U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H12N4O3S
Molecular Weight 280.3045
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SULFAMETER

SMILES

COc1cnc(nc1)NS(=O)(=O)c2ccc(cc2)N

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

Description
Curator's Comment:: description was created based on several sources, including: http://www.sigmaaldrich.com/catalog/product/sigma/s0383?lang=es®ion=ES http://www.medchemexpress.com/sulfameter.html

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
SULLA

Approved Use

Unknown

Launch Date

-1.10592E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
44.2 μg/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAMETER plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1599 μg × h/mL
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAMETER plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24 h
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SULFAMETER plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
250 mg/kg 1 times / day steady, oral
Recommended
Dose: 250 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 250 mg/kg, 1 times / day
Sources:
unhealthy, adult
n = 20
Health Status: unhealthy
Condition: chronic urinary-tract infection
Age Group: adult
Sex: unknown
Population Size: 20
Sources:
500 mg/kg 1 times / day steady, oral
Recommended
Dose: 500 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 500 mg/kg, 1 times / day
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: pustular acne vulgaris
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Disc. AE: Nasal stuffiness, Edema lip...
AEs leading to
discontinuation/dose reduction:
Nasal stuffiness (2 patients)
Edema lip (1 patient)
Leukopenia (1 patient)
Sources:
2 g single, oral
Studied dose
Dose: 2 g
Route: oral
Route: single
Dose: 2 g
Sources:
healthy, adult
n = 6
Health Status: healthy
Age Group: adult
Sex: unknown
Population Size: 6
Sources:
AEs

AEs

AESignificanceDosePopulation
Edema lip 1 patient
Disc. AE
500 mg/kg 1 times / day steady, oral
Recommended
Dose: 500 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 500 mg/kg, 1 times / day
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: pustular acne vulgaris
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Leukopenia 1 patient
Disc. AE
500 mg/kg 1 times / day steady, oral
Recommended
Dose: 500 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 500 mg/kg, 1 times / day
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: pustular acne vulgaris
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Nasal stuffiness 2 patients
Disc. AE
500 mg/kg 1 times / day steady, oral
Recommended
Dose: 500 mg/kg, 1 times / day
Route: oral
Route: steady
Dose: 500 mg/kg, 1 times / day
Sources:
unhealthy, adult
n = 43
Health Status: unhealthy
Condition: pustular acne vulgaris
Age Group: adult
Sex: unknown
Population Size: 43
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Anticryptosporidial activity is associated with specific sulfonamides in immunosuppressed rats.
1991 Apr
Monodrug efficacies of sulfonamides in prophylaxis for Pneumocystis carinii pneumonia.
1996 Apr
Hydrogen bonding in sulfonamides.
2001 Dec
Liquid chromatography-fluorescence detection for simultaneous analysis of sulfonamide residues in honey.
2003 Jun
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].
2005 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Simultaneous determination of 16 sulfonamides in honey by liquid chromatography/tandem mass spectrometry.
2005 Sep-Oct
Hapten synthesis and development of polyclonal antibody-based multi-sulfonamide immunoassays.
2006 Jun 28
Development of an immunochromatographic lateral-flow test strip for rapid detection of sulfonamides in eggs and chicken muscles.
2007 Mar 21
Analytical methods for multiresidue determination of sulfonamides and trimethoprim in meat and ground water samples by CE-MS and CE-MS/MS.
2007 Nov
ELISA for sulfonamides and its application for screening in water contamination.
2008 Aug 13
Characterization of integrons-mediated antimicrobial resistance among Escherichia coli strains isolated from bovine mastitis.
2008 Feb 5
Desolvation kinetics of sulfameter solvates.
2008 Jun
[Simultaneous determination of sulfonamides and fluoroquinolones residues in chicken by high performance liquid chromatography-electrospray tandem mass spectrometry].
2008 May
Multiresidue determination of sulfonamides in chicken meat by polymer monolith microextraction and capillary zone electrophoresis with field-amplified sample stacking.
2008 Sep 26
On-line coupling of dynamic microwave-assisted extraction to solid-phase extraction for the determination of sulfonamide antibiotics in soil.
2009 Aug 26
[Investigation of sulfonamides and tetracyclines antibiotics in soils from various vegetable fields].
2009 Jun 15
Analysis of sulfonamides in environmental water samples based on magnetic mixed hemimicelles solid-phase extraction coupled with HPLC-UV detection.
2009 Nov
Fast and selective extraction of sulfonamides from honey based on magnetic molecularly imprinted polymer.
2009 Nov 11
Determination of 76 pharmaceutical drugs by liquid chromatography-tandem mass spectrometry in slaughterhouse wastewater.
2009 Nov 20
A new and simple method to determine trace levels of sulfonamides in honey by high performance liquid chromatography with fluorescence detection.
2009 Oct 23
N-(4,6-Dimethyl-pyrimidin-2-yl)-4-(oxolan-2-ylamino)benzene-sulfonamide.
2009 Oct 28
Determination of sulfonamides in soil samples based on alumina-coated magnetite nanoparticles as adsorbents.
2010 Apr 30
Gene expression signature-based screening identifies new broadly effective influenza a antivirals.
2010 Oct 4
Patents

Sample Use Guides

In Vivo Use Guide
Sources: DOI: 10.1002/cpt1969104591
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
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
Name Type Language
SULFAMETER
MI   ORANGE BOOK   USAN  
USAN  
Official Name English
N(SUP 1)-(5-METHOXY-2-PYRIMIDINYL)SULFANILAMIDE
Systematic Name English
ULTRAX
Brand Name English
AHR-857
Code English
SULFAMETHOXYDIAZINE
Common Name English
SH-613
Code English
SULFAMETER [MI]
Common Name English
SULFAMETER [USAN]
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-(5-METHOXY-2-PYRIMIDINYL)-
Systematic Name English
SULFAMETHOXYPYRIMIDINE
Common Name English
BAY-5400
Code English
SULFAMETOXYDIAZINE
INN   WHO-DD  
INN  
Official Name English
SULFAMETOXYDIAZINE [INN]
Common Name English
SULFAMETER [ORANGE BOOK]
Common Name English
NSC-757874
Code English
NSC-683528
Code English
SULLA
Brand Name English
SULFAMETOXYDIAZINE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J01ED04
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
NCI_THESAURUS C29739
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C66568
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
DRUG CENTRAL
2511
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
CAS
651-06-9
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
ECHA (EC/EINECS)
211-480-8
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
MERCK INDEX
M10316
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY Merck Index
EPA CompTox
651-06-9
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
FDA UNII
3L179F09D6
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
PUBCHEM
5326
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
MESH
D013417
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
ChEMBL
CHEMBL1200359
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
WIKIPEDIA
SULFAMETOXYDIAZINE
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
DRUG BANK
DB06821
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
EVMPD
SUB10714MIG
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY
INN
1335
Created by admin on Fri Jun 25 21:54:52 UTC 2021 , Edited by admin on Fri Jun 25 21:54:52 UTC 2021
PRIMARY