N-acetylsulfamethoxazole
sulfamethoxazole
Conditions | Yield |
---|---|
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
4-aminobenzenesulfonyl chloride
sulfamethoxazole
Conditions | Yield |
---|---|
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
p-acetylaminobenzenesulfonyl chloride
sulfamethoxazole
Conditions | Yield |
---|---|
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
A
sulfamethoxazole
B
C10H11N3O3S
Conditions | Yield |
---|---|
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
sulfamethoxazole
Conditions | Yield |
---|---|
With hydrogen; nickel In sodium hydroxide Ambient temperature; |
Conditions | Yield |
---|---|
(i) NH2OH*HCl, aq. NaOH, EtOH, (ii) /BRN= 746676/, Py, (iii) aq. NaOH; Multistep reaction; |
2,3-dibromobutanenitrile
p-acetylaminobenzenesulfonyl chloride
sulfamethoxazole
Conditions | Yield |
---|---|
(i) NH2CONHOH, aq. NaOH, K2CO3, (ii) /BRN= 746676/, Py, (iii) aq. NaOH; Multistep reaction; |
N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
sulfamethoxazole
Conditions | Yield |
---|---|
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
nitroso derivative of sulfamethoxazole
A
sulfamethoxazole
B
glutathione disulfide
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 20h; Product distribution; |
5-methylisoxazol-3-ylamine
4-chlorosulfonylbenzene isocyanate
sulfamethoxazole
Conditions | Yield |
---|---|
solid phase synthesis; Yield given. Multistep reaction; |
sulphamethoxazole hydroxylamine
sulfamethoxazole
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
sulfamethoxazole
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine / 1 h / Heating 2: H2 / Raney-Ni / aq. NaOH / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
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
1-n-butyl-3-methylimidazolim bromide
C8H15N2(1+)*C10H10N3O3S(1-)
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
Stage #1: sulfamethoxazole With hydrogenchloride; sodium nitrite Green chemistry; Stage #2: pyrrolidine With potassium hydroxide Green chemistry; | 99% |
sulfamethoxazole
silver(I) trifluoromethanethiolate
4-isothiocyanato-N-(5-methylisoxazol-3-yl)benzenesulfonamide
Conditions | Yield |
---|---|
With potassium bromide In acetonitrile at 20℃; for 1h; | 97% |
4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one
sulfamethoxazole
C26H20N4O5S
Conditions | Yield |
---|---|
Stage #1: 4-(4-hydroxybenzylidene)-2-phenyloxazol-5(4H)-one; sulfamethoxazole at 140℃; for 1h; Stage #2: In acetone for 8h; Reflux; | 93% |
sulfamethoxazole
C12H23N2(1+)*C10H10N3O3S(1-)
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 16h; Reflux; | 93% |
sulfamethoxazole
(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
Conditions | Yield |
---|---|
With triethylamine In diethyl ether; benzene at 100℃; | 92% |
N-(2-chloropyrimidin-4-yl)-2,3-dimethyl-2H-indazol-6-amine
sulfamethoxazole
4-((4-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-2-yl)amino)-N-(5-methylisoxazol-3-yl)benzenesulfonamide
Conditions | Yield |
---|---|
With hydrogenchloride In water; isopropyl alcohol at 85℃; | 92% |
sulfamethoxazole
C20H39N2(1+)*C10H10N3O3S(1-)
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 11.5h; Reflux; | 92% |
Conditions | Yield |
---|---|
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
trimethylsulfoxonium iodide
4-amino-N-(5-methyl-3-isoxazolyl)-N-methylbenzenesulfonamide
Conditions | Yield |
---|---|
With aluminum oxide; potassium hydroxide at 130℃; for 0.0666667h; microwave irradiation; | 91% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 11.5h; Reflux; | 91% |
In N,N-dimethyl-formamide at 90 - 100℃; | 2.12 g |
sulfamethoxazole
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
With Kerr's catalyst; deuterium In chlorobenzene at 120℃; for 1h; | 91% |
Conditions | Yield |
---|---|
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
3-methoxy-2-hydroxybenzaldehyde
4-(2-hydroxy-3-methoxybenzylidenamine)-N-(5-methylisoxozaol-3-yl)benzenesulfonamide
Conditions | Yield |
---|---|
In tetrahydrofuran for 2h; | 90% |
With acetic acid In ethanol for 1h; Reflux; | 81% |
methyl 2-[4-(1H-indol-2-yl)phenoxy]acetate
sulfamethoxazole
2-[4-(1H-indol-2-yl)phenoxy]-N-{4-[N-(5-methylisoxazol-3-yl)sulfamoyl]phenyl}acetamide
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 10h; | 90% |
N-Hydroxymethylisatin
sulfamethoxazole
4-[(1-hydroxymethyl)-2-oxindolin-3-ylideneamino]-N-(5-methylisoxazol-3-yl)benzenesulphonamide
Conditions | Yield |
---|---|
In ethanol for 8h; Reflux; | 90% |
sulfamethoxazole
1-cyanoacetyl-3,5-dimethylpyrazole
2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide
Conditions | Yield |
---|---|
In toluene for 3h; Reflux; | 90% |
In 1,4-dioxane for 3h; Reflux; | 80% |
curcumin
sulfamethoxazole
3,5-disulfamethoxazole curcumin
Conditions | Yield |
---|---|
With acetic acid In ethanol at 60℃; for 2h; | 90% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 11.5h; Reflux; | 90% |
In N,N-dimethyl-formamide at 90 - 100℃; | 1.74 g |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With trichloroacetic acid at 140℃; for 0.25h; | 90% |
Conditions | Yield |
---|---|
In methanol Hg(II) acetate in methanol added dropwise with stirring; stirred (18 h,room temp.); filtered off; air dried; elem. anal.; | 89% |
sulfamethoxazole
4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone
C27H22N4O5S
Conditions | Yield |
---|---|
Stage #1: sulfamethoxazole; 4-(4-methoxybenzylidene)-2-phenyl-5(4H)-oxazolone at 140℃; for 1h; Stage #2: In acetone for 8h; Reflux; | 89% |
curcumin
sulfamethoxazole
3-sulfamethoxazole curcumin
Conditions | Yield |
---|---|
In ethanol at 60℃; for 4h; | 89% |
2,5-dioxopyrrolidin-1-yl methylcarbamate
sulfamethoxazole
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile for 24h; | 89% |
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 (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.
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. |
Hazard Codes: Xi,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
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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