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| CAS No.: | 723-46-6 |
|---|---|
| Name: | Sulfamethoxazole |
| Article Data: | 24 |
| Molecular Structure: | |
|
|
|
| Formula: | C10H11N3O3S |
| Molecular Weight: | 253.282 |
| 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; |
| EINECS: | 211-963-3 |
| Density: | 1.462 g/cm3 |
| Melting Point: | 166 °C |
| Boiling Point: | 482.1 °C at 760 mmHg |
| Flash Point: | 245.4 °C |
| Solubility: | Soluble in ethanol or acetone. Very slightly soluble in water |
| Appearance: | Crystals or white powder |
| Hazard Symbols: |
 Xn,  Xi
|
| Risk Codes: | 36/37/38-43-22 |
| Safety: | 26-36-36/37/39-22 |
| PSA: | 106.60000 |
| LogP: | 3.10100 |
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- 99170-93-1N-Methyl-2-oxazolamine
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- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
- 90221-55-92-bromo-5-methylbenzaldehyde
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- 21312-10-7
N-acetylsulfamethoxazole
- 723-46-6
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% |
- 1072-67-9
5-methylisoxazol-3-ylamine
- 24939-24-0
4-aminobenzenesulfonyl chloride
- 723-46-6
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% |
- 1072-67-9
5-methylisoxazol-3-ylamine
- 121-60-8
p-acetylaminobenzenesulfonyl chloride
- 723-46-6
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; |
- 13053-79-7
4-amino-N-(5-methyl-3-isoxazolyl)-benzene sulfonamide
A
- 723-46-6
sulfamethoxazole
B
- 954563-97-4
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% |
- 97254-40-5
N,N'-bis-(5-methyl-isoxazol-3-yl)-4,4'-diazenediyl-bis-benzenesulfonamide
- 723-46-6
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; |
- 25109-76-6
2,3-dibromobutanenitrile
- 121-60-8
p-acetylaminobenzenesulfonyl chloride
- 723-46-6
sulfamethoxazole
| Conditions | Yield |
|---|---|
| (i) NH2CONHOH, aq. NaOH, K2CO3, (ii) /BRN= 746676/, Py, (iii) aq. NaOH; Multistep reaction; |
- 29699-89-6
N-(5-methyl-isoxazol-3-yl)-4-nitro-benzenesulfonamide
- 723-46-6
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 |
- 128960-77-0
glutathione
- 131549-85-4
nitroso derivative of sulfamethoxazole
A
- 723-46-6
sulfamethoxazole
B
- 464195-31-1
glutathione disulfide
| Conditions | Yield |
|---|---|
| In dimethyl sulfoxide for 20h; Product distribution; |
- 1072-67-9
5-methylisoxazol-3-ylamine
- 6752-38-1
4-chlorosulfonylbenzene isocyanate
- 723-46-6
sulfamethoxazole
| Conditions | Yield |
|---|---|
| solid phase synthesis; Yield given. Multistep reaction; |
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Chemistry
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)
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.
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. |
Safety Profile
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
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.