1220-83-3

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes:

P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories:

Skin Irrit. 2 (100%)
Skin Sens. 1 (100%)
Eye Irrit. 2 (100%)
STOT SE 3 (100%)

Usage

Uses

1. Used in Pharmaceutical Industry:
Sulfamonomethoxine is used as an antimicrobial agent for treating various bacterial infections. Its application is based on its ability to inhibit bacterial enzyme activity, thus preventing the growth and proliferation of harmful bacteria.
2. Used in Veterinary Medicine:
Sulfamonomethoxine is used as a veterinary drug for treating porcine unknown hyperpyrexia, a severe, high fever in pigs. The application is due to its effectiveness in combating bacterial infections that may cause this condition.
3. Used in Combination Therapy:
Sulfamonomethoxine is often used in combination with Trimethoprim, another antimicrobial agent. This combination enhances the overall efficacy of the treatment by targeting different stages of bacterial enzyme inhibition. The synergistic effect of these two drugs helps in achieving a more potent and rapid response against bacterial infections.
4. Used in Enzyme Inhibition Studies:
Sulfamonomethoxine is also utilized in research and development as an inhibitor of bacterial enzymes. Its application in this context is to study the effects of enzyme inhibition on bacterial growth and to develop new strategies for combating antibiotic-resistant bacteria.

Synthesis Reference(s)

The Journal of Organic Chemistry, 26, p. 2764, 1961 DOI: 10.1021/jo01066a034

Biochem/physiol Actions

Sulfamonomethoxine is a competitive inhibitor of dihydropteroate synthetase used to block the synthesis of folic acid.

InChI:InChI=1/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)

Synthetic route

4-Nitrobenzenesulfonamido-6-methoxypyrimidine (1748-50-1) → sulfamonomethoxine (1220-83-3)

Conditions	Yield
With iron; ammonium chloride In water for 10h; Heating; Yield given;

4-nitrobenzenediazonium chloride (100-05-0) + benzothiophen-3-yl-glyoxal phenylhydrazone → sulfamonomethoxine (1220-83-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: SO2 / CuSO4 / acetic acid / 6 - 20 °C 2: 92 percent / pyridine / 2 h / 56 - 58 °C 3: Fe, NH4Cl / H2O / 10 h / Heating View Scheme

4-Nitrobenzenesulfonyl chloride (98-74-8) + (+-)-2-amino-5-butyl-thiazol-4-one → sulfamonomethoxine (1220-83-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / pyridine / 2 h / 56 - 58 °C 2: Fe, NH4Cl / H2O / 10 h / Heating View Scheme

2,4,6-trimethylpyrylium chlorate(VII) (940-93-2) + sulfamonomethoxine (1220-83-3) → 1-[4-(6-Methoxy-pyrimidin-4-ylsulfamoyl)-phenyl]-2,4,6-trimethyl-pyridinium; perchlorate

Conditions	Yield
In acetic acid for 2h; Heating;	97%

sulfamonomethoxine (1220-83-3) + glycyrrhyzic acid → C75H92N12O22S3

Conditions	Yield
pyridine; dicyclohexyl-carbodiimide In 1,4-dioxane at 20 - 22℃; for 24h; Condensation;	90.4%

(E)-3-(4-methoxyphenyl)propenoyl chloride (34446-64-5, 42996-84-9) + sulfamonomethoxine (1220-83-3) → p-methoxycinnamoyl sulfamonomethoxine

Conditions	Yield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;	85%

sulfamonomethoxine (1220-83-3) → 1,3-bis(N1-4-amino-6-methoxypyrimidinebenzenesulfonamide)-2,2,2,4,4,4-hexa-chlorocyclodiphosph(V)azane

Conditions	Yield
With phosphorus pentachloride In benzene at 15℃; for 0.5h;	81%

2,6-dimethyl-4-oxo-5-phenyl-1,3-oxazinium perchlorate (63673-58-5) + sulfamonomethoxine (1220-83-3) → 4-(2,6-dimethyl-4-oxo-5-phenyl-4H-pyrimidin-1-yl)-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

Conditions	Yield
In acetic acid for 48h; Ambient temperature;	65%

sulfamonomethoxine (1220-83-3) + (3R,5aS,6R,9R,10S,12R,12aR)-10-(3-bromopropoxy)-3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromene (165068-34-8) → 4-amino-N-(6-methoxypyrimidin-4-yl)-N-(3-((3,6,9-trimethyldecahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10-yl)oxy)propyl)benzenesulfonamide

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;	56%

3-(o-methoxyphenyl)-2,6-dimethyl-4-oxo-1,3-oxazinium perchlorate + sulfamonomethoxine (1220-83-3) → 4-[5-(2-methoxy-phenyl)-2,6-dimethyl-4-oxo-4H-pyrimidin-1-yl]-N-(6-methoxy-pyrimidin-4-yl)-benzenesulfonamide; compound with perchloric acid

Conditions	Yield
In acetic acid for 48h; Ambient temperature;	35%

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + sulfamonomethoxine (1220-83-3) → (Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)-N-(4-(N-(6-methoxypyrimidin-4-yl)sulfamoyl)phenyl)acetamide

Conditions	Yield
With pyridine; triethylamine In ethanol; dichloromethane at 20℃; Inert atmosphere;	32.7%

sulfamonomethoxine (1220-83-3) → 4-amino-N-(6-hydroxy-4-pyrimidinyl)benzenesulfonamide (14762-26-6)

Conditions	Yield
With sodium hydroxide for 14h; Heating;	16%
With sodium hydroxide at 80 - 90℃; for 50h; Yield given;

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + sulfamonomethoxine (1220-83-3) → C36H30N8O8S4

Conditions	Yield
With pyridine In 1,4-dioxane Ambient temperature;

tropaeolin O + sulfamonomethoxine (1220-83-3) → C23H18N7O8S2(1-)*Na(1+) (1312665-65-8)

Conditions	Yield
Stage #1: sulfamonomethoxine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h; Stage #2: tropaeolin O With sodium hydroxide In water pH=10.5;

4-acetoxyferuloyl chloride (55882-65-0, 108608-07-7, 50906-12-2) + sulfamonomethoxine (1220-83-3) → C23H22N4O7S

Conditions	Yield
With pyridine In tetrahydrofuran at 0 - 20℃; for 6h;

4-acetoxyferuloyl chloride (55882-65-0, 108608-07-7, 50906-12-2) + sulfamonomethoxine (1220-83-3) → N1-feruloylsulfamonomethoxine

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 6 h / 0 - 20 °C 2: hydrogenchloride / tetrahydrofuran / 1 h / 60 °C View Scheme

p-acetoxycinnamoyl chloride (53901-95-4, 108608-06-6, 58523-18-5) + sulfamonomethoxine (1220-83-3) → 4-acetoxycinnamoyl sulfamonomethoxine

Conditions	Yield
With pyridine In tetrahydrofuran for 25.5h; Cooling with ice;

Upstream product

• 1748-50-1 4-Nitrobenzenesulfonamido-6-methoxypyrimidine 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 1312665-65-8 C₂₃H₁₈N₇O₈S₂^(1-)*Na⁽¹⁺⁾ 
• 14762-26-6 4-amino-N-(6-hydroxy-4-pyrimidinyl)benzenesulfonamide 

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