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S9251

Sigma-Aldrich

Sulfanilamide

≥98%

Synonym(s):

4-aminobenzenesulfonamide, p-Aminobenzenesulfonamide

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About This Item

Linear Formula:
H2NC6H4SO2NH2
CAS Number:
63-74-1
Molecular Weight:
172.20
Beilstein:
511852
EC Number:
200-563-4
MDL number:
MFCD00007939
UNSPSC Code:
51283932
eCl@ss:
39093202
PubChem Substance ID:
24899829
NACRES:
NA.76

Quality Level

200

Assay

≥98%

form

powder or crystals

color

white to off-white

mp

164-166 °C (lit.)

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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

Gene Information

human ... CA1(759) , CA2(760) , CA5A(763) , CA5B(11238) , CA9(768)
mouse ... Car13(71934) , Car5a(12352)

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General description

Chemical structure: sulfonamide

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

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000388227
0000369391
0000369392
0000359051
0000369391

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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
Rajwinder Singh et al.
Biomedical optics express, 11(7), 3733-3752 (2020-10-06)
In pregnancy during an inflammatory condition, macrophages present at the feto-maternal junction release an increased amount of nitric oxide (NO) and pro-inflammatory cytokines such as TNF-α and INF-γ, which can disturb the trophoblast functions and pregnancy outcome. Measurement of the
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
Claudia Temperini et al.
Journal of medicinal chemistry, 53(2), 850-854 (2009-12-24)
Coumarins constitute a general and totally new class of inhibitors of the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), binding at the entrance of the active site cavity. We report here that the coumarin-binding site in CAs may interact with
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
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