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Basic Information

Molecular Structure:
CAS No.:	723-46-6
Name:	Sulfamethoxazole
Article Data:	24

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

Synthetic route

: 21312-10-7
N-acetylsulfamethoxazole

: 723-46-6
sulfamethoxazole

Conditions

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

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

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

C: C10H11N3O3S

Conditions

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%

...Expand

: 97254-40-5
N,N'-bis-(5-methyl-isoxazol-3-yl)-4,4'-diazenediyl-bis-benzenesulfonamide

: 723-46-6
sulfamethoxazole

Conditions

Conditions	Yield
With hydrogen; nickel In sodium hydroxide Ambient temperature;

: 13752-78-8
2-butynenitrile

: 121-60-8
p-acetylaminobenzenesulfonyl chloride

: 723-46-6
sulfamethoxazole

Conditions

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

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

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

C: (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

E: C20H26N6O10S2

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

Conditions

Conditions	Yield
In dimethyl sulfoxide for 20h; Product distribution;

...Expand

: 1072-67-9
5-methylisoxazol-3-ylamine

: 6752-38-1
4-chlorosulfonylbenzene isocyanate

: 723-46-6
sulfamethoxazole

Conditions

Conditions	Yield
solid phase synthesis; Yield given. Multistep reaction;

Raw Materials

98-74-8

121-60-8

Downstream Products

Total:209 Page 1 of 6 1 2 3 4 5 6 Next>>

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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: Irritant 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.