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S8751

Sigma-Aldrich

Sulfaguanidine

Synonym(s):

4-Amino-N-(aminoiminomethyl)benzenesulfonamide, 4-Amino-N-guanylbenzenesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C7H10N4O2S
CAS Number:
Molecular Weight:
214.24
Beilstein:
2695326
EC Number:
MDL number:
UNSPSC Code:
51283914
PubChem Substance ID:
NACRES:
NA.85

biological source

synthetic (Organic)

Quality Level

form

powder

color

white to off-white

solubility

1 M HCl: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

NC(=N)NS(=O)(=O)c1ccc(N)cc1

InChI

1S/C7H10N4O2S/c8-5-1-3-6(4-2-5)14(12,13)11-7(9)10/h1-4H,8H2,(H4,9,10,11)

InChI key

BRBKOPJOKNSWSG-UHFFFAOYSA-N

Gene Information

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General description

Chemical structure: sulfonamide

Application

Sulfaguanidine is used to block the synthesis of folic acid. It is used to study its effect on microsporidial growth and host cell viability.

Biochem/physiol Actions

Sulfaguanidine 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. Sulfaguanidine 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.Keep in a dry place.Storage class (TRGS 510): Non Combustible Solids

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 3

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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B W Clare et al.
Journal of enzyme inhibition, 16(1), 1-13 (2001-08-11)
A series of compounds has been prepared by reaction of dicyandiamide with alkyl/arylsulfonyl halides as well as arylsulfonylisocyanates to locate a lead for obtaining weakly basic thrombin inhibitors with sulfonyldicyandiamide moieties as the S1 anchoring group. The detected lead was
B Beauvais et al.
Antimicrobial agents and chemotherapy, 38(10), 2440-2448 (1994-10-01)
We have developed a new micromethod to study the effect of drugs on microsporidia, using MRC5 fibroblasts infected by 10(5) spores of Encephalitozoon cuniculi. After 3 days of incubation with various concentrations of drugs, parasitic foci were counted in stained
Vimal K Balakrishnan et al.
Journal of chromatography. A, 1131(1-2), 1-10 (2006-08-02)
In recent years, pharmaceutical and personal care products (PPCPs) have been detected in diverse environments (including groundwater, river water, and municipal wastewater). In order to evaluate their environmental impact, PPCPs must first be accurately determined. In this study, we focused
H Sasaki et al.
Journal of pharmacobio-dynamics, 13(3), 200-205 (1990-03-01)
The enhancing effect of pyrrolidone derivatives on the percutaneous penetration of sulfaguanidine, aminopyrine and sudan III was investigated using in vitro technique and excised rat skin. 1-Methyl (MP), 1-hexyl (HP) and 1-lauryl-2-pyrrolidone (LP) were used as penetration enhancers. Aminopyrine showed
Alan D Gift et al.
Journal of pharmaceutical sciences, 98(12), 4670-4683 (2009-05-21)
Active pharmaceutical ingredients (API) can undergo an anhydrate to hydrate transformation during wet granulation and this transformation may either result in mixed crystalline forms or an unwanted form in the final drug product. Previous studies have shown that it may

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