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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:
57-67-0
Molecular Weight:
214.24
Beilstein:
2695326
EC Number:
200-345-9
MDL number:
MFCD00038136
UNSPSC Code:
51283914
PubChem Substance ID:
24899810
NACRES:
NA.85

biological source

synthetic (Organic)

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

human ... F2(2147) , PRSS1(5644)

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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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
SLCP5182
SLBQ1293V
SLBD5155V
098K0683
026K0679

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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
Anna Białk-Bielińska et al.
Talanta, 80(2), 947-953 (2009-10-20)
One of the oldest groups of veterinary chemotherapeutic agents, sulfonamides have been widely used for more than 50 years, thanks to their low cost and their broad spectrum of activity in preventing or treating bacterial infections. Nowadays, those compounds are
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
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
R F Cross et al.
Journal of chromatography. A, 929(1-2), 113-121 (2001-10-12)
Two electrically neutral analytes previously observed to be separated from the neutral marker in capillary zone electrophoresis (CZE) experiments [sulphanilamide (SAA) and sulphaguanidine (SGW)] have been examined to determine the basis for separation. The degree of separation increases markedly with
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