All Photos(3)

S9251

Sigma-Aldrich

Sulfanilamide

≥98%

Synonym(s):
p-Aminobenzenesulfonamide
Linear Formula:
H2NC6H4SO2NH2
CAS Number:
Molecular Weight:
172.20
Beilstein:
511852
EC Number:
MDL number:
eCl@ss:
39093202
PubChem Substance ID:
NACRES:
NA.76

Quality Level

assay

≥98%

form

powder or crystals

color

white to off-white

mp

164-166 °C (lit.)

Mode of action

DNA synthesis | interferes
enzyme | inhibits

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

SMILES string

Nc1ccc(cc1)S(N)(=O)=O

InChI

1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)

InChI key

FDDDEECHVMSUSB-UHFFFAOYSA-N

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Related Categories

General description

Chemical structure: sulfonamide

Packaging

100, 500 g in poly bottle

Biochem/physiol Actions

Sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.
Mode of Action: A competitive inhibitor of dihydropteroate synthestase to block the synthesis of folic acid.
Anti-microbial Spectrum: Gram positive, Gram negative, Chlamydia
Mode of Resistance: Alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

I Meneau et al.
Antimicrobial agents and chemotherapy, 48(7), 2610-2616 (2004-06-25)
Failure of anti-Pneumocystis jiroveci prophylaxis with sulfa drugs is associated with mutations within the putative active site of the fungal dihydropteroate synthase (DHPS), an enzyme encoded by the multidomain FAS gene. This enzyme is involved in the essential biosynthesis of...
Edward E Knaus et al.
Bioorganic & medicinal chemistry letters, 21(19), 5892-5896 (2011-08-20)
A series of compounds incorporating regioisomeric phenylethynylbenzenesulfonamide moieties has been investigated for the inhibition of four human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IX and XII. Inhibition between the low nanomolar to the milliomolar range has been...
Daniela Vullo et al.
Bioorganic & medicinal chemistry letters, 20(7), 2178-2182 (2010-03-10)
A beta-carbonic anhydrase (CA, EC 4.2.1.1) from the bacterial pathogen Brucella suis, bsCA 1, has been cloned, purified characterized kinetically and for inhibition with a series of water soluble glycosylated sulfanilamides. bsCA 1 has appreciable activity as catalyst for the...
Daniela Vullo et al.
Bioorganic & medicinal chemistry letters, 15(4), 971-976 (2005-02-03)
The inhibition of a newly cloned human carbonic anhydrase (CA, EC 4.2.1.1), isozyme VII (hCA VII), has been investigated with a series of aromatic and heterocyclic sulfonamides, including some of the clinically used derivatives (acetazolamide, methazolamide, ethoxzolamide, dichlorophenamide, dorzolamide, brinzolamide...
Isao Nishimori et al.
Journal of medicinal chemistry, 48(24), 7860-7866 (2005-11-24)
A lately discovered carbonic anhydrase (hCA, EC 4.2.1.1), the mitochondrial hCA VB, was cloned, expressed, and purified. Kinetic parameters proved it to be 3.37 times more effective than hCA VA as a catalyst for the physiological reaction, with kcat =...

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