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S0383

Sigma-Aldrich

Sulfameter

Synonym(s):

5-Methoxysulfadiazine, N1-(5-Methoxypyrimidin-2-yl)sulfanilamide, Sulfamethoxydiazine

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About This Item

Empirical Formula (Hill Notation):
C11H12N4O3S
CAS Number:
Molecular Weight:
280.30
Beilstein:
621130
EC Number:
MDL number:
UNSPSC Code:
51283913
PubChem Substance ID:
NACRES:
NA.85

form

powder

Quality Level

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Light sensitive.)

color

white to faint yellow

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria
parasites

Mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

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

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)

InChI key

GPTONYMQFTZPKC-UHFFFAOYSA-N

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General description

Chemical structure: sulfonamide

Application

Sulfameter is a sulfonamide antibiotic used as a leprostatic agent and to treat urinary tract infections. It has been investigated as a potential therapy for chloroquine-resistant malaria during pregnancy.

Biochem/physiol Actions

Sulfameter is a sulfonamide antibiotic. 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. Sulfonamides are active against Gram positive bacteria and Gram negative bacteria. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Light sensitive.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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M Forland et al.
Diabetes care, 8(5), 499-506 (1985-09-01)
Forty-five women with diabetes mellitus and urinary tract infections have been followed an average of 34 mo on treatment protocols based on localization of infection as determined by the presence or absence of antibody-coated bacteria (ACB). Treatment was usually, but
Treatment of Chloroquine-Resistant Malaria During Pregnancy
Elliott K. Main, Denise M. Main, et al.
Journal of the American Medical Association, 249, 3207-3209 (1983)
Identification of polymorphs of sulfamethoxydiazine by optical and morphological methods.
T Yokoyama et al.
Chemical & pharmaceutical bulletin, 26(4), 1044-1048 (1978-04-01)
The effect of gastro-intestinal filling on the absorption of sulfametoxydiazine.
S Kaumeier et al.
International journal of clinical pharmacology and biopharmacy, 17(10), 412-415 (1979-10-01)
Ammar Khawam et al.
Journal of pharmaceutical sciences, 97(6), 2160-2175 (2007-11-03)
Solvates are often encountered in pharmaceutical solids and knowledge of their physical stability is necessary for their effective formulation. This work investigates the solid-state stability of five structurally related solvates of sulfameter (5-methoxysulfadiazine) by studying the kinetics of their desolvation

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