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723-46-6

Basic Information
CAS No.: 723-46-6
Name: Sulfamethoxazole
Molecular Structure:
Molecular Structure of 723-46-6 (Sulfamethoxazole)
Formula: C10H11N3O3S
Molecular Weight: 253.27
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: HarmfulXn, IrritantXi
Risk Codes: 36/37/38-43-22
Safety: 26-36-36/37/39-22
Transport Information:
PSA: 106.60000
LogP: 3.10100
Synthetic route
21312-10-7

N-acetylsulfamethoxazole

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%
1072-67-9

5-methylisoxazol-3-ylamine

24939-24-0

4-aminobenzenesulfonyl chloride

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%
1072-67-9

5-methylisoxazol-3-ylamine

121-60-8

p-acetylaminobenzenesulfonyl chloride

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;
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
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%
97254-40-5

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

723-46-6

sulfamethoxazole

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

2-butynenitrile

121-60-8

p-acetylaminobenzenesulfonyl chloride

723-46-6

sulfamethoxazole

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

sulphamethoxazole hydroxylamine

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;
121-60-8

p-acetylaminobenzenesulfonyl chloride

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
98-74-8

4-Nitrobenzenesulfonyl chloride

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
99447-77-5

4,4'-diazenediyl-bis-benzenesulfonyl chloride

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
103-84-4

Acetanilid

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
723-46-6

sulfamethoxazole

85100-77-2

1-n-butyl-3-methylimidazolim bromide

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%
123-75-1

pyrrolidine

723-46-6

sulfamethoxazole

C15H18N4O3S

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

sulfamethoxazole

811-68-7

silver(I) trifluoromethanethiolate

956576-66-2

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

Conditions
ConditionsYield
With potassium bromide In acetonitrile at 20℃; for 1h;97%
1226-71-7, 57427-89-1, 82301-52-8

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

723-46-6

sulfamethoxazole

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%
723-46-6

sulfamethoxazole

1-octyl-3-methyl-imidazolium bromide

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%
2631-77-8

3,5-diodosalicylaldehyde

723-46-6

sulfamethoxazole

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

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

sulfamethoxazole

19755-56-7

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

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%
444731-74-2

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

723-46-6

sulfamethoxazole

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

723-46-6

sulfamethoxazole

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%
110-78-1

Propyl isocyanate

723-46-6

sulfamethoxazole

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

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

sulfamethoxazole

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

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%
723-46-6

sulfamethoxazole

1774-47-6

trimethylsulfoxonium iodide

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%
723-46-6

sulfamethoxazole

3173-56-6

benzyl isothiocyanate

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
723-46-6

sulfamethoxazole

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%
723-46-6

sulfamethoxazole

C10H10(2)HN3O3S

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

formaldehyd

723-46-6

sulfamethoxazole

418790-13-3

N-(4-carbamoylphenyl)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%
723-46-6

sulfamethoxazole

148-53-8

3-methoxy-2-hydroxybenzaldehyde

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%
1357149-34-8

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

723-46-6

sulfamethoxazole

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%
50899-59-7

N-Hydroxymethylisatin

723-46-6

sulfamethoxazole

1393098-78-6

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

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

sulfamethoxazole

36140-83-7

1-cyanoacetyl-3,5-dimethylpyrazole

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%
723-46-6

sulfamethoxazole

1443768-38-4

3,5-disulfamethoxazole curcumin

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

sulfamethoxazole

103-71-9

phenyl isocyanate

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
723-46-6

sulfamethoxazole

90-02-8

salicylaldehyde

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;
723-46-6

sulfamethoxazole

126-81-8

dimedone

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%
723-46-6

sulfamethoxazole

1600-27-7

mercury(II) diacetate

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%
723-46-6

sulfamethoxazole

5429-22-1

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

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%
723-46-6

sulfamethoxazole

1443768-33-9

3-sulfamethoxazole curcumin

Conditions
ConditionsYield
In ethanol at 60℃; for 4h;89%
18342-66-0

2,5-dioxopyrrolidin-1-yl methylcarbamate

723-46-6

sulfamethoxazole

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

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

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.