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{{short description|Chemical used to treat pulmonary issues}}
{{Drugbox {{Drugbox
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 444121406 | verifiedrevid = 470472993
| IUPAC_name = 4-Amino-''N''-(3-methoxypyrazinyl)benzenesulfonamide | IUPAC_name = 4-Amino-''N''-(3-methoxypyrazinyl)benzenesulfonamide
| image = sulfalene.png | image = Sulfalene2DCSD.svg
| width = | width =
| alt = | alt =
| image2 = | image2 =
| width2 = | width2 =
| drug_name =
| imagename = <!-- else may use drug_name -->
| drug_name = <!-- else may use imagename -->
| caption = | caption =

<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Eadazine, Kelfizina, Kelfizine W, Longum
| Drugs.com = {{drugs.com|international|sulfametopyrazine}} | Drugs.com = {{drugs.com|international|sulfametopyrazine}}
| licence_EU = <!-- EMA requires brand name --> | licence_EU = <!-- EMA requires brand name -->
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| legal_status = | legal_status =
| dependency_liability = | dependency_liability =
| routes_of_administration = Oral<ref name="MIMS">{{cite web | url = http://www.cimsasia.com/USA/drug/info/sulfalene/?q = Sulphonamides&type = full | title = Sulfalene | work = MIMS Drug Information System | accessdate = 26 August 2011}}</ref> | routes_of_administration = Oral<ref name="MIMS">{{cite web | url = http://www.cimsasia.com/USA/drug/info/sulfalene/?q=Sulphonamides&type=full | title = Sulfalene | work = MIMS Drug Information System | access-date = 26 August 2011}}</ref>


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 152-47-6 | CAS_number = 152-47-6
| CAS_supplemental = | CAS_supplemental =
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| ATC_prefix = J01 | ATC_prefix = J01
| ATC_suffix = ED02 | ATC_suffix = ED02
| ATC_supplemental = | ATC_supplemental = {{ATCvet|J01|EQ19}}
| PubChem = 9047 | PubChem = 9047
| PubChemSubstance = | PubChemSubstance =
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| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}

<!--Chemical data--> <!--Chemical data-->
| C=11 | H=12 | N=4 | O=3 | S=1 | C=11 | H=12 | N=4 | O=3 | S=1
⚫ | SMILES = O=S(=O)(Nc1nccnc1OC)c2ccc(N)cc2
| molecular_weight = 280.304 g/mol
⚫ | smiles = O=S(=O)(Nc1nccnc1OC)c2ccc(N)cc2
| InChI = 1/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)
| InChIKey = KXRZBTAEDBELFD-UHFFFAOYAH
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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) | StdInChI = 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)
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}} }}


'''Sulfalene''' is a ] ] used for the treatment of ], ]s and ].<ref name="DrugBank">{{DrugBank|DB00664}}</ref> '''Sulfalene''' (], ]) or '''sulfametopyrazine''' (]) is a long-acting ] ] used for the treatment of ], ]s and ].<ref name="DrugBank">{{DrugBank|DB00664}}</ref><ref name = MD/> As of 2014 there were only two countries in which it is currently still marketed: ] and ].<ref name = MD>{{cite web|title=Sulfametopyrazine|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|date=9 May 2013|access-date=28 March 2014| veditors = Brayfield A |url=http://www.medicinescomplete.com/mc/martindale/current/4920-k.htm}}</ref>


It was discovered by researchers at ] and first published in 1960 and was marketed as Kelfizina.<ref name="pmid5332105">{{cite journal | vauthors = Baruffa G | title = Clinical trials in Plasmodium falciparum malaria with a long-acting sulphonamide | journal = Transactions of the Royal Society of Tropical Medicine and Hygiene | volume = 60 | issue = 2 | pages = 222–4 | date = 1966 | pmid = 5332105 | doi = 10.1016/0035-9203(66)90030-7 }}</ref><ref>Per prior citation, the first publication: {{cite journal | vauthors = Camerino B, Palamidessi G | date = 1960 | title = Derivati della parazina II. Sulfonamdopir |language=it | journal = Gazz Chim Ital | volume = 90 | pages = 1802–1815 }}</ref>

==See also==
*]
== References == == References ==
<references/> <references/>
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{{Sulfonamides and trimethoprim}} {{Sulfonamides and trimethoprim}}


] ]
] ]
] ]
] ]
]
]
]


{{antibiotic-stub}} {{antibiotic-stub}}

]

Latest revision as of 15:34, 8 October 2024

Chemical used to treat pulmonary issues Pharmaceutical compound
Sulfalene
Clinical data
Trade namesEadazine, Kelfizina, Kelfizine W, Longum
Other namesSulfametopyrazine
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Pharmacokinetic data
Protein binding60 to 80%
Elimination half-life60 to 65 hours
ExcretionUrinary
Identifiers
IUPAC name
  • 4-Amino-N-(3-methoxypyrazinyl)benzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.005.278 Edit this at Wikidata
Chemical and physical data
FormulaC11H12N4O3S
Molar mass280.30 g·mol
3D model (JSmol)
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.

See also

References

  1. ^ "Sulfalene". MIMS Drug Information System. Retrieved 26 August 2011.
  2. DrugBank DB00664
  3. ^ Brayfield A, ed. (9 May 2013). "Sulfametopyrazine". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 28 March 2014.
  4. 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.
  5. Per prior citation, the first publication: Camerino B, Palamidessi G (1960). "Derivati della parazina II. Sulfonamdopir". Gazz Chim Ital (in Italian). 90: 1802–1815.
Antibacterials that inhibit nucleic acid (J01E, J01M)
Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)
DHFR inhibitor
Sulfonamides
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Short-acting
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(inhibit bacterial
topoisomerase
and/or DNA gyrase,
thereby inhibiting
DNA replication)
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