Sulfalene: Difference between revisions

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	{{~~drugbox~~		{{Drugbox
			\| name = Sulfalene
	\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = T6BL4ZC15G
	\| verifiedrevid = 444121406
	\| IUPAC_name = 4-Amino-''N''-(3-methoxypyrazinyl)benzenesulfonamide		\| IUPAC_name = 4-Amino-''N''-(3-methoxypyrazinyl)benzenesulfonamide
	\| image = sulfalene.png		\| image = sulfalene.png
			\| width =
			\| alt =
			\| image2 =
			\| width2 =
			\| alt2 =
			\| imagename = <!-- else may use drug_name -->
			\| drug_name = <!-- else may use imagename -->
			\| caption =

			<!--Clinical data-->
			\| tradename =
			\| Drugs.com =
			\| MedlinePlus =
			\| licence_EU = <!-- EMA requires brand name -->
			\| licence_US = <!-- FDA may use generic name -->
			\| DailyMedID = <!-- preference to licence_US -->
			\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
			\| pregnancy_US = <!-- A / B / C / D / X -->
			\| pregnancy_category=
			\| 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_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_status =
			\| dependency_liability =
			\| routes_of_administration = Oral

			<!--Pharmacokinetic data-->
			\| bioavailability =
			\| protein_bound =
			\| metabolism =
			\| elimination_half-life =
			\| excretion =

			<!--Identifiers-->
			\| CAS_number = 152-47-6
			\| CAS_supplemental =
			\| ATCvet =
			\| ATC_prefix = J01
			\| ATC_suffix = ED02
			\| ATC_supplemental =
			\| PubChem = 9047
			\| PubChemSubstance =
			\| IUPHAR_ligand =
			\| DrugBank = DB00664
			\| ChemSpiderID = 8695
			\| UNII = T6BL4ZC15G
			\| KEGG = D01216
			\| ChEBI =
			\| ChEMBL =

			<!--Chemical data-->
			\| C=11 \| H=12 \| N=4 \| O=3 \| S=1
			\| 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}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 8695
	\| 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)		\| 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		\| InChIKey = KXRZBTAEDBELFD-UHFFFAOYAH
	\| smiles = O=S(=O)(Nc1nccnc1OC)c2ccc(N)cc2
	\| 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
	\| CAS_number = 152-47-6
	\| ATC_prefix = J01
	\| ATC_suffix = ED02
	\| PubChem = 9047
	\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}		\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = DB00664
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D01216
	\| C=11\|H=12\|N=4\|O=3\|S=1
	\| molecular_weight = 280.304 g/mol
	\| bioavailability =
	\| protein_bound =
	\| metabolism =
	\| elimination_half-life =
	\| excretion =
	\| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
	\| pregnancy_US = <!-- A / B / C / D / X -->
	\| pregnancy_category=
	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
	\| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
	\| legal_status =
	\| routes_of_administration = Oral
	}}		}}

Revision as of 04:56, 26 August 2011

Pharmaceutical compound

Sulfalene
Clinical data

Other names	Sulfametopyrazine
Routes of administration	Oral
ATC code	J01ED02 (WHO)
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	280.304 g/mol 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 is a sulfonamide antibacterial used for the treatment of chronic bronchitis, urinary tract infections and malaria.

References

DrugBank DB00664

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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