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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

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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K Nakanishi et al.
Journal of pharmacobio-dynamics, 13(12), 760-765 (1990-12-01)
The influence of suppository bases and adjuvants on the release rate of drugs and the absorption of non-absorbable drugs such as sulfanilic acid (SA) and sulfaguanidine (SG), was investigated following the rectal administration of suppositories. The suppository bases used were
Carmen M Sharaby
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 62(1-3), 326-334 (2005-11-01)
Novel hexachlorocyclodiphosph(V)azane of sulfaguanidine, H(4)L, l,3-[N'-amidino-sulfanilamide]-2,2,2,4,4,4-hexachlorocyclodiphosph(V)azane was prepared and its coordination behaviour towards the transition metal ions Fe(III), Fe(II), Co(II), Ni(II), Cu(II), Zn(II), Cd(II) and UO(2)(II) was studied. The structures of the isolated products are proposed based on elemental analyses
Erythema multiforme from sulfaguanidine.
Consolación de Frutos et al.
Contact dermatitis, 46(3), 186-187 (2002-05-10)
L S Wan et al.
Journal of microencapsulation, 12(4), 417-423 (1995-07-01)
Microspheres were formed when a solution of cellulose phthalate was extruded into 30% glacial acetic acid solution. Sulphonamides entrapped in such microspheres leached into the hardening solution because they dissolved freely in the acetic acid solution. This resulted in poor
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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