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Details

Stereochemistry ACHIRAL
Molecular Formula C11H12N4O3S
Molecular Weight 280.303
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAMETER

SMILES

COC1=CN=C(NS(=O)(=O)C2=CC=C(N)C=C2)N=C1

InChI

InChIKey=GPTONYMQFTZPKC-UHFFFAOYSA-N
InChI=1S/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

HIDE SMILES / InChI

Molecular Formula C11H12N4O3S
Molecular Weight 280.303
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Sulfametoxydiazine (INN) or sulfamethoxydiazine (USAN: sulfameter) is a long-acting sulfonamide antibacterial, shows bacteriostatic effects against Gram positive and Gram negative bacteria in vivo. It is used as a leprostatic agent and in the treatment of urinary tract infections. Orally active. Sulfonamides block the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfonamides are competitive inhibitors of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. Sulfameter is a dihydrofolate reductase (DHFR) inhibitor. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SULLA

Cmax

ValueDoseCo-administeredAnalytePopulation
44.2 μg/mL
1 g single, oral
SULFAMETER plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1599 μg × h/mL
1 g single, oral
SULFAMETER plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
24 h
1 g single, oral
SULFAMETER plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Loading dose first-day only (single dose): 1500 mg (3 tablets) Daily maintenance (single dose at 24 hour intervals): 500 mg (1 tablet).
Route of Administration: Oral
In Vitro Use Guide
Titrations of antibacterial activity were carried out by making twofold serial dilutions dilutions of plasma or serum and adding an equal volume (0.5 ml.) of a 10-5 dilution of an overnight culture of a strain of Escherichia coli which had been isolated from the peritoneal fluid of a patient with peritonitis and which was consistently sensitive to 0.30 mg. of sulfamethoxydiazine per 100 ml. of broth. Study of antibacterial titers showed that at 1: 64 the sulfonamide concentrations varied from 7 to 14 mg. per 100 ml
Substance Class Chemical
Record UNII
3L179F09D6
Record Status Validated (UNII)
Record Version