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Merck

S0383

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:
651-06-9
Molecular Weight:
280.30
UNSPSC Code:
51283913
NACRES:
NA.85
PubChem Substance ID:
24899422
EC Number:
211-480-8
Beilstein/REAXYS Number:
621130
MDL number:
MFCD00006067

InChI key

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)

SMILES string

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

form

powder

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

Quality Level

200

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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.

General description

Chemical structure: sulfonamide

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
107F0910

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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)
I U Asuzu et al.
Biochemical medicine and metabolic biology, 39(2), 158-167 (1988-04-01)
The interactions of aflatoxin B1 (AFB1) with vitamin K, phenylbutazone, and sulfamethoxine were investigated in albino rats. Vitamin K (5 mg/kg) was able to completely suppress the increase in whole blood clotting time caused by AFB1 (25 micrograms/kg). Phenylbutazone (50
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