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S9882

Sigma-Aldrich

Sulfachloropyridazine

Synonym(s):

4-Amino-N-(6-chloro-3-pyridazinyl)benzenesulfonamide, N1-(6-Chloro-3-pyridazinyl)sulfanilamide

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About This Item

Empirical Formula (Hill Notation):
C10H9ClN4O2S
CAS Number:
80-32-0
Molecular Weight:
284.72
Beilstein/REAXYS Number:
261558
EC Number:
201-269-9
MDL number:
MFCD00057371
UNSPSC Code:
51102829
PubChem Substance ID:
24899860
NACRES:
NA.85

form

powder

color

off-white to light yellow

solubility

0.5 M NaOH: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycoplasma

mode of action

DNA synthesis | interferes

SMILES string

Nc1ccc(cc1)S(=O)(=O)Nc2ccc(Cl)nn2

InChI

1S/C10H9ClN4O2S/c11-9-5-6-10(14-13-9)15-18(16,17)8-3-1-7(12)2-4-8/h1-6H,12H2,(H,14,15)

InChI key

XOXHILFPRYWFOD-UHFFFAOYSA-N

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Application

Sulfachloropyridazine is a sulfonamide antibiotic that is used to study kinetics, reaction pathways and toxicity evolution[1]. Sulfachloropyridazine has been used to treat acute urinary tract infections in pediatric patients[2].

Biochem/physiol Actions

Sulfachloropyridazine is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfachloropyridazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid[3]. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis. Sulfachloropyridazine is rapidly absorbed and rapidly excreted in the urine[4].

Other Notes

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

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

pcodes

P280

Hazard Classifications

Skin Sens. 1

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCC5271
SLBD3636V
070M1413
048K1249
045K0148

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[Sulfachloropyridazine in the treatment of acute infections of the urinary tract in childhood].
R C PEDRINAZZI et al.
Minerva pediatrica, 12, 1342-1347 (1960-10-27)
Absorption and Excretion of Sulfachloropyridazine
Wilfred F. Jones, Jr, Mohsen Ziai, et al.
Exp. Biol. Med, 95, 642-645 (1957)
Paul Kay et al.
Environmental toxicology and chemistry, 23(5), 1136-1144 (2004-06-08)
The environment may be exposed to veterinary medicines administered to livestock through the application of organic fertilizers to land. For other groups of substances that are applied to agricultural land (e.g., pesticides), preferential flow in underdrained clay soils has been
Paul A Blackwell et al.
Chemosphere, 67(2), 292-299 (2007-01-06)
The environmental fate of the antibiotics sulfachloropyridazine and oxytetracycline was investigated in a sandy loam soil. Liquid pig manure was fortified with the compounds and then applied to soil plots to investigate leaching, dissipation and surface run-off under field conditions.
Thomas L ter Laak et al.
Environmental toxicology and chemistry, 25(4), 904-911 (2006-04-25)
Antimicrobial agents are the most heavily used pharmaceuticals in intensive husbandry. Their usual discharge pathway is application to agricultural land as constituents of animal manure, which is used as fertilizer. Many of these compounds undergo pH-dependent speciation and, therefore, might
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