Product Name

  • Name

    Sulfamethoxazole

  • EINECS 211-963-3
  • CAS No. 723-46-6
  • Article Data24
  • CAS DataBase
  • Density 1.462 g/cm3
  • Solubility Soluble in ethanol or acetone. Very slightly soluble in water
  • Melting Point 166 °C
  • Formula C10H11N3O3S
  • Boiling Point 482.1 °C at 760 mmHg
  • Molecular Weight 253.282
  • Flash Point 245.4 °C
  • Transport Information
  • Appearance Crystals or white powder
  • Safety 26-36-36/37/39-22
  • Risk Codes 36/37/38-43-22
  • Molecular Structure Molecular Structure of 723-46-6 (Sulfamethoxazole)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms Sulfanilamide,N1-(5-methyl-3-isoxazolyl)- (6CI,8CI);3-(p-Aminobenzenesulfonamido)-5-methylisoxazole;3-Sulfanilamido-5-methylisoxazole;4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide;4-Amino-N-(5-methyl-3-isoxazolyl)benzensulfonamide;5-Methyl-3-sulfanilamidoisoxazole;Gantanol;N1-(5-Methyl-3-isoxazolyl)sulfanilamide;NSC 147832;Radonil;Ro 4-2130;STX608;Sinomin;Sulfamethoxazol;
  • PSA 106.60000
  • LogP 3.10100

Synthetic route

N-acetylsulfamethoxazole
21312-10-7

N-acetylsulfamethoxazole

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
With hydrogenchloride In methanol; diethyl ether at 75℃; for 0.25h; Microwave irradiation;100%
Stage #1: N-acetylsulfamethoxazole With sodium hydroxide; water at 80℃; for 1h;
Stage #2: With acetic acid In water pH=6;
96%
With sodium hydroxide In water for 4h; Reflux;93%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-aminobenzenesulfonyl chloride
24939-24-0

4-aminobenzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
Stage #1: 5-methylisoxazol-3-ylamine With ammonium hydroxide at 35 - 40℃; for 1h; Large scale;
Stage #2: 4-aminobenzenesulfonyl chloride at 15 - 20℃; for 4.5h; Large scale;
95%
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
Stage #1: 5-methylisoxazol-3-ylamine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: With sodium hydroxide for 2h; Inert atmosphere; Reflux;
60%
Stage #1: 5-methylisoxazol-3-ylamine; p-acetylaminobenzenesulfonyl chloride With pyridine In tetrahydrofuran at 20℃; for 6h;
Stage #2: With sodium hydroxide for 2h; Reflux;
4-amino-N-(5-methyl-3-isoxazolyl)-benzene sulfonamide
13053-79-7

4-amino-N-(5-methyl-3-isoxazolyl)-benzene sulfonamide

A

sulfamethoxazole
723-46-6

sulfamethoxazole

B

C10H11N3O3S
954563-97-4

C10H11N3O3S

C

C10H11N3O3S

C10H11N3O3S

Conditions
ConditionsYield
Stage #1: 4-amino-N-(5-methyl-3-isoxazolyl)-benzene sulfonamide With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; C8H9F3NO3S(1+)*CF3O3S(1-) In acetonitrile at 30℃; for 1h; Sealed tube; Irradiation;
Stage #2: With N-butylamine In acetonitrile at 23℃; for 12h; regioselective reaction;
A 13%
B 43%
C 12%
N,N'-bis-(5-methyl-isoxazol-3-yl)-4,4'-diazenediyl-bis-benzenesulfonamide
97254-40-5

N,N'-bis-(5-methyl-isoxazol-3-yl)-4,4'-diazenediyl-bis-benzenesulfonamide

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
With hydrogen; nickel In sodium hydroxide Ambient temperature;
2-butynenitrile
13752-78-8

2-butynenitrile

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
(i) NH2OH*HCl, aq. NaOH, EtOH, (ii) /BRN= 746676/, Py, (iii) aq. NaOH; Multistep reaction;
2,3-dibromobutanenitrile
25109-76-6

2,3-dibromobutanenitrile

p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
(i) NH2CONHOH, aq. NaOH, K2CO3, (ii) /BRN= 746676/, Py, (iii) aq. NaOH; Multistep reaction;
N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
29699-89-6

N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
With hydrogen; platinum In ethanol Ambient temperature;
Multi-step reaction with 2 steps
1: H2 / Pd-C / aq. NaOH / Ambient temperature
2: H2 / Raney-Ni / aq. NaOH / Ambient temperature
View Scheme
glutathione
128960-77-0

glutathione

nitroso derivative of sulfamethoxazole
131549-85-4

nitroso derivative of sulfamethoxazole

A

sulfamethoxazole
723-46-6

sulfamethoxazole

B

glutathione disulfide
464195-31-1

glutathione disulfide

C

(S)-2-Amino-4-[(S)-1-(carboxymethyl-carbamoyl)-2-sulfino-ethylcarbamoyl]-butyric acid

(S)-2-Amino-4-[(S)-1-(carboxymethyl-carbamoyl)-2-sulfino-ethylcarbamoyl]-butyric acid

D

(S)-2-Amino-4-((S)-1-(carboxymethyl-carbamoyl)-2-{N-[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenyl]aminosulfanyl}-ethylcarbamoyl)-butyric acid

(S)-2-Amino-4-((S)-1-(carboxymethyl-carbamoyl)-2-{N-[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenyl]aminosulfanyl}-ethylcarbamoyl)-butyric acid

E

C20H26N6O10S2

C20H26N6O10S2

F

(S)-2-Amino-4-{(S)-1-(carboxymethyl-carbamoyl)-2-[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenylsulfinamoyl]-ethylcarbamoyl}-butyric acid

(S)-2-Amino-4-{(S)-1-(carboxymethyl-carbamoyl)-2-[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenylsulfinamoyl]-ethylcarbamoyl}-butyric acid

Conditions
ConditionsYield
In dimethyl sulfoxide for 20h; Product distribution;
5-methylisoxazol-3-ylamine
1072-67-9

5-methylisoxazol-3-ylamine

4-chlorosulfonylbenzene isocyanate
6752-38-1

4-chlorosulfonylbenzene isocyanate

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
solid phase synthesis; Yield given. Multistep reaction;
sulphamethoxazole hydroxylamine
114438-33-4

sulphamethoxazole hydroxylamine

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
With 1,4-dihydronicotinamide adenine dinucleotide; human recombinant NADH cytochrome b5 reductase; cytochrome b5 In dimethyl sulfoxide pH=7.4; Enzyme kinetics; Further Variations:; Reagents;
With nicotinamide-adenin-dinucleotide reduced; recombinant human mitochondrial amidoxime reducing component-2 wild type protein In aq. buffer at 37℃; for 0.333333h; pH=6; Kinetics; Reagent/catalyst; Enzymatic reaction;
p-acetylaminobenzenesulfonyl chloride
121-60-8

p-acetylaminobenzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: aqueous NaOH
View Scheme
Multi-step reaction with 2 steps
1: pyridine / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: hydrogenchloride / diethyl ether; methanol / 0.25 h / 75 °C / Microwave irradiation
View Scheme
Multi-step reaction with 2 steps
1: pyridine; dmap / 12 h / 20 °C
2: sodium hydroxide / water / 4 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / acetonitrile / 2 h / Reflux
2: hydrogenchloride / water / 3 h
View Scheme
4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / 6 h / Ambient temperature
2: H2 / Pd-C / aq. NaOH / Ambient temperature
3: H2 / Raney-Ni / aq. NaOH / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: pyridine / 6 h / Ambient temperature
2: H2 / Pt / ethanol / Ambient temperature
View Scheme
4,4'-diazenediyl-bis-benzenesulfonyl chloride
99447-77-5

4,4'-diazenediyl-bis-benzenesulfonyl chloride

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / 1 h / Heating
2: H2 / Raney-Ni / aq. NaOH / Ambient temperature
View Scheme
Acetanilid
103-84-4

Acetanilid

sulfamethoxazole
723-46-6

sulfamethoxazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: chlorosulfonic acid / 10 h / 15 - 50 °C
2.1: sodium chloride / water / 40 °C
2.2: 5 h / 25 - 38 °C / pH 4
3.1: sodium hydroxide / water / 2 h / 104 °C / pH 14
View Scheme
sulfamethoxazole
723-46-6

sulfamethoxazole

1-n-butyl-3-methylimidazolim bromide
85100-77-2

1-n-butyl-3-methylimidazolim bromide

C8H15N2(1+)*C10H10N3O3S(1-)
1676076-93-9

C8H15N2(1+)*C10H10N3O3S(1-)

Conditions
ConditionsYield
Stage #1: 1-n-butyl-3-methylimidazolim bromide With Merck ion exchange resin III In water
Stage #2: sulfamethoxazole In water at 20℃; for 2h;
99%
pyrrolidine
123-75-1

pyrrolidine

sulfamethoxazole
723-46-6

sulfamethoxazole

C15H18N4O3S

C15H18N4O3S

Conditions
ConditionsYield
Stage #1: sulfamethoxazole With hydrogenchloride; sodium nitrite Green chemistry;
Stage #2: pyrrolidine With potassium hydroxide Green chemistry;
99%
sulfamethoxazole
723-46-6

sulfamethoxazole

silver(I) trifluoromethanethiolate
811-68-7

silver(I) trifluoromethanethiolate

4-isothiocyanato-N-(5-methylisoxazol-3-yl)benzenesulfonamide
956576-66-2

4-isothiocyanato-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
With potassium bromide In acetonitrile at 20℃; for 1h;97%
4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one
1226-71-7, 57427-89-1, 82301-52-8

4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one

sulfamethoxazole
723-46-6

sulfamethoxazole

C26H20N4O5S
843640-21-1

C26H20N4O5S

Conditions
ConditionsYield
Stage #1: 4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one; sulfamethoxazole at 140℃; for 1h;
Stage #2: In acetone for 8h; Reflux;
93%
sulfamethoxazole
723-46-6

sulfamethoxazole

1-octyl-3-methyl-imidazolium bromide

1-octyl-3-methyl-imidazolium bromide

C12H23N2(1+)*C10H10N3O3S(1-)
1676076-98-4

C12H23N2(1+)*C10H10N3O3S(1-)

Conditions
ConditionsYield
Stage #1: 1-octyl-3-methyl-imidazolium bromide With Merck ion exchange resin III In water
Stage #2: sulfamethoxazole In water at 20℃; for 2h;
93%
3,5-diodosalicylaldehyde
2631-77-8

3,5-diodosalicylaldehyde

sulfamethoxazole
723-46-6

sulfamethoxazole

4-[(2-hydroxy-3,5-diiodobenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide

4-[(2-hydroxy-3,5-diiodobenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
In methanol at 20℃; for 16h; Reflux;93%
sulfamethoxazole
723-46-6

sulfamethoxazole

(1,1,1,3,3,3-hexafluoro-2-methylprop-2-yl)isocyanate
19755-56-7

(1,1,1,3,3,3-hexafluoro-2-methylprop-2-yl)isocyanate

1-[4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl]-3-[2,2,2-trifluoro-1-methyl-1-(trifluoromethyl)ethyl]urea
355829-57-1

1-[4-[(5-methylisoxazol-3-yl)sulfamoyl]phenyl]-3-[2,2,2-trifluoro-1-methyl-1-(trifluoromethyl)ethyl]urea

Conditions
ConditionsYield
With triethylamine In diethyl ether; benzene at 100℃;92%
N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine
444731-74-2

N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine

sulfamethoxazole
723-46-6

sulfamethoxazole

4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide
1572439-33-8

4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
With hydrogenchloride In water; isopropyl alcohol at 85℃;92%
1-hexadecyl-3-methyl-3H-imidazol-1-ium; bromide

1-hexadecyl-3-methyl-3H-imidazol-1-ium; bromide

sulfamethoxazole
723-46-6

sulfamethoxazole

C20H39N2(1+)*C10H10N3O3S(1-)
1676077-01-2

C20H39N2(1+)*C10H10N3O3S(1-)

Conditions
ConditionsYield
Stage #1: 1-hexadecyl-3-methyl-3H-imidazol-1-ium; bromide With Merck ion exchange resin III In water
Stage #2: sulfamethoxazole In water at 20℃; for 2h;
92%
Propyl isocyanate
110-78-1

Propyl isocyanate

sulfamethoxazole
723-46-6

sulfamethoxazole

N-(5-methylisoxazol-3-yl)-4-(3-propylureido)benzenesulfonamide

N-(5-methylisoxazol-3-yl)-4-(3-propylureido)benzenesulfonamide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 11.5h; Reflux;92%
sulfamethoxazole
723-46-6

sulfamethoxazole

diazepam
439-14-5

diazepam

4-([4-{7-chloro-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl}phenyl]diazenyl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

4-([4-{7-chloro-1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl}phenyl]diazenyl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: sulfamethoxazole With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.0833333h; Green chemistry;
Stage #2: diazepam With sodium acetate In ethanol; water Green chemistry;
92%
sulfamethoxazole
723-46-6

sulfamethoxazole

trimethylsulfoxonium iodide
1774-47-6

trimethylsulfoxonium iodide

4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide
51543-31-8

4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide

Conditions
ConditionsYield
With aluminum oxide; potassium hydroxide at 130℃; for 0.0666667h; microwave irradiation;91%
sulfamethoxazole
723-46-6

sulfamethoxazole

benzyl isothiocyanate
3173-56-6

benzyl isothiocyanate

4-(3-benzylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

4-(3-benzylureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 11.5h; Reflux;91%
In N,N-dimethyl-formamide at 90 - 100℃;2.12 g
sulfamethoxazole
723-46-6

sulfamethoxazole

4-azido-N-(5-methylisoxazol-3-yl)benzenesulfonamide

4-azido-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: sulfamethoxazole With sulfuric acid In water at 0℃;
Stage #2: With sodium nitrite In water at 0 - 20℃; for 0.166667h;
Stage #3: With sodium azide; urea In water at 20℃;
91%
With sodium azide; tert.-butylnitrite In 1,4-dioxane; water at 50℃; for 0.333333h; Microwave irradiation;82%
sulfamethoxazole
723-46-6

sulfamethoxazole

C10H10(2)HN3O3S

C10H10(2)HN3O3S

Conditions
ConditionsYield
With Kerr's catalyst; deuterium In chlorobenzene at 120℃; for 1h;91%
formaldehyd
50-00-0

formaldehyd

sulfamethoxazole
723-46-6

sulfamethoxazole

N-(4-carbamoylphenyl)nicotinamide
418790-13-3

N-(4-carbamoylphenyl)nicotinamide

N-[4-({[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenylamino]-methyl}-carbamoyl)-phenyl]-nicotinamide

N-[4-({[4-(5-methyl-isoxazol-3-ylsulfamoyl)-phenylamino]-methyl}-carbamoyl)-phenyl]-nicotinamide

Conditions
ConditionsYield
Stage #1: formaldehyd; N-(4-carbamoyl-phenyl)-nicotinamide With hydrogenchloride In methanol at 0℃; for 0.5h; pH=3.5;
Stage #2: sulfamethoxazole Heating;
90%
sulfamethoxazole
723-46-6

sulfamethoxazole

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

4-(2-hydroxy-3-methoxybenzylidenamine)-N-(5-methylisoxozaol-3-yl)benzenesulfonamide
328026-18-2

4-(2-hydroxy-3-methoxybenzylidenamine)-N-(5-methylisoxozaol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
In tetrahydrofuran for 2h;90%
With acetic acid In ethanol for 1h; Reflux;81%
methyl 2-[4-(1H-indol-2-yl)phenoxy]acetate
1357149-34-8

methyl 2-[4-(1H-indol-2-yl)phenoxy]acetate

sulfamethoxazole
723-46-6

sulfamethoxazole

2-[4-(1H-indol-2-yl)phenoxy]-N-{4-[N-(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamide
1357149-22-4

2-[4-(1H-indol-2-yl)phenoxy]-N-{4-[N-(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamide

Conditions
ConditionsYield
With potassium carbonate In acetone for 10h;90%
N-Hydroxymethylisatin
50899-59-7

N-Hydroxymethylisatin

sulfamethoxazole
723-46-6

sulfamethoxazole

4-[(1-hydroxymethyl)-2-oxindolin-3-ylideneamino]-N-(5-methylisoxazol-3-yl)benzenesulphonamide
1393098-78-6

4-[(1-hydroxymethyl)-2-oxindolin-3-ylideneamino]-N-(5-methylisoxazol-3-yl)benzenesulphonamide

Conditions
ConditionsYield
In ethanol for 8h; Reflux;90%
sulfamethoxazole
723-46-6

sulfamethoxazole

1-cyanoacetyl-3,5-dimethylpyrazole
36140-83-7

1-cyanoacetyl-3,5-dimethylpyrazole

2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide
901373-59-9

2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide

Conditions
ConditionsYield
In toluene for 3h; Reflux;90%
In 1,4-dioxane for 3h; Reflux;80%
sulfamethoxazole
723-46-6

sulfamethoxazole

3,5-disulfamethoxazole curcumin
1443768-38-4

3,5-disulfamethoxazole curcumin

Conditions
ConditionsYield
With acetic acid In ethanol at 60℃; for 2h;90%
sulfamethoxazole
723-46-6

sulfamethoxazole

phenyl isocyanate
103-71-9

phenyl isocyanate

N-(5-methylisoxazol-3-yl)-4-(3-phenylureido)benzenesulfonamide

N-(5-methylisoxazol-3-yl)-4-(3-phenylureido)benzenesulfonamide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 11.5h; Reflux;90%
In N,N-dimethyl-formamide at 90 - 100℃;1.74 g
sulfamethoxazole
723-46-6

sulfamethoxazole

salicylaldehyde
90-02-8

salicylaldehyde

4-[(3-formyl-4-hydroxyphenyl)diazenyl]-N-(5-methylisoxazol-3-yl)benzenesulfonamide

4-[(3-formyl-4-hydroxyphenyl)diazenyl]-N-(5-methylisoxazol-3-yl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: sulfamethoxazole With hydrogenchloride; sodium nitrite at 0 - 5℃;
Stage #2: salicylaldehyde With sodium hydroxide In water
90%
Stage #1: sulfamethoxazole With hydrogenchloride In water for 0.5h;
Stage #2: With sodium nitrite In water at 0 - 5℃;
Stage #3: salicylaldehyde With hydrogenchloride; potassium hydroxide In water Cooling with ice;
sulfamethoxazole
723-46-6

sulfamethoxazole

dimedone
126-81-8

dimedone

4‐((5,5‐dimethyl‐3‐oxocyclohex‐1‐en‐1‐yl)amino)‐N‐(5‐methylisoxazol‐3‐yl)benzenesulfonamide

4‐((5,5‐dimethyl‐3‐oxocyclohex‐1‐en‐1‐yl)amino)‐N‐(5‐methylisoxazol‐3‐yl)benzenesulfonamide

Conditions
ConditionsYield
With trichloroacetic acid at 140℃; for 0.25h;90%
sulfamethoxazole
723-46-6

sulfamethoxazole

mercury(II) diacetate
1600-27-7

mercury(II) diacetate

Hg(sulfamethoxazolato)2

Hg(sulfamethoxazolato)2

Conditions
ConditionsYield
In methanol Hg(II) acetate in methanol added dropwise with stirring; stirred (18 h,room temp.); filtered off; air dried; elem. anal.;89%
sulfamethoxazole
723-46-6

sulfamethoxazole

4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
5429-22-1

4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone

C27H22N4O5S
843640-09-5

C27H22N4O5S

Conditions
ConditionsYield
Stage #1: sulfamethoxazole; 4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone at 140℃; for 1h;
Stage #2: In acetone for 8h; Reflux;
89%
sulfamethoxazole
723-46-6

sulfamethoxazole

3-sulfamethoxazole curcumin
1443768-33-9

3-sulfamethoxazole curcumin

Conditions
ConditionsYield
In ethanol at 60℃; for 4h;89%
2,5-dioxopyrrolidin-1-yl methylcarbamate
18342-66-0

2,5-dioxopyrrolidin-1-yl methylcarbamate

sulfamethoxazole
723-46-6

sulfamethoxazole

N-(5-methylisoxazol-3-yl)-4-(3-methylureido)benzenesulfonamide

N-(5-methylisoxazol-3-yl)-4-(3-methylureido)benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 24h;89%

Sulfamethoxazole Chemical Properties

IUPAC Name: 4-Amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
Synonyms of Sulfamethoxazole (CAS NO.723-46-6): 3-(p-Aminophenylsulfonamido)-5-methylisoxazole ; 3-(para-Aminophenylsulphonamido)-5-methylisoxazole ; 3-Sulfanilamido-5-methylisoxazole ; 5-Methyl-3-sulfanilamidoisoxazole ; Benzenesulfonamide, 4-amino-N-(5-methyl-3-isoxazolyl)- ; Sulphamethylisoxazole
CAS NO: 723-46-6
Molecular Formula: C10H11N3O3S
Molecular Weight: 253.27
Molecular Structure:
EINECS: 211-963-3
H bond acceptors: 6
H bond donors: 3
Freely Rotating Bonds: 2
Polar Surface Area: 75.03 Å2
Index of Refraction: 1.641
Molar Refractivity: 62.45 cm3
Molar Volume: 173.1 cm3
Surface Tension: 70.9 dyne/cm
Density: 1.462 g/cm3
Flash Point: 245.4 °C
Enthalpy of Vaporization: 74.7 kJ/mol
Boiling Point: 482.1 °C at 760 mmHg
Vapour Pressure: 1.87E-09 mmHg at 25°C
Melting point: 166-169°C
Storage temp: 0-6°C
Stability: Stable, but light sensitive. Incompatible with strong oxidizing agents
Appearance: Crystals or white powder
Water solubility: Insoluble in water
Product Categories of Sulfamethoxazole (CAS NO.723-46-6): Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use)

Sulfamethoxazole Uses

 Sulfamethoxazole (CAS NO.723-46-6) is a sulfonamide bacteriostatic antibiotic. Sulfamethoxazole is most often used as part of a synergistic combination with trimethoprim in a 5:1 ratio in co-trimoxazole. Besides it is commonly used to treat urinary tract infections and toxoplasmosis. In addition it can still be used as an alternative to amoxicillin-based antibiotics to treat sinusitis.

Sulfamethoxazole Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo oral 3gm/kg (3000mg/kg)   "Experimental Chemotherapy, Volume II," Schnitzer, R.J., and F. Hawking, eds. Academic Press New York, 1964Vol. 2, Pg. 249, 1964.
mouse LD50 intraperitoneal 2300mg/kg (2300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 21, Pg. 175, 1973.
mouse LD50 intravenous 1460mg/kg (1460mg/kg)   "Modern Pharmaceuticals of Japan, V," Tokyo, Japan Pharmaceutical, Medical and Dental Supply Exporters' Assoc., 1975Vol. -, Pg. 105, 1975.
mouse LD50 oral 2300mg/kg (2300mg/kg)   Chemotherapia. Vol. 8, Pg. 63, 1964.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
mouse LD50 unreported 5gm/kg (5000mg/kg)   Chemotherapia. Vol. 6, Pg. 273, 1963.
rat LD50 intraperitoneal 2690mg/kg (2690mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Chemotherapy Vol. 21, Pg. 175, 1973.
rat LD50 oral 6200mg/kg (6200mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Chemotherapy Vol. 21, Pg. 175, 1973.
women TDLo oral 160mg/kg/10D- (160mg/kg) ENDOCRINE: HYPOGLYCEMIA Archives of Internal Medicine. Vol. 143, Pg. 827, 1983.

Sulfamethoxazole Safety Profile

Hazard Codes: IrritantXi,Xn
Risk Statements: 36/37/38-43-22
R22: Harmful if swallowed. 
R43: May cause sensitization by skin contact. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-22
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: WP0700000
Hazard Note: Irritant
HazardClass: IRRITANT

Sulfamethoxazole Specification

Side effects of Sulfamethoxazole (CAS NO.723-46-6):
The most common side effect of Sulfamethoxazole is gastrointestinal upset. Allergies to sulfa-based medications typically cause skin rashes, hives, or trouble breathing or swallowing and warrant immediate discontinuation of the medication and contact with doctor immediately. In addition Sulfamethoxazole/trimethoprim is also known to increase blood concentrations of the drug warfarin and can cause an unexpected increase in clotting time and uncontrolled bleeding. Sulfamethoxazole can also bring adverse effects Neutropenia and thrombocytopenia if a patient is placed on long-term therapy.

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