Sulfalene: Difference between revisions

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Revision as of 05:08, 26 August 2011 editCheMoBot (talk \| contribs)Bots141,565 edits Updating {{drugbox}} (changes to watched fields - updated 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot← Previous edit		Latest revision as of 15:34, 8 October 2024 edit undoJWBE (talk \| contribs)Extended confirmed users10,129 edits removed Category:Anilines; added Category:4-Aminophenyl compounds using HotCat
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			{{short description\|Chemical used to treat pulmonary issues}}
	{{Drugbox		{{Drugbox
	\| Watchedfields = changed		\| Watchedfields = changed
		⚫	\| verifiedrevid = 470472993
	\| name = Sulfalene
	\| 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 =
	\| ~~alt2~~ =		\| drug_name =
		⚫	\| caption =
	\| imagename = <!-- else may use drug_name -->
	\| drug_name = <!-- else may use imagename -->
⚫	\| caption =

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename =		\| tradename = Eadazine, Kelfizina, Kelfizine W, Longum
	\| Drugs.com =		\| Drugs.com = {{drugs.com\|international\|sulfametopyrazine}}
			\| licence_EU = <!-- EMA requires brand name -->
	\| MedlinePlus =
	\| ~~licence_EU~~ = <!-- ~~EMA~~ ~~requires~~ ~~brand~~ name -->		\| licence_US = <!-- FDA may use generic name -->
	\| ~~licence_US~~ = <!-- ~~FDA~~ ~~may~~ ~~use generic name~~ -->		\| DailyMedID = <!-- preference to licence_US -->
	\| ~~DailyMedID~~ = ~~<!--~~ ~~preference~~ to ~~licence_US~~ -->		\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| ~~pregnancy_AU~~ = <!-- A / B1 / B2 / B3 / C / D / X -->		\| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	\| pregnancy_category =
	\| pregnancy_US = <!-- A / B / C / D / X -->
⚫	\| pregnancy_category=
	\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->		\| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
	\| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->		\| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
	\| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM -->		\| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM -->
	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->		\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	\| 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 \| access-date = 26 August 2011}}</ref>
	\| routes_of_administration = Oral

	<!--Pharmacokinetic data-->		<!--Pharmacokinetic data-->
	\| bioavailability =		\| bioavailability =
	\| protein_bound =		\| protein_bound = 60 to 80%<ref name="MIMS"/>
	\| metabolism =		\| metabolism =
	\| elimination_half-life =		\| elimination_half-life = 60 to 65 hours<ref name="MIMS"/>
	\| excretion =		\| excretion = ]<ref name="MIMS"/>

	<!--Identifiers-->		<!--Identifiers-->
		⚫	\| CAS_number_Ref = {{cascite\|correct\|??}}
	\| CAS_number = 152-47-6		\| CAS_number = 152-47-6
	\| CAS_supplemental =		\| CAS_supplemental =
	\| ATCvet =		\| ATCvet =
	\| 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 =
	\| IUPHAR_ligand =		\| IUPHAR_ligand =
⚫	\| DrugBank = DB00664
		⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
⚫	\| ChemSpiderID = 8695
		⚫	\| DrugBank = DB00664
⚫	\| UNII = T6BL4ZC15G
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
⚫	\| KEGG = D01216
		⚫	\| ChemSpiderID = 8695
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
		⚫	\| UNII = T6BL4ZC15G
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
		⚫	\| KEGG = D01216
	\| ChEBI_Ref = {{ebicite\|correct\|EBI}}		\| ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| ChEBI =
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL =

	<!--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
⚫	\| 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_comment =
⚫	\| StdInChIKey = KXRZBTAEDBELFD-UHFFFAOYSA-N
⚫	\| synonyms = Sulfametopyrazine
⚫	\| density =
⚫	\| melting_point =
⚫	\| melting_high =
⚫	\| melting_notes =
⚫	\| boiling_point =
⚫	\| boiling_notes =
⚫	\| solubility =
⚫	\| specific_rotation =
⚫	\| sec_combustion =

	<!-- ? -->
⚫	\| ~~UNII_Ref~~ = {{~~fdacite~~\|correct\|~~FDA~~}}
⚫	\| verifiedrevid = ~~444121406~~
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| 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)
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
		⚫	\| StdInChIKey = KXRZBTAEDBELFD-UHFFFAOYSA-N
⚫	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
		⚫	\| synonyms = Sulfametopyrazine
⚫	\| ~~KEGG_Ref~~ = {{~~keggcite~~\|correct\|~~kegg~~}}
		⚫	\| density =
		⚫	\| melting_point =
		⚫	\| melting_high =
		⚫	\| melting_notes =
		⚫	\| boiling_point =
		⚫	\| boiling_notes =
		⚫	\| solubility =
		⚫	\| specific_rotation =
		⚫	\| sec_combustion =
	}}		}}

	'''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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	{{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 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.

Antibacterials that inhibit nucleic acid (J01E, J01M)

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

DHFR inhibitor

2,4-Diaminopyrimidine

Sulfonamides
(DHPS inhibitor)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine (Sulfamethazine, Sulfadimerazine, Sulfadimezine) 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)

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	Secnidazole

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin Rifabutin Rifapentine Rifaximin Rifalazil
Lipiarmycins	Fidaxomicin

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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Categories:

Latest revision as of 15:34, 8 October 2024

See also

References