Sulfalene

Sulfalene
Systematic (IUPAC) name

4-Amino-N-(3-methoxypyrazinyl)benzenesulfonamide
Clinical data
Trade names	Eadazine, Kelfizina, Kelfizine W, Longum
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral^[1]
Pharmacokinetic data
Protein binding	60 to 80%^[1]
Biological half-life	60 to 65 hours^[1]
Excretion	Urinary^[1]
Identifiers
CAS Number	152-47-6^Y
ATC code	J01ED02 (WHO) QJ01EQ19 (WHO)
PubChem	CID 9047
DrugBank	DB00664^Y
ChemSpider	8695^Y
UNII	T6BL4ZC15G^Y
KEGG	D01216^Y
Synonyms	Sulfametopyrazine
Chemical data
Formula	C₁₁H₁₂N₄O₃S
Molar mass	280.304 g/mol
SMILES O=S(=O)(Nc1nccnc1OC)c2ccc(N)cc2
InChI InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)^Y Key:KXRZBTAEDBELFD-UHFFFAOYSA-N^Y
(verify)

Sulfalene (INN, USAN) or sulfametopyrazine (BAN) is a long-acting sulfonamide antibacterial used for the treatment of chronic bronchitis, urinary tract infections and malaria.^[2]^[3] As of 2014 there were only two countries in which it is currently still marketed: Thailand and Ireland.^[3]

It was discovered by researchers at Farmitalia and first published in 1960 and was marketed as Kelfizina.^[4]^[5]

References

1 2 3 4 "Sulfalene". MIMS Drug Information System. Retrieved 26 August 2011.
↑ DrugBank DB00664
1 2 Brayfield, A, ed. (9 May 2013). "Sulfametopyrazine". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 28 March 2014.
↑ Baruffa G. Clinical trials in Plasmodium falciparum malaria with a long-acting sulphonamide. Trans R Soc Trop Med Hyg. 1966;60(2):222-4. PMID 5332105
↑ Per prior citation, the first publication: Camerino B, Palamidessi G (1960) Derivati della parazina II. Sulfonamdopir (in Italian). Gazz Chim Ital 90:1802–1815

Antibacterials: nucleic acid inhibitors (J01E, J01M)

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

DHFR inhibitor

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

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Sulfalene

See also

References