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Merck

S8751

Sulfaguanidine

Synonym(s):

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

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25 G

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About This Item

Empirical Formula (Hill Notation):
C7H10N4O2S
CAS Number:
57-67-0
Molecular Weight:
214.24
UNSPSC Code:
51283914
NACRES:
NA.85
PubChem Substance ID:
24899810
EC Number:
200-345-9
Beilstein/REAXYS Number:
2695326
MDL number:
MFCD00038136

Key Documents

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InChI key

BRBKOPJOKNSWSG-UHFFFAOYSA-N

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)

SMILES string

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

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

Quality Level

200

Gene Information

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

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1 of 4

This Item
32402S1975600S8626
Sulfaguanidine

Sigma-Aldrich

S8751

Sulfaguanidine

Sulfaguanidine VETRANAL®, analytical standard

Supelco

32402

Sulfaguanidine

Sulfaguanidine European Pharmacopoeia (EP) Reference Standard

S1975600

Sulfaguanidine

Sulfadiazine 99.0-101.0%

Sigma-Aldrich

S8626

Sulfadiazine

mode of action

DNA synthesis | interferes, enzyme | inhibits

mode of action

-

mode of action

-

mode of action

DNA synthesis | interferes, enzyme | inhibits

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycoplasma

form

powder

form

-

form

-

form

powder or crystals

solubility

1 M HCl: soluble 50 mg/mL

solubility

-

solubility

-

solubility

96% ethanol: very slightly soluble, acetone: slightly soluble, water: practically insoluble

biological source

synthetic (Organic)

biological source

-

biological source

-

biological source

-

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

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[1].

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[2]. 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.

General description

Chemical structure: sulfonamide

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000491940
0000491940
0000489845
0000489845
SLCP5182

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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
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
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
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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