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Details

Stereochemistry ACHIRAL
Molecular Formula C10H11N3O3S
Molecular Weight 253.278
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAMETHOXAZOLE

SMILES

CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1

InChI

InChIKey=JLKIGFTWXXRPMT-UHFFFAOYSA-N
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)

HIDE SMILES / InChI

Description

Sulfamethoxazole is a synthetic antibacterial drug,which is used in combination with trimethoprim (Bactrim, Septra) for the treatment or prevention of infections that are proven or strongly suspected to be caused by bacteria. Sulfamethoxazole acts by inhibiting folic acid synthesis via enzyme called dihydropteroate synthase.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.71 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BACTRIM
Curative
BACTRIM
Curative
BACTRIM
Curative
BACTRIM
Curative
BACTRIM
Curative
BACTRIM

Cmax

ValueDoseCo-administeredAnalytePopulation
94.42 μg/mL
1200 mg single, oral
SULFAMETHOXAZOLE plasma
Homo sapiens
46.3 μg/mL
800 mg single, oral
SULFAMETHOXAZOLE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1202.5 μg × h/mL
1200 mg single, oral
SULFAMETHOXAZOLE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
12.8 h
800 mg single, oral
SULFAMETHOXAZOLE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
800 mg single, oral
SULFAMETHOXAZOLE plasma
Homo sapiens

Doses

AEs

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
The usual adult dosage in the treatment of urinary tract infections and otitis media is 1 DS (double strength) tablet (each DS tablets contains 800 mg sulfamethoxazole and 160 mg trimethoprim) every 12 hours for 10 to 14 days. An identical daily dosage is used for 5 days in the treatment of shigellosis. The recommended dose for children with urinary tract infections or acute otitis media is 40 mg/kg sulfamethoxazole and 8 mg/kg trimethoprim per 24 hours, given in two divided doses every 12 hours for 10 days. An identical daily dosage is used for 5 days in the treatment of shigellosis.The usual adult dosage in the treatment of acute exacerbations of chronic bronchitis is 1 DS tablet every 12 hours for 14 days. The recommended dosage for treatment of patients with documented Pneumocystis jiroveci pneumonia is 75 to 100 mg/kg sulfamethoxazole and 15 to 20 mg/kg trimethoprim per 24 hours given in equally divided doses every 6 hours for 14 to 21 days. The recommended dosage for prophylaxis in adults is 1 DS tablet daily. For the treatment of traveler’s diarrhea, the usual adult dosage is 1 DS tablet every 12 hours for 5 days.
Route of Administration: Oral
In Vitro Use Guide
Bacterias were treated with 23.75 ug sulfamethoxazole to test the susceptibility of microorganisms. MIC values were 38 mcg/ml (Enterobacteriaceae), 9.5 mcg/ml (Haemophilus influenzae), 9.5 mcg/ml (Streptococcus pneumoniae).