Sulfameter

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Cat Number

API0231643

CAS Number

651-06-9

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Product Detail Description Scientific Support Customer Q&A

CAS Number

651-06-9

EINECS

211-480-8

Storage

Store at room temperature

Synonyms

Sulfamethoxydiazine; Sulfametoxydiazine; 4-amino-N-(5-methoxypyrimidin-2-yl)benzenesulfonamide; Sulfamethoxypyrimidine

Molecular Formula

C11H12N4O3S

Molecular Weight

280.31

Smiles

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

Appearance

White to faint yellow crystalline powder

Melting Point

214-216℃

Boiling Point

539.4±56.0℃ (Predicted)

Relative Density

1.3936

General Description

Sulfameter (also known as sulfamethoxydiazine) is a long-acting sulfonamide antibiotic with a half-life of approximately 40 hours. It was used for urinary tract infections and as a prophylactic agent in rheumatic fever.

Mechanism of Action

Sulfameter inhibits bacterial folate synthesis by competing with PABA for dihydropteroate synthase, similar to other sulfonamides. Its long half-life is due to high protein binding and slow renal excretion. The drug has activity against gram-positive cocci, E. coli, and Proteus species. It does not kill bacteria but halts their growth, allowing immune clearance.

Application

Sulfameter was indicated for chronic urinary tract infections requiring prolonged therapy, as well as for acute uncomplicated UTIs when first-line agents failed. It was also used in leprosy combination regimens.

This review summarizes current knowledge on the biosynthesis of natural sulfonamide and sulfamate compounds isolated from actinomycetes, including ascamycin (a secondary sulfamate), sulfadixiamycin A (a tertiary sulfonamide), and SB‑203208 (a secondary sulfonamide). Each compound is produced by distinct and unique biosynthetic machineries that generate the characteristic S–N bond. Detailed understanding of these enzyme systems is crucial for creating second‑generation natural products through biosynthetic engineering. The authors also discuss the bioactivities and mechanisms of action of these highly potent natural products.

Fig. 1 Structural relationships of sulfonamides and sulfamates. (Awakawa T, et al., 2021)

References

Awakawa T, et al. Biosynthesis of sulfonamide and sulfamate antibiotics in actinomycete. J Ind Microbiol Biotechnol. 2021;48(3-4):kuab001.

Does Sulfameter require protection from light during long-term storage?

Yes, it is photosensitive. UV light can cause discoloration and degradation of the sulfonamide ring. Store in light-resistant containers.

What is the recommended storage temperature for Sulfameter?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which accelerates hydrolysis to sulfanilamide derivatives.

Is Sulfameter susceptible to moisture-induced degradation?

It is slightly hygroscopic. Under high humidity, it may absorb moisture and clump, but significant hydrolysis requires elevated temperatures. Store with desiccant.

How is the impurity sulfanilamide monitored during stability?

This primary degradation product is specifically quantified using a validated HPLC method, ensuring it remains below pharmacopoeial limits.