Sulfalene - Misplaced Pages

Chemical used to treat pulmonary issues Pharmaceutical compound

Sulfalene
Clinical data

Trade names	Eadazine, Kelfizina, Kelfizine W, Longum
Other names	Sulfametopyrazine
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	J01ED02 (WHO) QJ01EQ19 (WHO)
Pharmacokinetic data
Protein binding	60 to 80%
Elimination half-life	60 to 65 hours
Excretion	Urinary
Identifiers
IUPAC name 4-Amino-N-(3-methoxypyrazinyl)benzenesulfonamide
CAS Number	152-47-6
PubChem CID	9047
DrugBank	DB00664
ChemSpider	8695
UNII	T6BL4ZC15G
KEGG	D01216
CompTox Dashboard (EPA)	DTXSID2046179
ECHA InfoCard	100.005.278
Chemical and physical data
Formula	C₁₁H₁₂N₄O₃S
Molar mass	280.30 g·mol
3D model (JSmol)	Interactive image
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) Key:KXRZBTAEDBELFD-UHFFFAOYSA-N
(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. As of 2014 there were only two countries in which it is currently still marketed: Thailand and Ireland.

It was discovered by researchers at Farmitalia and first published in 1960 and was marketed as Kelfizina.

References

^ "Sulfalene". MIMS Drug Information System. Retrieved 26 August 2011.
DrugBank DB00664
^ Brayfield A, ed. (9 May 2013). "Sulfametopyrazine". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 28 March 2014.
Baruffa G (1966). "Clinical trials in Plasmodium falciparum malaria with a long-acting sulphonamide". Transactions of the Royal Society of Tropical Medicine and Hygiene. 60 (2): 222–4. doi:10.1016/0035-9203(66)90030-7. PMID 5332105.
Per prior citation, the first publication: Camerino B, Palamidessi G (1960). "Derivati della parazina II. Sulfonamdopir". Gazz Chim Ital (in Italian). 90: 1802–1815.

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

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

Other DHPS inhibitors

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

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)

Nitroimidazole derivatives	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin Rifabutin Rifapentine Rifaximin Rifalazil
Lipiarmycins	Fidaxomicin

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