Sulfamethoxypyridazine

Chemical compound

J01ED05 (WHO) QJ01EQ15 (WHO)

Identifiers

IUPAC name

4-amino-N-(6-methoxypyridazin-3-yl)benzenesulfonamide

CAS Number

80-35-3^N

PubChem CID

5330

ChemSpider

5139^Y

UNII

T034E4NS2Z

KEGG

D02439^Y

ChEBI

CHEBI:102516^Y

ChEMBL

ChEMBL268869^Y

CompTox Dashboard (EPA)

DTXSID5023611

ECHA InfoCard100.001.157

Chemical and physical dataFormulaC₁₁H₁₂N₄O₃SMolar mass280.30 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=S(=O)(Nc1nnc(OC)cc1)c2ccc(N)cc2

InChI

InChI=1S/C11H12N4O3S/c1-18-11-7-6-10(13-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)^Y
Key:VLYWMPOKSSWJAL-UHFFFAOYSA-N^Y

^NY (what is this?) (verify)

Sulfamethoxypyridazine is a sulfonamide antibacterial.^[1]

It is prescribed for vaginal irritation, and severe acute thrush.

It is also used in the treatment of Dermatitis herpetiformis,^[2] where it is an alternative therapy to Dapsone.

Sulfamethoxypyridazine is supplied as 500mg tablets.

References

^ Boger WP, Gylfe JM, Strickland CS (November 1956). "Sulfamethoxypyridazine (Kynex), a new long-acting sulfonamide". Antibiotic Medicine & Clinical Therapy. 3 (6). New York, NY: 378–87. PMID 13363378.
^ Vilanova X, De Moragas JM (October 1959). "[Treatment of dermatitis herpetiformis (Duhring) and herpes gestationis with sulfamethoxypyridazine]". Actas Dermo-sifiliograficas (in Spanish). 50: 439–42. PMID 13842251.

Antibacterials that inhibit nucleic acid (J01E, J01M)

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Brodimoprim
- Iclaprim^†
- Ormetoprim
- Pyrimethamine^#
- Tetroxoprim
- Trimethoprim^#

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole, Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Trimethoprim/sulfamethoxazole^#
Ormetoprim/sulfadimethoxine
Pyrimethamine/dapsone
Pyrimethamine/sulfadoxine

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)

1st generation

Fluoroquinolones

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡/Levonadifloxacin/Alalevonadifloxacin Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡

Newer non-fluorinated

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitroimidazole derivatives	Metronidazole^# Ornidazole Secnidazole Tinidazole
Nitrofuran derivatives	Furazolidone^‡ Nifuroxazide Nifurtoinol Nifurzide Nitrofurantoin^# Nitrofurazone