrile (80 + 20). Nitrofurans were detected at 375 nm (UV) isocratically with sodium acetate buffer solution-acetonitrile (80 + 20). For 50 ppb fortified milk, the average recoveries were (sulfathiazole) 65.52%; (sulfamerazine) 75.36%; (sulfamethazine) 93.94%; (sulfachlorpyridazine) 75.94%; (sulfamethoxazole) 85.18%; (sulfamonomethoxine) 83.45%; (chloramphenicol) 104.17%; (nitrofurazone) 91.81%; (furazolidone) 100.76%; and (furaltadone) 72.38%. Method detection limits ranged from 4 ppb (nitrofurazone) to 16 ppb (sulfamethazine).

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